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Synthesis of a novel lipopeptide with α‐melanocyte‐stimulating hormone peptide ligand and its effect on liposome stability
Author(s) -
Ogawa Yoshikatsu,
Kawahara Hidehiko,
Yagi Nobuhiro,
Kodaka Masato,
Tomohiro Takenori,
Okada Tomoko,
Konakahara Takeo,
Okuno Hiroaki
Publication year - 1999
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-999-0377-5
Subject(s) - liposome , lipopeptide , peptide , chemistry , receptor , phosphatidylglycerol , amphiphile , phosphatidylcholine , melanocyte stimulating hormone , biophysics , biochemistry , membrane , phospholipid , biology , organic chemistry , copolymer , genetics , bacteria , polymer
of liposomes into target cells is important for drug delivery systems. For this purpose, the surface of the liposome is equipped with ligand peptides, which may bind to specific receptors on the cell membrane. An artificial novel lipopeptide (MSH‐C4A2) containing the α‐melanocyte‐stimulating hormone (α‐MSH) sequence and two long alkyl chains was designed and synthesized, and the liposome, composed of egg phosphatidylcholine (EPC) and MSH‐C4A2, was prepared. The stability of the liposome was estimated by measuring calcein leakage from the liposome inner phase. The stability of the liposome decreased upon addition of MSH‐A4C2, which seemed to be attributable to the amphiphilic property of the peptide moiety (α‐MSH) of MSH‐A2C4. The stability was, however, recovered fairly well upon addition of cholesterol (Ch) or phosphatidylglycerol (PG). It was concluded therefore that the ternary system, MSH‐C4A2/Ch/EPC or MSH‐C4A2/PG/EPC, is suitable for preparing the functional liposome.