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Anticancer Original Research Paper

2-(4-methoxyphenylthio)-5,8-dimethoxy-1,4-naphthoquinone induces apoptosis via ROS-mediated MAPK and STAT3 signaling pathway in human gastric cancer cells

, , , , , , , , , , , , & ORCID Icon show all
Pages 214-226 | Received 03 Sep 2018, Accepted 18 Apr 2019, Published online: 10 May 2019

Reference

  • Mikami K, Hirano K, Futami K, Maekawa T. Gastrectomy with limited surgery for elderly patients with gastric cancer. Asian J Surg. 2018;41:65–72.
  • Wu QN, Liao YF, Lu YX, Wang Y, Lu JH, Zeng ZL. Pharmacological inhibition of DUSP6 suppresses gastric cancer growth and metastasis and overcomes cisplatin resistance. Cancer Lett. 2018;412:243–55.
  • Ahmed A, Al-Tamimi DM. Incorporation of p-53 mutation status and Ki-67 proliferating index in classifying Her2-neu positive gastric adenocarcinoma. Libyan J Med. 2018;13:1466573–8.
  • Bai F, Jiu M, You Y, Feng Y, Xin R, Liu X, et al. miR–29a–3p represses proliferation and metastasis of gastric cancer cells via attenuating HAS3 levels. Mol Med Rep. 2018;17:8145–52.
  • Chen JC, Hsieh MJ, Chen CJ, Lin JT, Lo YS, Chuang YC, et al. Polyphyllin G induce apoptosis and autophagy in human nasopharyngeal cancer cells by modulation of AKT and mitogen-activated protein kinase pathways in vitro and in vivo. Oncotarget. 2016;7:70276–89.
  • Sinha K, Das J, Pal PB, Sil PC. Oxidative stress: the mitochondria-dependent and mitochondria-independent pathways of apoptosis. Arch Toxicol. 2013;87:1157–1180.
  • Mukherjee AK, Saviola AJ, Mackessy SP. Cellular mechanism of resistance of human colorectal adenocarcinoma cells against apoptosis-induction by Russell's Viper venom L-amino acid oxidase (Rusvinoxidase). Biochimie. 2018;150:8–15.
  • Zuo D, Zhou Z, Wang H, Zhang T, Zang J, Yin F, et al. Alternol, a natural compound, exerts an anti-tumour effect on osteosarcoma by modulating of STAT3 and ROS/MAPK signalling pathways. J Cell Mol Med. 2017;21:208–21.
  • Liu J, Chang F, Li F, Fu H, Wang J, Zhang S, et al. Palmitate promotes autophagy and apoptosis through ROS-dependent JNK and p38 MAPK. Biochem Biophys Res Commun. 2015;463:262–7.
  • Wei L, Chen Q, Guo A, Fan J, Wang R, Zhang H. Asiatic acid attenuates CCl4-induced liver fibrosis in rats by regulating the PI3K/AKT/mTOR and Bcl-2/Bax signaling pathways. Int Immunopharmacol. 2018;60:1–8.
  • Liu L, Huang Z, Chen J, Wang J, Wang S. Protein phosphatase 2A mediates JS-K-induced apoptosis by affecting Bcl-2 family proteins in human hepatocellular carcinoma HepG2 cells. J Cell Biochem. 2018;119:6633–43.
  • Costa MCA, Ferreira M. Two-dimensional quantitative structure-activity relationship study of 1,4-naphthoquinone derivatives tested against HL-60 human promyelocytic leukaemia cells. SAR QSAR Environ Res. 2017;28:325–39.
  • Li K, Wang B, Zheng L, Yang K, Li Y, Hu M, et al. Target ROS to induce apoptosis and cell cycle arrest by 5,7-dimethoxy-1,4-naphthoquinone derivative. Bioorg Med Chem Lett. 2018;28:273–7.
  • Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ. Role of quinones in toxicology. Chem Res Toxicol. 2000;13:135–60.
