Leukotriene B4 photoaffinity probes: Design, synthesis and evaluation of new arylazide-1,3-disubstituted cyclohexanes

The synthesis and the binding affinities of new leukotriene B4 receptor photoaffinity probes, where a 1,3-disubstituted cyclohexane ring replaces the conjugated delta6,7 and delta8,9 double bonds of the natural eicosanoid, are described. One enantiomeric compound, 4b alpha, is specifically cross-lin...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2000-04, Vol.10 (8), p.811-814
Main Authors: DURAND, D, HULLOT, P, VIDAL, J.-P, GIRARD, J.-P, BANERES, J. L, PARELLO, J, MULLER, A, BONNE, C, ROSSI, J.-C
Format: Article
Language:English
Subjects:
Biological and medical sciences
Cell receptors
Cell structures and functions
Cyclohexanes - chemical synthesis
Cyclohexanes - chemistry
Drug Design
Drug Evaluation
Fundamental and applied biological sciences. Psychology
Humans
Leukotriene B4 - chemistry
Miscellaneous
Molecular and cellular biology
Molecular Probes
Photoaffinity Labels
Recombinant Proteins - chemistry
Stereoisomerism
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Summary:The synthesis and the binding affinities of new leukotriene B4 receptor photoaffinity probes, where a 1,3-disubstituted cyclohexane ring replaces the conjugated delta6,7 and delta8,9 double bonds of the natural eicosanoid, are described. One enantiomeric compound, 4b alpha, is specifically cross-linked upon photolysis to the recombinant leukotriene B4 receptor from human origin (h-BLTR) solubilized in a micellar medium. This probe appears as a good candidate for identifying the ligand binding site of this receptor.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(00)00103-7