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Phototoxicity of Some Bromine‐Substituted Rhodamine Dyes: Synthesis, Photophysical Properties and Application as Photosensitizers
Author(s) -
Pal Prabir,
Zeng Hualing,
Durocher Gilles,
Girard Denis,
Li Tiechao,
Gupta Ajay K.,
Giasson Richard,
Blanchard Louise,
Gaboury Louis,
Balassy Antonia,
Turmel Chantal,
Laperrière André,
Villeneuve Luc
Publication year - 1996
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.1751-1097.1996.tb03008.x
Subject(s) - singlet oxygen , photosensitizer , photochemistry , chemistry , phototoxicity , rhodamine , fluorescence , oxygen , organic chemistry , in vitro , biochemistry , physics , quantum mechanics
— The synthesis of some bromine‐substituted rhodamine derivatives viz. , 4,5‐dibromorhodamine methyl ester (dye 2) and 4,5‐dibromorhodamine n ‐butyl ester (dye 3) are reported. These dyes were synthesized to promote a more efficient cancer cell photosensitizer for potential use in in vitro bone marrow purging in preparation for autologous bone marrow transplantation. Spectroscopic and photo‐physical characterization of these dyes together with rhodamine 123 (dye 1) are reported in water, methanol, eth‐anol and also in a microheterogeneous system, sodium dodecyl sulfate. The possible mechanism of photosensi‐tization is characterized in terms of singlet oxygen efficiency of these dyes. Singlet oxygen quantum yields for bromine‐substituted dyes are in the range of 0.3‐0.5 depending on the solvent. For dye 1 no singlet oxygen production is found. The photodynamic actions of these dyes in different cell lines are tested. It was found that dye 2 and dye 3 are efficient photosensitizers and mediate eradication of K562, EM2, myeloid cell lines (CML) and the SMF‐AI rhabdomyosarcoma line.