MedKoo Cat#: 462584 | Name: Tubercidin 5'-triphosphate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tubercidin 5'-triphosphate, an ATP analog, is a substrate for the mitochondrial phosphotransferases from rat liver and beef heart.

Chemical Structure

Tubercidin 5'-triphosphate
Tubercidin 5'-triphosphate
CAS#10058-66-9

Theoretical Analysis

MedKoo Cat#: 462584

Name: Tubercidin 5'-triphosphate

CAS#: 10058-66-9

Chemical Formula: C11H17N4O13P3

Exact Mass: 506.0005

Molecular Weight: 506.19

Elemental Analysis: C, 26.10; H, 3.39; N, 11.07; O, 41.09; P, 18.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Tubercidin 5'-triphosphate
IUPAC/Chemical Name
5-(5-O-(Hydroxy((hydroxy(phosphonooxy)phosphinyl)oxy)phosphinyl)-beta-D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine
InChi Key
GVVRDIINMFAFEO-KCGFPETGSA-N
InChi Code
InChI=1S/C11H17N4O13P3/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(17)7(16)6(26-11)3-25-30(21,22)28-31(23,24)27-29(18,19)20/h1-2,4,6-8,11,16-17H,3H2,(H,21,22)(H,23,24)(H2,12,13,14)(H2,18,19,20)/t6-,7-,8-,11-/m1/s1
SMILES Code
Nc1ncnc2c1ccn2[C@@H]3O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]3O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 506.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Hulpia F, Campagnaro GD, Scortichini M, Van Hecke K, Maes L, de Koning HP, Caljon G, Van Calenbergh S. Revisiting tubercidin against kinetoplastid parasites: Aromatic substitutions at position 7 improve activity and reduce toxicity. Eur J Med Chem. 2019 Feb 15;164:689-705. doi: 10.1016/j.ejmech.2018.12.050. Epub 2018 Dec 21. PMID: 30677668. 2: Hulpia F, Mabille D, Campagnaro GD, Schumann G, Maes L, Roditi I, Hofer A, de Koning HP, Caljon G, Van Calenbergh S. Combining tubercidin and cordycepin scaffolds results in highly active candidates to treat late-stage sleeping sickness. Nat Commun. 2019 Dec 5;10(1):5564. doi: 10.1038/s41467-019-13522-6. PMID: 31804484; PMCID: PMC6895180. 3: Liu Y, Gong R, Liu X, Zhang P, Zhang Q, Cai YS, Deng Z, Winkler M, Wu J, Chen W. Discovery and characterization of the tubercidin biosynthetic pathway from Streptomyces tubercidicus NBRC 13090. Microb Cell Fact. 2018 Aug 28;17(1):131. doi: 10.1186/s12934-018-0978-8. PMID: 30153835; PMCID: PMC6112128. 4: DUVALL LR. TUBERCIDIN. Cancer Chemother Rep. 1963 Jul;30:61-2. PMID: 14051507. 5: Fustin JM, Doi M, Yamaguchi Y, Hida H, Nishimura S, Yoshida M, Isagawa T, Morioka MS, Kakeya H, Manabe I, Okamura H. RNA-methylation-dependent RNA processing controls the speed of the circadian clock. Cell. 2013 Nov 7;155(4):793-806. doi: 10.1016/j.cell.2013.10.026. PMID: 24209618. 6: Drew ME, Morris JC, Wang Z, Wells L, Sanchez M, Landfear SM, Englund PT. The adenosine analog tubercidin inhibits glycolysis in Trypanosoma brucei as revealed by an RNA interference library. J Biol Chem. 2003 Nov 21;278(47):46596-600. doi: 10.1074/jbc.M309320200. Epub 2003 Sep 12. PMID: 12972414. 7: Dovey HF, McKerrow JH, Wang CC. Action of tubercidin and other adenosine analogs on Schistosoma mansoni schistosomules. Mol Biochem Parasitol. 1985 Aug;16(2):185-98. doi: 10.1016/0166-6851(85)90086-6. PMID: 3929087. 8: el Kouni MH, Diop D, O'Shea P, Carlisle R, Sommadossi JP. Prevention of tubercidin host toxicity by nitrobenzylthioinosine 5'-monophosphate for the treatment of schistosomiasis. Antimicrob Agents Chemother. 