Phototoxicity of Some Bromine-Substituted Rhodamine Dyes: Synthesis, Photophysical Properties and Application as Photosensitizers |
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| Authors: | Prabir Pal Hualing Zeng Gilles Durocher Denis Girard Tiechao Li Ajay K Gupta Richard Giasson Louise Blanchard Louis Gaboury Antonia Balassy Chantal Turmel ré Laperrière Luc Villeneuve |
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| Institution: | Laboratoire de photophysique moléculaire, Universitéde Montréal, Montréal, Québec, Canada;Laboratoire de photochimie organique, Département de chimie, Universitéde Montréal, Montréal, Québec, Canada;Laboratoire de pathologie moléculaire, Département de pathologie, Universitéde Montréal, Montréal, Québec, Canada |
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| Abstract: | Abstract— 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. |
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