Cytotoxic Activity, Apoptosis Induction and Cell Cycle Arrest in Human Breast Cancer (MCF7) Cells by a Novel Fluorinated Tetrahydro-[1,2,4]Triazolo[3,4-a]Isoquinolin Chalcones

References

• Jacques Ferlay, Isabelle Soerjomataram, Rajesh Dikshit, Sultan Eser, Colin Mathers, Marise Rebelo, Donald Maxwell Parkin, David Forman, and Freddie Bray, “Cancer Incidence and Mortality Worldwide: Sources, Methods and Major Patterns in GLOBOCAN 2012,” International Journal of Cancer 136, no. 5 (2015): E359–386.
   PubMed Web of Science ®Google Scholar
• N. S. Khan, P. Khan, M. F. Ansari, S. Srivastava, G. M. Hasan, M. Husain, and M. I. Hassan, “Thienopyrimidine-Chalcone Hybrid Molecules Inhibit Fas-Activated Serine/Threonine Kinase: An Approach to Ameliorate Antiproliferation in Human Breast Cancer Cells,” Molecular Pharmaceutics 15, no. 9 (2018): 4173–89.
   PubMed Web of Science ®Google Scholar
• V. R. Solomon, and H. Lee, “Anti-Breast Cancer Activity of Heteroaryl Chalcone Derivatives,” Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie 66, no. 3 (2012): 213–20.
   PubMed Web of Science ®Google Scholar
• Zsuzsanna Rozmer, and Pál Perjési, “Naturally Occurring Chalcones and Their Biological Activities,” Phytochemistry Reviews 15, no. 1 (2016): 87–120.
   Web of Science ®Google Scholar
• E. J. Park, H. R. Park, J. S. Lee, and J. Kim, “Licochalcone A: An Inducer of Cell Differentiation and Cytotoxic Agent from Pogostemon Cablin,” Planta Medica 64, no. 5 (1998): 464–6.
   PubMed Web of Science ®Google Scholar
• H. H. Ko, L. T. Tsao, K. L. Yu, C. T. Liu, J. P. Wang, and C. N. Lin, “Structure-Activity Relationship Studies on Chalcone Derivatives: The Potent Inhibition of Chemical Mediators Release,” Bioorganic & Medicinal Chemistry 11, no. 1 (2003): 105–11.(02)00312-7.
   PubMed Web of Science ®Google Scholar
• G.-F. Yang, and X. Huang, “Development of Quantitative Structure-Activity Relationships and Its Application in Rational Drug Design,” Current Pharmaceutical Design 12, no. 35 (2006): 4601–11.
   PubMed Web of Science ®Google Scholar
• U. K. Jain, R. K. Bhatia, A. R. Rao, R. Singh, A. K. Saxena, and I. Sehar, “Design and Development of Halogenated Chalcone Derivatives as Potential Anticancer Agents,” Tropical Journal of Pharmaceutical Research 13, no. 1 (2014): 73–80.
   Web of Science ®Google Scholar
• T. A. Dias, C. L. Duarte, C. F. Lima, M. F. Proença, and C. Pereira-Wilson, “Superior Anticancer Activity of Halogenated Chalcones and Flavonols over the Natural Flavonol Quercetin,” European Journal of Medicinal Chemistry 65 (2013): 500–10.
   PubMed Web of Science ®Google Scholar
• J. Jasril, I. Ikhtiarudin, A. Zamri, H. Y. Teruna, and N. Frimayanti, “New Fluorinated Chalcone and Pyrazoline Analogs: Synthesis, Docking, and Molecular Dynamic Studies as Anticancer Agents,” Thai Journal of Pharmaceutical Sciences 41, no. 3 (2017): 93–8.
   Google Scholar
• S. Fulda, and K. Debatin, “Extrinsic versus Intrinsic Apoptosis Pathways in Anticancer Chemotherapy,” Oncogene 25, no. 34 (2006): 4798–811.
