title: From non-covalent binding to irreversible DNA lesions: nile blue and nile red as photosensitizing agents.
abstract: We report a molecular modeling study, coupled with spectroscopy experiments, on the behavior of two well known organic dyes, nile blue and nile red, when interacting with B-DNA. In particular, we evidence the presence of two competitive binding modes, for both drugs. However their subsequent photophysical behavior is different and only nile blue is able to induce DNA photosensitization via an electron transfer mechanism. Most notably, even in the case of nile blue, its sensitization capabilities strongly depend on the environment resulting in a single active binding mode: the minor groove. Fluorescence spectroscopy confirms the presence of competitive interaction modes for both sensitizers, while the sensitization via electron transfer, is possible only in the case of nile blue.
authors.affiliation: Université de Lorraine - Nancy, Theory-Modeling-Simulation SRSMC, Vandoeuvre-lès-Nancy, France.|CNRS, Theory-Modeling-Simulation SRSMC, Vandoeuvre-lès-Nancy, France.
authors.forename: Hugo
authors.initials: H
authors.lastname: Gattuso
authors.affiliation: Université de Lorraine - Nancy Santé, Biologie, Signal - CRAN, Vandoeuvre-lès-Nancy, France.|CNRS, Santé, Biologie, Signal, CRAN, Vandoeuvre-lès-Nancy, France.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Besancenot
authors.affiliation: Université de Lorraine - Nancy Santé, Biologie, Signal - CRAN, Vandoeuvre-lès-Nancy, France.|CNRS, Santé, Biologie, Signal, CRAN, Vandoeuvre-lès-Nancy, France.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Grandemange
authors.affiliation: Université de Lorraine - Nancy, Theory-Modeling-Simulation SRSMC, Vandoeuvre-lès-Nancy, France.|CNRS, Theory-Modeling-Simulation SRSMC, Vandoeuvre-lès-Nancy, France.
authors.forename: Marco
authors.initials: M
authors.lastname: Marazzi
authors.affiliation: Université de Lorraine - Nancy, Theory-Modeling-Simulation SRSMC, Vandoeuvre-lès-Nancy, France.|CNRS, Theory-Modeling-Simulation SRSMC, Vandoeuvre-lès-Nancy, France.
authors.forename: Antonio
authors.initials: A
authors.lastname: Monari
mesh_terms: D001665:Binding Sites; D001667:Binding, Competitive; D003198:Computer Simulation; D059371:DNA, B-Form / Q000737:chemistry*; D004579:Electron Transport; D005456:Fluorescent Dyes / Q000737:chemistry; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D010078:Oxazines / Q000737:chemistry*; D055668:Photochemical Processes; D017319:Photosensitizing Agents / Q000737:chemistry*; D011089:Polydeoxyribonucleotides / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry
chemical_list: D059371:DNA, B-Form; D005456:Fluorescent Dyes; D010078:Oxazines; D017319:Photosensitizing Agents; D011089:Polydeoxyribonucleotides; C008619:Nile Blue; C019530:poly(dC-dG); C044808:nile red