Nucleosides &amp; Nucleotides

Chemically reduced

Packaged based on NADPH content as determined by UV-Vis.

assay	~95%
Quality Level	200,
packaging	vial of 10 mg
InChI	1S/C21H30N7O17P3.4Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;;;;/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35);;;;/q;4*+1/p-4/t10-,11+,13-,14+,15-,16+,20-,21+;;;;/m0..../s1
InChI key	WYWWVJHQDVCHKF-MPUNMZHWSA-J

25, 100, 250, 500 mg in poly bottle
1 g in poly bottle

Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	3

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-Nicotinamide adenine dinucleotide 2-phosphate reduced tetrasodium salt hydrate

Empirical Formula (Hill Notation):	C₂₁H₂₆N₇Na₄O₁₇P₃ · xH₂O
CAS Number:	2646-71-1
Molecular Weight:	833.35 (anhydrous basis)
EC Number:	220-163-3
MDL number:	MFCD00036263
PubChem Substance ID:	24278049
NACRES:	NA.51

NADPH is an electron donor and a cofactor for many redox enzymes including nitric oxide synthetase.
-Nicotinamide adenine dinucleotide 2-phosphate (NADP+) and -Nicotinamide adenine dinucleotide 2-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).

Features and Benefits

This compound is also offered as part of Sigmas Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Chemically reduced

Packaged based on solid weight.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Quality Level	300
assay	≥97% (HPLC), ≥97% (spectrophotometric assay)
solubility	10 mM NaOH: soluble 50 mg/mL, clear
storage temp.	−20°C
SMILES string	[Na+].[Na+].[Na+].[Na+].NC(=O)C1=CN(C=CC1)[C@H]2O[C@@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@H](O)[C@@H]2O
InChI	1S/C21H30N7O17P3.4Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;;;;/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35);;;;/q;4*+1/p-4/t10-,11+,13-,14+,15-,16+,20-,21+;;;;/m0..../s1
InChI key	WYWWVJHQDVCHKF-MPUNMZHWSA-J

250 mg in poly bottle
1, 5 g in poly bottle
Packaged by solid weight.

Personal Protective Equipment	Eyeshields, Gloves, type N95 (US)
RIDADR	NONH for all modes of transport
WGK Germany	WGK 1
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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-Nicotinamide adenine dinucleotide hydrate

Empirical Formula (Hill Notation):	C₂₁H₂₇N₇O₁₄P₂ · xH₂O
CAS Number:	53-84-9
Molecular Weight:	663.43 (anhydrous basis)
EC Number:	200-184-4
MDL number:	MFCD00036253
eCl@ss:	39200202
PubChem Substance ID:	24897783
NACRES:	NA.55

Electron acceptor

This is the common form of NAD.

Quality Level	200,
biological source	yeast
product line	BioUltra
assay	98%
form	powder
impurities	0.1% Insoluble matter
color	white to off-white
solubility	H₂O: 0.1 M, clear, colorless to faintly yellow
anion traces	chloride (Cl^-): 0.2%, sulfate (SO₄^2-): 0.05%
cation traces	Al: 0.0005%, Ca: 0.005%, Cu: 0.001%, Fe: 0.001%, K: 0.005%, Mg: 0.0005%, NH₄⁺: 0.05%, Na: 0.005%, Pb: 0.001%, Zn: 0.0005%
storage temp.	20°C
SMILES string	NC1=NC=NC2=C1N=CN2.O[C@@H]3[C@@H](COP(O)(OP(OC[C@@H](O4)[C@@H](O)[C@@H](O)[C@H]4[N+]5=CC=CC(C(N)=O)=C5)([O-])=O)=O)OC[C@@H]3O
InChI	1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChI key	BAWFJGJZGIEFAR-NNYOXOHSSA-N
Gene Information	human ... ESR1(2099), ESR2(2100)

-Nicotinamide adenine dinucleotide phosphate hydrate is suitable for use in:

Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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-Nicotinamide adenine dinucleotide phosphate hydrate

Empirical Formula (Hill Notation):	C₂₁H₂₈N₇O₁₇P₃ · xH₂O
CAS Number:	53-59-8
Molecular Weight:	743.41 (anhydrous basis)
MDL number:	MFCD10567218
PubChem Substance ID:	24897747
NACRES:	NA.51

the measurement of Glucose-6-phosphate dehydrogenase activity
the Cytochrome P450 3A4 assay as a part of NADPH-regenerating system
the Cytochrome P450 2D6 assay as a part of NADPH-regenerating system
the determination of Glucose-6-phosphate content

1 g in glass bottle
100, 250, 500 mg in glass bottle

Packaged based on solid weight.
This is a common form of NADP.

Quality Level	200,
assay	95% (HPLC), 95% (spectrophotometric assay)
solubility	H₂O: soluble 50 mg/mL, clear, colorless to faintly yellow
cation traces	sodium and potassium: 0.04%
storage temp.	20°C
SMILES string	O.NC(=O)c1ccc[n+](c1)[C@@H]2O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](OP(O)(O)=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O
InChI	1S/C21H28N7O17P3.H2O/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39);1H2/t10-,11-,13-,14-,15-,16-,20-,21-;/m1./s1
InChI key	ZKJOXOJMGXFSPF-QYZPTAICSA-N

100, 500 mg in poly bottle
1, 5 g in poly bottle
Packaged by solid weight.

pictograms	GHS07
signalword	Warning
hcodes	H315 - H319 - H335
pcodes	P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
Target Organs	Respiratory system
Personal Protective Equipment	dust mask type N95 (US),, Eyeshields,, Gloves,
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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-Nicotinamide adenine dinucleotide phosphate sodium salt hydrate

Empirical Formula (Hill Notation):	C₂₁H₂₇N₇NaO₁₇P₃ · xH₂O
CAS Number:	698999-85-8
Molecular Weight:	765.39 (anhydrous basis)
MDL number:	MFCD00150480
PubChem Substance ID:	24897427
NACRES:	NA.51

Electron acceptor

This is the common form of NADP. Do not confuse with 3′−NADP or α-NADP.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N0505.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Quality Level	300
assay	98% (HPLC), 98% (spectrophotometric assay)
mp	175-178 °C (dec.) (lit.)
solubility	H₂O: soluble 50 mg/mL, clear, colorless to faintly yellow
storage temp.	20°C
SMILES string	O[C@H]1[C@@H](O)[C@H]([N+]2=CC(C(N)=O)=CC=C2)O[C@@H]1COP(OP(OC[C@H]3O[C@@H](N(C=N4)C5=C4C(N)=NC=N5)[C@H](OP(O)(O)=O)[C@@H]3O)([O-])=O)([O-])=O.O.[Na+]
InChI	1S/C21H28N7O17P3.Na.H2O/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;;/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39);;1H2/q;+1;/p-1/t10-,11-,13-,14-,15-,16-,20-,21-;;/m1../s1
InChI key	CYQLUFJYVTUUFN-WUEGHLCSSA-M

1, 5, 25 g in poly bottle

Pictograms	GHS07
Signal Word	Warning
Hazard Statements	H319
Precautionary Statements	P280 - P305 + P351 + P338 - P337 + P313
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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-Nicotinamide adenine dinucleotide sodium salt

Empirical Formula (Hill Notation):	C₂₁H₂₆N₇NaO₁₄P₂
CAS Number:	20111-18-6
Molecular Weight:	685.41
MDL number:	MFCD00148917
PubChem Substance ID:	24897433
NACRES:	NA.51

-Nicotinamide adenine dinucleotide (NAD+) and -Nicotinamide adenine dinucleotide, reduced (NADH) comprise a coenzyme redox pair (NAD+:NADH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. In addition to its redox function, NAD+/NADH is a donor of ADP-ribose units in ADP-ribosylaton (ADP-ribosyltransferases; poly(ADP-ribose) polymerases ) reactions and a precursor of cyclic ADP-ribose (ADP-ribosyl cyclases).

