Novel thiazolones for the simultaneous modulation of PPARγ, COX-2 and 15-LOX to address metabolic disease-associated portal inflammation

<p dir="ltr">A hybrid pharmacophore model, based on structural motifs previously identified by our team, was employed to generate ligands that simultaneously target COX-2, 15-LOX, and PPARγ in the context of metabolic dysfunction-associated fatty liver disease (MAFLD). Notable COX-2...

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Main Author: Mai S. El-Shoukrofy (19646815) (author)
Other Authors: Azza Ismail (10180577) (author), Reem H. Elhamammy (20448346) (author), Sherien A. Abdelhady (20837720) (author), Rasha Nassra (10180574) (author), Monica S. Makkar (20837723) (author), Mahmoud A. Agami (20837726) (author), Ahmed Wahid (15599036) (author), Hisham A. Nematalla (14798362) (author), Minh Sai (17049279) (author), Daniel Merk (1373682) (author), Ahmed F. El-Yazbi (10180589) (author), Ahmed S.F. Belal (20837729) (author), Ali H. Eid (5461829) (author), Perihan A. Elzahhar (10180568) (author)
Published: 2025
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Summary:<p dir="ltr">A hybrid pharmacophore model, based on structural motifs previously identified by our team, was employed to generate ligands that simultaneously target COX-2, 15-LOX, and PPARγ in the context of metabolic dysfunction-associated fatty liver disease (MAFLD). Notable COX-2 inhibitory activities (IC<sub>50</sub> = 0.065–0.24 μM) were observed relative to celecoxib (IC<sub>50</sub> = 0.049 μM). The two most effective 15-LOX inhibitors, <b>2a</b> and <b>2b</b>, exhibited 69 % and 57% of quercetin's action, respectively. Utilizing the rat hemi-diaphragm model to assess <i>in vitro</i> glucose uptake capacity, compounds <b>2a</b> and <b>2b</b> demonstrated significant glucose uptake potential in the absence of insulin, surpassing that of pioglitazone. Compound 2a activated PPARγ with an EC<sub>50</sub> value of 3.4 μM in a Gal4-hybrid reporter gene assay, indicating partial agonistic action. Interesting binding interactions with targets of interest were identified by molecular docking studies. As well, the expression levels of 20-HETE, Il-1β and TNF-α were decreased in LPS-challenged RAW264.7 macrophages upon treatment with compound <b>2a</b>. The pharmacokinetic analysis of <b>2a</b> and assessment of its in vivo efficacy in addressing hepatic impairment in rat models of diabetes and pre-diabetes were carried out. Together, these findings may offer preliminary insights into the potential of these compounds for further refinement in the existing therapeutic arsenals for metabolic diseases.</p><h2>Other Information</h2><p dir="ltr">Published in: European Journal of Medicinal Chemistry<br>License: <a href="http://creativecommons.org/licenses/by/4.0/" target="_blank">http://creativecommons.org/licenses/by/4.0/</a><br>See article on publisher's website: <a href="https://dx.doi.org/10.1016/j.ejmech.2025.117415" target="_blank">https://dx.doi.org/10.1016/j.ejmech.2025.117415</a></p>