Design, synthesis, and cytotoxic activities of isaindigotone derivatives as potential anti-gastric cancer agents

References

• Sung H, Ferlay J, Siegel RL, et al. Global cancer statistics 2020: Globocan estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin 2021;71:209–49.
   PubMed Web of Science ®Google Scholar
• Machlowska J, Baj J, Sitarz M, et al. Gastric cancer: epidemiology, risk factors, classification, genomic characteristics and treatment strategies. Int J Mol Sci 2020;21:453–61.
   PubMed Web of Science ®Google Scholar
• Liu P, Cheng H, Roberts TM, Zhao JJ. Targeting the phosphoinositide 3-kinase pathway in cancer. Nat Rev Drug Discov 2009;8:627–44.
   PubMed Web of Science ®Google Scholar
• Shimobayashi M, Hall MN. Making new contacts: the mTOR network in metabolism and signalling crosstalk. Nat Rev Mol Cell Biol 2014;15:155–62.
   PubMed Web of Science ®Google Scholar
• Thorpe LM, Yuzugullu H, Zhao JJ. Pi3k in cancer: divergent roles of isoforms, modes of activation and therapeutic targeting. Nat Rev Cancer 2015;15:7–24.
   PubMed Web of Science ®Google Scholar
• Lang SA, Gaumann A, Koehl GE, et al. Mammalian target of rapamycin is activated in human gastric cancer and serves as a target for therapy in an experimental model. Int J Cancer 2007;120:1803–10.
   PubMed Web of Science ®Google Scholar
• Wadhwa R, Song S, Lee JS, et al. Gastric cancer-molecular and clinical dimensions. Nat Rev Clin Oncol 2013;10:643–55.
   PubMed Web of Science ®Google Scholar
• Wong H, Yau T. Targeted therapy in the management of advanced gastric cancer: are we making progress in the era of personalized medicine? Oncologist 2012;17:346–58.
   PubMed Web of Science ®Google Scholar
• Yu G, Wang J, Chen Y, Wang X, et al. Overexpression of phosphorylated mammalian target of rapamycin predicts lymph node metastasis and prognosis of Chinese patients with gastric cancer. Clin Cancer Res 2009;15:1821–9.
   PubMed Web of Science ®Google Scholar
• He R, Xu B, Ping L, Lv X. Structural optimization towards promising β-methyl-4-acrylamido quinoline derivatives as PI3K/mTOR dual inhibitors for anti-cancer therapy: the in vitro and in vivo biological evaluation. Eur J Med Chem 2021;214:113249.
   PubMed Web of Science ®Google Scholar
• Liu T, Song S, Wang X, Hao J. Small-molecule inhibitors of breast cancer-related targets: potential therapeutic agents for breast cancer. Eur J Med Chem 2021;210:112954.
   PubMed Web of Science ®Google Scholar
• Viswanathan A, Kute D, Musa A, et al. 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma. Eur J Med Chem 2019;166:291–303.
   PubMed Web of Science ®Google Scholar
• Wu TT, Guo QQ, Chen ZL, et al. Design, synthesis and bioevaluation of novel substituted triazines as potential dual PI3K/mTOR inhibitors. Eur J Med Chem 2020;204:112637.
   PubMed Web of Science ®Google Scholar
• Xiang HY, Wang X, Chen YH, et al. Identification of methyl (5-(6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-2-yl)-4-(trifluoromethyl)pyridin-2-yl)carbamate (cyh33) as an orally bioavailable, highly potent, pi3k alpha inhibitor for the treatment of advanced solid tumors. Eur J Med Chem 2021;209:112913.
   PubMed Web of Science ®Google Scholar
• Yuan H, Ma Q, Ye L, Piao G. The traditional medicine and modern medicine from natural products. Molecules 2016;21:559.
   PubMed Web of Science ®Google Scholar
• Newman DJ, Cragg GM. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J Nat Prod 2020;83:770–803.
   PubMed Web of Science ®Google Scholar
• Molina P, Tárraga A, Gonzalez-Tejero A, et al. Inhibition of leukocyte functions by the alkaloid isaindigotone from isatis indigotica and some new synthetic derivatives. J Nat Prod 2001;64:1297–300.
   PubMed Web of Science ®Google Scholar
• Chung YC, Tang FY, Liao JW, et al. Isatis indigotica induces hepatocellular cancer cell death via caspase-independent apoptosis-inducing factor translocation apoptotic pathway in vitro and in vivo. Integr Cancer Ther 2011;10:201–14.
   PubMed Web of Science ®Google Scholar
• Xiaoyun W, Guowei Q, Kai CK, Fai CK. New alkaloids from isatis indigotica. Tetrahedron 1997;53:13323–8.
   Web of Science ®Google Scholar
• Shan C, Yan JW, Wang YQ, et al. Design, synthesis, and evaluation of isaindigotone derivatives to downregulate c-myc transcription via disrupting the interaction of nm23-h2 with g-quadruplex. J Med Chem 2017;60:1292–308.