This is the common form of NAD.

Quality Level	300
assay	95% (HPLC), 95% (enzymatic), 95% (spectrophotometric assay)
storage temp.	20°C
SMILES string	[Na].NC(=O)C1=CC=C[N](=C1)C2OC(COP(O)(=O)OP(O)(=O)OCC3OC(C(O)C3O)n4cnc5c(N)ncnc45)C(O)C2O
InChI	1S/C21H28N7O14P2.Na.H/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33;;/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25);;
InChI key	GSZRXOXBGUIRAU-UHFFFAOYSA-N
Gene Information	human ... ESR1(2099), ESR2(2100)

β-Nicotinamide adenine dinucleotide (NAD+) and β-Nicotinamide adenine dinucleotide, reduced (NADH) comprise a coenzyme redox pair (NAD+:NADH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. In addition to its redox function, NAD+/NADH is a donor of ADP-ribose units in ADP-ribosylaton (ADP-ribosyltransferases; poly(ADP-ribose) polymerases ) reactions and a precursor of cyclic ADP-ribose (ADP-ribosyl cyclases).

Pictograms	GHS07
Signal Word	Warning
Hazard Statements	H315 - H319 - H335
Precautionary Statements	P302 + P352 - P305 + P351 + P338
Target Organs	Respiratory system
Personal Protective Equipment	dust mask type N95 (US), Eyeshields, Gloves
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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-Nicotinamide adenine dinucleotide, reduced dipotassium salt

Empirical Formula (Hill Notation):	C₂₁H₂₇K₂N₇O₁₄P₂
Linear Formula:	C₂₁H₂₇N₇O₁₄P₂K₂
CAS Number:	104809-32-7
Molecular Weight:	741.62
MDL number:	MFCD00079494
PubChem Substance ID:	24897704
NACRES:	NA.51

100, 500 mg in poly bottle
1 g in poly bottle

Electron donor

Quality Level	200,
assay	≥95%
storage temp.	−20°C
SMILES string	[K].NC(=O)C1=CN(C=CC1)C2OC(COP(O)(=O)OP(O)(=O)OCC3OC(C(O)C3O)n4cnc5c(N)ncnc45)C(O)C2O
InChI	1S/C21H29N7O14P2.K.H/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33;;/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25);;
InChI key	KMRPNNQOKAHXEZ-UHFFFAOYSA-N
Gene Information	human ... IMPDH2(3615)

1, 5 g in poly bottle
50, 100, 500 mg in poly bottle
Packaged by solid weight.

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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-Nicotinamide adenine dinucleotide, reduced disodium salt hydrate

Empirical Formula (Hill Notation):	C₂₁H₂₇N₇Na₂O₁₄P₂ · xH₂O
CAS Number:	606-68-8
Molecular Weight:	709.40 (anhydrous basis)
EC Number:	210-123-3
MDL number:	MFCD03791273
PubChem Substance ID:	329818676
NACRES:	NA.51

NADH is a coenzyme that functions as a regenerating electron donor in catabolic processes including glycolysis, -oxidation and the citric acid cycle (Krebs cycle, TCA cycle). It participates in cell signaling events as well, for example as a substrate for the poly (ADP-ribose) polymerases (PARPs) during the DNA damage response. The NAD+/NADH dependent sirtuins play key roles in stress responses during events involving energy metabolism, with implications in cancer biology, diabetes and neurodegenerative disease.
As a reagent, NADH can be used in enzyme cycling assays to amplify detection of activity of biologically relevant enzymes or metabolites present in low concentrations.

Quality Level	300
assay	≥97% (HPLC), ≥97% (spectrophotometric assay)
storage temp.	−20°C
SMILES string	O.[Na+].[Na+].NC(=O)C1=CN(C=CC1)[C@@H]2O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O
InChI	1S/C21H29N7O14P2.2Na.H2O/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33;;;/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25);;;1H2/q;2*+1;/p-2/t10-,11-,13-,14-,15-,16-,20-,21-;;;/m1.../s1
InChI key	FWBNCIFELNNJCX-UHOVGGJYSA-L

100 mg in poly bottle
1, 5, 25 mg in glass bottle

Personal Protective Equipment	Eyeshields, Gloves, type N95 (US)
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3

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2,3-Dideoxyinosine

Empirical Formula (Hill Notation):	C₁₀H₁₂N₄O₃
CAS Number:	69655-05-6
Molecular Weight:	236.23
Beilstein/REAXYS Number:	3619529
MDL number:	MFCD00077728
PubChem Substance ID:	24893215
NACRES:	NA.55

Nucleotide antagonist

Quality Level	200,
assay	≥98% (HPLC)
storage temp.	−20°C
SMILES string	OC[C@@H]1CC[C@@H](O1)n2cnc3C(=O)NC=Nc23
InChI	1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
InChI key	BXZVVICBKDXVGW-NKWVEPMBSA-N

3-Isobutyl-1-methylxanthine, an inhibitor of adenosine 3,5-cyclic monophosphate phosphodiesterase (cAMP PDE), has been used:

Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	WGK 2
Flash Point F	Not applicable
Flash Point C	Not applicable

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3-Isobutyl-1-methylxanthine

Empirical Formula (Hill Notation):	C₁₀H₁₄N₄O₂
CAS Number:	28822-58-4
Molecular Weight:	222.24
Beilstein/REAXYS Number:	247859
EC Number:	249-259-3
MDL number:	MFCD00005584
PubChem Substance ID:	24896107
NACRES:	NA.77

for adipogenic differentiation
in tissue culture
3T3-L1 preadipocyte differentiation(

1 g in poly bottle

The increase in cAMP level as a result of phosphodiesterase inhibition by IBMX activates PKA, leading to decreased proliferation, increased differentiation, and induction of apoptosis. IBMX inhibits phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50: 1.3 µM). IBMX also serves as an adenosine receptor antagonist. IBMX has been shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. IBMX induces calcium release from intracellular stores in sensory neurons.

