Acylfulvenes, a new class of potent antitumor agents

被引:46
作者
McMorris, TC
Kelner, MJ
Wang, W
Diaz, MA
Estes, LA
Taetle, R
机构
[1] UNIV CALIF SAN DIEGO, DEPT PATHOL, LA JOLLA, CA 92093 USA
[2] UNIV ARIZONA, ARIZONA CANC CTR, DIV HEMATOL, TUCSON, AZ 85724 USA
来源
EXPERIENTIA | 1996年 / 52卷 / 01期
关键词
acylfulvene; illudin S; sesquiterpene; antitumor agents;
D O I
10.1007/BF01922420
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Acylfulvene, derived from the sesquiterpene illudin S by treatment with acid (reverse Prins reaction), is far less reactive to thiols than illudin S. However, it is reduced readily to an aromatic product, in the same way as illudin S. This may explain its greatly improved therapeutic index compared to that of the parent compound.
引用
收藏
页码:75 / 80
页数:6
相关论文
共 19 条
[1]   REVERSIBLE ADDITION OF THIOLS TO STEROID ALPHA,BETA-UNSATURATED CARBONYL GROUPS - POSSIBLE ROLE IN STEROID-PROTEIN INTERACTIONS [J].
FAHEY, RC ;
MYERS, PA ;
DISTEFANO, DL .
BIOORGANIC CHEMISTRY, 1980, 9 (03) :293-298
[2]  
FISHER JF, 1988, PROG DRUG RES, V32, P441
[3]  
FRENCH AL, 1988, CLIN TOXICOL, V26, P81
[4]   ANTIBIOTICS FROM BASIDIOMYCETES .36. LEAIANAFULVENE, A SESQUITERPENOID FULVENE DERIVATIVE FROM CULTURES OF MYCENA-LEAIANA [J].
HARTTIG, U ;
ANKE, T ;
SCHERER, A ;
STEGLICH, W .
PHYTOCHEMISTRY, 1990, 29 (12) :3942-3944
[5]   PRECLINICAL EVALUATION OF ILLUDINS AS ANTICANCER AGENTS - BASIS FOR SELECTIVE CYTOTOXICITY [J].
KELNER, MJ ;
MCMORRIS, TC ;
TAETLE, R .
JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1990, 82 (19) :1562-1565
[6]  
KELNER MJ, 1987, CANCER RES, V47, P3186
[7]  
KELNER MJ, 1995, IN PRESS CANCER RES
[8]   25 CASES OF POISONING BY MUSHROOM PLEUROTUS-OLEARIUS [J].
MARETIC, Z ;
RUSSELL, FE ;
GOLOBIC, V .
TOXICON, 1975, 13 (05) :379-381
[9]   STRUCTURE OF LAMPTEROL (ILLUDIN S) [J].
MATSUMOTO, T ;
SHIRAHAMA, H ;
ICHIHARA, A ;
FUKUOKA, Y ;
TAKAHASHI, Y ;
MORI, Y ;
WATANABE, M .
TETRAHEDRON, 1965, 21 (09) :2671-+
[10]   ISOLATION OF ILLUDIN S FROM THE MUSHROOM OMPHALOTUS-OLIVASCENS [J].
MCMORRIS, TC ;
MOON, S ;
UNGAB, G ;
KEREKES, RJ .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (02) :380-380