Document Detail

Synthesis, aggregation behavior and cholesterol solubilization studies of 16-epi-pythocholic acid (3 alpha,12 alpha,16 beta-trihydroxy-5 beta-cholan-24-oic acid).
MedLine Citation:
PMID:  20359489     Owner:  NLM     Status:  MEDLINE    
Synthesis, aggregation behavior and in vitro cholesterol solubilization studies of 16-epi-pythocholic acid (3 alpha,12 alpha,16 beta-trihydroxy-5 beta-cholan-24-oic acid, EPCA) are reported. The synthesis of this unnatural epimer of pythocholic acid (3 alpha,12 alpha,16 alpha-trihydroxy-5 beta-cholan-24-oic acid, PCA) involves a series of simple and selective chemical transformations with an overall yield of 21% starting from readily available cholic acid (CA). The critical micellar concentration (CMC) of 16-epi-pythocholate in aqueous media was determined using pyrene as a fluorescent probe. In vitro cholesterol solubilization ability was evaluated using anhydrous cholesterol and results were compared with those of other natural di- and trihydroxy bile acids. These studies showed that 16-epi-pythocholic acid (16 beta-hydroxy-deoxycholic acid) behaves similar to cholic acid (CA) and avicholic acid (3 alpha,7 alpha,16 alpha-trihydroxy-5 beta-cholan-24-oic acid, ACA) in its aggregation behavior and cholesterol dissolution properties.
Nonappa; Uday Maitra
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-03-30
Journal Detail:
Title:  Steroids     Volume:  75     ISSN:  1878-5867     ISO Abbreviation:  Steroids     Publication Date:  2010 Jul 
Date Detail:
Created Date:  2010-04-27     Completed Date:  2010-08-20     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0404536     Medline TA:  Steroids     Country:  United States    
Other Details:
Languages:  eng     Pagination:  506-12     Citation Subset:  IM    
Copyright Information:
(c) 2010 Elsevier Inc. All rights reserved.
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
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MeSH Terms
Bile Acids and Salts / chemical synthesis*,  chemistry*
Cholesterol / chemistry*
Cholic Acid / chemistry*
Cholic Acids / chemical synthesis*,  chemistry*
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Models, Chemical
Models, Molecular
Molecular Conformation
Molecular Structure
Reg. No./Substance:
0/3,12,16-trihydroxycholan-24-oic acid; 0/Bile Acids and Salts; 0/Cholic Acids; 57-88-5/Cholesterol; 81-25-4/Cholic Acid

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