Features and Benefits

Trace element testing by ICP
ICP testing for trace sulfur (as sulfate) and phosphorus (as phosphate) content
Ion chromatography testing for trace ammonium content

product line	BioUltra
Quality Level	200
assay	99%
impurities	<0.005% Phosphorus (P)
ign. residue	<0.1%
mp	200-201 °C (lit.)
solubility	DMSO: soluble 1 M (with gentle warning)
anion traces	sulfate (SO₄^2-): <0.05%
cation traces	Al: <0.0005%, Ca: <0.005%, Cu: <0.0005%, Fe: <0.005%, K: <0.05%, Mg: <0.005%, NH₄⁺: <0.05%, Na: <0.005%, Pb: <0.001%, Zn: <0.0005%
storage temp.	20°C
SMILES string	CC(C)CN1C(=O)N(C)C(=O)c2[nH]cnc12
InChI	1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)
InChI key	APIXJSLKIYYUKG-UHFFFAOYSA-N
Gene Information	rat ... Adora1(29290), Adora2a(25369)

3-Methyladenine (3-MA) is used to inhibit and study the mechanism of autophagy (lysosomal self-degradation) and apoptosis under various conditions. 3-MA inhibits autophagy by blocking autophagosome formation via the inhibition of type III Phosphatidylinositol 3-kinases (PI-3K). For use as an autophagy inhibitor, 3-MA is typically used at a concentration of 5 mM.
Standard for detection of nucleic acid methylation during carcinogenesis.

Personal Protective Equipment	dust mask type N95 (US), Eyeshields, Faceshields, Gloves
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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3-Methyladenine

Empirical Formula (Hill Notation):	C₆H₇N₅
CAS Number:	5142-23-4
Molecular Weight:	149.15
Beilstein/REAXYS Number:	146087
EC Number:	225-908-6
MDL number:	MFCD00010531
PubChem Substance ID:	24897326
NACRES:	NA.51

100, 500 mg in poly bottle

This product is soluble in DMF (10 mg/mL; may require gentle heating). It is also soluble in water, 95% ethanol, or 1 N NaOH at 30 mg/mL with heating, but upon cooling, the product precipitates from solution. Solutions of 3-MA may be prepared in DMSO at 100 mM.

Quality Level	300
assay	≥99% (HPLC)
form	powder
mp	~300 °C (dec.) (lit.)
solubility	DMF: 9.80-10.20 mg/mL, clear, colorless to light yellow
SMILES string	Cn1cnc(N)c2ncnc12
InChI	1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3
InChI key	FSASIHFSFGAIJM-UHFFFAOYSA-N

5-Bromo-2-deoxyuridine has been used:

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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SAE0107-10ML

3-Methyladenine Ready made solution SAE0107-10ML

General description
3-Methyladenine (3-MA) is a methylated derivative of adenine that has been used as an In vivo marker for the methylation of DNA. 3-Methyladenine and 7-methylguanine are the two main N-methylpurines formed in DNA upon exposure to methylating agents. 3-MA is removed from damaged DNA via the DNA base excision repair pathway, which begins with the enzyme N-methylpurine DNA glycosylase. The dependence of 3-MA repair on nucleotide excision repair in mammalian cell lines has been studied.3-MA have been widely used as autophagy inhibitor based on its inhibitory effect on class I and class III PI3K activity, which is known to be essential for induction of autophagy. 3-MA blocks class I PI3K persistently, whereas its suppressive effect on class III PI3K is transient, understanding the dual role of 3-MA in autophagy thus suggests that caution should be exercised in the application of 3-MA in autophagy study.
Furthermore, 3-MA is also capable of making the reduction of lymphocyte number caused by chronic stress rebound, implying that inhibition of autophagy can rescue chronic stress-induced immunosuppression.
Autophagy has been reported to play an important role in the 3, 4-Methylenedioxymethamphetamine MDMA-induced neurotoxicity in the mixed neuronal-glial primary culture and it was found that 3-MA ameliorate MDMA-induced autophagy, SERT loss, HPA axis dysfunction, and depressive behaviors.
Application
3-Methyladenine (3-MA) is used to inhibit and study the mechanism of autophagy (lysosomal self-degradation) and apoptosis under various conditions. 3-MA inhibits autophagy by blocking autophagosome formation via the inhibition of type III Phosphatidylinositol 3-kinases (PI-3K). For use as an autophagy inhibitor, 3-MA is typically used at a concentration of 5mM.
Preparation Note
3-Methyladenine ready made solution is provided at 50mM (7.5mg/mL) concentration in MES buffer.
It is recommended to store 3-methyladenine readymade solution at -20C.
In case percipitates are formed upon thaw, use sonication and heat to get the product back into solution.
It is recommended to avoid freeze thaw cycles.
When stored properly 3-Methyladenine readymade solution should be stable for 2 years.
Параметры

assay 98% (HPLC)

concentration 7.5 mg/mL

shipped in ambient

storage temp. 20°C

Safety Information

WGK Germany WGK 2

Flash Point F Not applicable

Flash Point C Not applicable

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5-Bromo-2-deoxyuridine

Empirical Formula (Hill Notation):	C₉H₁₁BrN₂O₅
CAS Number:	59-14-3
Molecular Weight:	307.10
Beilstein/REAXYS Number:	30395
EC Number:	200-415-9
MDL number:	MFCD00006529
PubChem Substance ID:	24278270
NACRES:	NA.51

as a supplement to study the effect of electroconvulsive seizures on hippocampal neurogenesis
as a supplement to study the loss-of-gene function in adult zebrafish heart
in T lymphocyte proliferation assay{133]

5-Bromo-2′-deoxyuridine (5-BrdU) is a thymidine analogue which is incorporated into DNA. 5-BrdU is routinely and extensively used to measure DNA synthesis and to label dividing cells. Consequently 5-BrdU is used to study cell signaling and other processes that induce cell proliferation.

1, 5, 100 g in glass bottle
100, 250, 500 mg in glass bottle

5-Bromo-2′-deoxyuridine (BrdU) is used to analyze cell proliferation, because of its facile incorporation into DNA during the S phase of the cell cycle. BrdU stimulates cellular differentiation and maturation in leukemia cell lines, while it inhibits differentiation of friend erythroleukemia cells. Studies of BrdU incorporation often subsequently use BrdU-specific antibodies with fluorescent tags, for detection of the incorporated BrdU, via such methods as flow cytometry or fluorescence microscopy.
Thymidine analog used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase.

Features and Benefits

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Quality Level	200
assay	99% (HPLC)
form	powder
mp	191-194 °C (dec.) (lit.)
solubility	DMSO: 50 mg/mL, clear, colorless to very faintly yellow
storage temp.	20°C
SMILES string	OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(Br)C(=O)NC2=O
InChI	1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
InChI key	WOVKYSAHUYNSMH-RRKCRQDMSA-N

Adenine hemisulfate salt has been used as a component of:

Pictograms	GHS08
Signal Word	Danger
Hazard Statements	H340 - H361fd
Precautionary Statements	P201 - P202 - P280 - P308 + P313 - P405 - P501
Personal Protective Equipment	Eyeshields, Gloves, type N95 (US)
RIDADR	NONH for all modes of transport
WGK Germany	WGK 2

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Adenine hemisulfate salt

Empirical Formula (Hill Notation):	C₅H₅N₅ · 0.5H₂O₄S
Linear Formula:	C₅H₅N₅ · 1/2H₂SO₄
CAS Number:	321-30-2
Molecular Weight:	184.17
Beilstein/REAXYS Number:	3820263
EC Number:	206-286-5
MDL number:	MFCD00213655
PubChem Substance ID:	24891230
NACRES:	NA.51

complete supplement mixture (CSM)
yeast extract with supplements (YES) medium for culturing S. pombe strain
synthetic complete glucose-based yeast media (SC) for S. cerevisiae cultures

