DNA interstrand cross-link formation by reductive activation of dehydropyrrolizidine progenitors

被引：7
|
作者：
Tepe, JJ [1 ]
Kosogof, C [1 ]
Williams, RM [1 ]
机构：
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
来源：
TETRAHEDRON | 2002年 / 58卷 / 18期
基金：
美国国家卫生研究院;
关键词：
DNA interstrand cross-link; reductive activation; dehydropyrrolizidine progenitors;
D O I：
10.1016/S0040-4020(02)00311-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pyrrolizidine alkaloids (PAs) are potent hepatotoxins and carcinogens isolated from a wide variety of plants. The hepatotoxicity of these agents is a manifestation of the initial production and release of the reactive dehydropyrrolizidine, which is the DNA-cross-linking species, generated in the liver by the mixed function cytochrome P450 oxidases. A separate class of DNA cross-linkers, including the clinically significant mitomycins and the related FR900482 and congeners are reductively activated in vivo forming a very similar pyrrolic-type intermediate responsible for the DNA cross-linking reactivity of these substances. We report here the synthesis and DNA cross-linking studies of a reductively activated dehydromonocrotaline progentior and its dicarbamate derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3553 / 3559
页数：7
相关论文
共 50 条
  • [21] Formation and Repair of an Interstrand DNA Cross-Link Arising from a Common Endogenous Lesion
    Housh, Kurt
    Jha, Jay S.
    Yang, Zhiyu
    Haldar, Tuhin
    Johnson, Kevin M.
    Yin, Jiekai
    Wang, Yinsheng
    Gates, Kent S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (37) : 15344 - 15357
  • [22] DNA interstrand cross-link formation by the 1,4-dioxobutane abasic lesion
    Guan, Lirui
    Greenberg, Marc M.
    Journal of the American Chemical Society, 2009, 131 (42): : 15225 - 15231
  • [23] The Fanconi anemia pathway and DNA interstrand cross-link repair
    Xiaoyu Su
    Jun Huang
    Protein & Cell, 2011, 2 (09) : 704 - 711
  • [24] The Fanconi anemia pathway and DNA interstrand cross-link repair
    Su, Xiaoyu
    Huang, Jun
    PROTEIN & CELL, 2011, 2 (09) : 704 - 711
  • [25] Bypass of a Psoralen DNA Interstrand Cross-Link by DNA Polymerases β, ι, and κ in Vitro
    Smith, Leigh A.
    Makarova, Alena V.
    Samson, Laura
    Thiesen, Katherine E.
    Dhar, Alok
    Bessho, Tadayoshi
    BIOCHEMISTRY, 2012, 51 (44) : 8931 - 8938
  • [26] Initiation of DNA Interstrand Cross-link Repair in Mammalian Cells
    Hlavin, Erica M.
    Smeaton, Michael B.
    Miller, Paul S.
    ENVIRONMENTAL AND MOLECULAR MUTAGENESIS, 2010, 51 (06) : 604 - 624
  • [27] Initiation of DNA Interstrand Cross-Link Repair in Mammalian Cells
    Miller, P. S.
    ENVIRONMENTAL AND MOLECULAR MUTAGENESIS, 2010, 51 (07) : 688 - 688
  • [28] FR66979 REQUIRES REDUCTIVE ACTIVATION TO CROSS-LINK DNA EFFICIENTLY
    HUANG, HF
    RAJSKI, SR
    WILLIAMS, RM
    HOPKINS, PB
    TETRAHEDRON LETTERS, 1994, 35 (52) : 9669 - 9672
  • [29] SEQUENCE SPECIFICITY OF DNA-DNA INTERSTRAND CROSS-LINK FORMATION BY CISPLATIN AND DINUCLEAR PLATINUM COMPLEXES
    ZOU, Y
    VANHOUTEN, B
    FARRELL, N
    BIOCHEMISTRY, 1994, 33 (18) : 5404 - 5410
  • [30] Cross-Link Structure Affects Replication-Independent DNA Interstrand Cross-Link Repair in Mammalian Cells
    Hlavin, Erica M.
    Smeaton, Michael B.
    Noronha, Anne M.
    Wilds, Christopher J.
    Miller, Paul S.
    BIOCHEMISTRY, 2010, 49 (18) : 3977 - 3988
12345