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Production of active oxygen species singlet oxygen and super oxide radical anion by psoralens and uv radiation 320 400 nanometers



Production of active oxygen species singlet oxygen and super oxide radical anion by psoralens and uv radiation 320 400 nanometers



Biochimica et Biophysica Acta 798(1): 115-126



Furocoumarins (psoralens) are potent skin photosensitizing agents that are used in combination with long-wavelength UV radiation (320-400 nm) in the treatment of psoriasis and other skin diseases. Linear and angular psoralens (12) capable of forming monofunctional and bifunctional adducts with DNA were examined with a view to elucidate the role of 1O2 and .**GRAPHIC**. in evoking skin photosensitization reactions and skin carcinogenesis. Both linear psoralens (capable of forming interstrand cross-links) and isopsoralens (angular, monofunctional type) and 3-carbethoxypsoralen (a linear and monofunctional type) produced 1O2 and .**GRAPHIC**. although at varying degrees. Psoralen and 3-carbethoxypsoralen produced 1O2 greater than isopsoralens (angelicins). Nonphotosensitizing angelicin, 5-methyl-angelicin, and 4,8-dimethyl-5'-carboxypsoralen produced 1O2 greater than 8-methoxypsoralen and 5-methoxypsoralen. The 3 monofunctional angelicin derivatives (isopsoralens) produced more .**GRAPHIC**. than 8-methoxypsoralen, 5-methoxypsoralen, and 3,4'-dimethyl-8-methoxypsoralen. 3-Carbethoxypsoralen, a potent generator of 1O2 and a moderate producer of .**GRAPHIC**. was highly photolabile. Until recently, skin photosensitization reactions (erythema, edema, damage to DNA or the membrane of cutaneous cells, the inhibition of scheduled DNA synthesis and skin carcinogenesis, etc.) were believed to involve photocyclo-addition of psoralens to DNA mediated by a type-I or anoxic reaction (a sensitizer-substrate interaction through the transfer of hydrogen atoms or electrons, but no direct involvement of molecular oxygen). Oxygen-dependent sensitized photodynamic reactions of type-II, involving the production of reactive oxygen (1O2 and .**GRAPHIC**. were believed not to mediate psoralen photosensitization reactions. 1O2 and .**GRAPHIC**. may also participate in skin photosensitization and cell membrane-damaging reactions. The fact that certain monofunctional isopsoralens produce 1O2 and .**GRAPHIC**. at rates comparable to or better than bifunctional psoralens suggests that these reactive moieties of oxygen could play a major role in explaining their recently observed carcinogenic property and cell membrane-damaging reactions (e.g., edema or inflammation, etc.).

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