25, 100 g in poly bottle
1 kg in poly bottle

Adenine is a purine nucleobase with a wide range of chemical and biochemical roles in vivo and in vitro. It is a regulatory molecule and a component of DNA, RNA, cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and signaling molecules (cAMP).

biological source	synthetic (organic)
Quality Level	200,
assay	≥99%
form	powder
solubility	0.5 M HCl: 10 mg/mL, clear, colorless
SMILES string	OS(O)(=O)=O.Nc1ncnc2[nH]cnc12.Nc3ncnc4[nH]cnc34
InChI	1S/2C5H5N5.H2O4S/c26-4-3-5(9-1-7-3)10-2-8-4;1-5(2,3)4/h21-2H,(H3,6,7,8,9,10);(H2,1,2,3,4)
InChI key	LQXHSCOPYJCOMD-UHFFFAOYSA-N

Adenosine 3′-phosphate 5′-phosphosulfate lithium salt has been used in a study that cloned and characterized a mammalian lithium-sensitive bisphosphate 3′-nucleotidase inhibited by inositol 1,4-bisphosphate. Adenosine 3′-phosphate 5′-phosphosulfate lithium salt has also been used in a study to assess the golgi-resident PAP-specific 3′-phosphatase-coupled sulfotransferase assays.
3′-Phosphoadenosine 5′-phosphosulfate (PAPS) is used as a universal sulfonate donor for in vivo sulfonation by sulfotransferases. PAPS is used for the sulfation of glycans. PAPS is also useful to study the distribution and function of its biological transporter(s).

pictograms	GHS06
signalword	Danger
hcodes	H301 - H319
pcodes	P264 - P270 - P280 - P301 + P310 - P305 + P351 + P338 - P337 + P313
Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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Adenosine 3-phosphate 5-phosphosulfate lithium salt hydrate

Empirical Formula (Hill Notation):	C₁₀H₁₅N₅O₁₃P₂S · xLi⁺ · yH₂O
CAS Number:	109434-21-1
Molecular Weight:	507.26 (free acid basis)
Beilstein/REAXYS Number:	8181191
eCl@ss:	32160414
NACRES:	NA.51

1, 5, 25 mg in glass bottle

Quality

Major impurities appear to be adenosine 3′,5′-diphosphate, sulfate and ammonia substitution products.

Rapid decomposition occurs when exposed to room temperature: up to 17% per day at 37 °C. We ship on dry ice to minimize decomposition in transit.

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A1651.pdf , Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.,

Quality Level	200,
assay	≥60%
shipped in	dry ice
storage temp.	−70°C

Adenosine 5-(,-imido)triphosphate lithium salt hydrate has been used in a study to research the effects of monovalent cations Li+, Na+, K+, NH4+, Rb+ and Cs+ on the solid and solution structures of the nucleic acid components. Adenosine 5-(,-imido)triphosphate lithium salt hydrate has also been used in a study to determine that antidepressants inhibit interferon--induced microglial production of IL-6 and nitric oxide.

pictograms	GHS07
signalword	Warning
hcodes	H315 - H319 - H335
pcodes	P302 + P352 - P305 + P351 + P338
Target Organs	Respiratory system
Personal Protective Equipment	dust mask type N95 (US),, Eyeshields,, Gloves,
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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Adenosine 5-(,-imido)triphosphate lithium salt hydrate

Empirical Formula (Hill Notation):	C₁₀H₁₇N₆O₁₂P₃ · xLi⁺ · yH₂O
CAS Number:	25612-73-1
Molecular Weight:	506.20 (free acid basis)
Beilstein/REAXYS Number:	6047109
PubChem Substance ID:	24890685
NACRES:	NA.51

100 mg in poly bottle
5, 25 mg in glass bottle

A non-hydrolyzable ATP analog. AMP-PNP competitively inhibits ATP-dependent enzyme systems, such as glutamine synthetase. It inhibits a number of enzymes which require the hydrolysis of ATP such as DNA topoisomerase II, SV40 large T-antigen helicase and a number of kinases. Blocks ATP-sensitive calcium-dependent potassium channels.

AMP-PNP is very unstable in acidic conditions; rapidly hydrolyzes to the phosphoramidate and inorganic phosphate.

Reconstitution

A 10 mg/mL stock solution may be made, aliquoted and stored at -70 °C for up to 3 months.

Quality Level	200,
assay	93% (HPLC)
form	powder
color	white
solubility	H₂O: 50 mg/mL
shipped in	dry ice
storage temp.	20°C
SMILES string	[Li+].[Li+].[Li+].[Li+].[H]O[H].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)NP([O-])([O-])=O)[C@@H](O)[C@H]3O

Adenosine 5′-diphosphate (5′-ADP or ADP) was used as a test compound for studying the endothelium-dependent vascular response in salt sensitive (DS) and salt resistant Dahl rats (DR). The product was used to study the different P2-purinergic receptor subtypes on canine vascular smooth muscle and endothelium.

Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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Adenosine 5-diphosphate

Empirical Formula (Hill Notation):	C₁₀H₁₅N₅O₁₀P₂
CAS Number:	58-64-0
Molecular Weight:	427.20
Beilstein/REAXYS Number:	67722
EC Number:	200-392-5
MDL number:	MFCD00066473
eCl@ss:	32160414
PubChem Substance ID:	57646699
NACRES:	NA.55

Adenosine 5′-diphosphate induces human platelet aggregation and non-competitively blocks the stimulated human platelet adenylate cyclase.

Bottomless glass bottle. Contents are inside inserted fused cone.

Quality Level	200,
assay	≥95% (HPLC)
impurities	≤15.0% water (KFT)
shipped in	dry ice
storage temp.	−20°C
SMILES string	Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]3O
InChI	1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
InChI key	XTWYTFMLZFPYCI-KQYNXXCUSA-N
Gene Information	human ... HSP90AA1(3320), P2RY1(5028)

Adenosine 5′-diphosphate (ADP) is an adenine nucleotide involved in energy storage and nucleic acid metabolism via its conversion into ATP by ATP synthases. ADP affects platelet activation through its interaction with ADP receptors P2Y1, P2Y12 and P2X1. Upon its conversion to adenosine by ecto-ADPases, platelet activation is inhibited via adenosine receptors.

Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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Adenosine 5-diphosphate sodium salt

Empirical Formula (Hill Notation):	C₁₀H₁₅N₅O₁₀P₂
CAS Number:	20398-34-9
Molecular Weight:	427.20
eCl@ss:	32160414
PubChem Substance ID:	24890690

100, 500 mg in poly bottle
1 g in poly bottle

Quality Level	300
biological source	bacterial
assay	≥95% (HPLC)
storage temp.	−20°C
SMILES string	[Na].Nc1ncnc2n(cnc12)C3OC(COP(O)(=O)OP(O)(O)=O)C(O)C3O
InChI	1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
InChI key	XTWYTFMLZFPYCI-KQYNXXCUSA-N
Gene Information	human ... HSP90AA1(3320), P2RY1(5028)

Adenosine 5′-triphosphate (ATP) is a central component of energy storage and metabolism in vivo. ATP is use in many cellular processes, respiration, biosynthetic reactions, motility, and cell division. ATP is a substrate of many kinases involved in cell signaling and of adenylate cyclase(s) that produce the second messenger cAMP. ATP provides the metabolic energy to drive metabolic pumps. ATP serves as a coenzyme in a wide array of enzymatic reactions.

