title: meso-Acetoxymethyl BODIPY dyes for photodynamic therapy: improved photostability of singlet oxygen photosensitizers.
abstract: We report two BODIPY based photosensitizers (Br2BOAc and I2BOAc) featuring an acetoxymethyl substituent at the meso-position. These photosensitizers show improved photostability against singlet oxygen, when compared to a BODIPY photosensitizer lacking the acetoxymethyl group. Both compounds were evaluated for photodynamic therapy against HeLa cells and photodynamic inactivation against E. coli bacteria. We show that the compounds readily embed in the lipid membranes of HeLa cervical cancer cells and efficiently induced light-dependent apoptosis at nanomolar concentration. Also, both compounds showed a substantial degree of photoinactivation of E. coli bacteria when used at low micromolar concentrations.
authors.affiliation: Department of Chemistry and Center for Self Assembled Chemical Structures, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada. Gonzalo.cosa@mcgill.ca.
authors.forename: R
authors.initials: R
authors.lastname: Lincoln
authors.affiliation: Department of Chemistry and Center for Self Assembled Chemical Structures, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada. Gonzalo.cosa@mcgill.ca.
authors.forename: A M
authors.initials: AM
authors.lastname: Durantini
authors.affiliation: Department of Chemistry and Center for Self Assembled Chemical Structures, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada. Gonzalo.cosa@mcgill.ca.
authors.forename: L E
authors.initials: LE
authors.lastname: Greene
authors.affiliation: Department of Chemistry and Center for Self Assembled Chemical Structures, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada. Gonzalo.cosa@mcgill.ca and Instituto Multidisciplinario de Biología Vegetal (IMBIV), CONICET, and Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba X5000HUA, Argentina.
authors.forename: S R
authors.initials: SR
authors.lastname: Martínez
authors.affiliation: Department of Chemistry and Center for Self Assembled Chemical Structures, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada. Gonzalo.cosa@mcgill.ca.
authors.forename: R
authors.initials: R
authors.lastname: Knox
authors.affiliation: Instituto Multidisciplinario de Biología Vegetal (IMBIV), CONICET, and Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba X5000HUA, Argentina.
authors.forename: M C
authors.identifier: 0000-0003-1585-2989
authors.initials: MC
authors.lastname: Becerra
authors.affiliation: Department of Chemistry and Center for Self Assembled Chemical Structures, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada. Gonzalo.cosa@mcgill.ca.
authors.forename: G
authors.initials: G
authors.lastname: Cosa
mesh_terms: D017209:Apoptosis / Q000187:drug effects / Q000528:radiation effects; D001896:Boron Compounds / Q000737:chemistry*; D004926:Escherichia coli / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D008027:Light; D008856:Microscopy, Fluorescence; D038761:Photobleaching; D017319:Photosensitizing Agents / Q000737:chemistry* / Q000494:pharmacology*; D026082:Singlet Oxygen / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D017319:Photosensitizing Agents; D026082:Singlet Oxygen