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N6660

β-Nicotinamide adenine dinucleotide, reduced disodium salt

Name: β-Nicotinamide adenine dinucleotide, reduced disodium salt
Brand: SIGMA

~98%, pkg of 0.2 mg (per vial)

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Synonym(s):

β-DPNH, β-NADH, Coenzyme I reduced disodium salt, Diphosphopyridine nucleotide reduced disodium salt

Empirical Formula (Hill Notation):

C₂₁H₂₇N₇Na₂O₁₄P₂

CAS Number:

606-68-8

Molecular Weight:

709.40

Beilstein:

5230241

EC Number:

210-123-3

MDL number:

MFCD00036200

PubChem Substance ID:

24897788

NACRES:

NA.51

Assay

~98%

Quality Level

200

form

powder

packaging

pkg of 0.2 mg (per vial)

SMILES string

[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/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);;/q;2*+1/p-2/t10-,11+,13-,14+,15-,16+,20-,21+;;/m0../s1

InChI key

QRGNQKGQENGQSE-QUWMEQBESA-L

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General description

β-Nicotinamide adenine dinucleotide (β-NAD) regulates energy metabolism and immunity. It is a cofactor for mitochondrial deacetylase sirtuin-3 enzyme and modulates inflammasome assembly. β-NAD supresses interleukin-1β levels in monocytic cells in inflammatory syndromes. β-NAD released by neurosecretory cells is a potential neurotransmitter. β-NAD is a vascular mediator in lung endothelial cells and may play a protective role against cytokine mediated inflammation.

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).

β-Nicotinamide adenine dinucleotide, reduced disodium salt has been used:

for the standard curve generation in neurotoxity assay of cortical neurons
in triosephosphate isomerase assay in jurkat JE6-1 cells
in lactate dehydrogenase assay

Biochem/physiol Actions

Electron donor

Reconstitution

Solutions should be prepared fresh and used promptly.

Other Notes

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

This is the common form of NADH; do not confuse with α-NADH.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Propionic acid secreted from propionibacteria induces NKG2D ligand expression on human-activated T lymphocytes and cancer cells

Andresen L, et al.

Journal of Immunology, jimmunol-j0803014 (2009)

beta-Nicotinamide adenine dinucleotide attenuates lipopolysaccharide-induced inflammatory effects in a murine model of acute lung injury

Umapathy N, et al.

Experimental Lung Research, 38(5), 223-232 (2012)

beta-Nicotinamide adenine dinucleotide is an enteric inhibitory neurotransmitter in human and nonhuman primate colons

Hwang SJ, et al.

Gastroenterology, 140(2), 608-617 (2011)

Deficiency of ATP13A2 leads to lysosomal dysfunction, alpha-synuclein accumulation, and neurotoxicity

Usenovic M, et al.

The Journal of Neuroscience, 32(12), 4240-4246 (2012)

13C MR Hyperpolarization of Lactate by Using ParaHydrogen and Metabolic Transformation in Vitro

Cavallari E, et al.

Chemistry?A European Journal , 23(5), 1200-1204 (2017)

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