RIDADR	NONH for all modes of transport
WGK Germany	nwg
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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Adenosine 5-triphosphate disodium salt hydrate

Empirical Formula (Hill Notation):	C₁₀H₁₄N₅Na₂O₁₃P₃ · xH₂O
CAS Number:	34369-07-8
Molecular Weight:	551.14 (anhydrous basis)
EC Number:	213-579-1
MDL number:	MFCD00150755
eCl@ss:	32160414
PubChem Substance ID:	24890761
NACRES:	NA.51

500 mg in poly bottle
1, 5, 10, 25, 100, 500 g in poly bottle

P2 purinergic agonist; increases activity of Ca2+-activated K+ channels; substrate for ATP-dependent enzyme systems

Quality Level	200,
biological source	microbial
type	Grade II
assay	97% (HPLC)
form	crystalline
solubility	H₂O: 50 mg/mL
storage temp.	20°C
SMILES string	O.[Na+].[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)OP([O-])(=O)OP(O)([O-])=O)[C@@H](O)[C@H]3O
InChI	1S/C10H16N5O13P3.2Na.H2O/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20;;;/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20);;;1H2/q;2*+1;/p-2/t4-,6-,7-,10-;;;/m1.../s1
InChI key	NTBQNWBHIXNPRU-MSQVLRTGSA-L

Adenosine 5-triphosphate magnesium salt has been used:

Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	WGK 2

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Adenosine 5-triphosphate magnesium salt

Empirical Formula (Hill Notation):	C₁₀H₁₆N₅O₁₃P₃ · xMg²⁺
CAS Number:	74804-12-9
Molecular Weight:	507.18 (free acid basis)
MDL number:	MFCD00084767
eCl@ss:	32160414
PubChem Substance ID:	24891422
NACRES:	NA.51

as a supplement in intracellular medium for Ca2+ retention assay and fluorescence wide field imaging analysis
as a component in potassium methane sulfonate-based internal solution for in vitro electrophysiology of cortical neurons
as a component in action potential intracellular solution

100, 500 mg in poly bottle
1 g in poly bottle

Adenosine 5-triphosphate (ATP) is a central component of energy storage and metabolism in vivo. ATP is use in many cellular processes, respiration, biosynthetic reactions, motility, and cell division. ATP is a substrate of many kinases involved in cell signaling and of adenylate cyclase(s) that produce the second messenger cAMP. ATP provides the metabolic energy to drive metabolic pumps. ATP serves as a coenzyme in a wide array of enzymatic reactions.
P2 purinergic agonist; increases activity of Ca2+-activated K+ channels; substrate for ATP-dependent enzyme systems

Quality Level	200
biological source	bacterial
assay	95%
solubility	H₂O: 50 mg/mL
storage temp.	20°C
SMILES string	[Mg].Nc1ncnc2n(cnc12)C3OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C3O
InChI	1S/C10H16N5O13P3.Mg.2H/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20;;;/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20);;;
InChI key	CPGAIACWYFBIFN-UHFFFAOYSA-N

Adenosine 5′-[γ-thio]triphosphate tetralithium salt has been used to treat the pollen grains to determine the inhibitory effect of adenosine triphosphate (ATP) or its hydrolysis product. It has also been used to select thiophosphorylate target protein.

Pictograms	GHS08
Signal Word	Warning
Hazard Statements	H371
Precautionary Statements	P260
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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Adenosine 5-[-thio]triphosphate tetralithium salt

Empirical Formula (Hill Notation):	C₁₀H₁₂Li₄N₅O₁₂P₃S
CAS Number:	93839-89-5
Molecular Weight:	546.98
Beilstein/REAXYS Number:	6265083
EC Number:	298-862-8
MDL number:	MFCD00077293
eCl@ss:	32160414
PubChem Substance ID:	24890536

25 mg in poly bottle
1, 5 mg in glass bottle

Adenosine 5-[-thio]triphosphate (ATP--S) is widely used as a non-hydrolyzed ATP analogue for studies on the effects of ATP binding to ATP sites in a wide range of processes including extracellular functions. ATP- -S is a P2 purinergic agonist which increases the activity of Ca2+-activated K+ channels. ATP- -S can substitute for ATP in kinase reactions yielding thiophosphorylated proteins that are resistant to protein phosphatases and modulate the ATP-dependent steps in the binding of ubiquitin conjugates to the 26S proteasome. ATP- -S differentially modulates Toll-like receptor 4-mediated cell survival and death.

Non-hydrolyzable ATP analog

Quality Level	200,
assay	75%
form	powder
color	white
solubility	H₂O: 25 mg/mL
shipped in	dry ice
storage temp.	20°C
SMILES string	[Li+].[Li+].[Li+].[Li+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=S)[C@@H](O)[C@H]3O
InChI	1S/C10H16N5O12P3S.4Li/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(25-10)1-24-28(18,19)26-29(20,21)27-30(22,23)31;;;;/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H,20,21)(H2,11,12,13)(H2,22,23,31);;;;/q;4*+1/p-4/t4-,6-,7-,10-;;;;/m1..../s1
InChI key	DWQFDOIBOYDYKH-KWIZKVQNSA-J

Flavin adenine dinucleotide (FAD) is used as a redox cofactor (electron carrier) by flavoproteins including succinate dehydrogenase (complex), α-ketoglutarate dehydrogenase, apoptosis-inducing factor 2 (AIF-M2, AMID), folate/FAD-dependent tRNA methyltransferases, and N-hydroxylating flavoprotein monooxygenases. FAD is a component of the pyruvate dehydrogenase complex.

Personal Protective Equipment	dust mask type N95 (US),, Eyeshields,, Gloves,
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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Flavin adenine dinucleotide disodium salt hydrate

Empirical Formula (Hill Notation):	C₂₇H₃₁N₉Na₂O₁₅P₂ · xH₂O
CAS Number:	84366-81-4
Molecular Weight:	829.51 (anhydrous basis)
Beilstein/REAXYS Number:	5326842
MDL number:	MFCD08277021
PubChem Substance ID:	24894909
NACRES:	NA.51

10, 25, 100, 250, 500 mg in poly bottle
1 g in poly bottle

Quality Level	200,
assay	≥95% (HPLC)
form	powder
color	yellow to orange-brown
storage temp.	−20°C
SMILES string	[Na+].[Na+].[H]O[H].Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])(=O)OP([O-])(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6c(N)ncnc56)c2cc1C
InChI	1S/C27H33N9O15P2.2Na.H2O/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36;;;/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43);;;1H2/q;2*+1;/p-2/t14-,15+,16+,19-,20+,21+,26+;;;/m0.../s1
InChI key	GXTPHHZYFMAGLX-UJXBNFGUSA-L

Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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Fluorouracil

Empirical Formula (Hill Notation):	C₄H₃FN₂O₂
CAS Number:	51-21-8
Molecular Weight:	130.08
Beilstein/REAXYS Number:	127172
EC Number:	200-085-6
MDL number:	MFCD00006018
PubChem Substance ID:	24894963
NACRES:	NA.71

Quality Level	200,
Agency/Method	USP/NF, meets USP testing specifications
mp	282-286 °C (dec.) (lit.)
Featured Industry	Pharmaceutical (small molecule)
SMILES string	FC1=CNC(=O)NC1=O
InChI	1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChI key	GHASVSINZRGABV-UHFFFAOYSA-N
Gene Information	human ... TYMS(7298)

