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Characterization of the Chemical Reactivity and Selectivity of DNA Bases Through the Use of DFT-Based Descriptors

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Book cover Structure, Bonding and Reactivity of Heterocyclic Compounds

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 38))

Abstract

In this chapter, the use of conceptual DFT descriptors for understanding the occurrence and likely mechanisms of formation of DNA lesions is reviewed. After a synthetic presentation of the principal DFT-based descriptors, the global reactivity and selectivity of DNA bases are investigated from global and local descriptors. Then, the formation of several DNA lesions is studied including cytosine compound deamination, intra-strand DNA cross-links, and pyrimidine dimer photoproducts. It appears from the use of the global and local DFT-based descriptors that most of the experimental facts can be theoretically rationalized.

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Acknowledgments

All the authors thank INSERM: “This research has benefited from ITMO cancer of Aviesan within the framework Plan Cancer 2009–2013.” Cette recherche a bénéficié de l’aide de l’ITMO cancer d’Aviesan dans le cadre du Plan Cancer 2009–2013.

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Authors and Affiliations

  1. Sorbonne Universités, UPMC Univ Paris 6, MONARIS, UMR 8233, 75005, Paris, France

    Vanessa Labet

  2. Université de Lyon 1, ISA, UMR 5280, 5 rue de la Doua, 69100, Villeurbanne, France

    Christophe Morell

  3. Normandie Université, COBRA, UMR6014 & FR 3038, Université de Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821, Mont-Saint-Aignan Cedex, France

    Vincent Tognetti, Olga A. Syzgantseva & Laurent Joubert

  4. Área Fisicoquímica, Facultad de Ciencias Exactas y Naturales y Agrimensura, UNNE, Campus Universitario, Av. Libertad 5400, (3400), Corrientes, Argentina

    Nelly Jorge

  5. CEA Grenoble -Institut Nanosciences et Cryogénie/SCIB/LAN (UMR-E n 3 CEA-UJF), CEA-Grenoble, 17, rue des Martyrs, 38054, Grenoble Cedex 9, France

    André Grand & Jean Cadet

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  1. Vanessa Labet
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  7. André Grand
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Correspondence to Christophe Morell .

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  1. Research Group of General Chemistry, Vrije Universiteit Brussel (VUB), Brussels, Belgium

    Frank De Proft

  2. Research Group of General Chemistry, Vrije Universiteit Brussel (VUB), Brussels, Belgium

    Paul Geerlings

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Labet, V. et al. (2014). Characterization of the Chemical Reactivity and Selectivity of DNA Bases Through the Use of DFT-Based Descriptors. In: De Proft, F., Geerlings, P. (eds) Structure, Bonding and Reactivity of Heterocyclic Compounds. Topics in Heterocyclic Chemistry, vol 38. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-45149-2_2

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