Regular ArticleMetabolic Activation of the Proestrogens trans-Stilbene and trans-Stilbene Oxide by Rat Liver Microsomes
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Discovery of novel ketoxime ether derivatives with potent FXR agonistic activity, oral effectiveness and high liver/blood ratio
2021, Bioorganic and Medicinal ChemistryDesign and identification of a new farnesoid X receptor (FXR) partial agonist by computational structure–activity relationship analysis: Ligand-induced H8 helix fluctuation in the ligand-binding domain of FXR may lead to partial agonism
2021, Bioorganic and Medicinal Chemistry LettersCitation Excerpt :To date, many FXR agonists based on GW4064 have been reported (Fig. S2).15–16,24–39 Some FXR agonists (Iso-2 to Iso-12 in Fig. S2) possess an alternative structure to the stilbene substituent which might elicit potential toxicity,26–28,40–45 while preserving isoxazole derivatives.15,24,26–34 From these analogs, tropifexor, a highly potent nonsteroidal FXR agonist, is undergoing clinical trials for the treatment of NASH.15,46
N<sup>1</sup>-Substituted benzimidazole scaffold for farnesoid X receptor (FXR) agonists accompanying prominent selectivity against vitamin D receptor (VDR)
2020, Bioorganic and Medicinal ChemistryCitation Excerpt :Figure 1) These portions of GW4064 (1) lie co-planar to each other, allowing the agonist to fit into a narrow region of the ligand binding domain (LBD) in FXR.31 Some FXR agonists (2–12) possess an alternative structure to the stilbene substituent which might elicit a potentially toxic15–17,32–37 while preserving isoxazole derivatives.13–24 ( Figure 1) From these analogs, tropifexor (2), a highly potent nonsteroidal FXR agonist, is undergoing clinical trials for the treatment of non-alcoholic steatohepatitis (NASH).14,38
Emerging targets and potential therapeutic agents in non-alcoholic fatty liver disease treatment
2020, European Journal of Medicinal ChemistryCitation Excerpt :The results of animal experiments indicated that the activation of GW4060 improved a series of liver injury characteristics in mouse models, such as levels of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST) and pro-inflammatory cytokines [94,95]. Unfortunately, the stilbene group of GW4060 had photosensitive property and degraded under light, which was possible to toxicity problems [96,97]. In a view of the short half-life of GW4064 and the toxicity of stilbene group, Akwabameyaw et al. modified the GW4064 by vinyl benzoic acid group and a chlorine atom on the intermediate benzene ring with hydrogen atom to obtain GSK8062 (Compound 17; Fig. 3)with better solubility and pharmacokinetic properties.
Estrogenic activity of multicyclic aromatic hydrocarbons in rainbow trout (Oncorhynchus mykiss) in vitro assays
2019, Aquatic ToxicologyCitation Excerpt :Had we terminated our concentration test range at -5 logM, we too would have missed the [3H]-E2 displacement. In addition, the Sugihara study ran assays for estrogenicity in the presence of rat microsomes and TSB was positive while CSB negative suggesting metabolic activation of TSB to trans-4-hydroxystilbene and trans-4,4’-dihydroxystilbene (Sugihara et al., 2000; Sanoh et al., 2002). By comparison, our system for the cytosol binding assay in rainbow trout has very limited metabolic capability and was not conducive to the oxidative ring-hydroxylation of parent chemical.
Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes
2017, Bioorganic and Medicinal Chemistry
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