Guanidine hydrochloride has been used:

pictograms	GHS06,GHS08
signalword	Danger
hcodes	H301 - H351
pcodes	P201 - P202 - P264 - P270 - P280 - P301 + P310
RIDADR	UN 2811 6.1 / PGIII
WGK Germany	WGK 3

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Guanidine hydrochloride

Empirical Formula (Hill Notation):	CH₅N₃ · HCl
Linear Formula:	NH₂C(=NH)NH₂ · HCl
CAS Number:	50-01-1
Molecular Weight:	95.53
Beilstein/REAXYS Number:	3591990
EC Number:	200-002-3
MDL number:	MFCD00013026
PubChem Substance ID:	24895119
NACRES:	NA.31

as a component of the extraction buffer for the extraction of proteoglycans
in extraction during protein fractionation of ATDC5 cell lines
as a chemical additive to study its effective absorbance spectra in structural analysis
to incubate the device chip to release prostate-specific antigen and for regeneration of aptamer
as a component of the 2,4-dinitrophenylhydrazine (DNPH) solution for detecting protein carbonyls by protein carbonylation study
in RNA isolation to dissociate nucleoproteins and inhibit RNase

Strong chaotropic agent useful for the denaturation and subsequent refolding of proteins. This strong denaturant can solubilize insoluble or denatured proteins such as inclusion bodies. This can be used as the first step in refolding proteins or enzymes into their active form. Urea and dithiothreitol (DTT) may also be necessary.

1, 2 kg in poly bottle
100, 500 g in poly bottle

Guanidine hydrochloride (GuHCl) is a small hydroscopic molecule. It plays a role in inhibiting heat shock protein 104 (Hsp104) adenosine triphosphatase (ATPase) activity in vivo. It is a potent denaturant and inactivator of several enzymes and proteins. GuHCl can inactivate aminoacylase and papain. It is involved in unfolding and inactivation of alkaline phosphatase in Haliotis diversicolor. At higher concentrations, GuHCl is involved in virus inactivation such as Herpes simplex virus 1 (HSV-1).

May agglomerate upon storage. The quality of the product does not appear to be affected and solutions prepared from the free-flowing and lumpy guanidine hydrochloride appear identical.

In order to make an 8M solution in water, one must heat the solution to 35 °C for approximately 30 minutes.
The maximum solubility of guanidine hydrochloride in water at room temperature is approximately 6M.

biological source	synthetic (organic)
Quality Level	400
grade	for molecular biology
assay	99%
form	crystalline powder
application(s)	RNA extraction: suitable
impurities	0.3% water (Karl Fischer)
color	white
pH	(25 °C, 4.6 - 6/573 g/L)
mp	180-185 °C (lit.)
solubility	H₂O: 6 M, clear, colorless
density	1.3 g/cm³ (lit.)
cation traces	Pb: 5 ppm
UV absorption	: 260 nm A_max: 0.10, : 290 nm A_max: 0.05
foreign activity	DNase, RNase, none detected
SMILES string	Cl[H].NC(N)=N
InChI	1S/CH5N3.ClH/c2-1(3)4;/h(H5,2,3,4);1H
InChI key	PJJJBBJSCAKJQF-UHFFFAOYSA-N
Gene Information	human ... KCNA1(3736), KCNA10(3744), KCNA2(3737), KCNA3(3738), KCNA4(3739), KCNA5(3741), KCNA6(3742), KCNA7(3743), KCNB1(3745), KCNB2(9312), KCNC1(3746), KCNC2(3747), KCNC3(3748), KCNC4(3749), KCND1(3750), KCND2(3751), KCND3(3752), KCNF1(3754), KCNG1(3755), KCNG2(26251), KCNG3(170850), KCNG4(93107), KCNH1(3756), KCNH2(3757), KCNH3(23416), KCNH4(23415), KCNH5(27133), KCNH6(81033), KCNH7(90134), KCNH8(131096), KCNQ1(3784), KCNQ2(3785), KCNQ3(3786), KCNQ4(9132), KCNQ5(56479), KCNS1(3787), KCNS2(3788), KCNS3(3790), KCNV1(27012), KCNV2(169522)

Pictograms	GHS07
Signal Word	Warning
Hazard Statements	H302 + H332 - H315 - H319
Precautionary Statements	P261 - P264 - P301 + P312 - P302 + P352 - P304 + P340 + P312 - P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US), Eyeshields, Faceshields, Gloves
RIDADR	NONH for all modes of transport
WGK Germany	WGK 1
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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Guanidine hydrochloride solution

Empirical Formula (Hill Notation):	CH₅N₃ · HCl
CAS Number:	50-01-1
Molecular Weight:	95.53
Beilstein/REAXYS Number:	3591990
MDL number:	MFCD00013026
PubChem Substance ID:	24895369
NACRES:	NA.55

Quality Level	200,
density	1.18 g/mL at 25 °C (lit.)
SMILES string	Cl.NC(N)=N
InChI	1S/CH5N3.ClH/c2-1(3)4;/h(H5,2,3,4);1H
InChI key	PJJJBBJSCAKJQF-UHFFFAOYSA-N
Gene Information	human ... KCNA1(3736), KCNA10(3744), KCNA2(3737), KCNA3(3738), KCNA4(3739), KCNA5(3741), KCNA6(3742), KCNA7(3743), KCNB1(3745), KCNB2(9312), KCNC1(3746), KCNC2(3747), KCNC3(3748), KCNC4(3749), KCND1(3750), KCND2(3751), KCND3(3752), KCNF1(3754), KCNG1(3755), KCNG2(26251), KCNG3(170850), KCNG4(93107), KCNH1(3756), KCNH2(3757), KCNH3(23416), KCNH4(23415), KCNH5(27133), KCNH6(81033), KCNH7(90134), KCNH8(131096), KCNQ1(3784), KCNQ2(3785), KCNQ3(3786), KCNQ4(9132), KCNQ5(56479), KCNS1(3787), KCNS2(3788), KCNS3(3790), KCNV1(27012), KCNV2(169522)

Guanidine thiocyanate has been used:

pictograms	GHS07
signalword	Warning
hcodes	H302 + H332 - H315 - H319
pcodes	P261 - P264 - P301 + P312 - P302 + P352 - P304 + P340 + P312 - P305 + P351 + P338
Personal Protective Equipment	Eyeshields,, Faceshields,, Gloves,, type ABEK (EN14387) respirator filter,
RIDADR	NONH for all modes of transport
WGK Germany	WGK 1
Flash Point F	Not applicable
Flash Point C	Not applicable

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Guanidine thiocyanate

Empirical Formula (Hill Notation):	CH₅N₃ · CHNS
Linear Formula:	NH₂C(=NH)NH₂ · HSCN
CAS Number:	593-84-0
Molecular Weight:	118.16
Beilstein/REAXYS Number:	3563461
EC Number:	209-812-1
MDL number:	MFCD00013027
PubChem Substance ID:	24895367
NACRES:	NA.31

for the lysis of colorectal adenocarcinoma cell line prior to RNA isolation
as a PCR inhibitor in triplex mitochondrial DNA (mtDNA) qPCR assay
for DNA extraction from cerebrospinal fluid (CSF)

Chaotropic agent and strong denaturant; solubilizes cells.

