Document Detail

Fluorescence properties of methyl 8-(2-anthroyl) octanoate, a solvatochromic lipophilic probe.
MedLine Citation:
PMID:  1790578     Owner:  NLM     Status:  MEDLINE    
Fluorescence excitation and emission spectra, relative fluorescence quantum yield phi r and fluorescence lifetime tau of methyl 8-(2-anthroyl)-octanoate have been studied in a set of organic solvents covering a large scale of polarity and in the presence of water. In this probe, the 2-anthroyl chromophore exhibits quite remarkable and unique fluorescence properties. Thus, when going from n-hexane to methanol, the maximum emission wavelength lambda em max shifts from 404 nm to 492 nm while phi r and tau increase from 1 to 17.7 and from 0.91 ns to 13.5 ns, respectively. These increments are still more accentuated in the presence of water with estimated values of 526 nm for lambda em max, 27 for phi r and 20 ns for tau in this solvent. Because of the presence of a keto group which is a hydrogen bond acceptor and which can conjugate with the aromatic ring so as to provide the chromophore with a high dipole moment, the fluorescence properties of the probe strongly depend on the polarity of the surrounding medium. They can be accounted for in terms of general solvent effects (dipolar solute/solvent interactions) in the presence of aprotic solvents and in terms of specific solvent effects (hydrogen bonding) in protic solvents. Such properties of solvatochromism make the 2-anthroyl chromophore, after 8-(2-anthroyl)octanoic acid has been attached to phospholipids (E. Perochon and J.F. Tocanne (1991) Chem. Phys. Lipids 58, 7-17) a potential tool for studying microenvironmental polarity in biological membranes.
E Perochon; A Lopez; J F Tocanne
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  59     ISSN:  0009-3084     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  1991 Aug 
Date Detail:
Created Date:  1992-03-30     Completed Date:  1992-03-30     Revised Date:  2006-04-17    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  17-28     Citation Subset:  IM    
Centre de Recherche de Biochimie et Génétique Cellulaires du CNRS 118, Toulouse, France.
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MeSH Terms
Indicators and Reagents
Membranes, Artificial*
Molecular Structure
Octanoic Acids / chemistry*
Spectrometry, Fluorescence
Reg. No./Substance:
0/Indicators and Reagents; 0/Membranes, Artificial; 0/Octanoic Acids; 0/Solvents; 86549-01-1/methyl-8-(2-anthroyl)octanoate

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