   PubMed Web of Science ®Google Scholar
• Wu WB, Chen SH, Hou JQ, et al. Disubstituted 2-phenyl-benzopyranopyrimidine derivatives as a new type of highly selective ligands for telomeric g-quadruplex DNA. Org Biomol Chem 2011;9:2975–86.
   PubMed Web of Science ®Google Scholar
• Deng J, Ma Y, He Y, et al. A network pharmacology-based investigation to the pharmacodynamic material basis and mechanisms of the anti-inflammatory and anti-viral effect of isatis indigotica. Drug Des Devel Ther 2021;15:3193–206.
   PubMed Web of Science ®Google Scholar
• Yang Q, Modi P, Newcomb T, et al. Idelalisib: first-in-class pi3k delta inhibitor for the treatment of chronic lymphocytic leukemia, small lymphocytic leukemia, and follicular lymphoma. Clin Cancer Res 2015;21:1537–42.
   PubMed Web of Science ®Google Scholar
• Li H, Mu J, Sun J, et al. Hydrogen sulfide releasing oridonin derivatives induce apoptosis through extrinsic and intrinsic pathways. Eur J Med Chem 2020;187:111978.
   PubMed Web of Science ®Google Scholar
• Ma ZJ, Lu L, Yang JJ, et al. Lariciresinol induces apoptosis in HepG2 cells via mitochondrial-mediated apoptosis pathway. Eur J Pharmacol 2018;821:1–10.
   PubMed Web of Science ®Google Scholar
• Bock FJ, Tait SWG. Mitochondria as multifaceted regulators of cell death. Nat Rev Mol Cell Biol 2020;21:85–100.
   PubMed Web of Science ®Google Scholar
• Rong L, Li Z, Leng X, et al. Salidroside induces apoptosis and protective autophagy in human gastric cancer AGS cells through the PI3K/AKT/mTOR pathway. Biomed Pharmacother 2020;122:109726.
   PubMed Web of Science ®Google Scholar
• Yang J, Pi C, Wang G. Inhibition of PI3K/AKT/mTOR pathway by apigenin induces apoptosis and autophagy in hepatocellular carcinoma cells. Biomed Pharmacother 2018;103:699–707.
   PubMed Web of Science ®Google Scholar
• Zhou J, Jiang YY, Chen H, Wu YC, et al. Tanshinone I attenuates the malignant biological properties of ovarian cancer by inducing apoptosis and autophagy via the inactivation of PI3K/AKT/mTOR pathway. Cell Prolif 2020;53:e12739.
   PubMed Web of Science ®Google Scholar
• Hunter KW, Crawford NPS, Alsarraj J. Mechanisms of metastasis. Breast Cancer Res 2008;10:S2.
   Google Scholar
• Flemban A, Qualtrough D. The potential role of hedgehog signaling in the luminal/basal phenotype of breast epithelia and in breast cancer invasion and metastasis. Cancers (Basel) 2015;7:1863–84.
   PubMed Web of Science ®Google Scholar
• Zou P, Koh HL. Determination of indican, isatin, indirubin and indigotin in isatis indigotica by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 2007;21:1239–46.
   PubMed Web of Science ®Google Scholar
• Ho YL, Chang YS. Studies on the antinociceptive, anti-inflammatory and anti pyretic effects of isatis indigotica root. Phytomedicine 2002;9:419–24.
   PubMed Web of Science ®Google Scholar
• You WC, Hsieh CC, Huang JT. Effect of extracts from indigowood root (isatis indigotica fort.) on immune responses in radiation-induced mucositis. J Altern Complement Med 2009;15:771–8.
   PubMed Web of Science ®Google Scholar
• Bae SH, Jung ES, Park YM, et al. Expression of cyclooxygenase-2 (cox-2) in hepatocellular carcinoma and growth inhibition of hepatoma cell lines by a cox-2 inhibitor, ns-398. Clin Cancer Res 2001;7:1410–8.
   PubMed Web of Science ®Google Scholar
• Hial V, De Mello MC, Horakova Z, Beaven MA. Antiproliferative activity of anti-inflammatory drugs in two mammalian cell culture lines. J Pharmacol Exp Ther 1977;202:446–54.
   PubMed Web of Science ®Google Scholar
• Kimoto T, Hino K, Koya-Miyata S, et al. Cell differentiation and apoptosis of monocytic and promyelocytic leukemia cells (U-937 and HL-60) by tryptanthrin, an active ingredient of polygonum tinctorium Lour. Pathol Int 2001;51:315–25.
   PubMed Web of Science ®Google Scholar
• Cipak L, Repicky A, Jantova S. Growth inhibition and apoptosis induced by 2-phenoxymethyl-3h-quinazolin-4-one in HL-60 leukemia cells. Exp Oncol 2007;29:13–7.
   PubMedGoogle Scholar