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Boronated Derivatives of Chlorin e6 and Fluoride-Containing Porphyrins as Penetrating Anions: a Study Using Bilayer Lipid Membranes

T. I. Rokitskaya1*, A. V. Zaitsev2, V. A. Ol’shevskaya2, V. N. Kalinin2, M. M. Moisenovich3, I. I. Agapov3, and Y. N. Antonenko1

1Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, 119991 Moscow, Russia; fax: (495) 939-3181; E-mail: rokitskaya@genebee.msu.ru

2Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, 119234 Moscow, Russia

3Biological Faculty, Lomonosov Moscow State University, 119991 Moscow, Russia

* To whom correspondence should be addressed.

Received March 22, 2012; Revision received May 23, 2012
Boronated derivatives of porphyrins are studied extensively as promising compounds for boron-neutron capture therapy and photodynamic therapy. Understanding of the mechanism of their permeation across cell membranes is a key step in screening for the most efficient compounds. In the present work, we studied the ability of boronated derivatives of chlorin e6 and porphyrins, which are mono-, di-, and tetra-anions, to permeate through planar bilayer lipid membranes (BLM). The translocation rate constants through the hydrophobic part of the lipid bilayer were estimated for monocarborane and its conjugate with chlorin e6 by the method of electrical current relaxation. They were similar, 6.6 and 6.8 sec–1, respectively. Conjugates of porphyrins carrying two and four carborane groups were shown to permeate efficiently through a BLM although they carry two charges and four charges, respectively. The rate of permeation of the tetraanion estimated by the BLM current had superlinear dependence on the BLM voltage. Because the resting potential of most mammalian cells is negative inside, it can be concluded that the presence of negatively-charged boronated groups in compounds should hinder the accumulation of the porphyrins in cells.
KEY WORDS: penetrating anions, monocarborane, bilayer lipid membrane, photosensitizer, chlorin e6, porphyrin

DOI: 10.1134/S0006297912090039