| pH-sensitive vesicles containing a lipidic beta-amino acid with two hydrophobic chains. | |
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MedLine Citation:
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PMID: 18205118 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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)]. |
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Authors:
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Stefania Capone; Peter Walde; Dieter Seebach; Takashi Ishikawa; Romualdo Caputo |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chemistry & biodiversity Volume: 5 ISSN: 1612-1880 ISO Abbreviation: Chem. Biodivers. Publication Date: 2008 Jan |
Date Detail:
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Created Date: 2008-01-30 Completed Date: 2008-03-31 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101197449 Medline TA: Chem Biodivers Country: Switzerland |
Other Details:
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Languages: eng Pagination: 16-30 Citation Subset: IM |
Affiliation:
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Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH-Zürich, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Alkylation Amino Acids / chemical synthesis, chemistry* Hydrogen-Ion Concentration Hydrophobicity Lipids / chemistry* Molecular Structure Phosphatidylcholines / chemistry* Phosphatidylglycerols / chemistry* Sensitivity and Specificity |
| Chemical | |
Reg. No./Substance:
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0/2-(aminomethyl)-2-pentadecylheptadecanoic acid; 0/Amino Acids; 0/Lipids; 0/Phosphatidylcholines; 0/Phosphatidylglycerols; 6753-55-5/1-palmitoyl-2-oleoylphosphatidylcholine; 81490-05-3/1-palmitoyl-2-oleoylglycero-3-phosphoglycerol |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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