In Vitro Cytotoxic Investigation of Some Synthesized 1,6-Disubstituted-1-Azacoumarin Derivatives as Anticancer Agents

References

• Soni JP , DeviP , ChemitikantiSet al. Design, synthesis and in vitro cytotoxic evaluation of β-carboline tethered quinoline-4-carboxamide conjugates as DNA-interactive Topo II inhibitors. J. Mol. Struct.1291, 136001 (2023).
   Web of Science ®Google Scholar
• Adel D , El-AdlK , NasrT , SakrTM , ZagharyW. Pyrazolo[3,4-d]pyrimidine derivatives as EGFRT790M and VEGFR-2 dual TK inhibitors: design, synthesis, molecular docking, ADMET profile and anticancer evaluations. J. Mol. Struct.1291, 136047 (2023).
   Web of Science ®Google Scholar
• Al-Warhi T , AlqahtaniLS , AlsharifGet al. Design, synthesis, and investigation of cytotoxic activity of cis-vinylamide-linked combretastatin analogues as potential anticancer agents. Symmetry14(10), 2088 (2022).
   Google Scholar
• Liu Y , QiY. Vildagliptin, a CD26/DPP4 inhibitor, ameliorates bleomycin-induced pulmonary fibrosis via regulating the extracellular matrix. Int. Immunopharmacol.87, 106774 (2020).
   PubMed Web of Science ®Google Scholar
• Carotenuto P , PecoraroA , PalmaG , RussoG , RussoA. Therapeutic approaches targeting nucleolus in cancer. Cells8(9), 1090 (2019).
   PubMed Web of Science ®Google Scholar
• Sereni MI , BaldelliE , GambaraGet al. Functional characterization of epithelial ovarian cancer histotypes by drug target based protein signaling activation mapping: Implications for personalized cancer therapy. Proteomics15(2–3), 365–373 (2015).
   PubMed Web of Science ®Google Scholar
• Patra P . A concise review on pyridocoumarin/azacoumarin derivatives: synthesis and biological activity. Chemistry Select4(7), 2024–2043 (2019).
   Google Scholar
• Bakare SB . Synthesis and anticancer evaluation of some coumarin and azacoumarin derivatives. Pol. J. Chem. Technol.23(2), 27–34 (2021).
   Web of Science ®Google Scholar
• Eggleston W . Coumarins. In: Reference Module in Biomedical Sciences.Elsevier (2023). www.sciencedirect.com/science/article/pii/B9780128243152005418
   Google Scholar
• Sirizi MAG , AlizadehGhalenoei J , AllahtavakoliM , ForouzanfarH , BagheriSM. Anticancer potential of Ferula assa-foetida and its constituents, a powerful plant for cancer therapy. World J. Biol. Chem.14(2), 28–39 (2023).
   PubMedGoogle Scholar
• Zeng Z , TianR , FengJ , YangN , YuanL. A systematic review on traditional medicine Toddalia asiatica (L.) Lam.: chemistry and medicinal potential. Saudi Pharm. J.29(8), 781–798 (2021).
   PubMed Web of Science ®Google Scholar
• Küpeli Akkol E , GençY , KarpuzB , Sobarzo-SánchezE , CapassoR. Coumarins and coumarin-related compounds in pharmacotherapy of cancer. Cancers12(7), 1959 (2020).
   PubMed Web of Science ®Google Scholar
• El-Deen IM , El-ZendMA , TantawyMA , BarakatLAA. Synthesis and cytotoxicity screening of some synthesized coumarin and aza-coumarin derivatives as anticancer agents. Russ. J. Bioorganic Chem.48(2), 380–390 (2022).
   Web of Science ®Google Scholar
• Sutar SM , SavanurHM , PatilCet al. Synthesis, molecular modelling studies and antimicrobial activity of coumarin and 1-azacoumarin linked 1,2,3-triazole. Chem. Data Collect28, 100480 (2020).
   Google Scholar
• Savanur HM , PawasheGM , KimKM , KalkhambkarRG. Synthesis and molecular modeling studies of coumarin- and 1-aza-coumarin-linked miconazole analogues and their antifungal activity. Chemistry Select3(33), 9648–9653 (2018).
   Google Scholar
• Abu Almaaty AH , ElgrahyNA , FayadEet al. Design, synthesis and anticancer evaluation of substituted cinnamic acid bearing 2-quinolone hybrid derivatives. Molecules26(16), 4724 (2021).
   PubMed Web of Science ®Google Scholar
• El-Aziz RMA , ZakiI , El-DeenIM , Abd-RahmanMS , MohammedFZ. In vitro anticancer evaluation of some synthesized 2H-quinolinone and halogenated 2H-quinolinone derivatives as therapeutic agents. Anticancer Agents Med. Chem.20(18), 2304–2315 (2020).
