Document Detail

Complexes between fluorescent cholic acid derivatives and human serum albumin. a photophysical approach to investigate the binding behavior.
MedLine Citation:
PMID:  20232881     Owner:  NLM     Status:  MEDLINE    
Interaction between bile acids and plasma proteins has attracted considerable attention over past decades. In fact, binding of bile acids to human serum albumin (HSA) determines their level in plasma, a value that can be used as a test for liver function. However, very little is known about the role that bile acids-HSA complexes play in hepatic uptake. In the present paper, we report on the utility of the singlet excited state properties of 4-nitrobenzo-2-oxa-1,3-diazole (NBD) fluorescent derivatives of cholic acid (ChA); namely, 3alpha-NBD-ChA, 3beta-NBD-ChA, 3beta-NBD-ChTau, 7alpha-NBD-ChA, and 7beta-NBD-ChA to clarify key aspects of bile acids-HSA interactions that remain poorly understood. On the basis of either absorption or emission measurements, formation of NBD-ChA@HSA complexes with 1:1 stoichiometry has been proven. Enhancement of the fluorescence emission upon addition of HSA has been used for determination of the binding constants, which are in the range of 10(4) M(-1). Energy transfer from tryptophan to NBD-ChA occurs by a FRET mechanism; the donor-acceptor distances have been determined according to Forster's theory. The estimated values (27-30 A) are compatible with both site I and site II occupancy and do not provide sufficient information for a safe assignment; however, fluorescence titration using warfarin (site I probe) and ibuprofen (site II probe) for displacement clearly indicates that the employed cholic acid derivatives bind to HSA at site I.
Jana Rohacova; M Luisa Marin; Miguel A Miranda
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The journal of physical chemistry. B     Volume:  114     ISSN:  1520-5207     ISO Abbreviation:  J Phys Chem B     Publication Date:  2010 Apr 
Date Detail:
Created Date:  2010-04-01     Completed Date:  2010-06-23     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101157530     Medline TA:  J Phys Chem B     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4710-6     Citation Subset:  IM    
Instituto Universitario Mixto de Tecnolog?a Qu?mica-Departamento de Qu?mica (UPV-CSIC), Avenida de los Naranjos s/n, E-46022, Valencia, Spain.
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MeSH Terms
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anticoagulants / chemistry
Binding Sites
Cholic Acid / chemistry*
Fluorescence Resonance Energy Transfer
Fluorescent Dyes / chemistry*
Ibuprofen / chemistry
Protein Binding
Serum Albumin / chemistry*
Spectrometry, Fluorescence
Warfarin / chemistry
Reg. No./Substance:
0/Anti-Inflammatory Agents, Non-Steroidal; 0/Anticoagulants; 0/Fluorescent Dyes; 0/Serum Albumin; 15687-27-1/Ibuprofen; 81-25-4/Cholic Acid; 81-81-2/Warfarin

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