Journal
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES
Volume 1838, Issue 3, Pages 793-801Publisher
ELSEVIER
DOI: 10.1016/j.bbamem.2013.11.012
Keywords
Photosensitizer; Tumor; Erythrocyte; Flip-flop; Bilayer lipid membrane; Gramicidin channel
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Funding
- Ministry of industry and Trade of the Russian Federation
- Federal Program Development of the Pharmaceutical and Medical Industry of the Russian Federation [11411.1008700.13.085]
- Access Centre of Lomonosov Moscow State University
- Ministry of Education and Science of Russian Federation [16.552.11.7081]
- Lomonosov Moscow State University Program of Development
- Russian Foundation for Basic Research [12-04-00199]
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Photodynamic tumor-destroying activity of the boronated chlorin e6 derivative BACE (chlorin e6 13 (1)-N-{2-[N-(1-carba-c/oso-dodecaboran-1-yl)methyl]aminoethyl}amide-15 (2), 17(3)-dimethyl ester), previously described in Moisenovich et al. (2010) PLoS ONE 5(9) e12717, was shown here to be enormously higher than that of unsubstituted chlorin e6, being supported by the data on much higher photocytotoxicity of BACE in M-1 sarcoma cell culture. To validate membrane damaging effect as the basis of the enhanced tumoricidal activity, BACE was compared with unsubstituted chlorin e6 in the potency to photosensitize dye leakage from liposomes, transbilayer lipid flip-flop, inactivation of gramicidin A ionic channels in planar lipid membranes and erythrocyte hemolysis. In all the models comprising artificial and cellular membranes, the photodynamic effect of BACE exceeded that of chlorin e6. BACE substantially differed from chlorin e6 in the affinity to liposomes and erythrocytes, as monitored by fluorescence spectroscopy, flow cytometry and centrifugation. The results support the key role of membrane binding in the photodynamic effect of the boronated chlorin e6 amide. (C) 2013 Elsevier B.V. All rights reserved.
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