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Biochemistry (Moscow)

, Volume 77, Issue 9, pp 975–982 | Cite as

Boronated derivatives of chlorin e 6 and fluoride-containing porphyrins as penetrating anions: a study using bilayer lipid membranes

  • T. I. RokitskayaEmail author
  • A. V. Zaitsev
  • V. A. Ol’shevskaya
  • V. N. Kalinin
  • M. M. Moisenovich
  • I. I. Agapov
  • Y. N. Antonenko
Article

Abstract

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 e 6 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 e 6 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 

Abbreviations

BLM

bilayer lipid membrane

BNCT

boronneutron capture therapy

PDT

photodynamic therapy

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Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • T. I. Rokitskaya
    • 1
    Email author
  • A. V. Zaitsev
    • 2
  • V. A. Ol’shevskaya
    • 2
  • V. N. Kalinin
    • 2
  • M. M. Moisenovich
    • 3
  • I. I. Agapov
    • 3
  • Y. N. Antonenko
    • 1
  1. 1.Belozersky Institute of Physico-Chemical BiologyLomonosov Moscow State UniversityMoscowRussia
  2. 2.Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia
  3. 3.Biological FacultyLomonosov Moscow State UniversityMoscowRussia

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