   PubMed Web of Science ®Google Scholar
• Nouria Al-Awadi, Ismail Abdelhamid, Ismail Abdelhamid, Alya Al-Etaibi, and Mohamed Elngadi, “Gas-Phase Pyrolysis in Organic Synthesis: Rapid Green Synthesis of 4-Quinolinones,” Synlett 2007, no. 14 (2007): 2205–8.
   Google Scholar
• N. A. Al-Awadi, M. R. Ibrahim, I. A. Abdelhamid, and M. H. Elnagdi, “Arylhydrazonals as the Aldehyde Component in Baylis-Hillman Reactions,” Tetrahedron 64, no. 35 (2008): 8202–5.
   Web of Science ®Google Scholar
• E. S. Darwish, I. A. Abdelhamid, M. A. Nasra, F. M. Abdel-Gallil, and D. H. Fleita, “A One-Pot Biginelli Synthesis of 6-Unsubstituted 5-Aroylpyrimidin-2(1H)- Ones and 6-Acetyl-1,2,4-Triazin-3(2H)-Ones,” Helvetica Chimica Acta 93, no. 6 (2010): 1204–8.
   Web of Science ®Google Scholar
• M. F. Mohamed, M. S. Mohamed, S. a Shouman, M. M. Fathi, and I. A. Abdelhamid, “Synthesis and Biological Evaluation of a Novel Series of Chalcones Incorporated Pyrazole Moiety as Anticancer and Antimicrobial Agents,” Applied Biochemistry and Biotechnology 168, no. 5 (2012): 1153–62.
   PubMed Web of Science ®Google Scholar
• S. K. Salama, M. F. Mohamed, A. F. Darweesh, A. H. M. Elwahy, and I. A. Abdelhamid, “Molecular Docking Simulation and Anticancer Assessment on Human Breast Carcinoma Cell Line Using Novel Bis(1,4-Dihydropyrano[2,3-c]Pyrazole-5-Carbonitrile) and bis(1,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-b]pyridine-6-carbonitrile) derivatives,” Bioorganic Chemistry 71 (2017): 19–29.
   PubMed Web of Science ®Google Scholar
• M. F. Mohamed, N. S. Ibrahim, A. H. M. Elwahy, and I. A. Abdelhamid, “Molecular Studies on Novel Antitumor Bis 1,4-Dihydropyridine Derivatives against Lung Carcinoma and Their Limited Side Effects on Normal Melanocytes,” Anti-Cancer Agents in Medicinal Chemistry 18, no. 15 (2018): 2156–68.
   PubMed Web of Science ®Google Scholar
• M. F. Mohamed, A. M. Abdelmoniem, A. H. M. Elwahy, and I. A. Abdelhamid, “DNA Fragmentation, Cell Cycle Arrest, and Docking Study of Novel Bis Spiro-Cyclic 2-Oxindole of Pyrimido[4,5-b]Quinoline-4,6-Dione Derivatives against Breast Carcinoma,” Current Cancer Drug Targets 18, no. 4 (2018): 372–81.
   PubMed Web of Science ®Google Scholar
• M. F. Mohamed, H. M. Hassaneen, and I. A. Abdelhamid, “Cytotoxicity, Molecular Modeling, Cell Cycle Arrest, and Apoptotic Induction Induced by Novel Tetrahydro-[1,2,4]Triazolo[3,4-a]Isoquinoline Chalcones,” European Journal of Medicinal Chemistry 143, no. 1 (2018): 532–41.
   PubMedGoogle Scholar
• M. F. Mohamed, A. A. Saddiq, T. M. Al-Shaikh, N. S. Ibrahim, and I. A. Abdelhamid, “Computational Studies and Sever Apoptotic Bioactivity of New Heterocyclic Cyanoacrylamide Based P-Fluorophenyl and p-Phenolic Compounds against Liver Carcinoma (Hepg2),” Bioorganic Chemistry 114 (2021): 105147.
   PubMed Web of Science ®Google Scholar
• G. H. Mansour, M. A. El-Magd, D. H. Mahfouz, I. A. Abdelhamid, M. F. Mohamed, N. S. Ibrahim, A. Hady A. Abdel Wahab, and E. M. Elzayat, “Bee Venom and Its Active Component Melittin Synergistically Potentiate the Anticancer Effect of Sorafenib against HepG2 Cells,” Bioorganic Chemistry 116, no. February (2021): 105329.
