Abstract
YM-216391, a novel cyclic peptide, was isolated from the cultured mycelium of Streptomyces nobilis JCM 4274. It was purified by solvent extraction, silica gel and ODS flash column chromatographies, followed by preparative HPLC. YM-216391 dose-dependently inhibited the growth of human cervical cancer HeLa S3 cells with an IC50 value of 14 nM. YM-216391 also showed potent cytotoxic activity against a human cancer cell line panel.
References
Baldacci E, Locci R, Farina G . Study of a new species of Streptomyces: Streptomyces nobilis sp. nov. and examination of related strains belonging to the genera Streptomyces, Streptoverticillium and Nocardia. Mycopathol Mycol Appl 26: 333–348 ( 1965)
Shin-ya K, Wierzba K, Matsuo K, Ohtani T, Yamada Y, Furihata K, Hayakawa Y, Seto H . Telomestatin, a novel telomerase inhibitor from Streptomyces anulatus. J Am Chem Soc 123: 1262–1263 ( 2001)
Nakajima A, Tauchi T, Sashida G, Sumi M, Abe K, Yamamoto K, Ohyashiki JH, Ohyashiki K . Telomerase inhibition enhances apoptosis in human acute leukemia cells: possibility of antitelomerase therapy. Leukemia 17: 560–567 ( 2003)
Shammas MA, Reis RJ, Li C, Koley H, Hurley LH, Anderson KC, Munshi NC . Telomerase inhibition and cell growth arrest after telomestatin treatment in multiple myeloma. Clin Cancer Res 10: 770–776 ( 2004)
Sumi M, Tauchi T, Sashida G, Nakajima A, Gotoh A, Shin-ya K, Ohyashiki JH, Ohyashiki K . A G-quadruplex-interactive agent, telomestatin (SOT-095), induces telomere shortening with apoptosis and enhances chemosensitivity in acute myeloid leukemia. Int J Oncol 24: 1481–1487 ( 2004)
Roesener JA, Scheuer PJ . Ulapualide A and B, extraordinary antitumor macrolides from nudibranch eggmasses. J Am Chem Soc 108: 846–847 ( 1986)
Matsunaga S, Fusetani N, Hashimoto K . Kabiramide C, a novel antifungal macrolide from nudibranch eggmasses. J Am Chem Soc 108: 847–849 ( 1986)
Fusetani N, Yasumuro K, Matsunaga S, Hashimoto K . Mycalolides A∼C, hybrid macrolides of ulapualides and halichondramide, from a sponge of the genus. Tetrahedron Lett 30: 2809–2812 ( 1989)
Matsunaga S, Fusetani N, Hashimoto K, Koseki K, Noma M, Noguchi H, Sankawa U . Bioactive marine metabolites. 25. Further kabiramides and halichondramides, cytotoxic macrolides embracing trisoxazole, from the Hexabranchus eggmasses. J Org Chem 54: 1360–1363 ( 1989)
Kobayashi J, Murata O, Shigemori H . Jaspisamides A~C, new cytotoxic macrolides from the Okinawan sponge Jaspis sp. J Nat Prod 56: 787–791 ( 1993)
Saito S, Watabe S, Ozaki H, Fusetani N, Karaki H . Mycalolide B, a novel actin depolymerizing agent. J Biol Chem 269: 29710–29714 ( 1994)
Spector I, Braet F, Shochet NR, Bubb MR . New anti-actin drugs in the study of the organization and function of the actin cytoskeleton. Microsc Res Tech 47: 18–37 ( 1999)
Jordan MA, Wilson L . Microtubules and actin filaments: dynamic targets for cancer chemotherapy. Curr Opin Cell Biol 10: 123–130 ( 1998)
Yeung KS, Paterson I . Actin-binding marine macrolides: total synthesis and biological importance. Angew Chem Int Ed Engl 41: 4632–4653 ( 2002)
Fenteany G, Zhu S . Small-molecule inhibitors of actin dynamics and cell motility. Curr Top Med Chem 3: 593–616 ( 2003)
Yamori T . Panel of human cancer cell lines provides valuable database for drug discovery and bioinformatics. Cancer Chemother Pharmacol 52 ( Suppl. 1): 74–79 ( 2003)
Dan S, Tsunoda T, Kitahara O, Yanagawa R, Zembutsu H, Katagiri T, Yamazaki K, Nakamura Y, Yamori T . An integrated database of chemosensitivity to 55 anticancer drugs and gene expression profiles of 39 human cancer cell lines. Cancer Res 62: 1139–1147 ( 2002)
Sohda K, Hiramoto M, Suzumura K, Takebayashi Y, Suzuki K, Tanaka A . YM-216391, a novel cytotoxic cyclic peptide from Streptomyces nobilis. II. Physico-chemical properties and structure elucidation. J Antibiot 58: 32–36 ( 2005)
Ishiyama M, Shiga M, Sasamoto K, Mizoguchi M, He P . A new sulfonated tetrazolium salt that produces a highly water-soluble formazan dye. Chem Pharm Bull 41: 1118–1122 ( 1993)
Yamori T, Matsunaga A, Sato S, Yamazaki K, Komi A, Ishizu K, Mita I, Edatsugi H, Matsuba Y, Takezawa K, Nakanishi O, Kohno H, Nakajima Y, Komatsu H, Andoh T, Tsuruo T . Potent antitumor activity of MS-247, a novel DNA minor groove binder, evaluated by an in vitro and in vivo human cancer cell line panel. Cancer Res 59: 4042–4049 ( 1999)
Shin-ya K . Telomerase. Saishin Igaku 56: 384–389 ( 2001) in Japanese
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Sohda, Ky., Nagai, K., Yamori, T. et al. YM-216391, a Novel Cytotoxic Cyclic Peptide from Streptomyces nobilis. J Antibiot 58, 27–31 (2005). https://doi.org/10.1038/ja.2005.2
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DOI: https://doi.org/10.1038/ja.2005.2
Keywords
- YM-216391
- cyclic peptide
- trisoxazole
- cytotoxic
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