TXNIP inhibition in the treatment of type 2 diabetes mellitus: design, synthesis, and biological evaluation of quinazoline derivatives

References

• International Diabetes Federation. IDF diabetes atlas. 10th ed. Brussels (Belgium): International Diabetes Federation; 2021.
   Google Scholar
• Papatheodorou K, Banach M, Bekiari E, Rizzo M, Edmonds M. Complications of diabetes 2017. J Diabetes Res. 2018; 2018:3086167.
   PubMed Web of Science ®Google Scholar
• Hu C, Jia W. Therapeutic medications against diabetes: what we have and what we expect. Adv Drug Deliv Rev. 2019;139:3–15.
   PubMed Web of Science ®Google Scholar
• Kathrin M. Beta cells in type 2 diabetes - a crucial contribution to pathogenesis. Diabetes Obes Metab. 2008;10(5):408–420.
   PubMed Web of Science ®Google Scholar
• Tatsuo T. Apoptosis in pancreatic β-islet cells in type 2 diabetes. Bosn J Basic Med Sci. 2016;16(3):162–179.
   PubMed Web of Science ®Google Scholar
• Grant B, Sandelson M, Agyemang-Prempeh B, Zalin A. Managing obesity in people with type 2 diabetes. Clin Med. 2021;21(4):e327–e231.
   PubMed Web of Science ®Google Scholar
• Carbone S, Del Buono MG, Ozemek C, Lavie CJ. Obesity, risk of diabetes and role of physical activity, exercise training and cardiorespiratory fitness. Prog Cardiovasc Dis. 2019;62(4):327–333.
   PubMed Web of Science ®Google Scholar
• Johnston LW, Harris SB, Retnakaran R, Giacca A, Liu Z, Bazinet RP, Hanley AJ. Association of NEFA composition with insulin sensitivity and beta cell function in the Prospective Metabolism and Islet Cell Evaluation (PROMISE) cohort. Diabetologia. 2018;61(4):821–830.
   PubMed Web of Science ®Google Scholar
• Chen G, Li Y, Zeng F, Deng G, Liang J, Wang J, Su Y, Chen Y, Mao L, Liu Z, et al. Biomarkers of fatty acids and risk of type 2 diabetes: a systematic review and meta-analysis of prospective cohort studies. Crit Rev Food Sci Nutr. 2021;61(16):2705–2718.
   PubMed Web of Science ®Google Scholar
• Forouhi NG, Koulman A, Sharp SJ, Imamura F, Kröger J, Schulze MB, Crowe FL, Huerta JM, Guevara M, Beulens JW, et al. Differences in the prospective association between individual plasma phospholipid saturated fatty acids and incident type 2 diabetes: the EPIC-InterAct case-cohort study. Lancet Diabetes Endocrinol. 2014;2(10):810–818.
   PubMed Web of Science ®Google Scholar
• Maedler K, Spinas GA, Dyntar D, Moritz W, Kaiser N, Donath MY. Distinct effects of saturated and monounsaturated fatty acids on beta-cell turnover and function. Diabetes. 2001;50(1):69–76.
   PubMed Web of Science ®Google Scholar
• Vetere A, Choudhary A, Burns SM, Wagner BK. Targeting the pancreatic β-cell to treat diabetes. Nat Rev Drug Discov. 2014;13(4):278–289.
   PubMed Web of Science ®Google Scholar
• Mahmood DF, Abderrazak A, El Hadri K, Simmet T, Rouis M. The thioredoxin system as a therapeutic target in human health and disease. Antioxid Redox Signal. 2013;19(11):1266–1303.
   PubMed Web of Science ®Google Scholar
• Lu J, Holmgren A. The thioredoxin antioxidant system. Free Radic Biol Med. 2014;66:75–87.
   PubMed Web of Science ®Google Scholar
• Yoshihara E, Chen Z, Matsuo Y, Masutani H, Yodoi J. Thiol redox transitions by thioredoxin and thioredoxin-binding protein-2 in cell signaling. Methods Enzymol. 2010;474:67–82.
   PubMed Web of Science ®Google Scholar
• Yoshihara E. TXNIP/TBP-2: a master regulator for glucose homeostasis. Antioxidants. 2020;9(8):765.
   Web of Science ®Google Scholar
• Alhawiti NM, Al Mahri S, Aziz MA, Malik SS, Mohammad S. TXNIP in metabolic regulation: physiological role and therapeutic outlook. Curr Drug Targets. 2017;18(9):1095–1103.
   PubMed Web of Science ®Google Scholar
• Chen J, Saxena G, Mungrue IN, Lusis AJ, Shalev A. Thioredoxin-interacting protein: a critical link between glucose toxicity and beta-cell apoptosis. Diabetes. 2008;57(4):938–944.
   PubMed Web of Science ®Google Scholar
• Chen J, Hui ST, Couto FM, Mungrue IN, Davis DB, Attie AD, Lusis AJ, Davis RA, Shalev A. Thioredoxin-interacting protein deficiency induces Akt/Bcl-xL signaling and pancreatic beta-cell mass and protects against diabetes. 2008;22(10):3581–3594.
