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Effect of C5-Methylation of Cytosine on the UV-Induced Reactivity of Duplex DNA: Conformational and Electronic Factors (29 views)

Banyasz A, Esposito L, Douki T, Perron M, Lepori C, Improta R, Markovitsi D

J Phys Chem B (ISSN: 1520-5207electronic, 1520-5207linking, 1520-6106), 2016 May 12; 120(18): 4232-4242.

Abstract
C5-methylation of cytosines is strongly correlated with UV-induced mutations detected in skin cancers. Mutational hot-spots appearing at TCG sites are due to the formation of pyrimidine cyclobutane dimers (CPDs). The present study, performed for the model DNA duplex (TCGTA)3.(TACGA)3 and the constitutive single strands, examines the factors underlying the effect of C5-methylation on pyrimidine dimerization at TCG sites. This effect is quantified for the first time by quantum yields varphi. They were determined following irradiation at 255, 267, and 282 nm and subsequent photoproduct analysis using HPLC coupled to mass spectrometry. C5-methylation leads to an increase of the CPD quantum yield up to 80% with concomitant decrease of that of pyrimidine(6-4) pyrimidone adducts (64PPs) by at least a factor of 3. The obtained varphi values cannot be explained only by the change of the cytosine absorption spectrum upon C5-methylation. The conformational and electronic factors that may affect the dimerization reaction are discussed in light of results obtained by fluorescence spectroscopy, molecular dynamics simulations, and quantum mechanical calculations. Thus, it appears that the presence of an extra methyl on cytosine affects the sugar puckering, thereby enhancing conformations of the TC step that are prone to CPD formation but less favorable to 64PPs. In addition, C5-methylation diminishes the amplitude of conformational motions in duplexes; in the resulting stiffer structure, pipi* excitations may be transferred from initially populated exciton states to reactive pyrimidines giving rise to CPDs.

Affiliations ▼
*** IBB - CNR Affiliation

LIDYL, CEA, CNRS, Universite Paris Saclay, F-91191 Gif-sur-Yvette, France., Istituto Biostrutture e Bioimmagini - CNR , 80134 Napoli, Italy., Universite Grenoble Alpes, INAC, LCIB, LAN & CEA, INAC, SCIB, LANF-38000 Grenoble, France.,

Details ▼
Impact factor: 3.177, 5-year impact factor: 3.177

Paper type: Journal Article,

Keywords: Not available.

Url: Not available.

References ▼
Not available.

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* UV-induced damage to DNA: effect of cytosine methylation on pyrimidine dimerization (9 views)
Martinez-fernandez L, Banyasz A, Esposito L, Markovitsi D, Improta R
Signal Transduction And Targeted Therapy, 2017 Jun; N/D: N/D-N/D.

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1 Records (1 excluding Abstracts and Conferences).
Total impact factor: 0 (0 excluding Abstracts and Conferences).
Total 5-year impact factor: 0 (0 excluding Abstracts and Conferences).



Your bibliography query: (([btitle, keywords, abstract] EFFECT AND [btitle, keywords, abstract] METHYLATION AND [btitle, keywords, abstract] CYTOSINE AND [btitle, keywords, abstract] INDUCED AND [btitle, keywords, abstract] REACTIVITY AND [btitle, keywords, abstract] DUPLEX AND [btitle, keywords, abstract] CONFORMATIONAL)) AND NOT [id] = 53281



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