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References |
1: Sameer H, Victor G, Katalin S, Henrik A. Elucidation of ligand binding and dimerization of NADPH:protochlorophyllide (Pchlide) oxidoreductase (POR) from pea (Pisum sativum L.) by structural analysis and simulations. Proteins. 2021 May 22. doi: 10.1002/prot.26151. Epub ahead of print. PMID: 34021929. 2: Chakraborty T, Polley S, Sinha D, Seal S, Sinha D, Mitra SK, Hazra J, Sau K, Pal M, Sau S. Structurally distinct unfolding intermediates formed from a staphylococcal capsule-producing enzyme retained NADPH binding activity. J Biomol Struct Dyn. 2021 May 12:1-18. doi: 10.1080/07391102.2021.1924269. Epub ahead of print. PMID: 33977860. 3: Dmitrieva VA, Domashkina VV, Ivanova AN, Sukhov VS, Tyutereva EV, Voitsekhovskaja OV. Regulation of plasmodesmata in leaves of Arabidopsis: ATP, NADPH and chlorophyll b levels matter. J Exp Bot. 2021 May 11:erab205. doi: 10.1093/jxb/erab205. Epub ahead of print. PMID: 33974689. 4: Rather GM, Pramono AA, Szekely Z, Bertino JR, Tedeschi PM. In cancer, all roads lead to NADPH. Pharmacol Ther. 2021 Apr 22;226:107864. doi: 10.1016/j.pharmthera.2021.107864. Epub ahead of print. PMID: 33894275. 5: Zhu J, Schwörer S, Berisa M, Kyung YJ, Ryu KW, Yi J, Jiang X, Cross JR, Thompson CB. Mitochondrial NADP(H) generation is essential for proline biosynthesis. Science. 2021 Apr 22:eabd5491. doi: 10.1126/science.abd5491. Epub ahead of print. PMID: 33888598. 6: Shen YP, Liao YL, Lu Q, He X, Yan ZB, Liu JZ. ATP and NADPH engineering of Escherichia coli to improve the production of 4-hydroxyphenylacetic acid using CRISPRi. Biotechnol Biofuels. 2021 Apr 20;14(1):100. doi: 10.1186/s13068-021-01954-6. PMID: 33879249; PMCID: PMC8056492. 7: Abdel-Hady GN, Ikeda T, Ishida T, Funabashi H, Kuroda A, Hirota R. Engineering Cofactor Specificity of a Thermostable Phosphite Dehydrogenase for a Highly Efficient and Robust NADPH Regeneration System. Front Bioeng Biotechnol. 2021 Apr 1;9:647176. doi: 10.3389/fbioe.2021.647176. PMID: 33869158; PMCID: PMC8047080. 8: Zhang J, Liu Z, Tian F, Chen Y. A novel ratiometric fluorescent probe from a hemicyanine derivative for detecting NAD(P)H in a cell microenvironment. Anal Methods. 2021 Apr 14;13(14):1681-1686. doi: 10.1039/d1ay00002k. Epub 2021 Mar 23. PMID: 33861234. 9: Diehl FF, Vander Heiden MG. Mitochondrial NADPH is a pro at Pro synthesis. Nat Metab. 2021 Apr;3(4):453-455. doi: 10.1038/s42255-021-00381-z. PMID: 33833464. 10: Hörl M, Fuhrer T, Zamboni N. Bifunctional Malic/Malolactic Enzyme Provides a Novel Mechanism for NADPH-Balancing in Bacillus subtilis. mBio. 2021 Apr 6;12(2):e03438-20. doi: 10.1128/mBio.03438-20. PMID: 33824210; PMCID: PMC8092299. 11: Milrad Y, Schweitzer S, Feldman Y, Yacoby I. Bi-directional electron transfer between H2 and NADPH mitigates light fluctuation responses in green algae. Plant Physiol. 2021 Feb 4:kiab051. doi: 10.1093/plphys/kiab051. Epub ahead of print. PMID: 33793951. 12: Yoshikawa Y, Nasuno R, Takagi H. An NADPH-independent mechanism enhances oxidative and nitrosative stress tolerance in yeast cells lacking glucose-6-phosphate dehydrogenase activity. Yeast. 2021 Mar 1. doi: 10.1002/yea.3558. Epub ahead of print. PMID: 33648021. 13: Deschoenmaeker F, Mihara S, Niwa T, Taguchi H, Wakabayashi KI, Toyoshima M, Shimizu H, Hisabori T. Thioredoxin pathway in anabaena sp. PCC 7120: activity of NADPH-thioredoxin reductase C. J Biochem. 2021 Feb 4:mvab014. doi: 10.1093/jb/mvab014. Epub ahead of print. PMID: 33537746. 14: Li S, Ye Z, Moreb EA, Hennigan JN, Castellanos DB, Yang T, Lynch MD. Dynamic control over feedback regulatory mechanisms improves NADPH flux and xylitol biosynthesis in engineered E. coli. Metab Eng. 2021 Mar;64:26-40. doi: 10.1016/j.ymben.2021.01.005. Epub 2021 Jan 16. PMID: 33460820. 