   Google Scholar
• Zhou R, Tardivel A, Thorens B, Choi I, Tschopp J. Thioredoxin-interacting protein links oxidative stress to inflammasome activation. Nat Immunol. 2010;11(2):136–140.
   PubMed Web of Science ®Google Scholar
• Sato Y, Fujimoto S, Mukai E, Sato H, Tahara Y, Ogura K, Yamano G, Ogura M, Nagashima K, Inagaki N. Palmitate induces reactive oxygen species production and β-cell dysfunction by activating nicotinamide adenine dinucleotide phosphate oxidase through Src signaling. J Diabetes Investig. 2014;5(1):19–26.
   PubMed Web of Science ®Google Scholar
• Oslowski CM, Hara T, O'Sullivan-Murphy B, Kanekura K, Lu S, Hara M, Ishigaki S, Zhu LJ, Hayashi E, Hui ST, et al. Thioredoxin-interacting protein mediates ER stress-induced β cell death through initiation of the inflammasome. Cell Metab. 2012;16(2):265–273.
   PubMed Web of Science ®Google Scholar
• Thielen LA, Chen J, Jing G, Moukha-Chafiq O, Xu G, Jo S, Grayson TB, Lu B, Li P, Augelli-Szafran CE, et al. Identification of an anti-diabetic, orally available small molecule that regulates TXNIP expression and glucagon action. Cell Metab. 2020;32(3):353.e8–365.e8.
   Web of Science ®Google Scholar
• Alber AB, Suter DM. Dynamics of protein synthesis and degradation through the cell cycle. Cell Cycle. 2019;18(8):784–794.
   PubMed Web of Science ®Google Scholar
• Trachootham D, Lu W, Ogasawara MA, Nilsa RD, Huang P. Redox regulation of cell survival. Antioxid Redox Signal. 2008;10(8):1343–1374.
   PubMed Web of Science ®Google Scholar
• Wehinger S, Ortiz R, Díaz MI, Aguirre A, Valenzuela M, Llanos P, Mc Master C, Leyton L, Quest AF. Phosphorylation of caveolin-1 on tyrosine-14 induced by ROS enhances palmitate-induced death of beta-pancreatic cells. Biochim Biophys Acta. 2015;1852(5):693–708.
   PubMed Web of Science ®Google Scholar
• Liu J, Chang F, Li F, Fu H, Wang J, Zhang S, Zhao J, Yin D. Palmitate promotes autophagy and apoptosis through ROS-dependent JNK and p38 MAPK. Biochem Biophys Res Commun. 2015;463(3):262–267.
   PubMed Web of Science ®Google Scholar
• Elsner M, Gehrmann W, Lenzen S. Peroxisome-generated hydrogen peroxide as important mediator of lipotoxicity in insulin-producing cells. Diabetes. 2011;60(1):200–208.
   PubMed Web of Science ®Google Scholar
• Schroder K, Zhou R, Tschopp J. The NLRP3 inflammasome: a sensor for metabolic danger? Science. 2010;327(5963):296–300.
   PubMed Web of Science ®Google Scholar
• Haneklaus M, O'Neill LA. NLRP3 at the interface of metabolism and inflammation. Immunol Rev. 2015;265(1):53–62.
   PubMed Web of Science ®Google Scholar
• Mori MA, Bezy O, Kahn CR. Metabolic syndrome: is Nlrp3 inflammasome a trigger or a target of insulin resistance? Circ Res. 2011;108(10):1160–1162.
   PubMed Web of Science ®Google Scholar
• Youm YH, Adijiang A, Vandanmagsar B, Burk D, Ravussin A, Dixit VD. Elimination of the NLRP3-ASC inflammasome protects against chronic obesity-induced pancreatic damage. Endocrinology. 2011;152(11):4039–4045.
   PubMed Web of Science ®Google Scholar
• Lytrivi M, Igoillo-Esteve M, Cnop M. Inflammatory stress in islet β-cells: therapeutic implications for type 2 diabetes? Curr Opin Pharmacol. 2018;43:40–45.
   PubMed Web of Science ®Google Scholar
• Igoillo-Esteve M, Marselli L, Cunha DA, Ladrière L, Ortis F, Grieco FA, Dotta F, Weir GC, Marchetti P, Eizirik DL, et al. Palmitate induces a pro-inflammatory response in human pancreatic islets that mimics CCL2 expression by beta cells in type 2 diabetes. Diabetologia. 2010;3(7):1395–1405.
   Google Scholar
• Inoue H, Shirakawa J, Togashi Y, Tajima K, Okuyama T, Kyohara M, Tanaka Y, Orime K, Saisho Y, Yamada T, et al. Signaling between pancreatic β cell and macrophages via S100 calcium-binding protein A8 exacerbates β-cell apoptosis and islet inflammation. J Biol Chem. 2018;293(16):5934–5946.
   PubMed Web of Science ®Google Scholar
• Jiang M, Qi L, Li L, Li Y. The caspase-3/GSDME signal pathway as a switch between apoptosis and pyroptosis in cancer. Cell Death Discov. 2020;6:112.
   PubMed Web of Science ®Google Scholar
• Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Nature Sci Rep. 2017;7:42717.
   PubMed Web of Science ®Google Scholar