Tunable DNA cleavage by intercalating peptidoconjugates

Chembiochem : a European Journal of Chemical Biology
Kerry P MahonShana O Kelley

Abstract

The properties of a novel family of peptide-based DNA-cleavage agents are described. Examination of the DNA-cleavage activities of a systematic series of peptide-intercalator conjugates revealed trends that show a strong dependence on peptide sequence. Conjugates differing by a single residue displayed reactivities that varied over a wide range. The cleavage activity was modulated by the electrostatic or steric qualities of individual amino acids. Isomeric conjugates that differed in the position of the tether also exhibited different reactivities. The mechanism of DNA cleavage for these compounds was also probed and was determined to involve hydrogen-atom abstraction from the DNA backbone. Previous studies of these compounds indicated that amino acid peroxides were the active agents in the cleavage reaction; in this report, the chemistry underlying the reaction is characterized. The results reported provide insight into how peptide sequences can be manipulated to produce biomimetic compounds.

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Citations

Sep 25, 2010·Oligonucleotides·Netanel Kolevzon, Eylon Yavin
Jan 17, 2016·Chemistry : a European Journal·Sina BerndlHans-Achim Wagenknecht
Dec 22, 2009·Physical Chemistry Chemical Physics : PCCP·Christa PrunklHans-Achim Wagenknecht
May 11, 2007·BioTechniques·Marc D Roy
Aug 29, 2018·Journal of Alzheimer's Disease : JAD·Sakae YumotoAkira Ishikawa
May 17, 2019·Current Protein & Peptide Science·Tamara ŠmidlehnerIvo Piantanida
Mar 30, 2010·Bioconjugate Chemistry·Adva BitonEylon Yavin
Apr 30, 2008·The Journal of Organic Chemistry·Florian MenacherHans-Achim Wagenknecht
Sep 22, 2021·Chemical Reviews·Vivian M LechnerMatthew J Gaunt
Oct 31, 2021·Angewandte Chemie·Soumen DasM G Finn

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