Natural Chlorins Modified with Cholesterol Moiety. Synthesis, Characteristics, Copper Complexes, and Entrapping in Phospholipid Vesicles

Irina A. Nikolaeva,^a Julia V. Morozova,^a Maria G. Zavialova,^a Roman A. Novikov,^b Yaroslav V. Tkachev,^b Vladimir P. Timofeev,^b Alexander Yu. Misharin,^a and Gelii V. Ponomarev^a@

^aV. N. Orekhovich Institute of Biomedical Chemistry RAMS, 119121 Moscow, Russia

^bV. A. Engelhardt Institute of Molecular Biology RAS, 119991 Moscow, Russia

^@Corresponding author E-mail: gelii@yandex.ru

DOI: 10.6060/mhc2010.2-3.150

The chemical synthesis and characteristics of two natural chlorins modified with cholesterol moieties: 17’’[(cholest-5-en)-3β-yloxyethoxycarbamoyl]pyropheophorbide a and 13’[(cholest-5-en)-3b-yloxyethoxycarbamoyl]chlorin are presented, as well as the preparation of the related copper complexes. Both conjugates obtained, as well as their copper complexes, may be simply incorporated in phosphatidylcholine vesicles. Being entrapping in vesicles all these conjugates are considered to be novel potential sensitizers for photodynamic therapy, while copper complexes of conjugates are considered to be spin probes for membrane studies, providing important structural and dynamical information.

Keywords: Chlorins, cholesterol derivatives, bioconjugates.

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