1,12-Substituted tetracyclines as antioxidant agents

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DOIResolve DOI: http://doi.org/10.1016/j.bmc.2005.04.032
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TypeArticle
Journal titleBioorganic and Medicinal Chemistry
Volume13
Issue15
Pages46274637; # of pages: 11
Subjectcomplications; env; pha; Stress
AbstractNovel hydroxypyrazoline derivatives of tetracycline and minocycline have been synthesized through the reaction of these tetracyclines with hydrazine. The formation of a new chiral center at C12 is stereospecific to give 12S-12 -hydroxy-1,12-pyrazolino-tetracycline. A reaction mechanism for the formation of these novel tetracycline derivatives has been proposed. Hydroxypyrazoli -notetracyclines exhibit no binding to Mg2+ and Zn2+, features that are required for antibiotic activity and matrix metalloproteinase (MMP) inhibitions, respectively. The modification toward their hydroxypyrazolino derivatives significantly improved the antioxidant activities of tetracycline and minocycline, as shown by three commonly used assays (DPPH, ABTS(+), and superoxide scavenging). 12S-Hydroxy-1,12-pyrazolinominocycline is a promising tetracycline-based antioxidant devoid of antibiotic properties and MMP inhibitory activity, which could be beneficial in the treatment of complications related to oxidative stress. Crown Copyright (c) 2005 Published by Elsevier Ltd. All rights reserved
Publication date
LanguageEnglish
AffiliationNRC Biotechnology Research Institute; National Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
NRC number47469
NPARC number3539511
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Record identifier8c851111-700a-401f-9259-ff47ba789184
Record created2009-03-01
Record modified2016-05-09
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