100, 250, 500 g in poly bottle

Guanidine thiocyanate is a denaturing agent and is used routinely in RNA isolation. It is used as a storage buffer for whole blood samples. Guanidine thiocyanate inactivates nucleases and is ideal for storing and freezing fecal samples for DNA studies. It is used in combination with phenol−chloroform in RNA extraction.

Quality Level	200
biological source	synthetic (organic)
grade	for molecular biology
assay	99%
form	powder or crystals
application(s)	RNA extraction: suitable
color	colorless to white,
mp	120-122 °C (lit.)
solubility	water: 100 mg/mL, clear, colorless
cation traces	Ba: 5 ppm, Fe: 5 ppm, Na: 0.5%, heavy metals (as Pb): 5 ppm
Featured Industry	Agriculture
foreign activity	DNase, RNase, none detected
SMILES string	SC#N.NC(N)=N
InChI	1S/CH5N3.CHNS/c2-1(3)4;2-1-3/h(H5,2,3,4);3H
InChI key	ZJYYHGLJYGJLLN-UHFFFAOYSA-N

Guanosine 5-diphosphate sodium salt has been used:

Pictograms	GHS05,GHS07
Signal Word	Danger
Hazard Statements	H302 + H312 + H332 - H314 - H412
Precautionary Statements	P260 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
Supp Hazards	EUH032
Personal Protective Equipment	dust mask type N95 (US), Eyeshields, Gloves
RIDADR	UN 1759 8 / PGIII
WGK Germany	WGK 2
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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Guanosine 5-diphosphate sodium salt

Empirical Formula (Hill Notation):	C₁₀H₁₅N₅O₁₁P₂
CAS Number:	43139-22-6
Molecular Weight:	443.20
MDL number:	MFCD00070121
PubChem Substance ID:	24895291
NACRES:	NA.51

in GTP--35S functional assays
in Y1 agonist-stimulated [35S]- guanosine-5-O-(3-thio)triphosphate (GTPS) functional binding
in the expression and purification of recombinant proteins

10 mg in glass bottle
25, 100, 500 mg in poly bottle
1 g in poly bottle

Guanosine 5′-diphosphate (GDP) is the diphosphate nucleoside of the purine guanine. GDP and GTP are involved in and may be used to study cell signaling via G-coupled protein receptors (GCPR) and guanine nucleotide exchange factors (GEF) and a variety of GTPases.

Quality Level	200
type	Type I
assay	≥96% (HPLC)
shipped in	dry ice
storage temp.	−20°C
SMILES string	[Na].NC1=NC(=O)c2ncn(C3OC(COP(O)(=O)OP(O)(O)=O)C(O)C3O)c2N1
InChI	1S/C10H15N5O11P2.Na.H/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21;;/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18);;
InChI key	PVMPTWQLNDHIEV-UHFFFAOYSA-N

Guanosine 5′-[β,γ-imido]triphosphate (GMP-PNP, Gpp(NH)p) is a non-hydrolyzable analog of GTP that binds and irreversibly activates G proteins. Gpp(NH)p is used in a variety of applications that involve GTP binding, including GTP-activation, GTP-inhibition, GTP transport, GTP hydrolysis, and GTP structure stabilization. Since a cycle of GTP binding, hydrolysis, and release is required for the initiation of protein translocation across the endoplasmic reticulum, guanosine 5′-[β,γ-imido]triphosphate is often used in studies of protein synthesis. Gpp(NH)p is used to activate ADP-ribosylation factors and to modulate G proteins involved in cell signaling, protein synthesis and other metabolic processes.

Personal Protective Equipment	Eyeshields, Gloves, type N95 (US)
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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Guanosine 5-[,-imido]triphosphate trisodium salt hydrate

Empirical Formula (Hill Notation):	C₁₀H₁₄N₆Na₃O₁₃P₃ · xH₂O
CAS Number:	148892-91-5
Molecular Weight:	588.14 (anhydrous basis)
MDL number:	MFCD00084770
PubChem Substance ID:	24895020
NACRES:	NA.51

Application

Guanosine 5-[,-imido]triphosphate trisodium salt hydrate has been used: to study K-RAS interactions with the membrane, for the crystallization of Mycobacterium tuberculosis FtsZ, as a translation initiation inhibitor for the analysis of the 48S pre-initiation complex.
Non-hydrolyzable analog of GTP; the preferred GTP analog to activate ADP-ribosylation factor.

5 mg in glass bottle
25, 100 mg in poly bottle

Guanosine 5′-[,γ-imido]triphosphate binds and irreversibly activates G proteins. Since a cycle of GTP binding, hydrolysis, and release is required for the initiation of protein translocation across the endoplasmic reticulum, this non-hydrolyzable GTP analog is often used in studies of protein synthesis.

Quality Level	200,
assay	85% (HPLC)
form	powder
color	white
solubility	H₂O: 50 mg/mL
shipped in	dry ice
storage temp.	70°C
SMILES string	[Na+].[Na+].[Na+].Nc1nc(O)c2ncn([C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)NP(O)([O-])=O)[C@@H](O)[C@H]3O)c2n1
InChI	1S/C10H17N6O13P3.3Na/c11-10-13-7-4(8(19)14-10)12-2-16(7)9-6(18)5(17)3(28-9)1-27-32(25,26)29-31(23,24)15-30(20,21)22;;;/h2-3,5-6,9,17-18H,1H2,(H,25,26)(H3,11,13,14,19)(H4,15,20,21,22,23,24);;;/q;3*+1/p-3/t3-,5-,6-,9-;;;/m1.../s1
InChI key	QGJNRMUNXAROIT-CYCLDIHTSA-K

Dibutyryl CAMP is a cell-permeable CAMP analogue that activates CAMP dependent protein kinase (PKA) or the CAMP/PKA signaling pathway. Dibutyryl CAMP is used as a morphological differentiation inducer and cell signaling modulator in cells such as Schwann cells. Dibutyrl cAMP is used in a variety of differentiation studies, such as neuron differentiation / neuronal differentiation.

pictograms	GHS07
signalword	Warning
hcodes	H315 - H319 - H335
pcodes	P302 + P352 - P305 + P351 + P338
Target Organs	Respiratory system
Personal Protective Equipment	dust mask type N95 (US),, Eyeshields,, Gloves,
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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N6,2-O-Dibutyryladenosine 3,5-cyclic monophosphate sodium salt

Empirical Formula (Hill Notation):	C₁₈H₂₃N₅NaO₈P
Linear Formula:	C₁₈H₂₃N₅O₈PNa
CAS Number:	16980-89-5
Molecular Weight:	491.37
EC Number:	241-059-4
MDL number:	MFCD00005843
PubChem Substance ID:	24893246
NACRES:	NA.51

1 g in poly bottle
25, 100, 250 mg in poly bottle

Cell-permeable cAMP analog that activates cAMP dependent protein kinase (PKA).

