دورية أكاديمية
S-Dihydrodaidzein and 3-(1,3-benzoxazol-2-yl)-benzamide, Two New Potential β-estrogen Receptor Ligands with Anti-adipogenic Activity.
| العنوان: | S-Dihydrodaidzein and 3-(1,3-benzoxazol-2-yl)-benzamide, Two New Potential β-estrogen Receptor Ligands with Anti-adipogenic Activity. |
|---|---|
| المؤلفون: | Torres-Rojas MF; Laboratorio de Biomedicina Molecular 2, Escuela Nacional de Medicina y Homeopatía, Instituto Politécnico Nacional, Guillermo Massieu Helguera No. 239, La Escalera Ticoman, 07320, Ciudad de México, México., Mandujano-Lazaro G; Laboratorio de Biomedicina Molecular 2, Escuela Nacional de Medicina y Homeopatía, Instituto Politécnico Nacional, Guillermo Massieu Helguera No. 239, La Escalera Ticoman, 07320, Ciudad de México, México., Lopez-Camarillo C; Posgrado en Ciencias Genómicas, Universidad Autónoma de la Ciudad de México, Calle San Lorenzo 290, Col. del Valle Sur, Benito Juárez, 03100, Ciudad de México, México., Ramirez-Moreno E; Laboratorio de Biomedicina Molecular 2, Escuela Nacional de Medicina y Homeopatía, Instituto Politécnico Nacional, Guillermo Massieu Helguera No. 239, La Escalera Ticoman, 07320, Ciudad de México, México., Mendez-Alvarez D; Laboratorio de Biotecnología Farmacéutica, Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Bulevard del Maestro S/N Esquina Elías Piña. Col. Narciso Mendoza, 88710, Reynosa, Tamaulipas, México., Rivera G; Laboratorio de Biotecnología Farmacéutica, Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Bulevard del Maestro S/N Esquina Elías Piña. Col. Narciso Mendoza, 88710, Reynosa, Tamaulipas, México., Marchat LA; Laboratorio de Biomedicina Molecular 2, Escuela Nacional de Medicina y Homeopatía, Instituto Politécnico Nacional, Guillermo Massieu Helguera No. 239, La Escalera Ticoman, 07320, Ciudad de México, México. |
| المصدر: | Medicinal chemistry (Shariqah (United Arab Emirates)) [Med Chem] 2024; Vol. 20 (4), pp. 434-442. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Bentham Science Publishers Country of Publication: Netherlands NLM ID: 101240303 Publication Model: Print Cited Medium: Internet ISSN: 1875-6638 (Electronic) Linking ISSN: 15734064 NLM ISO Abbreviation: Med Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Amsterdam : Bentham Science Publishers Original Publication: Sharjah, U.A.E.; San Francisco, CA : Bentham Science Publishers |
| مواضيع طبية MeSH: | Adipogenesis*/drug effects , Benzamides*/pharmacology , Benzamides*/chemistry , Benzamides*/chemical synthesis , Estrogen Receptor beta*/metabolism , Estrogen Receptor beta*/genetics, Animals ; Mice ; 3T3-L1 Cells ; Anti-Obesity Agents/pharmacology ; Anti-Obesity Agents/chemistry ; Anti-Obesity Agents/chemical synthesis ; Benzoxazoles/pharmacology ; Benzoxazoles/chemistry ; Benzoxazoles/chemical synthesis ; Cell Survival/drug effects ; Isoflavones/pharmacology ; Isoflavones/chemistry ; Ligands ; Molecular Docking Simulation ; Molecular Structure ; Structure-Activity Relationship |
| مستخلص: | Background: The elucidation of molecular pathways associated with adipogenesis has evidenced the relevance of estrogen and estrogen receptor beta (ERβ). The positive effects of ERβ ligands on adipogenesis, energy expenditure, lipolysis, food intake, and weight loss, make ERβ an attractive target for obesity control. From ligand-based virtual screening, molecular docking, and molecular dynamic simulations, six new likely ERβ ligands (C1 to C6) have been reported with potential for pharmacological obesity treatment. Objective: In this study, the effect of molecules C1-C6 on adipogenesis using the murine 3T3-L1 cell line was evaluated. Methods: Cell viability was assessed by MTT assays. Lipid accumulation and gene expression were investigated by ORO staining and real-time quantitative RT-PCR experiments, respectively. Results: Cell viability was not significantly affected by C1-C6 at concentrations up to 10 μM. Interestingly, treatment with 10 μM of C1 (S-Dihydrodaidzein) and C2 (3-(1,3-benzoxazol-2-yl)- benzamide) for 72 h inhibited adipocyte differentiation; moreover, ORO staining evidenced a reduced intracellular lipid accumulation (40% at day 7). Consistently, mRNA expression of the adipogenic markers, PPARγ and C/EBPα, was reduced by 50% and 82%, respectively, in the case of C1, and by 83% and 59%, in the case of C2. Conclusion: Altogether, these results show the two new potential β-estrogen receptor ligands, C1 and C2, to exhibit anti-adipogenic activity. They could further be used as lead structures for the development of more efficient drugs for obesity control. (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.) |
