The lipidic beta-amino acid 2-(aminomethyl)-2-pentadecylheptadecanoic acid (1) was synthesized via the alkylation of the C(alpha)-atom of fully protected beta-alanine. Mixed large unilamellar vesicles with a diameter between 100 and 200 nm containing POPC (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) and 1 at a molar ratio of 9 : 1 were prepared and found to have a surface charge which is dependent on pH. At slightly acidic pH, the vesicles were positively charged, and at alkaline pH negatively charged. Dynamic light scattering, zeta potential, and cryo-transmission electron-microscopy measurements indicated that the mixed vesicles fused at pH 4-5 with negatively charged mixed vesicles composed of POPC and POPG (9.8 : 1, molar ratio), POPG being 1-palmitoyl-2-oleoyl-sn-glycero-3-[phospho-rac-(1-glycerol)].
pH-sensitive vesicles containing a lipidic beta-amino acid with two hydrophobic chains. Publishing Authors By Initials
pH-sensitive vesicles containing a lipidic beta-amino acid with two hydrophobic chains. Journal Published:
PUBLICATION TYPE: Research Support, Non-U.S. Gov
Journal: Chemistry & biodiversity
VOLUME: 5
Page Numbers: 16-30
Journal Abbreviation: Chem. Biodivers.
ISSN: 1612-1880
DAY: 30
MONTH: Jan
YEAR: 2008
pH-sensitive vesicles containing a lipidic beta-amino acid with two hydrophobic chains. Information
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LANGUAGE: eng
NlmUniqueID: 101197449
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Grant and Affiliation Information for pH-sensitive vesicles containing a lipidic beta-amino acid with two hydrophobic chains.
AFFILIATION: Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH-Zürich, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich.
Country: Switzerland
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MEDLINETA: Chem Biodivers
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