DNA alkylation promoted by an electron-rich quinone methide intermediate

2016, Volume 10, Issue 2

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Frontiers of Chemical Science and Engineering >> 2016, Volume 10, Issue 2 doi: 10.1007/s11705-015-1541-3

DNA alkylation promoted by an electron-rich quinone methide intermediate

. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.. Sichuan Institute of Geological Engineering Investigation, Chengdu 610072, China.. Department of Chemistry, Johns Hopkins University, Baltimore, MD 21218, USA

Accepted: 2015-11-20 Available online: 2016-05-19

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Abstract

Biological application of conjugates derived from oligonucleotides and quinone methides have previously been limited by the slow exchange of their covalent self-adducts and subsequent alkylation of target nucleic acids. To enhance the rates of these processes, a new quinone methide precursor with an electron donating substituent has been prepared. Additionally, this substituent has been placed to the nascent -methylene group of the quinone methide for maximum effect. A conjugate made from this precursor and a 5'-aminohexyloligonucleotide accelerates formation of its reversible self-adduct and alkylation of its complementary DNA as predicted from prior model studies.

Keywords

quione methide ; DNA alkylation ; reversible covalent reaction ; bioconjugation ; target-directed modification of nucleic acids

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