15: Shlosberg Y, Eichenbaum B, Tóth TN, Levin G, Liveanu V, Schuster G, Adir N. NADPH performs mediated electron transfer in cyanobacterial-driven bio- photoelectrochemical cells. iScience. 2020 Dec 4;24(1):101892. doi: 10.1016/j.isci.2020.101892. PMID: 33364581; PMCID: PMC7750406. 16: Qin N, Li L, Ji X, Li X, Zhang Y, Larsson C, Chen Y, Nielsen J, Liu Z. Rewiring Central Carbon Metabolism Ensures Increased Provision of Acetyl-CoA and NADPH Required for 3-OH-Propionic Acid Production. ACS Synth Biol. 2020 Dec 18;9(12):3236-3244. doi: 10.1021/acssynbio.0c00264. Epub 2020 Nov 13. PMID: 33186034. 17: Assil-Companioni L, Büchsenschütz HC, Solymosi D, Dyczmons-Nowaczyk NG, Bauer KKF, Wallner S, Macheroux P, Allahverdiyeva Y, Nowaczyk MM, Kourist R. Engineering of NADPH Supply Boosts Photosynthesis-Driven Biotransformations. ACS Catal. 2020 Oct 16;10(20):11864-11877. doi: 10.1021/acscatal.0c02601. Epub 2020 Sep 4. PMID: 33101760; PMCID: PMC7574619. 18: Ju HQ, Lin JF, Tian T, Xie D, Xu RH. NADPH homeostasis in cancer: functions, mechanisms and therapeutic implications. Signal Transduct Target Ther. 2020 Oct 7;5(1):231. doi: 10.1038/s41392-020-00326-0. PMID: 33028807; PMCID: PMC7542157. 19: Wei X, Lu Z, Li L, Zhang H, Sun F, Ma H, Wang L, Hu Y, Yan Z, Zheng H, Yang G, Liu D, Tepel M, Gao P, Zhu Z. Reducing NADPH Synthesis Counteracts Diabetic Nephropathy through Restoration of AMPK Activity in Type 1 Diabetic Rats. Cell Rep. 2020 Sep 29;32(13):108207. doi: 10.1016/j.celrep.2020.108207. PMID: 32997989. 20: Moon SJ, Dong W, Stephanopoulos GN, Sikes HD. Oxidative pentose phosphate pathway and glucose anaplerosis support maintenance of mitochondrial NADPH pool under mitochondrial oxidative stress. Bioeng Transl Med. 2020 Sep 8;5(3):e10184. doi: 10.1002/btm2.10184. PMID: 33005744; PMCID: PMC7510474.
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Molecular Formula |
C21H30N7O17P3
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Molecular Weight |
745.42
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Exact Mass |
745.09
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Elemental Analysis |
C, 33.84; H, 4.06; N, 13.15; O, 36.49; P, 12.47
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CAS # |
53-57-6
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Related CAS # |
53-57-6 (free acid);604-79-5 (oxidized);2646-71-1 (sodium);100929-71-3 (ammonium); 100929-71-3 (Cy4N);
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Appearance |
Solid powder
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SMILES |
NC(C1=CN(C=CC1)[C@@H]2O[C@H](COP(O)(OP(O)(OC[C@H]3O[C@H]([C@H](OP(O)(O)=O)[C@@H]3O)N4C=NC5=C4N=CN=C5N)=O)=O)[C@@H](O)[C@H]2O)=O
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InChi Key |
ACFIXJIJDZMPPO-NNYOXOHSSA-N
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InChi Code |
InChI=1S/C21H30N7O17P3/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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
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Chemical Name |
Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
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Synonyms |
Codehydrase II reduced; Codehydrogenase II reduced; Coenzyme II reduced; Cozymase II reduced; Dihydrocodehydrogenase II.
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 1.3415 mL | 6.7076 mL | 13.4153 mL | |
5 mM | 0.2683 mL | 1.3415 mL | 2.6831 mL | |
10 mM | 0.1342 mL | 0.6708 mL | 1.3415 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.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.