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Research Articles

A novel anticancer chromeno-pyrimidine analogue inhibits epithelial-mesenchymal transition in lung adenocarcinoma cells

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Pages 401-412 | Received 20 Oct 2020, Accepted 06 Mar 2021, Published online: 05 Apr 2021

References

  • Abdelhafez OM, Amin KM, Batran RZ, Maher TJ, Nada SA, Sethumadhavan S. 2010. Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives. Bioorg Med Chem. 18(10):3371–3378.
  • Akrami H, Safavi M, Mirjalili BF, Ashkezari MD, Dadfar F, Mohaghegh N, Emami S, Salehi F, Nadri H, Ardestani SK, et al. 2017. Facile synthesis and antiproliferative activity of 7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amines. Eur J Med Chem. 127:128–136.
  • Alblewi FF, Okasha RM, Hritani ZM, Mohamed HM, El-Nassag MAA, Halawa AH, Mora A, Fouda AM, Assiri MA, Al-Dies AM, et al. 2019. Antiproliferative effect, cell cycle arrest and apoptosis generation of novel synthesized anticancer heterocyclic derivatives based 4H-benzo[h]chromene. Bioorg Chem. 87:560–571.
  • Al-Majedy YK, Al-Amiery AA, Kadhum AAH, Mohamad AB. 2016. Antioxidant activities of 4-methylumbelliferone derivatives. PLoS One. 11(5):e0156625.
  • Al-Warhi T, Sabt A, Elkaeed EB, Eldehna WM. 2020. Recent advancements of coumarin-based anticancer agents: an up-to-date review. Bioorg Chem. 103:104163
  • Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. 2018. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 68(6):394–424.
  • Bubols GB, da Rocha Vianna D, Medina-Remon A, von PG, Lamuela-Raventos RM, EiflerLima VL, Garcia SC. 2013. The antioxidant activity of coumarins and flavonoids. Mini Rev Med Chem. 13(3):318–334.
  • Budzisz E, Brzezinska E, Krajewska U, Rozalski M. 2003. Cytotoxic effects, alkylating properties and molecular modeling of coumarin derivatives (I) and their phosphonic analogues (II) and (III). chemInform. Eur J Med Chem. 38(6):597–603.
  • Chaffer CL, Weinberg RA. 2011. A perspective on cancer cell metastasis. Science. 331(6024):1559–1564.
  • Chia CY, Kumari U, Casey PJ. 2014. Breast cancer cell invasion mediated by Gα12 signaling involves expression of interleukins-6 and -8, and matrix metalloproteinase-2. J Mol Signal. 9:6.
  • El-Bakhshawangy NM, El-Nassan HB, Kassab AE, Taher AT. 2018. Design, synthesis and biological evaluation of chromenopyrimidines as potential cytotoxic agents. Future Med Chem. 10(12):1465–1481.
  • Fang W, Li H, Kong L, Niu G, Gao Q, Zhou K, Zheng J, Wu B. 2003. Role of matrix metalloproteinases (MMPs) in tumor invasion and metastasis: serial studies on MMPs and TIMPs. Beijing Da Xue Xue Bao Yi Xue Ban. 35(4):441–443.
  • Galmarini CM, Mackey JR, Dumontet C. 2002. Nucleoside analogues and nucleobases in cancer treatment. Lancet Oncol. 3(7):415–424.
  • Gherghi IC, Girousi ST, Voulgaropoulos AN, Tzimou-Tsitouridou R. 2003. Study of interactions between DNA-ethidium bromide (EB) and DNA-acridine orange (AO), in solution, using hanging mercury drop electrode (HMDE). Talanta. 61(2):103–112.
  • Green DR, Reed JC. 1998. Mitochondria and apoptosis. Science. 281(5381):1309–1312.