| References: | Sallis J.F.; Glanz K.; Physical activity and food environments: Solutions to the obesity epidemic. Milbank Q 2009,87(1),123-154. (PMID: 10.1111/j.1468-0009.2009.00550.x19298418) Mauvais-Jarvis F.; Clegg D.J.; Hevener A.L.; The role of estrogens in control of energy balance and glucose homeostasis. Endocr Rev 2013,34(3),309-338. (PMID: 10.1210/er.2012-105523460719) Ko S.H.; Jung Y.; Energy metabolism changes and dysregulated lipid metabolism in postmenopausal women. Nutrients 2021,13(12),4556. (PMID: 10.3390/nu1312455634960109) Lovre D.; Lindsey S.H.; Mauvais-Jarvis F.; Effect of menopausal hormone therapy on components of the metabolic syndrome. Ther Adv Cardiovasc Dis 2017,11(1),33-43. (PMID: 10.1177/175394471664935827234158) Kumar R.; Zakharov M.N.; Khan S.H.; Miki R.; Jang H.; Toraldo G.; Singh R.; Bhasin S.; Jasuja R.; The dynamic structure of the estrogen receptor. J Amino Acids 2011,2011,1-7. (PMID: 10.4061/2011/81254022312471) Warner M.; Huang B.; Gustafsson J.A.; Estrogen receptor β as a pharmaceutical target. Trends Pharmacol Sci 2017,38(1),92-99. (PMID: 10.1016/j.tips.2016.10.00627979317) Heine P.A.; Taylor J.A.; Iwamoto G.A.; Lubahn D.B.; Cooke P.S.; Increased adipose tissue in male and female estrogen receptor-α knockout mice. Proc Natl Acad Sci USA 2000,97(23),12729-12734. (PMID: 10.1073/pnas.97.23.1272911070086) González-Granillo M.; Savva C.; Li X.; Fitch M.; Pedrelli M.; Hellerstein M.; Parini P.; Korach-André M.; Gustafsson J.Å.; ERβ activation in obesity improves whole body metabolism via adipose tissue function and enhanced mitochondria biogenesis. Mol Cell Endocrinol 2019,479,147-158. (PMID: 10.1016/j.mce.2018.10.00730342056) Yi K.W.; Shin J.H.; Seo H.S.; Lee J.K.; Oh M.J.; Kim T.; Saw H.S.; Kim S.H.; Hur J.Y.; Role of estrogen receptor-alpha and -beta in regulating leptin expression in 3T3-L1 adipocytes. Obes 2008,16,2393-2399. (PMID: 10.1038/oby.2008.389) Dieudonné M.N.; Leneveu M.C.; Giudicelli Y.; Pecquery R.; Evidence for functional estrogen receptors α and β in human adipose cells: Regional specificities and regulation by estrogens. Am J Physiol Cell Physiol 2004,286(3),C655-C661. (PMID: 10.1152/ajpcell.00321.200314761887) Kramarova T.V.; Dahlman Wright K.; Pongratz I.; The role of the estrogen receptors in obesity. Drug Discov Today Dis Mech 2009,6(1-4),e49-e54. (PMID: 10.1016/j.ddmec.2009.11.001) Mueller S.; Korach K.S.; Estrogen receptors and endocrine diseases: Lessons from estrogen receptor knockout mice. Curr Opin Pharmacol 2001,1(6),613-619. (PMID: 10.1016/S1471-4892(01)00105-911757817) Ng C.W.; Wong K.K.; Impact of estrogen receptor expression on prognosis of ovarian cancer according to antibody clone used for immunohistochemistry: A meta-analysis. J Ovarian Res 2022,15(1),63. (PMID: 10.1186/s13048-022-01001-435610648) Andersen C.L.; Sikora M.J.; Boisen M.M.; Ma T.; Christie A.; Tseng G.; Park Y.; Luthra S.; Chandran U.; Haluska P.; Mantia-Smaldone G.M.; Odunsi K.; McLean K.; Lee A.V.; Elishaev E.; Edwards R.P.; Oesterreich S.; Active estrogen receptor-alpha signaling in ovarian cancer models and clinical specimens. Clin Cancer Res 2017,23(14),3802-3812. (PMID: 10.1158/1078-0432.CCR-16-150128073843) Liu A.; Zhang D.; Yang X.; Song Y.; Estrogen receptor alpha activates MAPK signaling pathway to promote the development of endometrial cancer. J Cell Biochem 2019,120(10),17593-17601. (PMID: 10.1002/jcb.2902731140648) Ponnusamy S.; Tran Q.T.; Harvey I.; Smallwood H.S.; Thiyagarajan T.; Banerjee S.; Johnson