Document Detail

Synthesis and preliminary biological evaluation of beta-carotene and retinoic acid oxidation products.
MedLine Citation:
PMID:  16908162     Owner:  NLM     Status:  MEDLINE    
Synthesis of the beta-carotene oxidation product, 2,3-dihydro-5,8-endoperoxy-beta-apo-carotene-13-one (1) was achieved in six steps starting from beta-ionone. Photo-oxygenation of all trans-retinoic acid (8) and 13-cis-retinoic acid (9) produced a mixture of 5S*,8S*-epidioxy-5,8-dihydroretinoic acid (10) and 13-cis-5S*,8S*-epidioxy-5,8-dihydroretinoic acid (11). Methylation of the crude photo-oxygenation mixture afforded the corresponding methyl esters 12 and 13, respectively, both of which underwent ready aerial oxidation yielding hitherto unknown oxidation products of retinoic acid identified as methyl 5S*,8S*-epidioxy-9,10beta-epoxy-5,8,9,10-tetrahydroretinoate (14) and methyl 13-cis-5S*,8S*-epidioxy-9,10beta-epoxy-5,8,9,10-tetrahydroretinoate (15). Evaluation of 1, all trans-retinoic acid (8), 13-cis-retinoic acid (9), and the photo-oxygenation products 10-15 in a panel of five cancer cell lines showed 1 to be inactive and that 11 is significantly cytotoxic compared with the other retinoic acid analogs suggesting the requirement of the carboxylic acid moiety and the cis-geometry of the 13(14) double bond for cytotoxic activity.
E M Kithsiri Wijeratne; Manping X Liu; Narendra B Kantipudi; Claudia B Brochini; A A Leslie Gunatilaka; Louise M Canfield
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  14     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2006 Dec 
Date Detail:
Created Date:  2006-10-23     Completed Date:  2007-01-30     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  7875-9     Citation Subset:  IM    
Southwest Center for Natural Products Research and Commercialization, Office of Arid Lands Studies, College of Agriculture and Life Sciences, The University of Arizona, Tucson, AZ 85706-6800, USA.
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MeSH Terms
Antineoplastic Agents / chemical synthesis*,  chemistry,  pharmacology
Cell Line, Tumor
Cell Survival / drug effects
Drug Screening Assays, Antitumor
Norisoprenoids / chemistry
Structure-Activity Relationship
Tretinoin / chemical synthesis*,  chemistry
beta Carotene / chemical synthesis*,  chemistry
Reg. No./Substance:
0/Antineoplastic Agents; 0/Norisoprenoids; 14901-07-6/beta-ionone; 302-79-4/Tretinoin; 7235-40-7/beta Carotene

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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