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MedKoo Cat#: 461770 | Name: Sangivamycin

Description:

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

Sangivamycin is a structural analog of adenosine and antibiotic exhibiting antitumor and antivirus activities. It inhibits protein kinase C and the synthesis of both DNA and RNA.

Chemical Structure

Sangivamycin
Sangivamycin
CAS#18417-89-5 (free base)

Theoretical Analysis

MedKoo Cat#: 461770

Name: Sangivamycin

CAS#: 18417-89-5 (free base)

Chemical Formula: C12H15N5O5

Exact Mass: 309.1073

Molecular Weight: 309.28

Elemental Analysis: C, 46.60; H, 4.89; N, 22.64; O, 25.86

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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Related CAS #
Sangivamycin hydrate 18417-89-5 (free base)
Synonym
Sangivamycin; B 90912; B-90912; B90912; B-14437; B 14437; B14437;
IUPAC/Chemical Name
4-amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide
InChi Key
OBZJZDHRXBKKTJ-JTFADIMSSA-N
InChi Code
InChI=1S/C12H15N5O5/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16)/t5-,7-,8-,12-/m1/s1
SMILES Code
O=C(C1=CN([C@H]2[C@@H]([C@@H]([C@@H](CO)O2)O)O)C3=NC=NC(N)=C31)N
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 309.28 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: Wakao K, Watanabe T, Takadama T, Ui S, Shigemi Z, Kagawa H, Higashi C, Ohga R, Taira T, Fujimuro M. Sangivamycin induces apoptosis by suppressing Erk signaling in primary effusion lymphoma cells. Biochem Biophys Res Commun. 2014 Feb 7;444(2):135-40. doi: 10.1016/j.bbrc.2014.01.017. Epub 2014 Jan 14. PubMed PMID: 24434142. 2: Komi Y, Ohno O, Suzuki Y, Shimamura M, Shimokado K, Umezawa K, Kojima S. Inhibition of tumor angiogenesis by targeting endothelial surface ATP synthase with sangivamycin. Jpn J Clin Oncol. 2007 Nov;37(11):867-73. Epub 2007 Oct 23. PubMed PMID: 17956898. 3: Ohno O, Shima Y, Ikeda Y, Kondo SI, Kato K, Toi M, Umezawa K. Selective growth inhibition by sangivamycin of human umbilical vein endothelial cells. Int J Oncol. 2001 May;18(5):1009-15. PubMed PMID: 11295049. 4: Dolloff NG, Allen JE, Dicker DT, Aqui N, Vogl D, Malysz J, Talamo G, El-Deiry WS. Sangivamycin-like molecule 6 exhibits potent anti-multiple myeloma activity through inhibition of cyclin-dependent kinase-9. Mol Cancer Ther. 2012 Nov;11(11):2321-30. doi: 10.1158/1535-7163.MCT-12-0578. Epub 2012 Sep 10. PubMed PMID: 22964485; PubMed Central PMCID: PMC3502072. 5: Cohen MB, Glazer RI. Comparison of the cellular and RNA-dependent effects of sangivamycin and toyocamycin in human colon carcinoma cells. Mol Pharmacol. 1985 Mar;27(3):349-55. PubMed PMID: 2579317. 6: Lee SA, Jung M. The nucleoside analog sangivamycin induces apoptotic cell death in breast carcinoma MCF7/adriamycin-resistant cells via protein kinase Cdelta and JNK activation. J Biol Chem. 2007 May 18;282(20):15271-83. Epub 2007 Mar 19. PubMed PMID: 17371872. 7: O'Brien WJ, Taylor JL, O'Malley TP, Ritch PS. The antiherpesvirus activity and cytotoxicity of sangivamycin. Curr Eye Res. 1987 Jan;6(1):255-7. PubMed PMID: 3030647. 