| Cytoplasmic delivery of liposomal contents mediated by an acid-labile cholesterol-vinyl ether-PEG conjugate. | |
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MedLine Citation:
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PMID: 19072698 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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An acid-cleavable PEG lipid, 1'-(4'-cholesteryloxy-3'-butenyl)-omega-methoxy-polyethylene[112] glycolate (CVEP), has been developed that produces stable liposomes when dispersed as a minor component (0.5-5 mol %) in 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE). Cleavage of CVEP at mildly acidic pHs results in dePEGylation of the latently fusogenic DOPE liposomes, thereby triggering the onset of content release. This paper describes the synthesis of CVEP via a six-step sequence starting from the readily available precursors 1,4-butanediol, cholesterol, and mPEG acid. The hydrolysis rates and release kinetics from CVEP/DOPE liposome dispersions as a function of CVEP loading, as well as the cryogenic transmission electron microscopy and pH-dependent monolayer properties of 9:91 CVEP/DOPE mixtures, also are reported. When folate receptor-positive KB cells were exposed to calcein-loaded 5:95 CVEP/DOPE liposomes containing 0.1 mol % folate-modified 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-polyethylene[76] glycolamide (folate-PEG-DSPE), delivery of the calcein cargo to the cytoplasm of the cells was observed as determined by fluorescence microscopy and flow cytometry. Fluorescence resonance energy transfer analysis of lipid mixing in these cells was consistent with membrane-membrane fusion between the liposome and endosomal membranes. |
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Authors:
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Jeremy A Boomer; Marquita M Qualls; H Dorota Inerowicz; Robert H Haynes; V Srilakshmi Patri; Jong-Mok Kim; David H Thompson |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural |
Journal Detail:
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Title: Bioconjugate chemistry Volume: 20 ISSN: 1520-4812 ISO Abbreviation: Bioconjug. Chem. Publication Date: 2009 Jan |
Date Detail:
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Created Date: 2009-01-21 Completed Date: 2009-03-23 Revised Date: 2012-01-09 |
Medline Journal Info:
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Nlm Unique ID: 9010319 Medline TA: Bioconjug Chem Country: United States |
Other Details:
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Languages: eng Pagination: 47-59 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-1393, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Cholesterol* Cytoplasm / metabolism* Fluoresceins / administration & dosage* Fluorescence Resonance Energy Transfer Humans Kinetics Liposomes / pharmacokinetics* Polyethylene Glycols* Vinyl Compounds* |
| Grant Support | |
ID/Acronym/Agency:
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GM55266/GM/NIGMS NIH HHS; R01 GM055266-02/GM/NIGMS NIH HHS; R01 GM055266-03/GM/NIGMS NIH HHS; R01 GM055266-04/GM/NIGMS NIH HHS; R01 GM087016-04/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Fluoresceins; 0/Liposomes; 0/Polyethylene Glycols; 0/Vinyl Compounds; 109-93-3/vinyl ether; 1461-15-0/fluorexon; 57-88-5/Cholesterol |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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