Photosensitized damage to calf thymus DNA by a hypocrellin derivative: mechanisms under aerobic and anaerobic conditions.
The di-cysteine substituted hypocrellin B (DCHB) derivative has been found to be a potential phototherapeutic agent and exhibit photosensitized damage to DNA. Electronic paramagnetic resonance (EPR) and spectrophotometry demonstrate that one-electron transfer from calf thymus DNA to triplet DCHB induces the generation of the reduced form of DCHB (DCHB*- radical), followed by the second electron transfer from DNA to DCHB*- or the disproportionation of DCHB*- to form the hydroquinone of DCHB (DCHBH2) in anaerobic conditions. This electron transfer process induces the direct damage to DNA in oxygen-free media and contributes partly to the damage of DNA in aerobic media. Superoxide radical and hydroxyl radical are formed with enhanced efficiencies while singlet oxygen is generated with a reduced efficiency from irradiation of DCHB and DNA solution under aerobic conditions as compared with the case in the absence of DNA. All of three reactive oxygen species play an evident role in the photosensitized damage to DNA in aerobic system in addition to the direct electron-transfer damage.
He
Y Y
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Institute of Photographic Chemistry, Academia Sinica, Beijing, PR China.
Jiang
L J
LJ
D000332:Aerobiosis; D000693:Anaerobiosis; D000818:Animals; D002417:Cattle; D004247:DNA / Q000737:chemistry* / Q000187:drug effects / Q000528:radiation effects; D004249:DNA Damage; D004578:Electron Spin Resonance Spectroscopy; D004583:Electrons; D008027:Light; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D017319:Photosensitizing Agents / Q000737:chemistry / Q000494:pharmacology*; D013053:Spectrophotometry; D013843:Thiazines / Q000737:chemistry / Q000494:pharmacology*; D013950:Thymus Gland
D017319:Photosensitizing Agents; D013843:Thiazines; C417049:di-cysteine substituted hypocrellin B; D010569:Perylene; D004247:DNA