PeptideDB

NAD sodium (β-DPN sodium; β-NAD sodium; β-Nicotinamide Adenine Dinucleotide sodium) 20111-18-6

NAD sodium (β-DPN sodium; β-NAD sodium; β-Nicotinamide Adenine Dinucleotide sodium) 20111-18-6

CAS No.: 20111-18-6

NAD (β-Nicotinamide Adenine Dinucleotide) sodium is an analog of NAD. NAD sodium can be reduced to β-nicotinamide aden
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NAD (β-Nicotinamide Adenine Dinucleotide) sodium is an analog of NAD. NAD sodium can be reduced to β-nicotinamide adenine dinucleotide (NADH) when coupled to an oxidative reaction with an organic substrate. NAD sodium can be converted into β-nicotinamide adenine dinucleotide (NADH) and delivered to the interior of mitochondria to indirectly produce ATP.

Physicochemical Properties


Molecular Formula C21H26N7NAO14P2
Molecular Weight 685.41
Exact Mass 685.091
Elemental Analysis C, 36.80; H, 3.82; N, 14.31; Na, 3.35; O, 32.68; P, 9.04
CAS # 20111-18-6
Related CAS # NAD+-d4; 53-84-9 (free acid); 20111-18-6 (sodium); 58-68-4 (reduced)
PubChem CID 72710628
Appearance White to off-white solid powder
Hydrogen Bond Donor Count 6
Hydrogen Bond Acceptor Count 18
Rotatable Bond Count 11
Heavy Atom Count 45
Complexity 1110
Defined Atom Stereocenter Count 8
SMILES

C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)([O-])OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O)C(=O)N.[Na+]

InChi Key OGCURMAMSJFXSG-QYZPTAICSA-M
InChi Code

InChI=1S/C21H27N7O14P2.Na/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);/q;+1/p-1/t10-,11-,13-,14-,15-,16-,20-,21-;/m1./s1
Chemical Name

sodium;[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Synonyms

beta-Nicotinamide adenine dinucleotide sodium salt from Saccharomyces cerevisiae; 683-623-6; Nadide sodium; 20111-18-6; Nad sodium salt; UNII-B1N53L892B; B1N53L892B; Nicotinamide-adenine dinucleotide monosodium salt;
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


Targets Endogenous metabolite
ln Vitro Poly(aniline)–poly(styrenesulfonate) composite-coated glassy carbon electrodes are shown to produce a stable, reproducible amperometric response to NADH in citrate–phosphate buffer at pH 7. These responses have been studied as a function of electrode potential, film thickness and both NADH and NAD+ concentration. The results show that the oxidation of NADH occurs throughout the whole of the film and that NAD+, the reaction product, reversibly inhibits the reaction. Rate constants for the different processes have been obtained by kinetic modelling and compared with those previously determined for poly(aniline)–poly(vinylsulfonate) films. Preliminary comparisons imply that diffusion within ‘pores’ in these poly(aniline) composite matrices is important in determining the magnitude of the amperometric responses [1].
Electropolymerisation of aniline in the presence of poly(styrenesulfonate) produces films which are not only stable and electroactive at neutral pH but that are also electrocatalytic surfaces for NADH oxidation. Analysis of the variation of the currents for NADH oxidation as a function of the film thickness, the concentration of NADH, the concentration of NAD+, and the electrode potential shows that NADH oxidation on the poly(aniline)–poly(styrenesulfonate) composite films follows the same mechanism as the reaction on the poly(aniline)–poly(vinylsulfonate) composite films. However, currents for the oxidation of NADH on the poly(aniline)–poly(styrenesulfonate) films are typically three to ten times less than those for the poly(aniline)–poly(vinylsulfonate) films under comparable conditions. From the detailed kinetic analysis this difference in response appears to be mainly due to the lower diffusion coefficient for NADH within the poly(aniline)–poly(styrenesulfonate) film coupled with a lower partition coefficient for NADH into the film. In our previous paper, we pointed out that treating the film as a uniform medium through which NADH was diffusing was an oversimplification and that NADH diffusion was more likely to occur through aqueous pores within the composite film matrix. This proposal receives considerable support from this kinetic analysis which indicates that the more porous poly(aniline)–poly(vinylsulfonate) film, as assessed from SEM measurements, has larger apparent partition and diffusion coefficients for NADH within the film. The comparison between the results obtained for the two different poly(aniline) films highlights the important effect that the physical structures of the films can have on their electrocatalytic properties.[1]
References

[1]. The oxidation of β-nicotinamide adenine dinucleotide (NADH) at poly(aniline)-coated electrodes: Part II. Kinetics of reaction at poly(aniline)–poly(styrenesulfonate) composites. 2022 May 22;486(1):23-31.

Additional Infomation Nicotinamide adenine dinucleotide (NAD+) is a coenzyme for redox reactions, making it central to energy metabolism. NAD+ is also an essential cofactor for non-redox NAD+-dependent enzymes, including sirtuins, CD38 and poly(ADP-ribose) polymerases. NAD+ can directly and indirectly influence many key cellular functions, including metabolic pathways, DNA repair, chromatin remodelling, cellular senescence and immune cell function. These cellular processes and functions are critical for maintaining tissue and metabolic homeostasis and for healthy ageing. Remarkably, ageing is accompanied by a gradual decline in tissue and cellular NAD+ levels in multiple model organisms, including rodents and humans. This decline in NAD+ levels is linked causally to numerous ageing-associated diseases, including cognitive decline, cancer, metabolic disease, sarcopenia and frailty. Many of these ageing-associated diseases can be slowed down and even reversed by restoring NAD+ levels. Therefore, targeting NAD+ metabolism has emerged as a potential therapeutic approach to ameliorate ageing-related disease, and extend the human healthspan and lifespan. However, much remains to be learnt about how NAD+ influences human health and ageing biology. This includes a deeper understanding of the molecular mechanisms that regulate NAD+ levels, how to effectively restore NAD+ levels during ageing, whether doing so is safe and whether NAD+ repletion will have beneficial effects in ageing humans. https://pubmed.ncbi.nlm.nih.gov/33353981/

Solubility Data


Solubility (In Vitro) H2O: 125 mg/mL (182.37 mM)
Solubility (In Vivo) Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)

Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.4590 mL 7.2949 mL 14.5898 mL
5 mM 0.2918 mL 1.4590 mL 2.9180 mL
10 mM 0.1459 mL 0.7295 mL 1.4590 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.