| 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). | |
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MedLine Citation:
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PMID: 20359489 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Nonappa; Uday Maitra |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-03-30 |
Journal Detail:
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Title: Steroids Volume: 75 ISSN: 1878-5867 ISO Abbreviation: Steroids Publication Date: 2010 Jul |
Date Detail:
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Created Date: 2010-04-27 Completed Date: 2010-08-20 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0404536 Medline TA: Steroids Country: United States |
Other Details:
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Languages: eng Pagination: 506-12 Citation Subset: IM |
Copyright Information:
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(c) 2010 Elsevier Inc. All rights reserved. |
Affiliation:
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Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. nonappa@jyu.fi |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Bile Acids and Salts
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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 Solubility |
| Chemical | |
Reg. No./Substance:
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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 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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