   PubMedGoogle Scholar
• N. M. Elwan, H. A. Abdelhadi, T. A. Abdallah, and H. M. Hassaneen, “Synthesis of [1,2,4]Triazolo[3,4-a]Isoquinolines and Pyrrolo[2,1-a]Isoquinolines Using α-Keto Hydrazonoyl Halides,” Tetrahedron 52, no. 10 (1996): 3451–6.
   Web of Science ®Google Scholar
• H. M. Hassaneen, H. M. E. Hassaneen, Y. S. Mohammed, and R. M. Pagni, “Synthesis, Reactions and Antibacterial Activity of 3-Acetyl[1,2,4]Triazolo[3,4-a]Isoquinoline Derivatives Using Chitosan as Heterogeneous Catalyst under Microwave Irradiation,” Zeitschrift Für Naturforschung B 66, no. 3 (2011): 299–310.
   Google Scholar
• L. J. Michelini, M. R. C. Castro, J. M. F. Custodio, L. F. N. Naves, W. F. Vaz, G. S. Lobón, F. T. Martins, C. N. Perez, and H. B. Napolitano, “A Novel Potential Anticancer Chalcone: Synthesis, Crystal Structure and Cytotoxic Assay,” Journal of Molecular Structure 1168 (2018): 309–15.
   Web of Science ®Google Scholar
• H. Zhang, J. J. Liu, J. Sun, X. H. Yang, T. T. Zhao, X. Lu, H. Bin Gong, and H. L. Zhu, “Design, Synthesis and Biological Evaluation of Novel Chalcone Derivatives as Antitubulin Agents,” Bioorganic & Medicinal Chemistry 20, no. 10 (2012): 3212–8.
   PubMed Web of Science ®Google Scholar
• C. Jin, Y. J. Liang, H. He, and L. Fu, “Synthesis and Antitumor Activity of Novel Chalcone Derivatives,” Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie 67, no. 3 (2013): 215–7.
   PubMed Web of Science ®Google Scholar
• X. Fang, B. Yang, Z. Cheng, M. Yang, N. Su, L. Zhou, and J. Zhou, “Synthesis and Antitumor Activity of Novel Nitrogen Mustard-Linked Chalcones,” Archiv Der Pharmazie 346, no. 4 (2013): 292–9.
   PubMed Web of Science ®Google Scholar
• D. A. Gschwend, A. C. Good, and I. D. Kuntz, “Molecular Docking towards Drug Discovery,” Journal of Molecular Recognition 9, no. 2 (1996): 175–86.
   PubMed Web of Science ®Google Scholar
• K. Yamane, K. Tateishi, R. J. Klose, J. Fang, L. A. Fabrizio, H. Erdjument-Bromage, J. Taylor-Papadimitriou, P. Tempst, and Y. Zhang, “Article PLU-1 is an H3K4 Demethylase Involved in Transcriptional Repression and Breast Cancer Cell Proliferation,” Molecular Cell 25, no. 6 (2007): 801–12.
   PubMed Web of Science ®Google Scholar
• Q. Zhang, Y. Yoshimatsu, J. Hildebrand, S. M. Frisch, and R. H. Goodman, “Homeodomain Interacting Protein Kinase 2 Promotes Apoptosis by Downregulating the Transcriptional Corepressor CtBP,” Cell 115, no. 2 (2003): 177–86.(03)00802-X.
   PubMed Web of Science ®Google Scholar
• L. F. B. Bortolotto, F. R. Barbosa, G. Silva, T. A. Bitencourt, R. O. Beleboni, S. J. Baek, M. Marins, and A. L. Fachin, “Cytotoxicity of Trans-Chalcone and Licochalcone a against Breast Cancer Cells is Due to Apoptosis Induction and Cell Cycle Arrest,” Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie 85 (2017): 425–33.
