| Benzoselenazolinone derivatives designed to be glutathione peroxidase mimetics feature inhibition of cyclooxygenase/5-lipoxygenase pathways and anti-inflammatory activity. | |
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MedLine Citation:
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PMID: 8071938 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Two series of compounds, substituted benzoselenazolinones and their opened analogs, diselenides, were prepared. The diselenides were designed according to the available SAR about glutathione peroxidase mimics and were expected to have activity. An initial series of tests was performed in order to assess the glutathione peroxidase and antioxidant activity of the diselenides compared to their cyclized analogs. The diselenides were shown to be very potent (up to 3 times the activity of ebselen), whereas the benzoselenazolinones were inactive, thus confirming our hypothesis. A second series of tests was done to determine the anti-inflammatory potency of the two series. Both were found to be potent on cyclooxygenase and 5-lipoxygenase pathways (up to 95% inhibition at 10(-5) M). Some compounds were selective, and the variations in the activity allowed us to draft some structure-activity relationships. The most interesting compound of each series, 6-benzoylbenzoselenazolinone and bis[(2-amino-5-benzoyl)phenyl] diselenide, was tested in vivo on the rat foot edema induced with different phlogistic agents and was shown to have some anti-inflammatory properties. |
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Authors:
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V Galet; J L Bernier; J P Hénichart; D Lesieur; C Abadie; L Rochette; A Lindenbaum; J Chalas; J F Renaud de la Faverie; B Pfeiffer |
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Publication Detail:
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Type: In Vitro; Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 37 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 1994 Sep |
Date Detail:
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Created Date: 1994-09-23 Completed Date: 1994-09-23 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 2903-11 Citation Subset: IM |
Affiliation:
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Institut de Chimie Pharmaceutique de Lille, France. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*, pharmacology Antioxidants / chemical synthesis, pharmacology Azoles / chemical synthesis*, pharmacology* Cyclooxygenase Inhibitors / chemical synthesis*, pharmacology Glutathione Peroxidase / metabolism* Hemolysis / drug effects Humans Lipid Peroxidation / drug effects Lipoxygenase Inhibitors / chemical synthesis*, pharmacology Male Organoselenium Compounds / chemical synthesis*, pharmacology* Rats Rats, Wistar Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Anti-Inflammatory Agents, Non-Steroidal; 0/Antioxidants; 0/Azoles; 0/Cyclooxygenase Inhibitors; 0/Lipoxygenase Inhibitors; 0/Organoselenium Compounds; 60940-34-3/ebselen; EC 1.11.1.9/Glutathione Peroxidase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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