1989 Jun;33(6):824-7. doi: 10.1128/aac.33.6.824. PMID: 2764531; PMCID: PMC284239. 9: Kolassa N, Jakobs ES, Buzzell GR, Paterson AR. Manipulation of toxicity and tissue distribution of tubercidin in mice by nitrobenzylthioinosine 5'-monophosphate. Biochem Pharmacol. 1982 May 15;31(10):1863-74. doi: 10.1016/0006-2952(82)90489-0. PMID: 7104018. 10: Dirice E, Walpita D, Vetere A, Meier BC, Kahraman S, Hu J, Dančík V, Burns SM, Gilbert TJ, Olson DE, Clemons PA, Kulkarni RN, Wagner BK. Inhibition of DYRK1A Stimulates Human β-Cell Proliferation. Diabetes. 2016 Jun;65(6):1660-71. doi: 10.2337/db15-1127. Epub 2016 Mar 7. PMID: 26953159; PMCID: PMC4878416. 11: Aoki JI, Yamashiro-Kanashiro EH, Ramos DC, Cotrim PC. Efficacy of the tubercidin antileishmania action associated with an inhibitor of the nucleoside transport. Parasitol Res. 2009 Jan;104(2):223-8. doi: 10.1007/s00436-008-1177-z. Epub 2008 Sep 12. PMID: 18787843. 12: Bergstrom DE, Brattesani AJ, Ogawa MK, Reddy PA, Schweickert MJ, Balzarini J, De Clercq E. Antiviral activity of C-5 substituted tubercidin analogues. J Med Chem. 1984 Mar;27(3):285-92. doi: 10.1021/jm00369a010. PMID: 6699874. 13: Zhao LX, Huang SX, Tang SK, Jiang CL, Duan Y, Beutler JA, Henrich CJ, McMahon JB, Schmid T, Blees JS, Colburn NH, Rajski SR, Shen B. Actinopolysporins A-C and tubercidin as a Pdcd4 stabilizer from the halophilic actinomycete Actinopolyspora erythraea YIM 90600. J Nat Prod. 2011 Sep 23;74(9):1990-5. doi: 10.1021/np200603g. Epub 2011 Aug 26. PMID: 21870828; PMCID: PMC3179765. 14: Kazimierczuk Z, Revankar GR, Robins RK. Total synthesis of certain 2-, 6-mono- and 2,6-disubstituted-tubercidin derivatives. Synthesis of tubercidin via the sodium salt glycosylation procedure. Nucleic Acids Res. 1984 Jan 25;12(2):1179-92. doi: 10.1093/nar/12.2.1179. PMID: 6694909; PMCID: PMC318564. 15: Sandau US, Yahya M, Bigej R, Friedman JL, Saleumvong B, Boison D. Transient use of a systemic adenosine kinase inhibitor attenuates epilepsy development in mice. Epilepsia. 2019 Apr;60(4):615-625. doi: 10.1111/epi.14674. Epub 2019 Feb 27. PMID: 30815855; PMCID: PMC6713278. 16: Seela F, Peng X, Eickmeier H, Reuter H. 2-Amino-7-chloro-2'-deoxytubercidin. Acta Crystallogr C. 2006 Oct;62(Pt 10):o593-5. doi: 10.1107/S0108270106032227. Epub 2006 Sep 12. PMID: 17008745. 17: Aoki JI, Coelho AC, Muxel SM, Zampieri RA, Sanchez EM, Nerland AH, Floeter- Winter LM, Cotrim PC. Characterization of a Novel Endoplasmic Reticulum Protein Involved in Tubercidin Resistance in Leishmania major. PLoS Negl Trop Dis. 2016 Sep 8;10(9):e0004972. doi: 10.1371/journal.pntd.0004972. PMID: 27606425; PMCID: PMC5015992. 18: Pope LH, Shotton MW, Forsyth T, Hughes DJ, Denny RC, Fuller W. Structural polymorphism in a tubercidin analogue of the DNA double helix. Biophys Chem. 1998 Feb 16;70(2):161-72. doi: 10.1016/s0301-4622(97)00132-4. PMID: 9540207. 19: Lynch TP, Jakobs ES, Paran JH, Paterson AR. Treatment of mouse neoplasms with high doses of tubercidin. Cancer Res. 1981 Aug;41(8):3200-4. PMID: 7248975. 20: Nishimura N, Kato A, Maeba I. Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin. Carbohydr Res. 2001 Mar 9;331(1):77-82. doi: 10.1016/s0008-6215(01)00017-9. PMID: 11284507.