title: 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.affiliation: CNR, Istituto di Metodologie Chimiche and Universita degli Studi di Roma "La Sapienza", P.le A. Moro 5, 00185 Roma, Italy.
authors.forename: Cecilia
authors.initials: C
authors.lastname: Bombelli
authors.forename: Annarita
authors.initials: A
authors.lastname: Stringaro
authors.forename: Stefano
authors.initials: S
authors.lastname: Borocci
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Bozzuto
authors.forename: Marisa
authors.initials: M
authors.lastname: Colone
authors.forename: Luisa
authors.initials: L
authors.lastname: Giansanti
authors.forename: Rosa
authors.initials: R
authors.lastname: Sgambato
authors.forename: Laura
authors.initials: L
authors.lastname: Toccaceli
authors.forename: Giovanna
authors.initials: G
authors.lastname: Mancini
authors.forename: Agnese
authors.initials: A
authors.lastname: Molinari
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D004134:Dimyristoylphosphatidylcholine / Q000737:chemistry; D016503:Drug Delivery Systems; D005909:Glioblastoma / Q000188:drug therapy / Q000378:metabolism; D006801:Humans; D008081:Liposomes / Q000737:chemistry; D008652:Mesoporphyrins / Q000008:administration & dosage* / Q000493:pharmacokinetics; D051379:Mice; D018613:Microscopy, Confocal; D015394:Molecular Structure; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000008:administration & dosage* / Q000493:pharmacokinetics; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry
chemical_list: D008081:Liposomes; D008652:Mesoporphyrins; D017319:Photosensitizing Agents; D013501:Surface-Active Agents; C072269:temoporfin; D004134:Dimyristoylphosphatidylcholine