Academic Journal
Stereoselective Fluorescence Quenching in the Electron Transfer Photooxidation of Nucleobase-Related Azetidines by Cyanoaromatics
| العنوان: | Stereoselective Fluorescence Quenching in the Electron Transfer Photooxidation of Nucleobase-Related Azetidines by Cyanoaromatics |
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| المؤلفون: | Fraga-Timiraos, Ana Belén, Rodríguez Muñiz, Gemma María, Peiro-Penalba, Vicente, Miranda Alonso, Miguel Ángel, Lhiaubet, Virginie Lyria |
| المساهمون: | Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química, Universitat Politècnica de València. Departamento de Química - Departament de Química, Generalitat Valenciana, Ministerio de Economía y Competitividad |
| بيانات النشر: | MDPI AG |
| سنة النشر: | 2016 |
| المجموعة: | Universitat Politécnica de Valencia: RiuNet / Politechnical University of Valencia |
| مصطلحات موضوعية: | DNA repair, Energy and charge transfer, Nucleobase analogues, Photolyase, Redox potential, QUIMICA ORGANICA |
| الوصف: | [EN] Electron transfer involving nucleic acids and their derivatives is an important field in bioorganic chemistry, specifically in connection with its role in the photo-driven DNA damage and repair. Four-membered ring heterocyclic oxetanes and azetidines have been claimed to be the intermediates involved in the repair of DNA (6-4) photoproduct by photolyase. In this context, we examine here the redox properties of the two azetidine isomers obtained from photocycloaddition between 6-aza-1,3-dimethyluracil and cyclohexene. Steady-state and time-resolved fluorescence experiments using a series of photoreductants and photooxidants have been run to evaluate the efficiency of the electron transfer process. Analysis of the obtained quenching kinetics shows that the azetidine compounds can act as electron donors. Additionally, it appears that the cis isomer is more easily oxidized than its trans counterpart. This result is in agreement with electrochemical studies performed on both azetidine derivatives. ; Spanish Government (CTQ2015-70164-P, RIRAAF RETICS RD12/0013/0009, Red de Fotoquimica Biologica CTQ2015-71896-REDT, Severo Ochoa program/SEV-2012-0267 and SVP-2013-068057 for A. B. F.-R. grant) and Generalitat Valenciana (Prometeo II/2013/005) are gratefully acknowledged. ; Fraga-Timiraos, AB.; Rodríguez Muñiz, GM.; Peiro-Penalba, V.; Miranda Alonso, MÁ.; Lhiaubet, VL. (2016). Stereoselective Fluorescence Quenching in the Electron Transfer Photooxidation of Nucleobase-Related Azetidines by Cyanoaromatics. Molecules. 21(12). https://doi.org/10.3390/molecules21121683 ; S ; 21 ; 12 ; Arnold, A. R., Grodick, M. A., & Barton, J. K. (2016). DNA Charge Transport: from Chemical Principles to the Cell. Cell Chemical Biology, 23(1), 183-197. doi:10.1016/j.chembiol.2015.11.010 ; Jia, C., Ma, B., Xin, N., & Guo, X. (2015). Carbon Electrode–Molecule Junctions: A Reliable Platform for Molecular Electronics. Accounts of Chemical Research, 48(9), 2565-2575. doi:10.1021/acs.accounts.5b00133 ; Beratan, D. N., Liu, C., ... |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| تدمد: | 1420-3049 |
| Relation: | Molecules; info:eu-repo/grantAgreement/MINECO//SEV-2012-0267/; info:eu-repo/grantAgreement/MINECO//SVP-2013-068057/ES/SVP-2013-068057/; info:eu-repo/grantAgreement/MINECO//CTQ2015-70164-P/ES/LESIONES DEL ADN COMO FOTOSENSIBILIZADORES INTRINSECOS - CONCEPTO DE CABALLO DE TROYA/; info:eu-repo/grantAgreement/GVA//PROMETEOII%2F2013%2F005/ES/ESPECIES FOTOACTIVAS Y SU INTERACCION CON BIOMOLECULAS/; info:eu-repo/grantAgreement/MINECO//CTQ2015-71896-REDT/ES/RED DE FOTOQUIMICA BIOLOGICA/; info:eu-repo/grantAgreement/MINECO//RD12%2F0013%2F0009/; http://doi.org/10.3390/molecules21121683; urn:issn:1420-3049; http://hdl.handle.net/10251/151282; PMC6273614 |
| DOI: | 10.3390/molecules21121683 |
| الاتاحة: | http://hdl.handle.net/10251/151282 https://doi.org/10.3390/molecules21121683 |
| Rights: | http://creativecommons.org/licenses/by/4.0/ ; info:eu-repo/semantics/openAccess |
| رقم الانضمام: | edsbas.F7643FD1 |
| قاعدة البيانات: | BASE |
Full Text Finder | تدمد: | 14203049 |
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| DOI: | 10.3390/molecules21121683 |