8: Smee DF, McKernan PA, Alaghamandan HA, Frank KB, Ramasamy K, Revankar GR, Robins RK. Antiviral activities of 2'-deoxyribofuranosyl and arabinofuranosyl analogs of sangivamycin against retro- and DNA viruses. Antiviral Res. 1988 Dec 11;10(6):263-77. PubMed PMID: 2854957. 9: Loomis CR, Bell RM. Sangivamycin, a nucleoside analogue, is a potent inhibitor of protein kinase C. J Biol Chem. 1988 Feb 5;263(4):1682-92. PubMed PMID: 3338987. 10: Kang J, Lee DK, Lee CH. Cell cycle arrest and cytochrome c-mediated apoptotic induction in human lung cancer A549 cells by MCS-C2, an analogue of sangivamycin. J Microbiol Biotechnol. 2010 Feb;20(2):433-7. PubMed PMID: 20208452. 11: Gupta PK, Daunert S, Nassiri MR, Wotring LL, Drach JC, Townsend LB. Synthesis, cytotoxicity, and antiviral activity of some acyclic analogues of the pyrrolo[2,3-d]pyrimidine nucleoside antibiotics tubercidin, toyocamycin, and sangivamycin. J Med Chem. 1989 Feb;32(2):402-8. PubMed PMID: 2913300. 12: Cappellini A, Chiarini F, Ognibene A, McCubrey JA, Martelli AM. The cyclin-dependent kinase inhibitor roscovitine and the nucleoside analog sangivamycin induce apoptosis in caspase-3 deficient breast cancer cells independent of caspase mediated P-glycoprotein cleavage: implications for therapy of drug resistant breast cancers. Cell Cycle. 2009 May 1;8(9):1421-5. Epub 2009 May 2. PubMed PMID: 19342873; PubMed Central PMCID: PMC3813519. 13: Ritch PS, Glazer RI. Preferential incorporation of sangivamycin into ribonucleic acid in Sarcoma 180 cells in vitro. Biochem Pharmacol. 1982 Jan 15;31(2):259-61. PubMed PMID: 7059368. 14: McCarty RM, Bandarian V. Deciphering deazapurine biosynthesis: pathway for pyrrolopyrimidine nucleosides toyocamycin and sangivamycin. Chem Biol. 2008 Aug 25;15(8):790-8. doi: 10.1016/j.chembiol.2008.07.012. PubMed PMID: 18721750; PubMed Central PMCID: PMC2603307. 15: Osada H, Sonoda T, Tsunoda K, Isono K. A new biological role of sangivamycin; inhibition of protein kinases. J Antibiot (Tokyo). 1989 Jan;42(1):102-6. PubMed PMID: 2921215. 16: Stockwin LH, Yu SX, Stotler H, Hollingshead MG, Newton DL. ARC (NSC 188491) has identical activity to Sangivamycin (NSC 65346) including inhibition of both P-TEFb and PKC. BMC Cancer. 2009 Feb 20;9:63. doi: 10.1186/1471-2407-9-63. PubMed PMID: 19232100; PubMed Central PMCID: PMC2651907. 17: Lebioda L, Hargrave PA, Palczewski K. X-ray crystal structure of sangivamycin, a potent inhibitor of protein kinases. FEBS Lett. 1990 Jun 18;266(1-2):102-4. PubMed PMID: 2365059. 18: Saffer JD, Glazer RI. Inhibition of histone H1 phosphorylation by sangivamycin and other pyrrolopyrimidine analogues. Mol Pharmacol. 1981 Jul;20(1):211-7. PubMed PMID: 7290086. 19: Gupta PK, Nassiri MR, Coleman LA, Wotring LL, Drach JC, Townsend LB. Synthesis, cytotoxicity, and antiviral activity of certain 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine nucleosides related to toyocamycin and sangivamycin. J Med Chem. 1989 Jul;32(7):1420-5. PubMed PMID: 2500527. 20: Glazer RI, Hartman KD. In vitro translational activity of messenger RNA following treatment of human colon carcinoma cells with sangivamycin. Mol Pharmacol. 1983 Nov;24(3):509-12. PubMed PMID: 6633511.