Loses 2′-O-butyryl group at pH 8.5

Quality Level	200
biological source	synthetic (organic)
assay	96% (HPLC)
form	powder
impurities	0.5% Cyclic AMP, 3% monobutyryl derivatives
color	off-white
solubility	H₂O: 100 mg/mL
storage temp.	20°C
SMILES string	[Na+].CCCC(=O)Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3OC(=O)CCC
InChI	1S/C18H24N5O8P.Na/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14;/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);/q;+1/p-1/t10-,14-,15-,18-;/m1./s1
InChI key	KRBZRVBLIUDQNG-JBVYASIDSA-M

Thymidine is also referred to as pyrimidine deoxynucleoside. Deoxythymidine is a nucleoside present in DNA. In a DNA double stranded structure, thymidine pairs with deoxyadeninosine. It is useful in cell synchronization during S-phase. In the salvage pathway of pyrimidines, pyrimidine phosphorylase reversibly converts thymine to thymidine.

Personal Protective Equipment	Eyeshields, Gloves, type N95 (US)
RIDADR	NONH for all modes of transport
WGK Germany	WGK 2
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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poly(C)

CAS Number: 26936-40-3

MDL number: MFCD00131956

NACRES: NA.55

Кат. номер

P4903-10MG

P4903-10MG-PW

P4903-25MG-PW

P4903-25MG

P4903-100MG-PW

P4903-100MG

P4903-1G

P4903-5MG

Packaging
10, 25, 100 mg in glass bottle
Preparation Note
Prepared from CDP using polynucleotide phosphorylase
Параметры

storage temp. −20°C

Quality Level 200,

Safety Information

Personal Protective Equipment Eyeshields,, Gloves,, type N95 (US),

RIDADR NONH for all modes of transport

WGK Germany WGK 3

Flash Point F Not applicable

Flash Point C Not applicable

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Thymidine

Empirical Formula (Hill Notation):	C₁₀H₁₄N₂O₅
CAS Number:	50-89-5
Molecular Weight:	242.23
Beilstein/REAXYS Number:	89285
EC Number:	200-070-4
MDL number:	MFCD00006537
PubChem Substance ID:	24900588
NACRES:	NA.51

Application

Thymidine has been used:

as a supplement in HL5-modified medium for cell culture
to incubate cells in cell-cycle analysis
in cell synchronization

1, 5, 10, 25 g in poly bottle

biological source	synthetic (organic)
Quality Level	200,
assay	≥99%
form	powder
mp	186-188 °C (lit.)
solubility	water: 50 mg/mL, clear, colorless
SMILES string	CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O
InChI	1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1
InChI key	IQFYYKKMVGJFEH-XLPZGREQSA-N
Gene Information	human ... DTYMK(1841)

Personal Protective Equipment	Eyeshields,, Gloves,, type N95 (US),
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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Uric acid

Empirical Formula (Hill Notation):	C₅H₄N₄O₃
CAS Number:	69-93-2
Molecular Weight:	168.11
Beilstein/REAXYS Number:	156158
EC Number:	200-720-7
MDL number:	MFCD00005712
PubChem Substance ID:	24900634
NACRES:	NA.55

Uric acid has been used:

in inducing hyperuricemia in mice
as a component of digestion fluid for the simulation of in vitro human digestion model
in selectivity test of the glucose sensor in sweat-based diabetes monitoring

25, 100 g in poly bottle
1 kg in poly bottle

Uric acid is an insoluble catabolite produced by adenine and guanine metabolism. Accumulation of uric acid leads to gout, hyperuricemia, arthritis and renal failure. Elevated uric acid levels contributes to hypertension and pathogenesis of cardiovascular disease. Low uric acid levels associated with Parkinson′s disease and multiple sclerosis, may elicit protective functionality. High levels of uric acid in patients with chronic obstructive pulmonary disease (COPD) may serve as potential marker for diagnosis.

Quality Level	100
assay	≥99%
form	crystalline
mp	>300 °C (lit.)
SMILES string	O=C1NC(=O)C2=C(N1)NC(=O)N2
InChI	1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)
InChI key	LEHOTFFKMJEONL-UHFFFAOYSA-N

Uridine 5-diphosphoglucuronic acid (UDPGA) is a cofactor, synthesized from UDPglucose and nicotinamide adenine dinucleotide (NAD+) intracellularly by the catalytic activity of UDPglucose dehydrogenase. The concentration of UDPGA in a number of liver preparations ranges from 0.3-0.5 mM.

Personal Protective Equipment	Eyeshields, Gloves, type N95 (US)
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

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Uridine 5-diphosphoglucuronic acid ammonium salt

Empirical Formula (Hill Notation):	C₁₅H₂₂N₂O₁₈P₂ · xNH₃
CAS Number:	43195-60-4
Molecular Weight:	580.29 (free acid basis)
PubChem Substance ID:	24900657
NACRES:	NA.51

Application

Uridine 5-diphosphoglucuronic acid ammonium salt has been used in the initiation of UDP-glucuronosyl transferase (UDGPT) assay towards 14C-testosterone in the liver S9 protein. It is suitable for use in UDGPT assay.

100, 250, 500 mg in poly bottle
1 g in poly bottle

Uridine 5′-diphosphoglucuronic acid (UDGPA) is the glucuronic acid donor for the conjugation of bilirubin in the endoplasmic recticulum.

Quality Level	200,
assay	98-100%
storage temp.	20°C
SMILES string	N.O[C@@H]1[C@@H](O)[C@H](O[C@@H]([C@H]1O)C(O)=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O
InChI	1S/C15H22N2O18P2.H3N/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25;/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26);1H3/t4-,6-,7+,8+,9-,10-,11+,12-,14-;/m1./s1
InChI key	WMWKTCPGFOEPBD-YGIWDPDDSA-N

Uridine 5′-diphosphoglucuronic acid trisodium salt has been used in optimization of incubation assay and glucuronidation assay.

pictograms	GHS07
signalword	Warning
hcodes	H315 - H319 - H335
pcodes	P302 + P352 - P305 + P351 + P338
Target Organs	Respiratory system
Personal Protective Equipment	Eyeshields,, Faceshields,, Gloves,, type P2 (EN 143) respirator cartridges,
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point F	Not applicable
Flash Point C	Not applicable

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Uridine 5-diphosphoglucuronic acid trisodium salt

Empirical Formula (Hill Notation):	C₁₅H₁₉N₂Na₃O₁₈P₂
CAS Number:	63700-19-6
Molecular Weight:	646.23
MDL number:	MFCD03452710
PubChem Substance ID:	24900659
NACRES:	NA.51

25, 100, 250, 500 mg in poly bottle
1 g in poly bottle

Uridine 5′-diphosphate-glucuronic acid (UDP-GlcA) is a carboxylic acid-formed sugar nucleotide. It participates in the biosynthesis of numerous cell components. UDP-GlcA is a glycosyl donor for glycosyltransferases in the biosynthesis of several cell components like glycosaminoglycans, some N- and O-linked glycans, glycosphingolipids and pectins.

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. U6751.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Quality Level	200
assay	98-100%
storage temp.	−20°C
SMILES string	[Na+].[Na+].[Na+].O[C@@H]1[C@@H](O)[C@H](O[C@@H]([C@H]1O)C([O-])=O)OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O
InChI	1S/C15H22N2O18P2.3Na/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25;;;/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26);;;/q;3*+1/p-3/t4-,6-,7+,8+,9-,10-,11+,12-,14-;;;/m1.../s1
InChI key	XXXUNWUNTOMVIG-QWGSIYABSA-K