   PubMed Web of Science ®Google Scholar
• Trifonov AV , GazizovAS , TapalovaASet al. Synthesis and anticancer evaluation of novel 7-aza-coumarine-3-carboxamides. Int. J. Mol. Sci.24(12), 9927 (2023).
   PubMed Web of Science ®Google Scholar
• Sokmen BB , AydinG , GumusAet al. Synthesis, antielastase, antioxidant and radical scavenging activities of 4-(aza substituted) methylene substituted dihydroxy coumarines. J. Enzyme Inhib. Med. Chem.28(4), 870–875 (2013).
   PubMed Web of Science ®Google Scholar
• Abdelhameid MK , ZakiI , MohammedMR , MohamedKO. Design, synthesis, and cytotoxic screening of novel azole derivatives on hepatocellular carcinoma (HepG2 Cells). Bioorganic Chem.101, 103995 (2020).
   PubMed Web of Science ®Google Scholar
• Ghasemi A , KhanzadehT , ZadiHeydarabad Met al. Evaluation of BAX and BCL-2 gene expression and apoptosis induction in acute lymphoblastic leukemia cell line CCRFCEM after high-dose prednisolone treatment. Asian Pac. J. Cancer Prev.19(8), 2319–2323 (2018).
   Google Scholar
• Peña-Blanco A , García-SáezAJ. Bax, Bak and beyond – mitochondrial performance in apoptosis. FEBS J.285(3), 416–431 (2018).
   PubMed Web of Science ®Google Scholar
• Ramadan MA , ShawkeyAE , RabehMA , AbdellatifAO. Expression of P53, BAX, and BCL-2 in human malignant melanoma and squamous cell carcinoma cells after tea tree oil treatment in vitro. Cytotechnology71(1), 461–473 (2019).
   PubMed Web of Science ®Google Scholar
• Venkatachalam P , NadumaneVK. Modulation of Bax and Bcl-2 genes by secondary metabolites produced by Penicillium rubens JGIPR9 causes the apoptosis of cancer cell lines. Mycology12(2), 69–81 (2021).
   Google Scholar
• Mourad MAE , AboElmaaty A , ZakiIet al. Novel topoisomerase II/EGFR dual inhibitors: design, synthesis and docking studies of naphtho[2′,3′:4,5]thiazolo[3,2-a]pyrimidine hybrids as potential anticancer agents with apoptosis inducing activity. J. Enzyme Inhib. Med. Chem.38(1), 2205043 (2023).
   PubMed Web of Science ®Google Scholar
• Skok Ž , ZidarN , KikeljD , IlašJ. Dual inhibitors of human DNA topoisomerase II and other cancer-related targets. J. Med. Chem.63(3), 884–904 (2020).
   PubMed Web of Science ®Google Scholar
• Chen S-F , HuangN-L , LinJ-Het al. Structural insights into the gating of DNA passage by the topoisomerase II DNA-gate. Nat. Commun.9(1), 3085 (2018).
   PubMedGoogle Scholar
• Matias-Barrios VM , RadaevaM , SongYet al. Discovery of new catalytic topoisomerase ii inhibitors for anticancer therapeutics. Front. Oncol.10, 633142 (2021).
   PubMed Web of Science ®Google Scholar
• Okoro CO , FatokiTH. A mini review of novel topoisomerase II inhibitors as future anticancer agents. Int. J. Mol. Sci.24(3), 2532 (2023).
   PubMed Web of Science ®Google Scholar
• Macieja A , KopaP , GalitaG , PastwaE , MajsterekI , PoplawskiT. Comparison of the effect of three different topoisomerase II inhibitors combined with cisplatin in human glioblastoma cells sensitized with double strand break repair inhibitors. Mol. Biol. Rep.46(4), 3625–3636 (2019).
   PubMed Web of Science ®Google Scholar
• Behery ME , El-DeenIM , El-ZendMA , BarakatLAA. Design, synthesis and evaluation the bioactivities of novel 8-methoxy-1-azacoumarin-3-carboxamide derivatives as anti-diabetic agents. J. Mol. Struct.1294, 136486 (2023).
   Google Scholar
• Mohammed FZ , RizzkYW , El-DeenIM , GadEM , El-BeheryM , MahdyARE. Discovery of 2-amino-4H-1,3,4-thiadiazine-5(6H)-one derivatives and their in vitro antitumor investigation. Chemistry Select7(7), e202104333 (2022).
   Google Scholar
• Mourad AAE , RizzkYW , ZakiI , MohammedFZ , El-BeheryM. Synthesis and cytotoxicity screening of some synthesized hybrid nitrogen molecules as anticancer agents. J. Mol. Struct.1242, 130722 (2021).
