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N8129

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide, reduced disodium salt hydrate

≥97% (HPLC)

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Synonym(s):
β-DPNH, β-NADH, DPNH, Diphosphopyridine nucleotide, reduced form, NADH
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

Quality Level

300

Assay

≥97% (HPLC)
≥97% (spectrophotometric assay)

form

powder

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

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Application

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).
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.

Biochem/physiol Actions

NADH is a coenzyme that functions as a regenerating electron donor in catabolic processes including glycolysis, β-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.

Packaging

Packaged by solid weight.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Hypoxia-induced miR-210 modulates tissue response to acute peripheral ischemia.
Zaccagnini G, Maimone B, Di Stefano V, et al.
Antioxidants & Redox Signaling, 21(8), 1177-1188 (2014)
Valentina Vacca et al.
Toxins, 12(8) (2020-08-06)
Botulinum neurotoxin type A (BoNT/A) is a major therapeutic agent that has been proven to be a successful treatment for different neurological disorders, with emerging novel therapeutic indications each year. BoNT/A exerts its action by blocking SNARE complex formation and
Ernesto Arias-Palomo et al.
Molecular cell, 74(1), 173-184 (2019-02-25)
In cells, dedicated AAA+ ATPases deposit hexameric, ring-shaped helicases onto DNA to initiate chromosomal replication. To better understand the mechanisms by which helicase loading can occur, we used cryo-EM to determine sub-4-Å-resolution structures of the E. coli DnaB⋅DnaC helicase⋅loader complex with
Lifeng Yang et al.
Cell metabolism, 31(4), 809-821 (2020-03-19)
NADH provides electrons for aerobic ATP production. In cells deprived of oxygen or with impaired electron transport chain activity, NADH accumulation can be toxic. To minimize such toxicity, elevated NADH inhibits the classical NADH-producing pathways: glucose, glutamine, and fat oxidation.
Erica N Parker et al.
Nature microbiology, 5(1), 67-75 (2019-11-20)
Gram-negative bacterial infections are a significant public health concern, and the lack of new drug classes for these pathogens is linked to the inability of most drug leads to accumulate inside Gram-negative bacteria1-7. Here, we report the development of a
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