DNA alkylation properties of yatakemycin

被引：78
作者：
Parrish, JP
Kastrinsky, DB
Wolkenberg, SE
Igarashi, Y
Boger, DL
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Toyama Perfectural Univ, Biotechnol Res Ctr, Toyama 9390398, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 36期
关键词：
D O I：
10.1021/ja035984h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Yatakemycin represents the newest and now most potent member of a class of naturally occurring antitumor compounds that includes CC-1065 and the duocarmycins, which derive their biological properties from a characteristic DNA alkylation reaction. Herein, the first description of the yatakemycin DNA alkylation properties is detailed, constituting the first such study of a naturally occurring "sandwiched" member of this class. Thus, the event, sequence selectivity, relative rate and efficiency, and reversibility of the DNA alkylation reaction of yatakemycin are described.
引用
收藏
页码：10971 / 10976
页数：6
相关论文
共 44 条
[11]   Synthesis and evaluation of 1,2,8,8a-tetrahydrocyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one, the parent alkylation subunit of CC-1065 and the duocarmycins:: Impact of the alkylation subunit substituents and its implications for DNA alkylation catalysis [J].
Boger, DL ;
Santillan, A ;
Searcey, M ;
Brunette, SR ;
Wolkenberg, SE ;
Hedrick, MP ;
Jin, Q .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) :4101-4111
[12]   AN ALTERNATIVE AND CONVENIENT STRATEGY FOR GENERATION OF SUBSTANTIAL QUANTITIES OF SINGLY 5'-P-32-END-LABELED DOUBLE-STRANDED DNA FOR BINDING-STUDIES - DEVELOPMENT OF A PROTOCOL FOR EXAMINATION OF FUNCTIONAL FEATURES OF (+)-CC-1065 AND THE DUOCARMYCINS THAT CONTRIBUTE TO THEIR SEQUENCE-SELECTIVE DNA ALKYLATION PROPERTIES [J].
BOGER, DL ;
MUNK, SA ;
ZARRINMAYEH, H ;
ISHIZAKI, T ;
HAUGHT, J ;
BINA, M .
TETRAHEDRON, 1991, 47 (14-15) :2661-2682
[13]   Reversed and sandwiched analogs of duocarmycin SA: Establishment of the origin of the sequence-selective alkylation of DNA and new insights into the source of catalysis [J].
Boger, DL ;
Bollinger, B ;
Hertzog, DL ;
Johnson, DS ;
Cai, H ;
Mesini, P ;
Garbaccio, RM ;
Jin, Q ;
Kitos, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4987-4998
[14]   Parallel synthesis and evaluation of 132 (+)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI) analogues of CC-1065 and the duocarmycins defining the contribution of the DNA-binding domain [J].
Boger, DL ;
Schmitt, HW ;
Fink, BE ;
Hedrick, MP .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6654-6661
[15]   THE DUOCARMYCINS - SYNTHETIC AND MECHANISTIC STUDIES [J].
BOGER, DL .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :20-29
[16]  
BOGER DL, 1996, ANGEW CHEM INT EDIT, V35, P1439
[17]  
DUOCARMYCIN A, 1990, J ORG CHEM, V55, P4499
[18]  
Duocarmycin S. A., 1994, J AM CHEM SOC, V116, P1635
[19]   High resolution solution structure of a DNA duplex alkylated by the antitumor agent duocarmycin SA [J].
Eis, PS ;
Smith, JA ;
Rydzewski, JM ;
Case, DA ;
Boger, DL ;
Chazin, WJ .
JOURNAL OF MOLECULAR BIOLOGY, 1997, 272 (02) :237-252
[20]   Metal cation complexation and activation of reversed CPyI analogues of CC-1065 and duocarmycin SA: Partitioning the effects of binding and catalysis [J].
Ellis, DA ;
Wolkenberg, SE ;
Boger, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9299-9306
12345