| Design, synthesis, and fluorescence studies of fluorenyl fatty acids as new depth-dependent fluorescent probes for membranes: getting over the looping-back problem. | |
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MedLine Citation:
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PMID: 3233217 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Fluorescent fatty acids have proved very useful in studying the membrane hydrophobic core. They readily partition into membranes or can be converted to phospholipids, which form integral components of membranes. By attaching the fluorescent chromophore to different positions along the alkyl chain of fatty acids, e.g., an anthroyloxy group attached via an ester linkage to n-hydroxystearic acid, membranes have been probed at different depths. While this is an interesting approach and has been extensively used, relatively little attention has been paid to the molecular design of these probes in order to have minimal membrane perturbation. In the present study we have looked into the general problem of design of such depth-dependent membrane probes. We report here a series of fluorenyl fatty acids with varying fatty acid chain lengths, i.e., (2-fluorenyl)acetic acid, -butyric acid, -hexanoic acid, and -octanoic acid, in order to obtain information at different depths in the membrane hydrophobic core. To see the effect of attachment of a hydrophobic tail on the orientation of such fatty acids in membranes, an n-butyl group was linked to the C-7 position of fluorene in (2-fluorenyl)butyric acid to get 4-(7-n-butylfluoren-2-yl)butyric acid. Further, to assess their ability to act as depth-dependent fluorescent probes, these fatty acids were incorporated in vesicles prepared from egg phosphatidylcholine, and their fluorescence quenching was studied with potassium iodide, Cu(II), 9,10-dibromostearic acid, and 12-bromostearic acid.(ABSTRACT TRUNCATED AT 250 WORDS) |
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Authors:
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A K Lala; R R Dixit; V Koppaka; S Patel |
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Publication Detail:
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Type: Comparative Study; Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Biochemistry Volume: 27 ISSN: 0006-2960 ISO Abbreviation: Biochemistry Publication Date: 1988 Dec |
Date Detail:
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Created Date: 1989-05-01 Completed Date: 1989-05-01 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 0370623 Medline TA: Biochemistry Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 8981-9 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Indian Institute of Technology, Bombay, Powai. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Cell Membrane
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physiology Chemical Phenomena Chemistry Fatty Acids / chemical synthesis* Fluorenes / chemical synthesis* Fluorescence Polarization Fluorescent Dyes* Liposomes Membrane Fluidity Spectrometry, Fluorescence Spectrophotometry, Ultraviolet Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Fatty Acids; 0/Fluorenes; 0/Fluorescent Dyes; 0/Liposomes |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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