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Chaturvedi R, Long EC. Mechanistic studies of dinucleotide and oligonucleotide model cyclobutane pyrimidine dimer (CPD) DNA lesions under alkaline conditions. Bioorg Med Chem. 2021;54:116499doi: 10.1016/j.bmc.2021.116499.
Chaturvedi, R., & Long, E. C. (2021). Mechanistic studies of dinucleotide and oligonucleotide model cyclobutane pyrimidine dimer (CPD) DNA lesions under alkaline conditions. Bioorganic & medicinal chemistry, 54116499. https://doi.org/10.1016/j.bmc.2021.116499
Chaturvedi, Ritu, and Long, Eric C. "Mechanistic studies of dinucleotide and oligonucleotide model cyclobutane pyrimidine dimer (CPD) DNA lesions under alkaline conditions." Bioorganic & medicinal chemistry vol. 54 (2021): 116499. doi: https://doi.org/10.1016/j.bmc.2021.116499
Chaturvedi R, Long EC. Mechanistic studies of dinucleotide and oligonucleotide model cyclobutane pyrimidine dimer (CPD) DNA lesions under alkaline conditions. Bioorg Med Chem. 2021 Nov 10;54:116499. doi: 10.1016/j.bmc.2021.116499. Epub 2021 Nov 10. PMID: 34922308.
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Bioorg Med Chem. 2021 Nov 10;54:116499. doi: 10.1016/j.bmc.2021.116499. Epub 2021 Nov 10.

Mechanistic studies of dinucleotide and oligonucleotide model cyclobutane pyrimidine dimer (CPD) DNA lesions under alkaline conditions.

Bioorganic & medicinal chemistry

Ritu Chaturvedi, Eric C Long

Affiliations

  1. Department of Chemistry & Chemical Biology, Indiana University-Purdue University Indianapolis (IUPUI), 402 N. Blackford St., Indianapolis, IN 46202, United States. Electronic address: [email protected].
  2. Department of Chemistry & Chemical Biology, Indiana University-Purdue University Indianapolis (IUPUI), 402 N. Blackford St., Indianapolis, IN 46202, United States. Electronic address: [email protected].

PMID: 34922308 DOI: 10.1016/j.bmc.2021.116499

Abstract

Cyclobutane pyrimidine dimers (CPDs) are the most abundant mutagenic DNA lesions formed in mammalian cells upon exposure to UV-B radiation (280-315 nm) in sunlight. These lesions are thought to be chemically stable and to withstand high concentrations of acids and bases.While earlier investigations of DNA lesions containing saturated pyrimidines have shown that the C4 carbonyl is a potential target of nucleophilic attack, similar reactions with thymine nucleobase model CPDs clearly showed that the cis-syn CPD (major isomer) is stable in the presence of a high concentration of alkali at room temperature. Here is described the alkaline reactivity of these lesions when contained within a dinucleotide CPD model system. Results using cis-syn CPD formed from dinucleotide 5'-TpT-3' combined with [

Copyright © 2021 Elsevier Ltd. All rights reserved.

Keywords: Alkaline reactivity; Cyclobutane pyrimidine dimer; DNA damage; DNA strand break; Hemiaminal

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