Reveromycin A
- Structure
- InChI=1S/C36H52O11/c1-6-7-19-35(47-34(44)17-16-32(40)41)21-22-36(46-30(35)14-10-25(3)23-33(42)43)20-18-27(5)29(45-36)13-9-24(2)8-12-28(37)26(4)11-15-31(38)39/h8-12,14-15,23,26-30,37H,6-7,13,16-22H2,1-5H3,(H,38,39)(H,40,41)(H,42,43)/b12-8+,14-10+,15-11+,24-9+,25-23+/t26-,27-,28-,29?,30?,35+,36-/m0/s1
- InChIKey=ZESGNAJSBDILTB-FAKCWQBJSA-N
- Synonyms
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- Origin
- Streptomyces reveromyceticus
- Biological activities
- epidermal growth factor inhibitor (Eukaryota)
Inhibition of eukaryotic protein synthesis (Eukaryota)
protein synthesis inhitibion (Eukaryota)
- Therapeutic
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Anticancer
Antifungal
Osteoporosis
- Target
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Ile-tRNA synthase (IleRS)
- Assay information
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Inhibition of isoleucyl-tRNA synthetase (IC50 = 2-12 nM)
Inhibition of protein synthesis in eukaryotic cells (IC50 = 40 nM)
Growth inhibition against osteoclasts (IC50 = 0.2 μM)
Growth inhibition against cancer cells (IC50 [μM]): KB (3) K562 (3), HL60 (20), HeLa (78)
Antifungal activity (MIC [μM]): C. albicans (3.7, pH3)
- References
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Fremlin L, Farrugia M, Piggott AM, Khalil Z, Lacey E, Capon RJ
Reveromycins revealed: new polyketide spiroketals from Australian marine-derived and terrestrial Streptomyces spp. A case of natural products vs. artifacts.
Org Biomol Chem, 9(4): 1201-1211 (2011) 21152660 doi: 10.1039/c0ob00654h
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Shimizu T, Usui T, Fujikura M, Kawatani M, Satoh T, Machida K, Kanoh N, Woo JT, Osada H, Sodeoka M
Synthesis and biological activities of reveromycin A and spirofungin A derivatives.
Bioorg Med Chem Lett, 18(13): 3756-3760 (2008) 18519164 doi: 10.1016/j.bmcl.2008.05.054
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Woo JT, Kawatani M, Kato M, Shinki T, Yonezawa T, Kanoh N, Nakagawa H, Takami M, Lee KH, Stern PH, Nagai K, Osada H
Reveromycin A, an agent for osteoporosis, inhibits bone resorption by inducing apoptosis specifically in osteoclasts.
Proc Natl Acad Sci U S A, 103(12): 4729-4734 (2006) 16537392 doi: 10.1073/pnas.0505663103
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Shimizu T, Usui T, Machida K, Furuya K, Osada H, Nakata T
Chemical modification of reveromycin A and its biological activities.
Bioorg Med Chem Lett, 12(23): 3363-3366 (2002) 12419362
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Miyamoto Y, Machida K, Mizunuma M, Emoto Y, Sato N, Miyahara K, Hirata D, Usui T, Takahashi H, Osada H, Miyakawa T
Identification of Saccharomyces cerevisiae isoleucyl-tRNA synthetase as a target of the G1-specific inhibitor Reveromycin A.
J Biol Chem, 277(32): 28810-28814 (2002) 12050165 doi: 10.1074/jbc.M203827200
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Takahashi H, Osada H, Koshino H, Sasaki M, Onose R, Nakakoshi M, Yoshihama M, Isono K
Reveromycins, new inhibitors of eukaryotic cell growth. II. Biological activities.
J Antibiot, 45(9): 1414-1419 (1992) 1429226
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Osada H;Koshino H;Isono K;Takahashi H;Kawanishi G
Reveromycin A, a new antibiotic which inhibits the mitogenic activity of epidermal growth factor.
J Antibiot, 44(2): 259-261 (1991) 2010365