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T7375

Sigma-Aldrich

Thionicotinamide adenine dinucleotide

≥90%

Synonym(s):

Thionicotinamide-DPN

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About This Item

Linear Formula:
C21H27N7O13SP2
CAS Number:
4090-29-3
Molecular Weight:
679.49
MDL number:
MFCD00079609
UNSPSC Code:
41106305
PubChem Substance ID:
24900446
NACRES:
NA.51

Quality Level

200

Assay

≥90%

storage temp.

−20°C

SMILES string

NC(=S)C1=CC=C[N](=C1)C2OC(COP(O)(=O)OP(O)(=O)OCC3OC(C(O)C3O)n4cnc5c(N)ncnc45)C(O)C2O

InChI

1S/C21H28N7O13P2S/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(40-21)6-38-43(35,36)41-42(33,34)37-5-10-13(29)15(31)20(39-10)27-3-1-2-9(4-27)18(23)44/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H2,23,44)(H,33,34)(H,35,36)(H2,22,24,25)

InChI key

JFOSDPGFZXVRDA-UHFFFAOYSA-N

Application

Thionicotinamide adenine dinucleotide has been used as a substrate analog in S-adenosyl-l-homocysteine (AdoHcy) hydrolases (SAHH) inhibition assay and in NAD+ glycohydrolase activity.

Biochem/physiol Actions

Thionicotinamide adenine dinucleotide (sNAD) is an analog of coenzyme nicotinamide adenine dinucleotide (NAD) and NADH. sNAD is a potential inhibitor of NAD+ kinase. NAD+ kinase modulates NAD levels, contributing to cytotoxicity in cancer cells.

Linkage

Analog of NAD

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000321863
0000319507
0000319506
0000311731
0000311731

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R A Laun et al.
Clinical and experimental medicine, 1(4), 201-209 (2002-03-29)
The arterial ketone body ratio is calculated as the ratio of arterial levels of acetoacetate/beta-hydroxybutyrate. It correlates with survival in experimental hemorrhagic shock and outcome after liver surgery and myocardial infarction. Procedures for determination of ketone bodies are often laborious
Suppression of cytosolic NADPH pool by thionicotinamide increases oxidative stress and synergizes with chemotherapy
Tedeschi PM, et al.
Molecular Pharmacology, 88(4), 720?727-720?727 (2015)
Comparative kinetics of cofactor association and dissociation for the human and trypanosomal S-adenosylhomocysteine hydrolases. 1. Basic features of the association and dissociation processes
Li QS, et al
Biochemistry, 46(19), 5798-5809 (2007)
Simultaneous determination of multiple forms of lactate dehydrogenase based on NAD and thio-NAD.
S Hosaki et al.
Clinica chimica acta; international journal of clinical chemistry, 157(3), 321-322 (1986-06-30)
D M Kiick et al.
Biochemistry, 25(1), 227-236 (1986-01-14)
The pH dependence of the kinetic parameters and the primary deuterium isotope effects with nicotinamide adenine dinucleotide (NAD) and also thionicotinamide adenine dinucleotide (thio-NAD) as the nucleotide substrates were determined in order to obtain information about the chemical mechanism and
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