| New BODIPY lipid probes for fluorescence studies of membranes. | |
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MedLine Citation:
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PMID: 17416929 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Many fluorescent lipid probes tend to loop back to the membrane interface when attached to a lipid acyl chain rather than embedding deeply into the bilayer. To achieve maximum embedding of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorophore into the bilayer apolar region, a series of sn-2 acyl-labeled phosphatidylcholines was synthesized bearing 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-yl (Me(4)-BODIPY-8) at the end of C(3)-, C(5)-, C(7)-, or C(9)-acyl. A strategy was used of symmetrically dispersing the methyl groups at BODIPY ring positions 1, 3, 5, and 7 to decrease fluorophore polarity. Iodide quenching of the phosphatidylcholine probes in bilayer vesicles confirmed that the Me(4)-BODIPY-8 fluorophore was embedded in the bilayer. Parallax analysis of Me(4)-BODIPY-8 fluorescence quenching by phosphatidylcholines containing iodide at different positions along the sn-2 acyl chain indicated that the penetration depth of Me(4)-BODIPY-8 into the bilayer was determined by the length of the linking acyl chain. Evaluation using monolayers showed minimal perturbation of <10 mol% probe in fluid-phase and cholesterol-enriched phosphatidylcholine. Spectral characterization in monolayers and bilayers confirmed the retention of many features of other BODIPY derivatives (i.e., absorption and emission wavelength maxima near 498 nm and approximately 506-515 nm) but also showed the absence of the 620-630 nm peak associated with BODIPY dimer fluorescence and the presence of a 570 nm emission shoulder at high Me(4)-BODIPY-8 surface concentrations. We conclude that the new probes should have versatile utility in membrane studies, especially when precise location of the reporter group is needed. |
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Authors:
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Ivan A Boldyrev; Xiuhong Zhai; Maureen M Momsen; Howard L Brockman; Rhoderick E Brown; Julian G Molotkovsky |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2007-04-07 |
Journal Detail:
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Title: Journal of lipid research Volume: 48 ISSN: 0022-2275 ISO Abbreviation: J. Lipid Res. Publication Date: 2007 Jul |
Date Detail:
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Created Date: 2007-06-21 Completed Date: 2007-10-15 Revised Date: 2009-11-18 |
Medline Journal Info:
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Nlm Unique ID: 0376606 Medline TA: J Lipid Res Country: United States |
Other Details:
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Languages: eng Pagination: 1518-32 Citation Subset: IM |
Affiliation:
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Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, 117997 Russia. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Boron Compounds
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diagnostic use* Chemistry, Physical Fluorescent Dyes / diagnostic use* Lipid Bilayers / chemistry* Membrane Lipids / chemistry* Phosphatidylcholines / chemistry* Physicochemical Phenomena Spectrometry, Fluorescence Unilamellar Liposomes / chemistry |
| Grant Support | |
ID/Acronym/Agency:
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GM45928/GM/NIGMS NIH HHS; HL49180/HL/NHLBI NIH HHS; R01 GM045928-07/GM/NIGMS NIH HHS; R01 GM045928-08/GM/NIGMS NIH HHS; R01 GM045928-09/GM/NIGMS NIH HHS; R01 GM045928-10/GM/NIGMS NIH HHS; R01 GM045928-11/GM/NIGMS NIH HHS; R01 GM045928-12/GM/NIGMS NIH HHS; R01 GM045928-13/GM/NIGMS NIH HHS; R01 GM045928-14A1/GM/NIGMS NIH HHS; R01 GM045928-15/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; 0/Boron Compounds; 0/Fluorescent Dyes; 0/Lipid Bilayers; 0/Membrane Lipids; 0/Phosphatidylcholines; 0/Unilamellar Liposomes |
| Comments/Corrections | |
Erratum In:
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J Lipid Res. 2007 Aug;48(8):1900 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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