Efficiency of liposomes in the delivery of a photosensitizer controlled by the stereochemistry of a gemini surfactant component.

Abstract	Liposomes formulated with dimyristoyl-sn-glycero-phosphatidylcholine, DMPC, and either one of the cationic gemini surfactants (S,S)-2,3-dimethoxy-1,4-bis(N-hexadecyl-N,N-dimethylammonio)butane bromide, 1a, and (S,R)-2,3-dimethoxy-1,4-bis(N-hexadecyl-N,N-dimethylammonio)butane bromide, 1b, were investigated as vehicles of the photosensitizer m-tetrahydroxyphenylchlorin, m-THPC, to cell models of malignant glioma. The delivery efficiency of DMPC/1a and DMPC/1b liposome formulations were evaluated on the murine glioblastoma cell line C6 and on the human glioblastoma cell line LN229 by flow cytometry and laser scanning confocal microscopy. The stereochemistry of the spacer of the gemini was found to strongly influence the delivery efficiency of m-THPC to cells, the mode of interaction with the cell membrane, and the intracellular distribution of m-THPC. The physicochemical features of liposomes were investigated with the aim of explaining the parameters that control their biological features. Differences that could account for the different biological activity of the formulations concern the values of surface potential and the environment of m-THPC at the water/liposome interface.
Authors	Cecilia Bombelli, Annarita Stringaro, Stefano Borocci, Giuseppina Bozzuto, Marisa Colone, Luisa Giansanti, Rosa Sgambato, Laura Toccaceli, Giovanna Mancini, Agnese Molinari
Journal	Molecular pharmaceutics (Mol Pharm) Vol. 7 Issue 1 Pg. 130-7 (Feb 01 2010) ISSN: 1543-8392 [Electronic] United States
PMID	19929006 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References	Liposomes Mesoporphyrins Photosensitizing Agents Surface-Active Agents temoporfin Dimyristoylphosphatidylcholine
Topics	Animals Cell Line, Tumor Dimyristoylphosphatidylcholine (chemistry) Drug Delivery Systems Glioblastoma (drug therapy, metabolism) Humans Liposomes (chemistry) Mesoporphyrins (administration & dosage, pharmacokinetics) Mice Microscopy, Confocal Molecular Structure Photochemotherapy Photosensitizing Agents (administration & dosage, pharmacokinetics) Stereoisomerism Surface-Active Agents (chemistry)

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