  • Ollinger K, Brunmark A. Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes. J Biol Chem. 1991;266:21496–503.
  • Vertogradova TP, Gol'dberg LE, Filippos'iants ST, Belova IP, Stepanova ES. The mechanism of the toxic effect of the antitumor antibiotic carminomycin. Antibiotiki. 1974; 19:50–7.
  • Liu C, Shen GN, Luo YH, Piao XJ, Jiang XY, Meng LQ, et al. Novel 1,4-naphthoquinone derivatives induce apoptosis via ROS-mediated p38/MAPK, Akt and STAT3 signaling in human hepatoma Hep3B cells. Int J Biochem Cell Biol. 2018;96:9–19.
  • Chang G, Zhou Y, Zhu RZ, Liu ZH, Cao YB, Cao RB. Naphthalene was synthesized by molten salt. China. 2017; 201710669130.8.
  • Xu DF, Guo XJ, Xu ZH, Li SS. A novel total synthesis of (±) shikonin. Chin Chem Lett. 2006;17:871–3.
  • Huot R, Brassard P. Friedel-Crafts condensations with maleic anhydrides. III. The synthesis of polyhydroxylated naphthoquinones. Can J Chem. 1974;52:838–42.
  • Sun HN, Shen GN, Jin YZ, Jin Y, Han YH, Feng L, et al. 2-cyclohexylamino-5,8-dimethoxy-1,4-naphthoquinone inhibits LPS-induced BV2 microglial activation through MAPK/NF-kB signaling pathways. Heliyon. 2016;2:e00132.
  • Shen GN, Choi JH, Gajulapati K, Lee JH, Kim YK, Rho MC, et al. 2-substitiuted thio- and amino-5,8-dimethoxy-1,4-naphthoquinones as a novel class of acyl-CoA: cholestrol acyltransferase inhibitors. Bull. Korean Chem Soc. 2009;30:1088–92.
  • Tabrizi L, Chiniforoshan H. Designing new iridium (iii) arene complexes of naphthoquinone derivatives as anticancer agents: a structure-activity relationship study. Dalton Trans. 2017;46:2339–49.
  • Beretta GL, Ribaudo G, Menegazzo I, Supino R, Capranico G, Zunino F, et al. Synthesis and evaluation of new naphthalene and naphthoquinone derivatives as anticancer agents. Arch Pharm (Weinheim). 2016;349:1–15.
  • And JJI, Chignell CF. Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Chem Res Toxicol. 2004;17:55–62.
  • Elmore S. Apoptosis: a review of programmed cell death. Toxicol Pathol. 2007;35:495–516.
  • Shin DY, Kim GY, Lee JH, Choi BT, Yoo YH, Choi YH, et al. Apoptosis induction of human prostate carcinoma DU145 cells by diallyl disulfide via modulation of JNK and PI3K/AKT signaling pathways. IJMS. 2012;13:14158–71.
  • Ashkenazi A, Holland P, Eckhardt SG. Ligand-based targeting of apoptosis in cancer: the potential of recombinant human apoptosis ligand 2/Tumor necrosis factor-related apoptosis-inducing ligand (rhApo2L/TRAIL). J Clin Oncol. 2008;26:3621–30.
  • Lim ES, Rhee YH, Park MK, Shim BS, Ahn KS, Kang H, et al. DMNQ S-64 induces apoptosis via caspase activation and cyclooxygenase-2 inhibition in human nonsmall lung cancer cells. Ann N Y Acad Sci. 2007;1095:7–18.
  • Zhao H, Yan L, Xu X, Jiang C, Shi J, Zhang Y, et al. Potential of Bacillus subtilis lipopeptides in anti-cancer I: induction of apoptosis and paraptosis and inhibition of autophagy in K562 cells. AMB Express. 2018;8:78–93.
  • Ghosh SK, Ganta A, Spanjaard RA. Discovery and cellular stress pathway analysis of 1,4-naphthoquinone derivatives with novel, highly potent broad-spectrum anticancer activity. J Biomed Sci. 2018;25:12–22.
