Quinone Methides and Their Biopolymer Conjugates as Reversible DNA Alkylating Agents

被引：13
作者：
Wang, Huan [1 ,2 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China
[2] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
来源：
CURRENT ORGANIC CHEMISTRY | 2014年 / 18卷 / 01期
关键词：
Alkylation; Cross-linking; Nucleic Acids; Peptide Nucleic Acids; Quinone Methide; Reversibility; Sequence Specificity; Strand Exchange; CROSS-LINKING AGENTS; PEPTIDE NUCLEIC-ACIDS; THYMINE-SUBSTITUTED POLYAMIDE; HYPERVALENT IODINE OXIDATION; PYRROLE-IMIDAZOLE POLYAMIDE; TARGET-PROMOTED ALKYLATION; NITROGEN-MUSTARD; DUPLEX DNA; DEOXYGUANOSINE RESIDUES; POTENTIAL APPLICATIONS;
D O I：
10.2174/138527281801140121122736
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this review, we discuss the advances in understanding the reactivity of quinone methide (QM) intermediates and the reversibility of DNA alkylation by QMs in the past two decades. QMs react with strong nucleophiles of DNA under kinetic control but reversibly. The effective lifetime of QMs can be extended through repeated capture and release from DNA adducts. A QM-acridine conjugate DNA cross-linking agent remains dynamic and "migrates" among DNA strands through multiple strand exchange reactions until forming stable adducts irreversibly. Self-adducts of QM-biopolymer conjugates exhibit strong capability to alkylate complementary DNA strands in a sequence specific manner.
引用
收藏
页码：44 / 60
页数：17
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