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Chemical Compound Review

Sanzivamycin     5-amino-9-[(2R,3R,4S,5R)-3,4- dihydroxy-5...

Synonyms: sangivamycin, CHEMBL101892, SureCN195540, CPD-13052, NSC-65346, ...
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Disease relevance of SKI 27013


High impact information on SKI 27013

  • Sangivamycin at the same concentration that inhibited PKC translocation by 52% completely inhibited PTH-stimulated 1,25(OH)2D3 secretion [6].
  • The underlying mechanisms were studied in functionally intact detached rod outer segments by testing the effect of either sangivamycin, an inhibitor of rhodopsin kinase, or phytic acid, an inhibitor of 48K protein binding to phosphorylated rhodopsin, on light responses recorded in whole-cell voltage clamp [7].
  • Sangivamycin (10 and 50 microM) also reduced PTH-stimulated PKC translocation, but did not alter PKA activity ratio [6].
  • Using a series of inhibitors with known specificities and established rank-orders of potency for different kinases, we determined that the c-myc response to Epo was blocked with the following rank order: staurosporine much greater than H7 greater than sangivamycin greater than H8 [8].
  • The phosphorylation of rhodopsin by protein kinase C is inhibited by the protein kinase C-selective inhibitor sangivamycin [9].

Chemical compound and disease context of SKI 27013


Biological context of SKI 27013

  • Certain oncogene products resemble elements involved in transmembrane signaling, elevate cellular sn-1,2-diacylglycerol second messenger levels, and activate protein kinase C. Sangivamycin was unique among the nucleoside compounds tested in its ability to potently inhibit protein kinase C activity [11].
  • Three lines of evidence suggest that protein kinase-C (PKC) mediates serum-stimulated PES gene expression: 1) 12-tetradecanoyl phorbol 13-acetate mimicked the serum response; 2) PES gene expression by serum was attenuated in cells depleted of PKC; and 3) a PKC inhibitor, sangivamycin, blocked serum-stimulated PES gene induction [12].
  • Exposure for 24 hr to toyocamycin caused an exponential type of cell lethality resulting in a 4-log reduction of cell viability, while sangivamycin produced a gradual and self-limiting type of cell lethality resulting in a 1-log reduction of cell viability [13].
  • Ara-sangivamycin, for example, inhibited virus replication 10(5)-fold at a concentration (10 microM) which produced only partial inhibition of cell growth and labeled precursor incorporation [14].
  • Phorbol esters activated PC hydrolysis in both myocytes and adipocytes, but insulin-induced stimulation of PC hydrolysis was not dependent upon activation of PKC, since this hydrolysis was not inhibited by 500 microM sangivamycin, an effective PKC inhibitor [15].

Anatomical context of SKI 27013


Associations of SKI 27013 with other chemical compounds


Gene context of SKI 27013


Analytical, diagnostic and therapeutic context of SKI 27013

  • The degree of LTP was significantly potentiated by the inclusion of picrotoxin in the perfusion medium but induction was prevented by D-2-amino-5-phosphonopentanoate (25 microM), L-2-amino-3-phosphonopropionate (125 microM), 5-(isoquinolinyl-sulphonyl)-2-methylpiperazine (50 microM), sangivamycin (25 microM) and thapsigargin (1 microM) [28].
  • Nontoxic concentrations of sangivamycin (10 nM) and staurosporine (1 nM), added to cell cultures from 1 to 7 h before X irradiation, enhanced cell killing by radiation in both cell lines [20].
  • Several of the sangivamycin analogs were tested in animal models using a twice-a-day treatment regimen [29].


