Design and synthesis of tricyclic terpenoid derivatives as novel PTP1B inhibitors with improved pharmacological property and in vivo antihyperglycaemic efficacy

References

• Chen L, Magliano DJ, Zimmet PZ. The worldwide epidemiology of type 2 diabetes mellitus-present and future perspectives. Nat Rev Endocrinol 2012;8:228–36.
   Web of Science ®Google Scholar
• van Dieren S, Beulens JWJ, van der Schouw YT, et al. The global burden of diabetes and its complications: an emerging pandemic. Eur J Cardiov Prev R 2010;17:S3–S8.
   PubMed Web of Science ®Google Scholar
• Zinman B, Wanner C, Lachin JM, et al. Investigators, empagliflozin, cardiovascular outcomes, and mortality in type 2 diabetes. New Engl J Med 2015;373:2117–28.
   PubMed Web of Science ®Google Scholar
• Catanzaro R, Lorenzetti A, Allegri F, et al. Inhibiting insulin resistance mechanisms by DTS phytocompound: an experimental study on metabolic syndrome-prone adipocytes. Acta bio-medica Atenei Parmensis 2012;83:95–102.
   PubMedGoogle Scholar
• Bonner C, Kerr-Conte J, Gmyr V, et al. Inhibition of the glucose transporter SGLT2 with dapagliflozin in pancreatic alpha cells triggers glucagon secretion. Nat Med 2015;21:512–U139.
   PubMed Web of Science ®Google Scholar
• Green JB, Bethel MA, Armstrong PW, et al. Effect of sitagliptin on cardiovascular outcomes in type 2 diabetes. New Engl J Med 2015;373:232–42.
   PubMed Web of Science ®Google Scholar
• Jia Y, Lao Y, Zhu H, et al. Is metformin still the most efficacious first-line oral hypoglycaemic drug in treating type 2 diabetes? A network meta-analysis of randomized controlled trials. Obes Rev 2019;20:1–12.
   PubMed Web of Science ®Google Scholar
• Gouni-Berthold I, Berthold HK. Pharmacologic therapy for cardiovascular risk reduction in patients with the metabolic syndrome. Curr Pharm Des 2014;20:5025–38.
   PubMed Web of Science ®Google Scholar
• Rajasurya V, Anjum H, Surani S. Metformin use and metformin-associated lactic acidosis in intensive care unit patients with diabetes. Cureus 2019;11:UNSP e4739.
   PubMed Web of Science ®Google Scholar
• Ji WJ, Chen XL, Lv J, et al. Liraglutide exerts antidiabetic effect via PTP1B and PI3K/Akt2 signaling pathway in skeletal muscle of KKAy mice. Int J Endocrinol 2014;9:312452.
   Google Scholar
• Panzhinskiy E, Hua Y, Culver B, et al. Endoplasmic reticulum stress upregulates protein tyrosine phosphatase 1B and impairs glucose uptake in cultured myotubes. Diabetologia 2013;56:598–607.
   PubMed Web of Science ®Google Scholar
• Hsu MF, Meng TC. Enhancement of insulin responsiveness by nitric oxide-mediated inactivation of protein-tyrosine phosphatases. J Biol Chem 2010;285:7919–28.
   PubMed Web of Science ®Google Scholar
• Elchebly M, Payette P, Michaliszyn E, et al. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science 1999;283:1544–8.
   PubMed Web of Science ®Google Scholar
• Delibegovic M, Zimmer D, Kauffman C, et al. Liver-specific deletion of protein-tyrosine phosphatase 1B (PTP1B) improves metabolic syndrome and attenuates diet-induced endoplasmic reticulum stress. Diabetes 2009;58:590–9.
   PubMed Web of Science ®Google Scholar
• Bence KK, Delibegovic M, Xue B, et al. Neuronal PTP1B regulates body weight, adiposity and leptin action. Nat Med 2006;12:917–24.
   PubMed Web of Science ®Google Scholar
• Fernandez-Ruiz R, Vieira E, Garcia-Roves PM, et al. Protein tyrosine phosphatase-1B modulates pancreatic beta-cell mass. PLoS One 2014;9:e90344.
   PubMed Web of Science ®Google Scholar
• Liu SM, Xi YN, Bettaieb A, et al. Disruption of protein-tyrosine phosphatase 1B expression in the pancreas affects beta-cell function. Endocrinology 2014;155:3329–38.
   PubMed Web of Science ®Google Scholar
• Qian S, Zhang M, He Y, et al. Recent advances in the development of protein tyrosine phosphatase 1B inhibitors for type 2 diabetes. Fut Med Chem 2016;8:1239–58.
   PubMed Web of Science ®Google Scholar
• Yu M, Liu Z, Liu Y, et al. PTP1B markedly promotes breast cancer progression and is regulated by miR-193a-3p. Febs J 2019;286:1136–53.
   PubMed Web of Science ®Google Scholar
• Garcia-Ruiz I, Blanes Ruiz N, Rada P, et al. Protein tyrosine phosphatase 1B deficiency protects against hepatic fibrosis by modulating NADPH oxidases. Redox Bio 2019;26:101263.
   PubMed Web of Science ®Google Scholar
• Liu H, Sun D, Du H, et al. Synthesis and biological evaluation of tryptophan-derived rhodanine derivatives as PTP1B inhibitors and anti-bacterial agents. Eur J Med Chem 2019;172:163–73.
   PubMed Web of Science ®Google Scholar
• Yu X, Sun JP, He Y, et al. Structure, inhibitor, and regulatory mechanism of Lyp, a lymphoid-specific tyrosine phosphatase implicated in autoimmune diseases. Proc Natl Acad Sci USA 2007;104:19767–772.
