title: DNA photocleavage by a cationic BODIPY dye through both singlet oxygen and hydroxyl radical: new insight into the photodynamic mechanism of BODIPYs.
abstract: Two new NIR-absorbing BODIPY dyes, each bearing two pyridinium groups, are synthesized and their DNA-binding affinities and DNA photocleavage abilities examined in depth. While one BODIPY dye photocleaves DNA mainly through singlet oxygen, the other photocleaves DNA through both singlet oxygen and hydroxyl radical. To the best of our knowledge, this is the first example of a hydroxyl radical being involved in the photodynamic behavior of BODIPY-type dyes. EPR experiments confirm the ability of these and several related BODIPYs to generate superoxide anion radical and hydroxyl radical. This finding may shed light on the mechanism of BODIPY-based photodynamic therapy (PDT) and open a new avenue for development of more efficient BODIPY-type PDT agents.
authors.affiliation: Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Jianguang
authors.initials: J
authors.lastname: Wang
authors.forename: Yuanjun
authors.initials: Y
authors.lastname: Hou
authors.forename: Wanhua
authors.initials: W
authors.lastname: Lei
authors.forename: Qianxiong
authors.initials: Q
authors.lastname: Zhou
authors.forename: Chao
authors.initials: C
authors.lastname: Li
authors.forename: Baowen
authors.initials: B
authors.lastname: Zhang
authors.forename: Xuesong
authors.initials: X
authors.lastname: Wang
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D004578:Electron Spin Resonance Spectroscopy; D005456:Fluorescent Dyes / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry*; D008027:Light; D010782:Photolysis; D017319:Photosensitizing Agents / Q000737:chemistry*; D026082:Singlet Oxygen / Q000737:chemistry*
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D002412:Cations; D005456:Fluorescent Dyes; D017319:Photosensitizing Agents; D026082:Singlet Oxygen; D017665:Hydroxyl Radical; D004247:DNA