Sangivamycin

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

MedKoo CAT#: 461770

CAS#: 18417-89-5

Description: 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

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Sangivamycin
CAS# 18417-89-5

Theoretical Analysis

MedKoo Cat#: 461770
Name: Sangivamycin
CAS#: 18417-89-5
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 not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

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

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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.