  • Heerboth S, Housman G, Leary M, Longacre M, Byler S, Lapinska K, Willbanks A, Sarkar S. 2015. EMT and tumor metastasis. Clin Trans Med. 4:6–6.
  • Jain M, Surin WR, Misra A, Prakash P, Singh V, Khanna V, Kumar S, Siddiqui HH, Raj K, Barthwal MK, et al. 2013. Antithrombotic activity of a newly synthesized coumarin derivative 3-(5-hydroxy-2,2-dimethyl-chroman-6-yl)-N-{2-[3-(5-hydroxy-2,2-dimethyl-chroman-6-yl)-propionylamino]-ethyl}-propionamide. Chem Biol Drug Des. 81(4):499–508.
  • Kaufhold S, Bonavida B. 2014. Central role of Snail1 in the regulation of EMT and resistance in cancer: a target for therapeutic intervention. J Exp Clin Cancer Res. 33(1):62
  • Keri RS, Sasidhar BS, Nagaraja BM, Santos MA. 2015. Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents. Eur J Med Chem. 100:257–269.
  • Khan KM, Saify ZS, Khan MZ, Zia U, Choudhary MI, Ur RA, Perveen S, Chohan ZH, Supuran CT. 2004. Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J Enzyme Inhib Med Chem. 19(4):373–379.
  • King TD, Zhang W, Suto MJ, Li Y. 2012. Frizzled7 as an emerging target for cancer therapy. Cell Signal. 24(4):846–851.
  • Kontogiorgis CA, Hadjipavlou-Litina DJ. 2005. Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem. 48(20):6400–6408.
  • Kostova I. 2005. Synthetic and natural coumarins as cytotoxic agents. Curr Med Chem Anticancer Agents. 5(1):29–46.
  • Kwon OS, Choi JS, Islam MN, Kim YS, Kim HP. 2011. Inhibition of 5-lipoxygenase and skin inflammation by the aerial parts of Artemisia capillaris and its constituents. Arch Pharm Res. 34(9):1561–1569.
  • Li H, Huang J, Yang B, Xiang T, Yin X, Peng W, Cheng W, Wan J, Luo F, Li H, et al. 2013. Mangiferin exerts antitumor activity in breast cancer cells by regulating matrix metalloproteinases, epithelial to mesenchymal transition, and β-catenin signaling pathway. Toxicol Appl Pharmacol. 272(1):180–190.
  • MacDonald BT, Tamai K, He X. 2009. Wnt/beta-catenin signaling: components, mechanisms, and diseases. Dev Cell. 17(1):9–26.
  • Matsumoto T, Takahashi K, Kanayama S, Nakano Y, Imai H, Kibi M, Imahori D, Hasei T, Watanabe T. 2017. Structures of antimutagenic constituents in the peels of Citrus limon. J Nat Med. 71(4):735–744.
  • Merchant N, Nagaraju GP, Rajitha B, Lammata S, Jella KK, Buchwald ZS, Lakka SS, Ali AN. 2017. Matrix metalloproteinases: their functional role in lung cancer. Carcinogenesis. 38(8):766–780.
  • Mirunalini S, Deepalakshmi K, Manimozhi J. 2014. Antiproliferative effect of coumarin by modulating oxidant/antioxidant status and inducing apoptosis in Hep2 cells. Biomed Aging Pathol. 4(2):131–135.
  • Morsy SA, Farahat AA, Nasr MNA, Tantawy AS. 2017. Synthesis, molecular modeling and anticancer activity of new coumarin containing compounds. Saudi Pharm J. 25(6):873–883.
  • Nagaraj NS, Datta PK. 2010. Targeting the transforming growth factor-beta signaling pathway in human cancer. Expert Opin Investig Drugs. 19(1):77–91.
  • Najmanová I, Doseděl M, Hrdina R, Anzenbacher P, Filipský T, Říha M, Mladěnka P. 2015. Cardiovascular effects of coumarins besides their antioxidant activity. Curr Top Med Chem. 15(9):830–849.
