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Literature DB >> 27572158

Investigation of the mechanisms of photo-induced formation of cyclobutane dimers of cytosine and 2,4-diaminopyrimidine.

Abstract

The mechanisms of the formation of cyclobutane dimers (CBD) of cytosine and 2,4-diaminopyrimidine were studied at the CC2 theoretical level and cc-pVDZ basis functions. Four orientations of the two monomers are explored: cys-syn, cis-anti, trans-syn, and trans-anti. The research revealed that in all cases the cyclobutane structures are formed along the (1)ππ* excited-state reaction paths of the stacked aggregates. We localized the S1/S0 conical intersections mediating those transformations. The results obtained agree well with the previously reported investigations on the cis-syn cyclodimer formations of other pyrimidines.

Entities: Chemical Gene

Keywords: Ab initio calculations; Cyclobutane photodimers; Excited states; Nucleic acid bases; Photo-induced cyclodimerization

Mesh：

Substances：

Year: 2016 PMID： 27572158 DOI： 10.1007/s00894-016-3087-9

Source DB: PubMed Journal: J Mol Model ISSN： 0948-5023 Impact factor: 1.810

31 in total

1. Unified model for the ultrafast decay of pyrimidine nucleobases.

Authors: Manuela Merchán; Remedios González-Luque; Teresa Climent; Luis Serrano-Andrés; Elena Rodríguez; Mar Reguero; Daniel Peláez
Journal: J Phys Chem B Date: 2006-12-28 Impact factor: 2.991

2. Involvement of 5-methylcytosine in sunlight-induced mutagenesis.

Authors: Y H You; C Li; G P Pfeifer
Journal: J Mol Biol Date: 1999-10-29 Impact factor: 5.469

3. Quantum chemical investigation of the electronic spectra of the keto, enol, and keto-imine tautomers of cytosine.

Authors: Katarina Tomić; Jörg Tatchen; Christel M Marian
Journal: J Phys Chem A Date: 2005-09-22 Impact factor: 2.781

4. Effect of substituents on the excited-state dynamics of the modified DNA bases 2,4-diaminopyrimidine and 2,6-diaminopurine.

Authors: Zsolt Gengeliczki; Michael P Callahan; Nathan Svadlenak; Csaba István Pongor; Bálint Sztáray; Leo Meerts; Dana Nachtigallová; Pavel Hobza; Mario Barbatti; Hans Lischka; Mattanjah S de Vries
Journal: Phys Chem Chem Phys Date: 2010-04-08 Impact factor: 3.676

5. Radiationless decay mechanism of cytosine: an ab initio study with comparisons to the fluorescent analogue 5-methyl-2-pyrimidinone.

Authors: Kurt A Kistler; Spiridoula Matsika
Journal: J Phys Chem A Date: 2007-03-17 Impact factor: 2.781

6. Analysis of mutation spectra in UVB-exposed mouse skin epidermis and dermis: frequent occurrence of C-->T transition at methylated CpG-associated dipyrimidine sites.

Authors: Hironobu Ikehata; Toshinari Masuda; Hiroyuki Sakata; Tetsuya Ono
Journal: Environ Mol Mutagen Date: 2003 Impact factor: 3.216

7. Formation of the main UV-induced thymine dimeric lesions within isolated and cellular DNA as measured by high performance liquid chromatography-tandem mass spectrometry.

Authors: T Douki; M Court; S Sauvaigo; F Odin; J Cadet
Journal: J Biol Chem Date: 2000-04-21 Impact factor: 5.157

Investigation of the mechanisms of photo-induced formation of cyclobutane dimers of cytosine and 2,4-diaminopyrimidine.

1. Unified model for the ultrafast decay of pyrimidine nucleobases.

2. Involvement of 5-methylcytosine in sunlight-induced mutagenesis.

3. Quantum chemical investigation of the electronic spectra of the keto, enol, and keto-imine tautomers of cytosine.

4. Effect of substituents on the excited-state dynamics of the modified DNA bases 2,4-diaminopyrimidine and 2,6-diaminopurine.

5. Radiationless decay mechanism of cytosine: an ab initio study with comparisons to the fluorescent analogue 5-methyl-2-pyrimidinone.

6. Analysis of mutation spectra in UVB-exposed mouse skin epidermis and dermis: frequent occurrence of C-->T transition at methylated CpG-associated dipyrimidine sites.

7. Formation of the main UV-induced thymine dimeric lesions within isolated and cellular DNA as measured by high performance liquid chromatography-tandem mass spectrometry.

8. Modeling thymine photodimerizations in DNA: mechanism and correlation diagrams.

9. Ultrafast internal conversion of excited cytosine via the lowest pipi electronic singlet state.

10. Deamination of 5-methylcytosines within cyclobutane pyrimidine dimers is an important component of UVB mutagenesis.

1. Theoretical Study of Light-Induced Crosslinking Reaction Between Pyrimidine DNA Bases and Aromatic Amino Acids.