  1. Kinetic effects of sangivamycin in sarcoma 180 in vitro. Ritch, P.S., Glazer, R.I., Cunningham, R.E., Shackney, S.E. Cancer Res. (1981) [Pubmed]
  2. Utilization of signal transduction pathway by the human T-cell leukemia virus type I transcriptional activator tax. Tan, T.H., Jia, R., Roeder, R.G. J. Virol. (1989) [Pubmed]
  3. Design, synthesis and antiviral activity of novel 4,5-disubstituted 7-(beta-D-ribofuranosyl)pyrrolo[2,3-d][1,2,3]triazines and the novel 3-amino-5-methyl-1-(beta-D-ribofuranosyl)- and 3-amino-5-methyl-1-(2-deoxy-beta-D-ribofuranosyl)-1,5-dihydro-1,4,5,6,7,8-hexaazaacenaphthylene as analogues of triciribine. Migawa, M.T., Drach, J.C., Townsend, L.B. J. Med. Chem. (2005) [Pubmed]
  4. Antagonism of the cytotoxic but not antiviral effects of ara-sangivamycin by adenosine. Birch, G.M., Krawczyk, S.H., Townsend, L.B., Drach, J.C. Antimicrob. Agents Chemother. (1989) [Pubmed]
  5. Pyrrolopyrimidine nucleosides. 18. Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine-5-carboxamide (3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine-5-carboxamide (2'-deoxysangivamycin). Maruyama, T., Wotring, L.L., Townsend, L.B. J. Med. Chem. (1983) [Pubmed]
  6. Role of protein kinase C in parathyroid hormone stimulation of renal 1,25-dihydroxyvitamin D3 secretion. Janulis, M., Tembe, V., Favus, M.J. J. Clin. Invest. (1992) [Pubmed]
  7. The influence of arrestin (48K protein) and rhodopsin kinase on visual transduction. Palczewski, K., Rispoli, G., Detwiler, P.B. Neuron (1992) [Pubmed]
  8. c-myc is an erythropoietin early response gene in normal erythroid cells: evidence for a protein kinase C-mediated signal. Spangler, R., Sytkowski, A.J. Blood (1992) [Pubmed]
  9. Kinetics and localization of the phosphorylation of rhodopsin by protein kinase C. Greene, N.M., Williams, D.S., Newton, A.C. J. Biol. Chem. (1995) [Pubmed]
  10. Shape changes and chemokinesis of Walker carcinosarcoma cells: effects of protein kinase inhibitors (HA-1004, polymyxin B, sangivamycin and tamoxifen) and an inhibitor of diacylglycerol kinase (R 59022). Zimmermann, A., Keller, H. Anticancer Res. (1993) [Pubmed]
  11. Sangivamycin, a nucleoside analogue, is a potent inhibitor of protein kinase C. Loomis, C.R., Bell, R.M. J. Biol. Chem. (1988) [Pubmed]
  12. Regulation of prostaglandin endoperoxide synthase gene expression in cultured rat mesangial cells: induction by serum via a protein kinase-C-dependent mechanism. Simonson, M.S., Wolfe, J.A., Konieczkowski, M., Sedor, J.R., Dunn, M.J. Mol. Endocrinol. (1991) [Pubmed]
  13. Comparison of the cellular and RNA-dependent effects of sangivamycin and toyocamycin in human colon carcinoma cells. Cohen, M.B., Glazer, R.I. Mol. Pharmacol. (1985) [Pubmed]
  14. Pyrrolo[2,3-d]pyrimidine nucleosides as inhibitors of human cytomegalovirus. Turk, S.R., Shipman, C., Nassiri, R., Genzlinger, G., Krawczyk, S.H., Townsend, L.B., Drach, J.C. Antimicrob. Agents Chemother. (1987) [Pubmed]
  15. Differential effects of pertussis toxin on insulin-stimulated phosphatidylcholine hydrolysis and glycerolipid synthesis de novo. Studies in BC3H-1 myocytes and rat adipocytes. Hoffman, J.M., Standaert, M.L., Nair, G.P., Farese, R.V. Biochemistry (1991) [Pubmed]
  16. Egr-1 expression in surface Ig-mediated B cell activation. Kinetics and association with protein kinase C activation. Seyfert, V.L., McMahon, S., Glenn, W., Cao, X.M., Sukhatme, V.P., Monroe, J.G. J. Immunol. (1990) [Pubmed]
  17. In vitro translational activity of messenger RNA following treatment of human colon carcinoma cells with sangivamycin. Glazer, R.I., Hartman, K.D. Mol. Pharmacol. (1983) [Pubmed]
  18. Selective growth inhibition by sangivamycin of human umbilical vein endothelial cells. Ohno, O., Shima, Y., Ikeda, Y., Kondo, S.I., Kato, K., Toi, M., Umezawa, K. Int. J. Oncol. (2001) [Pubmed]
  19. Phorbol myristate acetate induces ruffling of the acrosome of human sperm. Liu, d.e. .Y., Martic, M., Grkovic, I., Garrett, C., Dunlop, M.E., Baker, H.W. Fertil. Steril. (2002) [Pubmed]
  20. Inhibition of protein kinases sensitizes human tumor cells to ionizing radiation. Hallahan, D.E., Virudachalam, S., Schwartz, J.L., Panje, N., Mustafi, R., Weichselbaum, R.R. Radiat. Res. (1992) [Pubmed]
  21. Effect of protein kinase C inhibitors on the actions of phorbol esters on vascular tone and adrenergic transmission in the isolated rat kidney. Sehic, E., Malik, K.U. J. Pharmacol. Exp. Ther. (1990) [Pubmed]
  22. X-ray crystal structure of sangivamycin, a potent inhibitor of protein kinases. Lebioda, L., Hargrave, P.A., Palczewski, K. FEBS Lett. (1990) [Pubmed]
  23. Progesterone-stimulated intracellular calcium increase in human spermatozoa is protein kinase C-independent. Bonaccorsi, L., Krausz, C., Pecchioli, P., Forti, G., Baldi, E. Mol. Hum. Reprod. (1998) [Pubmed]
  24. Platelet-activating factor enhances production of insulin-like growth factor binding proteins in a human adenocarcinoma cell line (HEC-1A). Giannini, S., Maggi, M., Cresci, B., Finetti, G., Bonaccorsi, L., Luconi, M., Rotella, C.M., Forti, G., Serio, M., Baldi, E. Gynecol. Oncol. (1996) [Pubmed]
  25. Tumor promotion and depletion of protein kinase C in epidermal JB6 cells. Kischel, T., Harbers, M., Stabel, S., Borowski, P., Müller, K., Hilz, H. Biochem. Biophys. Res. Commun. (1989) [Pubmed]
  26. Regulation of VCAM-1 expression and involvement in cell adhesion to murine microvascular endothelium. Bereta, J., Bereta, M., Cohen, S., Cohen, M.C. Cell. Immunol. (1993) [Pubmed]
  27. Protein tyrosine kinase, mitogen-activated protein kinase and protein kinase C are involved in the mitogenic signaling of platelet-activating factor (PAF) in HEC-1A cells. Bonaccorsi, L., Luconi, M., Maggi, M., Muratori, M., Forti, G., Serio, M., Baldi, E. Biochim. Biophys. Acta (1997) [Pubmed]
  28. The characteristics and pharmacology of olfactory cortical LTP induced by theta-burst high frequency stimulation and 1S,3R-ACPD. Collins, G.G. Neuropharmacology (1994) [Pubmed]
  29. Antiviral activities of 2'-deoxyribofuranosyl and arabinofuranosyl analogs of sangivamycin against retro- and DNA viruses. Smee, D.F., McKernan, P.A., Alaghamandan, H.A., Frank, K.B., Ramasamy, K., Revankar, G.R., Robins, R.K. Antiviral Res. (1988) [Pubmed]
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