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Hydrophilicity vs hydrophobicity — varying the amphiphilic structure of porphyrins related to the photosensitizer m-THPC

ARNO WIEHE

Humboldt Universität zu Berlin, Institut für Physik, Invalidenstr. 110, D-11115 Berlin, Germany

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EKATERINA J. SIMONENKO

Humboldt Universität zu Berlin, Institut für Physik, Invalidenstr. 110, D-11115 Berlin, Germany

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MATHIAS O. SENGE

Freie Universität Berlin, Institut für Chemie, Organische Chemie, Takustr. 3, D-14195 Berlin, Germany

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, and

BEATE RÖDER

Humboldt Universität zu Berlin, Institut für Physik, Invalidenstr. 110, D-11115 Berlin, Germany

Corresponding author, Humboldt Universität zu Berlin, Institut für Physik, Invalidenstr. 110, D-11115 Berlin, Germany.

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https://doi.org/10.1002/jpp.389Cited by:39 (Source: Crossref)

Abstract

A total of 21 different porphyrins, some of them closely related to the photosensitizer meta-tetrahydroxyphenylchlorin (m-THPC) with a varied degree of hydrophilic/lipophilic substitution were synthesized employing conventional porphyrin condensation procedures and modern functionalization via organolithium reagents. For 14 of them, the photodynamic therapy (PDT) related photophysical properties were determined in isotropic solution and in liposome membrane-model systems. The photophysical data indicate that the localization of m-THPC may be fine-tuned by carefully changing the substitution pattern.

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