   Web of Science ®Google Scholar
• Mohammed FZ , RizzkYW , El-DeenIM , MouradAAE , El-BeheryM. Design, synthesis, cytotoxic screening and molecular docking studies of novel hybrid thiosemicarbazone derivatives as anticancer agents. Chem. Biodivers18(12), e2100580 (2021).
   PubMed Web of Science ®Google Scholar
• Rizzk YW , El-DeenIM , MohammedFZ , AbdelhamidMS , KhedrAIM. In vitro antitumor evaluation of some hybrid molecules containing coumarin and quinolinone moieties. Anticancer Agents Med. Chem.19(16), 2010–2018 (2020).
   Web of Science ®Google Scholar
• Wu C-C , LiT-K , FarhLet al. Structural basis of type II topoisomerase inhibition by the anticancer drug etoposide. Science333(6041), 459–462 (2011).
   PubMed Web of Science ®Google Scholar
• Thomsen R , ChristensenMH. MolDock: a new technique for high-accuracy molecular docking. J. Med. Chem.49(11), 3315–3321 (2006).
   PubMed Web of Science ®Google Scholar
• Gaber A , AlsanieWF , AlhomraniM , AlamriAS , El-DeenIM , RefatMS. Synthesis and characterization of some new coumarin derivatives as probable breast anticancer MCF-7 drugs. Crystals11(5), 565 (2021).
   Web of Science ®Google Scholar
• Sherif MH , YossefAM. Synthesis and anticancer evaluation of some fused coumarino-[4,3-d]-pyrimidine derivatives. Res. Chem. Intermed.41(1), 383–390 (2015).
   Web of Science ®Google Scholar
• Jingwen B , YaochenL , GuojunZ. Cell cycle regulation and anticancer drug discovery. Cancer Biol. Med.14(4), 348 (2017).
   PubMed Web of Science ®Google Scholar
• Kouroshnia A , ZeinaliS , IraniS , SadeghiA. Induction of apoptosis and cell cycle arrest in colorectal cancer cells by novel anticancer metabolites of Streptomyces sp. 801. Cancer Cell Int.22(1), 235 (2022).
   PubMed Web of Science ®Google Scholar
• Mukherjee S , MitraI , ReddyVPet al. Effect of Pt(II) complexes on cancer and normal cells compared to clinically used anticancer drugs: cell cycle analysis, apoptosis and DNA/BSA binding study. J. Mol. Liq.247, 126–140 (2017).
   Web of Science ®Google Scholar
• Abbady AQ , TwairA , AliB , MuradH. Characterization of annexin V fusion with the superfolder GFP in liposomes binding and apoptosis detection. Front. Physiol.8, 317 (2017).
   PubMed Web of Science ®Google Scholar
• Fink SL , CooksonBT. Apoptosis, pyroptosis, and necrosis: mechanistic description of dead and dying eukaryotic cells. Infect. Immun.73(4), 1907–1916 (2005).
   PubMed Web of Science ®Google Scholar
• Lakshmanan I , BatraS. Protocol for apoptosis assay by flow cytometry using annexin V staining method. BIO-Protoc.3(6), 1–3 (2013).
   PubMedGoogle Scholar
• Brentnall M , Rodriguez-MenocalL , DeGuevara RL , CeperoE , BoiseLH. Caspase-9, caspase-3 and caspase-7 have distinct roles during intrinsic apoptosis. BMC Cell Biol.14(1), 32 (2013).
   PubMedGoogle Scholar
• Shim MK , YoonHY , LeeSet al. Caspase-3/-7-specific metabolic precursor for bioorthogonal tracking of tumor apoptosis. Sci. Rep.7(1), 16635 (2017).
   PubMedGoogle Scholar
• Radwan EM , Abo-ElabassE , AbdEl-Baky AEet al. Unveiling the antitumor potential of novel N-(substituted-phenyl)-8-methoxycoumarin-3-carboxamides as dual inhibitors of VEGFR2 kinase and cytochrome P450 for targeted treatment of hepatocellular carcinoma. Front. Chem.11, 1231030 (2023).
   PubMed Web of Science ®Google Scholar
• Terefe EM , GhoshA. Molecular docking, validation, dynamics simulations, and pharmacokinetic prediction of phytochemicals isolated from croton dichogamus against the HIV-1 reverse transcriptase. Bioinforma. Biol. Insights16, 117793222211256 (2022).
   Web of Science ®Google Scholar
• Meng X-Y , ZhangH-X , MezeiM , CuiM. Molecular docking: a powerful approach for structure-based drug discovery. Curr. Comput. Aided-Drug Des.7(2), 146–157 (2011).
   PubMed Web of Science ®Google Scholar
• Pantsar T , PosoA. Binding affinity via docking: fact and fiction. Molecules23(8), 1899 (2018).
   PubMed Web of Science ®Google Scholar