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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Quinone Methides as DNA Alkylating Agents: An Overview on Efficient Activation Protocols for Enhanced Target Selectivity

Author(s): Claudia Percivalle, Filippo Doria and Mauro Freccero

Volume 18 , Issue 1 , 2014

Page: [19 - 43] Pages: 25

DOI: 10.2174/13852728113176660135

open access plus


The following review analyzes the most effective activation protocols for the generation of transient electrophilic quinone methides, merged into the recent strategies to achieve recognition and alkylation of nucleic acids. The covalent targeting has to be specific for selected oligonucleotide sequences (sequence-specificity) or for those oligonucleotides capable to fold into supramolecular structures, such as G-quadruplexes (structure-specificity). The reversibility of the DNA alkylation process by QM is reviewed underlining the opportunities (in term of selectivity and delivery) and drawbacks (in term of product characterization of the covalent damage) in the DNA targeting.

Keywords: Alkylation, cross-linking, nucleic acids, quinone methides, reversibility, sequence-specificity, structure-specificity.

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