   PubMed Web of Science ®Google Scholar
• Olivier M, Hsiung CA, Chuang LM, et al. Single nucleotide polymorphisms in protein tyrosine phosphatase 1 beta (PTPN1) are associated with essential hypertension and obesity. Hum Mol Genet 2004;13:1885–92.
   PubMed Web of Science ®Google Scholar
• Combs AP. Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity, and cancer. J Med Chem 2010;53:2333–44.
   PubMed Web of Science ®Google Scholar
• Jiang CS, Liang LF, Guo YW. Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades. Acta Pharmacol Sin 2012;33:1217–45.
   PubMed Web of Science ®Google Scholar
• Li J, Bai L, Wei F, et al. Therapeutic mechanisms of herbal medicines against insulin resistance: a review. Front Pharmacol 2019;10:661.
   PubMed Web of Science ®Google Scholar
• Wang LJ, Jiang B, Wu N, et al. Natural and semisynthetic protein tyrosine phosphatase 1B (PTP1B) inhibitors as anti-diabetic agents. RSC Adv 2015;5:48822–834.
   Web of Science ®Google Scholar
• Qian S, Li H, Chen Y, et al. Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B. J Nat Prod 2010;73:1743–50.
   PubMed Web of Science ®Google Scholar
• Qian S, Chen QL, Guan JL, et al. Synthesis and biological evaluation of raddeanin A, a triterpene saponin isolated from Anemone raddeana. Chem Pharm Bull 2014;62:779–85.
   PubMed Web of Science ®Google Scholar
• Qian S, Wu Y, He YX, et al. Synthesis and biological evaluation of oleanane triterpenoid with gamma-lactone functionality in ring C. Chem J Chin Univ 2012;33:969–75.
   Web of Science ®Google Scholar
• Pei SC, Wu JB, Lei F, et al. Synthesis of oleanolic disaccharide derivatives. Chin Chem Lett 2012;23:403–6.
   Web of Science ®Google Scholar
• Chen L, Wu JB, Lei F, et al. Synthesis and biological evaluation of oleanolic acid derivatives as antitumor agents. J Asian Nat Prod Res 2012;14:355–63.
   PubMed Web of Science ®Google Scholar
• Qian S, Li JH, Zhang YW, et al. Synthesis and alpha-glucosidase inhibitory activity of oleanolic acid derivatives. J Asian Nat Prod Res 2010;12:20–29.
   PubMed Web of Science ®Google Scholar
• Moretto AF, Kirincich SJ, Xu WX, et al. Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors. Bioorg Med Chem 2006;14:2162–77.
   PubMed Web of Science ®Google Scholar
• Puius YA, Zhao Y, Sullivan M, et al. Identification of a second aryl phosphate-binding site in protein-tyrosine phosphatase 1B: a paradigm for inhibitor design. Proc Natl Acad Sci USA 1997;94:13420–25.
   PubMed Web of Science ®Google Scholar
• Abad A, Arno M, Domingo LR, et al. Synthesis of (+)-podocarp-8(14)-en-13-one and methyl-(+)-13-oxo-podocarp-8(14)-en-18-oate from abietic acid. Tetrahedron 1985;41:4937–40.
   Web of Science ®Google Scholar
• Alvarez-Manzaneda EJ, Chahboun R, Guardia JJ, et al. New route to 15-hydroxydehydroabietic acid derivatives: application to the first synthesis of some bioactive abietane and nor-abietane type terpenoids. Tetrahedron Lett 2006;47:2577–80.
   Web of Science ®Google Scholar
• Gonzalez MA, Correa-Royero J, Agudelo L, et al. Synthesis and biological evaluation of abietic acid derivatives. Eur J Med Chem 2009;44:2468–72.
   PubMed Web of Science ®Google Scholar
• Boger DL, Coleman RS. Benzylic hydroperoxide rearrangement - observations on a viable and convenient alternative to the Baeyer-Villiger rearrangement. J Org Chem 1986;51:5436–39.
   Web of Science ®Google Scholar
• Lee HJ, Ravn MM, Coates RM. Synthesis and characterization of abietadiene, levopimaradiene, palustradiene, and neoabietadiene: hydrocarbon precursors of the abietane diterpene resin acids. Tetrahedron 2001;57:6155–67.
   Web of Science ®Google Scholar
• Liu ZQ, Liu T, Chen C, et al. Fumosorinone, a novel PTP1B inhibitor, activates insulin signaling in insulin-resistance HepG2 cells and shows anti-diabetic effect in diabetic KKAy mice. Toxicol Appl Pharmacol 2015;285:61–70.
   PubMed Web of Science ®Google Scholar
• Xu F, Wang F, Wang Z, et al. Glucose uptake activities of bis (2, 3-dibromo-4,5-dihydroxybenzyl)ether, a novel marine natural product from red alga Odonthalia corymbifera with protein tyrosine phosphatase 1B inhibition, in vitro and in vivo. PLoS One 2016;11:e0147748.
   PubMed Web of Science ®Google Scholar
• Cui DS, Lipchock JM, Brookner D, et al. Uncovering the molecular interactions in the catalytic loop that modulate the conformational dynamics in protein tyrosine phosphatase 1B. J Am Chem Soc 2019;141:12634–47.
   PubMed Web of Science ®Google Scholar
• Hann MM, Oprea TI. Pursuing the leadlikeness concept in pharmaceutical research. Curr Opin Chem Biol 2004;8:255–63.
   PubMed Web of Science ®Google Scholar
• Jose Ramirez-Espinosa J, Yolanda Rios M, Paoli P, et al. Synthesis of oleanolic acid derivatives: In vitro, in vivo and in silico studies for PTP-1B inhibition. Eur J Med Chem 2014;87:316–27.
   PubMed Web of Science ®Google Scholar