Potency ranking of triterpenoids as inducers of a cytoprotective enzyme and as inhibitors of a cellular inflammatory response via their electron affinity and their electrophilicity index.
Details
Serval ID
serval:BIB_6F4428BA3DD2
Type
Article: article from journal or magazin.
Collection
Publications
Institution
Title
Potency ranking of triterpenoids as inducers of a cytoprotective enzyme and as inhibitors of a cellular inflammatory response via their electron affinity and their electrophilicity index.
Journal
Chemico-biological interactions
ISSN
1872-7786 (Electronic)
ISSN-L
0009-2797
Publication state
Published
Issued date
30/07/2010
Peer-reviewed
Oui
Volume
186
Number
2
Pages
118-126
Language
english
Notes
Publication types: Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
Publication Status: ppublish
Publication Status: ppublish
Abstract
Electron affinity (EA) and electrophilicity index (omega) of 16 synthetic triterpenoids (TP), previously identified as inducers of cytoprotective enzymes and as inhibitors of cellular inflammatory responses, have been calculated by the molecular orbital method. Linear correlations were obtained by plotting the values of EA, as well as those of omega versus (i) the potencies of induction of NAD(P)H quinone reductase (NQO1, EC 1.6.99.2), a cytoprotective enzyme, expressed via the concentration of TP required to double the specific activity of NQO1 (CD value) and (ii) the values of their anti-inflammatory activity expressed via the IC-50 of TP for suppression of upregulation of inducible nitric oxide synthase (iNOS, EC 1.14.13.39), both previously experimentally determined. The observed correlations demonstrate quantitatively for a series of triterpenoids that their electrophilicity is a major factor determining their potency as inducers of the cytoprotective phase 2 response and as inhibitors of inflammatory processes.
Keywords
Anti-Inflammatory Agents, Non-Steroidal/chemistry, Anti-Inflammatory Agents, Non-Steroidal/pharmacology, Binding Sites, Enzyme Induction/drug effects, Humans, Hydrophobic and Hydrophilic Interactions, In Vitro Techniques, Ligands, Models, Chemical, NAD(P)H Dehydrogenase (Quinone)/biosynthesis, Nitric Oxide Synthase Type II/antagonists & inhibitors, Oleanolic Acid/analogs & derivatives, Oleanolic Acid/chemistry, Oleanolic Acid/pharmacology, Static Electricity, Structure-Activity Relationship, Triterpenes/chemistry, Triterpenes/pharmacology
Pubmed
Web of science
Create date
05/02/2018 15:53
Last modification date
20/08/2019 15:28
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