| Synthesis and preliminary biological evaluation of beta-carotene and retinoic acid oxidation products. | |
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MedLine Citation:
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PMID: 16908162 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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E M Kithsiri Wijeratne; Manping X Liu; Narendra B Kantipudi; Claudia B Brochini; A A Leslie Gunatilaka; Louise M Canfield |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 14 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2006 Dec |
Date Detail:
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Created Date: 2006-10-23 Completed Date: 2007-01-30 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 7875-9 Citation Subset: IM |
Affiliation:
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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. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Antineoplastic Agents
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chemical synthesis*,
chemistry,
pharmacology Cell Line, Tumor Cell Survival / drug effects Drug Screening Assays, Antitumor Humans Norisoprenoids / chemistry Oxidation-Reduction Photochemistry Structure-Activity Relationship Tretinoin / chemical synthesis*, chemistry beta Carotene / chemical synthesis*, chemistry |
| Chemical | |
Reg. No./Substance:
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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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