   PubMed Web of Science ®Google Scholar
• H. Gil, D. Koh, Y. Lim, Y. Han, and S. Young, “The Synthetic Chalcone Derivative 2-Hydroxy-3',5,5'-Trimethoxychalcone Induces Unfolded Protein Response-Mediated Apoptosis in A549 Lung Cancer Cells,” Bioorganic & Medicinal Chemistry Letters 28, no. 17 (2018): 2969–75.
   PubMed Web of Science ®Google Scholar
• F.-F. Gan, R. Zhang, H.-L. Ng, M. Karuppasamy, W. Seah, W. H. Yeap, S.-M. Ong, E. Hadadi, S.-C. Wong, W.-K. Chui, et al. “Novel Dual-Targeting anti-Proliferative Dihydrotriazine-Chalcone Derivatives Display Suppression of Cancer Cell Invasion and Inflammation by Inhibiting the NF-κB Signaling Pathway,” Food and Chemical Toxicology : An International Journal Published for the British Industrial Biological Research Association 116, no. Pt B (2018): 238–48.
   PubMedGoogle Scholar
• Y.-Q. Zhang, Z.-H. Wen, K. Wan, D. Yuan, X. Zeng, G. Liang, J. Zhu, B. Xu, and H. Luo, “A Novel Synthesized 3', 5'-Diprenylated Chalcone Mediates the Proliferation of Human Leukemia Cells by Regulating Apoptosis and Autophagy Pathways,” Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie 106 (2018): 794–804.
   PubMed Web of Science ®Google Scholar
• Y. L. Hsu, P. L. Kuo, W. S. Tzeng, and C. C. Lin, “Chalcone Inhibits the Proliferation of Human Breast Cancer Cell by Blocking Cell Cycle Progression and Inducing Apoptosis,” Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association 44, no. 5 (2006): 704–13.
   PubMed Web of Science ®Google Scholar
• Z. A. Wani, A. S. Pathania, G. Mahajan, A. Behl, M. J. Mintoo, S. K. Guru, A. Viswanath, F. Malik, A. Kamal, and D. M. Mondhe, “Anticancer Activity of a Novel Quinazolinone-Chalcone Derivative through Cell Cycle Arrest in Pancreatic Cancer Cell Line,” Journal of Solid Tumors 5, no. 2 (2015): 73–85.
   Google Scholar
• M. Perro, S. Cravo, R. T. Lima, M. H. Vasconcelos, M. S. José, A. M. S. Silva, M. Pinto, H. Cidade, and A. G. Corrêa, “Bioorganic & Medicinal Chemistry Solid-Phase Synthesis of 2’-Hydroxychalcones. Effects on Cell Growth Inhibition, Cell Cycle and Apoptosis of Human Tumor Cell Lines,” Bioorganic and Medicinal Chemistry 20, no. 1 (2012): 25–33.
   PubMedGoogle Scholar
• R. Romagnoli, F. Prencipe, L. C. Lopez-Cara, P. Oliva, S. Baraldi, P. G. Baraldi, F. Estévez-Sarmiento, J. Quintana, and F. Estévez, “Synthesis and Biological Evaluation of Alpha-Bromoacryloylamido Indolyl Pyridinyl Propenones as Potent Apoptotic Inducers in Human Leukaemia Cells,” Journal of Enzyme Inhibition and Medicinal Chemistry 33, no. 1 (2018): 727–42.
   PubMed Web of Science ®Google Scholar
• M. J. Ramaiah, S. N. C. V. L. Pushpavalli, G. R. Krishna, P. Sarma, D. Mukhopadhyay, A. Kamal, U. Bhadra, and M. P. Bhadra, “Chalcone-Imidazolone Conjugates Induce Apoptosis through DNA Damage Pathway by Affecting Telomeres,” Cancer Cell International 11 (2011): 11.
   PubMed Web of Science ®Google Scholar
• R. De Vincenzo, C. Ferlini, M. Distefano, C. Gaggini, A. Riva, E. Bombardelli, P. Morazzoni, P. Valenti, F. Belluti, F. O. Ranelletti, et al. “In Vitro Evaluation of Newly Developed Chalcone Analogues in Human Cancer Cells,” Cancer Chemother Pharmacol 46, no. 4 (2000): 305–12.
   PubMed Web of Science ®Google Scholar