Document Detail

Synthesis of charged amphipathic nitroxide lipid spin labels and an example of their application in membrane studies.
MedLine Citation:
PMID:  6297818     Owner:  NLM     Status:  MEDLINE    
The synthesis of a series of amphipathic nitroxide lipid spin labels is reported. Thus, 12-proxylhexadecanol has been converted into the versatile fatty acid spin label 14-proxylstearic acid. This substance was used to prepare 14-proxylstearyltrimethylammonium methanesulfonate, a positively charged label, and 14-proxylstearylmethyl phosphate sodium salt, a negatively charged label. Also prepared in the doxyl series were quaternary ammonium salts derived from 16-doxyl- and 7-doxylstearic acid. The positively charged and negatively charged proxyl labels were used in a preliminary experiment to investigate the role of charge in their interaction with reconstituted cytochrome oxidase. The average binding affinity of the negatively charged label is approximately 2-fold higher than that of the positively charged label at pH 7.4. At pH 5.5 the average relative affinity for negatively charged label is about 3.5-fold higher than that of positively charged label, suggesting that the ionizable group(s) on the protein can interact with the lipid headgroup.
J F Keana; S A Boyd; D A McMillen; E M Bernard; P C Jost
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  31     ISSN:  0009-3084     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  1982 Dec 
Date Detail:
Created Date:  1983-04-15     Completed Date:  1983-04-15     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  339-49     Citation Subset:  IM    
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MeSH Terms
Cyclic N-Oxides / chemical synthesis*,  pharmacology
Electron Spin Resonance Spectroscopy / methods
Electron Transport Complex IV / metabolism
Indicators and Reagents
Membrane Lipids / analysis
Membrane Proteins / analysis
Membranes / ultrastructure*
Spin Labels / chemical synthesis*
Grant Support
25698//PHS HHS; 27137//PHS HHS; GM 24951/GM/NIGMS NIH HHS
Reg. No./Substance:
0/Cyclic N-Oxides; 0/Indicators and Reagents; 0/Membrane Lipids; 0/Membrane Proteins; 0/Spin Labels; EC Transport Complex IV

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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