  • Nargotra A, Sharma S, Alam MI, Ahmed Z, Bhagat A, Taneja SC, Qazi GN, Koul S. 2011. In silico identification of viper phospholipaseA2 inhibitors: validation by in vitro, in vivo studies. J Mol Model. 17(12):3063–3073.
  • Nawrocki-Raby B, Gilles C, Polette M, Martinella-Catusse C, Bonnet N, Puchelle E, Foidart JM, Roy FV, Birembaut P. 2003. E-Cadherin mediates MMP down-regulation in highly invasive bronchial tumor cells. Am J Pathol. 163(2):653–661.
  • Neyts J, Clercq ED, Singha R, Chang YH, Das AR, Chakraborty SK, Hong SC, Tsay SC, Hsu MH, Hwu JR. 2009. Structure-activity relationship of new anti-hepatitis C virus agents: heterobicycle-coumarin conjugates. J Med Chem. 52(5):1486–1490.
  • Pajaniradje S, Mohankumar K, Pamidimukkala R, Subramanian S, Rajagopalan R. 2014. Antiproliferative and apoptotic effects of Sesbania grandiflora leaves in human cancer cells. Biomed Res Int. 2014:474953.
  • Parkin DM, Pisani P, Ferlay J. 1993. Estimates of the worldwide incidence of eighteen major cancers in 1985. Int J Cancer. 54(4):594–606.
  • Parsons SL, Watson SA, Collins HM, Griffin NR, Clarke PA, Steele RJ. 1998. Gelatinase (MMP-2 and -9) expression in gastrointestinal malignancy. Br J Cancer. 78(11):1495–1502.
  • Patil PO, Bari SB, Firke SD, Deshmukh PK, Donda ST, Patil DA. 2013. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer’s disease. Bioorg Med Chem. 21(9):2434–2450.
  • Penta S. 2016. Advances in structure and activity relationship of coumarin derivatives. Massachusetts (MA): Academic Press. Chapter 3, Antitumor Agents; p. 47–76.
  • Safranek J, Pesta M, Holubec L, Kulda V, Dreslerova J, Vrzalova J, Topolcan O, Pesek M, Finek J, Treska V. 2009. Expression of MMP-7, MMP-9, TIMP-1 and TIMP-2 mRNA in lung tissue of patients with non-small cell lung cancer (NSCLC) and benign pulmonary disease. Anticancer Res. 29(7):2513–2517.
  • Sashidhara KV, Kumar A, Kumar M, Sarkar J, Sinha S. 2010. Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents. Bioorg Med Chem Lett. 20(24):7205–7211.
  • Shirasaka T. 2008. Development history and concept of an oral anticancer agent S-1 (TS-1): its clinical usefulness and future vistas. Jpn J Clin Oncol. 39(1):2–15.
  • Simon HU, Haj-Yehia A, Levi-Schaffer F. 2000. Role of reactive oxygen species (ROS) in apoptosis induction. Apoptosis. 5(5):415–418.
  • Xu J, Lamouille S, Derynck R. 2009. TGF-beta-induced epithelial to mesenchymal transition. Cell Res. 19(2):156–172.
  • Zappa C, Mousa SA. 2016. Non-small cell lung cancer: current treatment and future advances. Transl Lung Cancer Res. 5(3):288–300.
  • Zhang W, Wang F, Xu P, Miao C, Zeng X, Cui X, Lu C, Xie H, Yin H, Chen F, et al. 2014. Perfluorooctanoic acid stimulates breast cancer cells invasion and up-regulates matrix metalloproteinase-2/-9 expression mediated by activating NF-kappaB. Toxicol Lett. 229(1):118–125.
  • Zhu YY, Huang HY, Wu YL. 2015. Anticancer and apoptotic activities of oleanolic acid are mediated through cell cycle arrest and disruption of mitochondrial membrane potential in HepG2 human hepatocellular carcinoma cells. Mol Med Rep. 12(4):5012–5018.

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