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BIOLOGICAL ACTIVITIES OF PHTHALOCYANINES—IV. TYPE II SENSITIZED PHOTOOXIDATION OF L‐TRYPTOPHAN AND CHOLESTEROL BY SULFONATED METALLO PHTHALOCYANINES
Author(s) -
Langlots R.,
Ali H.,
Brasseur N.,
Wagner J. R.,
Lier J. E. van
Publication year - 1986
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1986.tb03574.x
Subject(s) - chemistry , singlet oxygen , rose bengal , photochemistry , tryptophan , hematoporphyrin , phthalocyanine , aqueous solution , indole test , manganese , porphyrin , oxygen , photosensitizer , metal , stereochemistry , photodynamic therapy , organic chemistry , amino acid , biochemistry
— Sulfonated phthalocyanine and a series of its metal chelates in combination with red light irradiation led to the degradation of L‐tryptophan in oxygenated aqueous solution. The photoproducts and the rate of transformation of L‐tryptophan are compared with hematoporphyrin and rose bengal sensitized photooxidation. In all cases the primary photoproducts are characterized as cis and trans ‐3a‐hydroperoxy‐l,2,3,3a,8,8a‐hexahydropyrrolo[2,3‐b]indole‐2‐carboxylic acid. Support for the involvement of singlet excited oxygen is obtained from azide inhibition and the formation of the specific singlet oxygen product with cholesterol. We observed the contribution of another pathway in the case of the manganese complex.