D.L.; Dalton J.T.; Sullivan R.D.; Miller D.D.; Bridges D.; Narayanan R.; Pharmacologic activation of estrogen receptor α increases mitochondrial function, energy expenditure, and brown adipose tissue. FASEB J 2017,31(1),266-281. (PMID: 10.1096/fj.201600787rr27733447) Setchell K.D.R.; Clerici C.; Lephart E.D.; Cole S.J.; Heenan C.; Castellani D.; Wolfe B.E.; Nechemias-Zimmer L.; Brown N.M.; Lund T.D.; Handa R.J.; Heubi J.E.; S-Equol, a potent ligand for estrogen receptor β, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora1–4. Am J Clin Nutr 2005,81(5),1072-1079. (PMID: 10.1093/ajcn/81.5.107215883431) Mandujano-Lázaro G.; Galaviz-Hernández C.; Reyes-López C.A.; Almanza-Pérez J.C.; Giacoman-Martínez A.; López-Camarillo C.; Huang F.; Marchat L.A.; A short S-equol exposure has a long-term inhibitory effect on adipogenesis in mouse 3T3-L1 cells. Appl Sci 2021,11(20),9657. (PMID: 10.3390/app11209657) Méndez-Álvarez D.; Torres-Rojas M.F.; Lara-Ramirez E.E.; Marchat L.A.; Rivera G.; Ligand-based virtual screening, molecular docking, and molecular dynamic simulations of new β-estrogen receptor activators with potential for pharmacological obesity treatment. Molecules 2023,28(11),4389. (PMID: 10.3390/molecules2811438937298864) Turner J.V.; Agatonovic-Kustrin S.; Glass B.D.; Molecular aspects of phytoestrogen selective binding at estrogen receptors. J Pharm Sci 2007,96(8),1879-1885. (PMID: 10.1002/jps.2098717518366) Setchell K.D.R.; Clerici C.; Equol: History, chemistry, and formation. J Nutr 2010,140(7),1355S-1362S. (PMID: 10.3945/jn.109.11977620519412) Mayo B.; Vázquez L.; Flórez A.B.; Equol: A bacterial metabolite from the daidzein isoflavone and its presumed beneficial health effects. Nutrients 2019,11(9),2231. (PMID: 10.3390/nu1109223131527435) Kuiper G.G.J.M.; Lemmen J.G.; Carlsson B.; Corton J.C.; Safe S.H.; van der Saag P.T.; van der Burg B.; Gustafsson J.Å.; Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 1998,139(10),4252-4263. (PMID: 10.1210/endo.139.10.62169751507) Fuentes N.; Silveyra P.; Estrogen receptor signaling mechanisms. Adv Protein Chem Struct Biol 2019,116,135-170. (PMID: 10.1016/bs.apcsb.2019.01.00131036290) Singh S.; Veeraswamy G.; Bhattarai D.; Goo J.I.; Lee K.; Choi Y.; Recent advances in the development of pharmacologically active compounds that contain a benzoxazole scaffold. Asian J Org Chem 2015,4(12),1338-1361. (PMID: 10.1002/ajoc.201500235) Chan K.K.L.; Siu M.K.Y.; Jiang Y.; Wang J.; Leung T.H.Y.; Ngan H.Y.S.; Estrogen receptor modulators genistein, daidzein and ERB-041 inhibit cell migration, invasion, proliferation and sphere formation via modulation of FAK and PI3K/AKT signaling in ovarian cancer. Cancer Cell Int 2018,18(1),65. (PMID: 10.1186/s12935-018-0559-229743815) Hwang J.T.; Kim S.; Choi I.; Choi S.Y.; 3,5-Dimethoxy-(4-methoxyphenyl)benzamide suppresses adipogenesis in 3T3-L1 cells. Acta Pol Pharm 2014,71(1),35-38. (PMID: 24779192) Sharma D.; Sharma S.; Chauhan P.; Kumar A.; Sharma A.; Kumari N.; Acetylation of histone and modification of gene expression via HDAC inhibitors affects the obesity. Biomed Pharmacol J 2021,14(1),153-161. (PMID: 10.13005/bpj/2110) Zaib M.; Malik M.N.H.; Shabbir R.; Mushtaq M.N.; Younis W.; Jahan S.; Ahmed I.; Kharl H.A.A.; Imine derivatives of benzoxazole attenuate high-fat diet-induced hyperlipidemia by modulation of lipid-regulating genes. ACS Omega 2023,8(17),15306-15317. (PMID: 10.1021/acsomega.3c0044337151544) |
| معلومات مُعتمدة: | SIP20210843, SIP20220687, SIP20230858 BEIFI-IPN; 1038496 CONACYT |
| فهرسة مساهمة: | Keywords: 3T3-L1 cells; MTT assays.; adipogenesis; estrogen receptor beta ligand; mRNA; obesity |
| المشرفين على المادة: | 0 (Anti-Obesity Agents) 0 (Benzamides) 0 (Benzoxazoles) 0 (Estrogen Receptor beta) 0 (Isoflavones) 0 (Ligands) |
| تواريخ الأحداث: | Date Created: 20240109 Date Completed: 20240708 Latest Revision: 20240731 |
| رمز التحديث: | 20240731 |
| DOI: | 10.2174/0115734064285786231230185457 |
| PMID: | 38192145 |
| قاعدة البيانات: | MEDLINE |
| تدمد: | 1875-6638 |
|---|---|
| DOI: | 10.2174/0115734064285786231230185457 |