  • Wang C, Chen K, Xia Y, Dai W, Wang F, Shen M, et al. N-acetylcysteine attenuates ischemia-reperfusion-induced apoptosis and autophagy in mouse liver via regulation of the ROS/JNK/Bcl-2 pathway. PLoS One. 2014;9:e108855.
  • Rushworth GF, Megson IL. Existing and potential therapeutic uses for N-acetylcysteine: the need for conversion to intracellular glutathione for antioxidant benefits. Pharmacol Ther. 2014;141:150–9.
  • Lu Y, Cederbaum A. The mode of cisplatin-induced cell death in CYP2E1-overexpressing HepG2 cells: modulation by ERK, ROS, glutathione, and thioredoxin. Free Radic Biol Med. 2007;43:1061–75.
  • Filomeni G, Aquilano K, Rotilio G, Ciriolo MR. Glutathione-related systems and modulation of extracellular signal-regulated kinases are involved in the resistance of AGS adenocarcinoma gastric cells to diallyl disulfide-induced apoptosis. Cancer Res. 2005;65:11735–42.
  • Wilke J, Kawamura T, Watanabe N, Osada H, Ziegler S, Waldmann H. Identification of cytotoxic, glutathione-reactive moieties inducing accumulation of reactive oxygen species via glutathione depletion. Bioorg Med Chem. 2018;26:1453–61.
  • Wang ZH, Zhan-Sheng H. Catalpol inhibits migration and induces apoptosis in gastric cancer cells and in athymic nude mice. Biomed Pharmacother. 2018;103:1708–19.
  • Meng LQ, Liu C, Luo YH, Piao XJ, Wang Y, Zhang Y, et al. Quinalizarin exerts an anti-tumour effect on lung cancer A549 cells by modulating the Akt, MAPK, STAT3 and p53 signalling pathways. Mol Med Rep. 2018;17:2626–34.
  • Cheng X, Peuckert C, Wölfl S. Essential role of mitochondrial Stat3 in p38MAPK mediated apoptosis under oxidative stress. Sci Rep. 2017;7:15388–98.
  • Ahn J, Won M, Choi JH, Kim YS, Jung CR, Im DS, et al. Reactive oxygen species-mediated activation of the Akt/ASK1/p38 signaling cascade and p21(Cip1) downregulation are required for shikonin-induced apoptosis. Apoptosis. 2013;18:870–81.
  • Zhao Q, Assimopoulou AN, Klauck SM, Damianakos H, Chinou I, Kretschmer N, et al. Inhibition of c-MYC with involvement of ERK/JNK/MAPK and AKT pathways as a novel mechanism for shikonin and its derivatives in killing leukemia cells. Oncotarget. 2015;6:38934–38951.
  • Zhen Y, Wu Q, Ding Y, Zhang W, Zhai Y, Lin X, et al. Exogenous hydrogen sulfide promotes hepatocellular carcinoma cell growth by activating the STAT3-COX-2 signaling pathway. Oncol Lett. 2018;15:6562–70.
  • Mukthavaram R, Ouyang X, Saklecha R, Jiang P, Nomura N, Pingle SC, et al. Effect of the JAK2/STAT3 inhibitor SAR317461 on human glioblastoma tumorspheres. J Transl Med. 2015;13:269–78.
  • Aggarwal BB, Kunnumakkara AB, Harikumar KB, Gupta SR, Tharakan ST, Koca C, et al. Signal transducer and activator of transcription-3, inflammation and cancer: How intimate is the relationship?. Ann N Y Acad Sci. 2009;1171:59–76.
  • Fathi N, Rashidi G, Khodadadi A, Shahi S, Sharifi S. STAT3 and apoptosis challenges in cancer. Int J Biol Macromol. 2018;117:993–1001.
  • Jing N, Tweardy DJ. Targeting Stat3 in cancer therapy. Anticancer Drugs. 2005;16:601–7.
  • Bai E, Yang L, Xiang Y, Hu W, Li C, Lin J, et al. L61H46 shows potent efficacy against human pancreatic cancer through inhibiting STAT3 pathway. CMAR. 2018; 10:565–81.

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