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Photophysical and Redox Properties of a Series of Phthalocyanines: Relation with Their Photodynamic Activities on TF‐1 and Daudi Leukemic Cells
Author(s) -
Daziano JeanPierre,
Steenken Steen,
Chaban Christian,
Mani Patrice,
Cha Michel,
Julliard Michel
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.tb03129.x
Subject(s) - phthalocyanine , photochemistry , flash photolysis , chemistry , singlet oxygen , excited state , electron acceptor , photodynamic therapy , reaction rate constant , oxygen , kinetics , organic chemistry , physics , quantum mechanics , nuclear physics
— The photodynamic therapy (PDT) efficiency of five phthalocyanines, chloroaluminum phthalocyanine (AlPc), dichlorosilicon phthalocyanine (SiPc), bis (tri‐ n ‐hexylsi‐loxy)silicon phthalocyanine (PcHEX), bis (triphenyl‐siloxy)silicon phthalocyanine (PcPHE) and nickel phthalocyanine (NiPc), was assessed on two leukemic cell lines TF‐1 and erythroieukemic and B lymphoblastic cell lines, Daudi, respectively. AlPc showed the best photocytotox‐icity leading to 0.008 surviving fraction at 2 × 10 −9 M for TF‐1 and 4 × 10 −9 M for Daudi. At 5 × 10 −7 M , SiPc and PcHEX induced a significant photokilling, whereas NiPc and PcPHE were inactive. Laser flash photolysis and photoredox properties of the phthalocyanines were investigated to try to relate these parameters with the biological effects. AlPc showed the longest triplet lifetime: 484 fis in dimethyl sulfoxide/H 2 O. This value was increased up to 820 u.s when AlPc was complexed with human serum albumin used as a membrane model. Such an enhancement was not observed with the silicon phthalocyanines. Upon irradiation, all the phthalocyanines generated singlet oxygen with 0.29–0.37 quantum yield values. The reduction potentials of the excited states obtained from measurement in the ground state and energy of the excited triplets show that AlPc is the best electron acceptor. The in vitro photocytotoxicity observed and the measured parameters are in agreement with a key role of electron transfer in PDT assays involving these phthalocyanines.