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Triphenylphosphonium-substituted phthalocyanine: Design, synthetic strategy, photoproperties and photodynamic activity

Chemistry Department, Gebze Technical University, Gebze, 41400 Kocaeli, Turkey

Faculté Des Sciences de Bizerte, Université de Carthage, UR17ES01 Didactique des Sciences Expérimentales, et de chimie supramoléculaire, 7021 Zarzouna Bizerte, Tunisia

Laboratoire de Chimie des Substances Naturelles EA 1069 Université de Limoges, Faculté des Sciences, et Techniques, 123 Av. Albert Thomas, 87060 Limoges, France

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Denis Durand

Institut de Biomolécules Max Mousseron, UMR 5247, Université de Montpellier, Avenue Charles Flahault, 34093 Montpellier Cedex 05, France

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Emel Önal

Chemistry Department, Gebze Technical University, Gebze, 41400 Kocaeli, Turkey

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Dina Aggad

Institut de Biomolécules Max Mousseron, UMR 5247, Université de Montpellier, Avenue Charles Flahault, 34093 Montpellier Cedex 05, France

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Ümit İşci

Chemistry Department, Gebze Technical University, Gebze, 41400 Kocaeli, Turkey

SPP full member in good standing

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Gülçin Ekineker

Chemistry Department, Gebze Technical University, Gebze, 41400 Kocaeli, Turkey

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Frédérique Brégier

Laboratoire de Chimie des Substances Naturelles EA 1069 Université de Limoges, Faculté des Sciences, et Techniques, 123 Av. Albert Thomas, 87060 Limoges, France

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Bassem Jamoussi

Université Tunis el Manar, UR17ES01 Didactique des Sciences Expérimentales et de Chimie Supramoléculaire, Tunis, Tunisia

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Vincent Sol

Laboratoire de Chimie des Substances Naturelles EA 1069 Université de Limoges, Faculté des Sciences, et Techniques, 123 Av. Albert Thomas, 87060 Limoges, France

E-mail Address: vincent.sol@unilim.fr

Correspondence to: Vincent Sol, tel.: +33 5 55 45 74 90

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Magali Gary-Bobo

Institut de Biomolécules Max Mousseron, UMR 5247, Université de Montpellier, Avenue Charles Flahault, 34093 Montpellier Cedex 05, France

E-mail Address: magali.gary-bobo@inserm.fr

Correspondence to: Magali Gary-Bobo, tel.: +33 4 11 75 96 17

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, and

Fabienne Dumoulin

Chemistry Department, Gebze Technical University, Gebze, 41400 Kocaeli, Turkey

E-mail Address: fdumoulin@gtu.edu.tr

Correspondence to: Fabienne Dumoulin, tel.: +90 262 605 30 22

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https://doi.org/10.1142/S1088424618500554Cited by:20 (Source: Crossref)

Abstract

In line with current efforts to direct PDT photosensitizers to specific organelles such as mitochondria, a triphenylphosphonium-tetrasubstituted Zn phthalocyanine was designed, taking into account synthetic constraints. Triphenylphosphonium moieties were successfully introduced on alkyl bromide substituents on a pre-formed phthalocyanine. Photophysical and photochemical measurements showed that the photoproperties of the Zn phthalocyanine core were not affected by the triphenylphosphonium groups. Biological investigations demonstrated the dark innocuousness of the phthalocyanine up to 1 $μ$ $μ$ M, a concentration that exhibited a powerful phototoxicity. Cell death was confirmed to be photodynamically induced thanks to reactive oxygen species detection experiments. Nonetheless, the triphenylphosphonium moieties did not promote the accumulation of the phthalocyanine in mitochondria as significantly as expected.

Dedicated to Dr. Dominique Lafont

Keywords:

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