Biostructural features of additional jasplakinolide (jaspamide) analogues.
The cyclodepsipeptide jasplakinolide (1) (aka jaspamide), isolated previously from the marine sponge Jaspis splendens, is a unique cytotoxin and molecular probe that operates through stabilization of filamentous actin (F-actin). We have recently disclosed that two analogues of 1, jasplakinolides B (3) and E, were referred to the National Cancer Institute's (NCI) Biological Evaluation Committee, and the objective of this study was to reinvestigate a Fijian collection of J. splendens in an effort to find jasplakinolide congeners with similar biological properties. The current efforts have afforded six known jasplakinolide analogues (4-7, 9, 10), two structures requiring revision (8 and 14), and four new congeners of 1 (11-13, 15) including open-chain derivatives and structures with modified β-tyrosine residues. Compounds were evaluated for biological activity in the NCI's 60 cell line screen and in a microfilament disruption assay in both HCT-116 and HeLa cells. These two phenotypic screens provide evidence that each cytotoxic analogue, including jasplakinolide B (3), operates by modification of microfilaments. The new structure jasplakinolide V (13) has also been selected for study by the NCI's Biological Evaluation Committee. In addition, the results of a clonogenic dose-response study on jasplakinolide are presented.
Department of Chemistry and Biochemistry, University of California, Santa Cruz, Santa Cruz, California 95064, United States.
Katharine R
KR
Watts
Brandon I
BI
Morinaka
Taro
T
Amagata
Sarah J
SJ
Robinson
Karen
K
Tenney
Walter M
WM
Bray
Nadine C
NC
Gassner
R Scott
RS
Lokey
Joseph
J
Media
Frederick A
FA
Valeriote
Phillip
P
Crews
D000199:Actins / Q000378:metabolism; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005367:Fiji; D045325:HCT116 Cells; D006367:HeLa Cells; D006801:Humans; D008386:Marine Biology; D015394:Molecular Structure; D054547:National Cancer Institute (U.S.); D010456:Peptides, Cyclic; D013237:Stereoisomerism; D014481:United States
D000199:Actins; D000970:Antineoplastic Agents; D003603:Cytotoxins; D047630:Depsipeptides; D010456:Peptides, Cyclic; C118105:jaspamide B; C558230:jasplakinolide E; C558231:jasplakinolide V; C057531:jasplakinolide
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