ACTIVATION OF NEOCARZINOSTATIN-CHROMOPHORE BY 4-HYDROXYTHIOPHENOL - INTRAMOLECULAR RADICAL TRAPPING OF BIRADICAL INTERMEDIATE

被引:7
作者
SUGIYAMA, H
FUJIWARA, T
SAITO, I
机构
[1] Department of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University, Kyoto
关键词
D O I
10.1016/S0040-4039(00)78508-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of neocarzinostatin chromphore (1) with 4-hydroxythiophenol under DNA-cleaving conditions was investigated. It was found that a novel cyclization product (5) is formed as a major product together with a minor amount of normal cyclization product 4b. Tritium was incorporated into 4b and 5 from [H-3]-labeled poly(dA-dT), implying that both processes giving 4b and 5 are actually involved in the DNA cleavage reaction.
引用
收藏
页码:8825 / 8828
页数:4
相关论文
共 20 条
[1]   INTERNAL HYDROGEN ABSTRACTION BY ACTIVATED NEOCARZINOSTATIN - QUENCHING OF THE RADICAL AT C2 BY HYDROGEN-ATOM TRANSFER FROM THE ALPHA-CARBON OF THE ADDUCTED THIOL [J].
CHIN, DH ;
GOLDBERG, IH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1914-1915
[2]   FREE-RADICAL MECHANISMS INVOLVED IN THE FORMATION OF SEQUENCE-DEPENDENT BISTRANDED DNA LESIONS BY THE ANTITUMOR ANTIBIOTICS BLEOMYCIN, NEOCARZINOSTATIN, AND CALICHEAMICIN [J].
DEDON, PC ;
GOLDBERG, IH .
CHEMICAL RESEARCH IN TOXICOLOGY, 1992, 5 (03) :311-332
[3]   INFLUENCE OF THIOL STRUCTURE ON NEOCARZINOSTATIN ACTIVATION AND EXPRESSION OF DNA DAMAGE [J].
DEDON, PC ;
GOLDBERG, IH .
BIOCHEMISTRY, 1992, 31 (07) :1909-1917
[4]   THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM [J].
EDO, K ;
MIZUGAKI, M ;
KOIDE, Y ;
SETO, H ;
FURIHATA, K ;
OTAKE, N ;
ISHIDA, N .
TETRAHEDRON LETTERS, 1985, 26 (03) :331-334
[5]   MECHANISM OF NEOCARZINOSTATIN ACTION - ROLE OF DNA MICROSTRUCTURE IN DETERMINATION OF CHEMISTRY OF BISTRANDED OXIDATIVE DAMAGE [J].
GOLDBERG, IH .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) :191-198
[6]   BIFUNCTIONAL INVOLVEMENT OF THE HYDROXYNAPHTHOATE ESTER MOIETY IN THE ACTIVATION OF NEOCARZINOSTATIN CHROMOPHORE IN DNA-MEDIATED SITE-SPECIFIC CLEAVAGE [J].
HENSENS, OD ;
HELMS, GL ;
ZINK, DL ;
CHIN, DH ;
KAPPEN, LS ;
GOLDBERG, IH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11030-11031
[7]   NEOCARZINOSTATIN CHROMOPHORE - PRESENCE OF A HIGHLY STRAINED ETHER RING AND ITS REACTION WITH MERCAPTAN AND SODIUM-BOROHYDRIDE [J].
HENSENS, OD ;
DEWEY, RS ;
LIESCH, JM ;
NAPIER, MA ;
REAMER, RA ;
SMITH, JL ;
ALBERSSCHONBERG, G ;
GOLDBERG, IH .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1983, 113 (02) :538-547
[8]  
ISHIDA N, 1965, J ANTIBIOT, V18, P68
[9]   CHEMISTRY OF NEOCARZINOSTATIN-MEDIATED DEGRADATION OF D(GCATGC) - MECHANISM OF SPONTANEOUS THYMINE RELEASE [J].
KAWABATA, H ;
TAKESHITA, H ;
FUJIWARA, T ;
SUGIYAMA, H ;
MATSUURA, T ;
SAITO, I .
TETRAHEDRON LETTERS, 1989, 30 (32) :4263-4266
[10]   10-MEMBERED NEOCARZINOSTATIN CHROMOPHORE ANALOGS LEADING TO SIGMA,SIGMA-BIRADICAL VIA A CUMULENE INTERMEDIATE [J].
KAWATA, S ;
OISHI, T ;
HIRAMA, M .
TETRAHEDRON LETTERS, 1994, 35 (26) :4595-4598