Refine your search:     
Report No.

Synthesis of radioiodinated antitumor cyclic peptide, [$$^{125}$$I]-sansalvamide A derivative

Watanabe, Shigeki; Yamada, Keiichi*; Tsukui, Narutaka*; Hanaoka, Hirofumi*; Ohshima, Yasuhiro; Yamaguchi, Aiko*; Oku, Hiroyuki*; Ishioka, Noriko

Sansalvamide A (SA), a penta cyclic peptide isolated marine fungus, is a lead compound of anti-cancer reagent because the peptide has cytotoxicity against various cancer cell lines. Halogenated SA derivatives (SA-X, X = Cl, Br, I) was prepared and remarkable cytotocity against malignant human breast cancer. In this study, a radiohalogenated SA derivative [$$^{125}$$I]SA-I was prepared to conduct in vivo evaluation of SA derivatives. Synthetic scheme of [$$^{125}$$I]SA-I are as follows: an iodinated linear peptide, Boc-F(p-I)LLVL-OMe, was prepared by the conventional solid phase peptide synthesis. After preparation of stannylated peptide, Boc-F(p-SnBu$$_{3}$$)LLVL-OMe, $$^{125}$$I was labeled with electrophilic destannylation in the presence of oxidizing reagent. After deprotection of N- and C-termius, [$$^{125}$$I]SA-I was obtained successfully by macrocyclization in liquid phase. Overall labeled yield was 7%. To our best knowledge, this report is the first on the synthesis of radiolabeled SA derivative. In vivo evaluation of the SA derivative using [$$^{125}$$I]SA-I is being undertaken.



- Accesses





[CLARIVATE ANALYTICS], [WEB OF SCIENCE], [HIGHLY CITED PAPER & CUP LOGO] and [HOT PAPER & FIRE LOGO] are trademarks of Clarivate Analytics, and/or its affiliated company or companies, and used herein by permission and/or license.