N-thioalkylcarbazoles derivatives as new anti-proliferative agents: synthesis, characterisation and molecular mechanism evaluation

References

• Caruso A, Iacopetta D, Puoci F, et al. Carbazole derivatives: a promising scenario for breast cancer treatment. Mini Rev Med Chem 2016;16:630–43.
   PubMed Web of Science ®Google Scholar
• Caruso A, Chimento A, El-Kashef H, et al. Antiproliferative activity of some 1,4-dimethylcarbazoles on cells that express estrogen receptors: Part I. J Enzyme Inhib Med Chem 2012;27:609–13.
   PubMed Web of Science ®Google Scholar
• Gluszynska A. Biological potential of carbazole derivatives. Eur J Med Chem 2015;94:405–26.
   PubMed Web of Science ®Google Scholar
• Carocci A, Catalano A, Sinicropi MS. Melatonergic drugs in development. Clin Pharmacol 2014;6:127–37.
   PubMedGoogle Scholar
• Saturnino C, Iacopetta D, Sinicropi MS, et al. N-Alkyl carbazole derivatives as new tools for Alzheimer's disease: preliminary studies. Molecules 2014;19:9307–17.
   PubMed Web of Science ®Google Scholar
• Zhu D, Chen M, Li M, et al. Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity. Eur J Med Chem 2013;68:81–8.
   PubMed Web of Science ®Google Scholar
• Bashir M, Bano A, Ijaz AS, Chaudhary BA. Recent developments and biological activities of N-substituted carbazole derivatives: a review. Molecules 2015;20:13496–517.
   PubMed Web of Science ®Google Scholar
• Iacopetta D, Rosano C, Puoci F, et al. Multifaceted properties of 1,4-dimethylcarbazoles: Focus on trimethoxybenzamide and trimethoxyphenylurea derivatives as novel human topoisomerase II inhibitors. Eur J Pharmaceut Sci: Off J Eur Feder Pharmaceut Sci 2017;96:263–72.
   PubMed Web of Science ®Google Scholar
• Vann KR, Ergun Y, Zencir S, et al. Inhibition of human DNA topoisomerase IIalpha by two novel ellipticine derivatives. Bioorg Med Chem Lett 2016;26:1809–12.
   PubMed Web of Science ®Google Scholar
• Maji B, Kumar K, Muniyappa K, Bhattacharya S. New dimeric carbazole-benzimidazole mixed ligands for the stabilization of human telomeric G-quadruplex DNA and as telomerase inhibitors. A remarkable influence of the spacer. Org Biomol Chem 2015;13:8335–48.
   PubMed Web of Science ®Google Scholar
• Andrews WJ, Panova T, Normand C, et al. Old drug, new target: ellipticines selectively inhibit RNA polymerase I transcription. J Biol Chem 2013;288:4567–82.
   PubMed Web of Science ®Google Scholar
• Sinicropi MS, Lappano R, Caruso A, et al. Bromo-1,4-dimethyl-9H-carbazol-3-yl-methylene)-hydrazine (carbhydraz) acts as a GPER agonist in breast cancer cells. Curr Top Med Chem 2015;15:1035–42.
   PubMed Web of Science ®Google Scholar
• Parisi OI, Morelli C, Puoci F, et al. Magnetic molecularly imprinted polymers (MMIPs) for carbazole derivative release in targeted cancer therapy. J Mater Chem B 2014;2:6619–25.
   PubMed Web of Science ®Google Scholar
• Stiborova M, Frei E. Ellipticines as DNA-targeted chemotherapeutics. Curr Med Chem 2014;21:575–91.
   PubMed Web of Science ®Google Scholar
• Isah T. Rethinking Ginkgo biloba L.: medicinal uses and conservation. Pharmacogn Rev 2015;9:140–8.
   PubMedGoogle Scholar
• Deane FM, O'Sullivan EC, Maguire AR, et al. Synthesis and evaluation of novel ellipticines as potential anti-cancer agents. Organ Biomol Chem 2013;11:1334–44.
   PubMed Web of Science ®Google Scholar
• Miller CM, O'Sullivan EC, Devine KJ, McCarthy FO. Synthesis and biological evaluation of novel isoellipticine derivatives and salts. Organ Biomol Chem 2012;10:7912–21.
   PubMed Web of Science ®Google Scholar
• Deane FM, O'Sullivan EC, Maguire AR, et al. Synthesis and evaluation of novel ellipticines as potential anti-cancer agents. Org Biomol Chem 2013;11:1334–44.
   PubMed Web of Science ®Google Scholar
• Harding MM, Grummitt AR. 9-hydroxyellipticine and derivatives as chemotherapy agents. Mini Rev Med Chem 2003;3:67–76.
   PubMed Web of Science ®Google Scholar
• Saturnino C, Buonerba M, Boatto G, et al. Synthesis and preliminary biological evaluation of a new pyridocarbazole derivative covalently linked to a thymidine nucleoside as a potential targeted antitumoral agent. I. Chem Pharm Bull (Tokyo) 2003;51:971–4.
   PubMed Web of Science ®Google Scholar
• Caruso A, Voisin-Chiret AS, Lancelot JC, et al. Efficient and simple synthesis of 6-aryl-1,4-dimethyl-9H-carbazoles. Molecules 2008;13:1312–20.
   PubMed Web of Science ®Google Scholar
• Caruso A, Sinicropi MS, Lancelot JC, et al. Synthesis and evaluation of cytotoxic activities of new guanidines derived from carbazoles. Bioorg Med Chem Lett 2014;24:467–72.
   PubMed Web of Science ®Google Scholar
• Sinicropi MS, Caruso A, Conforti F, et al. Synthesis, inhibition of NO production and antiproliferative activities of some indole derivatives. J Enzyme Inhib Med Chem 2009;24:1148–53.
   PubMed Web of Science ®Google Scholar
• Cresteil T, Rault S, Aubert G, Lancelot JC, Caruso A, A. L, inventors. 2012.
   Google Scholar
• Panno A, Sinicropi MS, Caruso A, et al. New trimethoxybenzamides and trimethoxyphenylureas derived from dimethylcarbazole as cytotoxic agents. J Heterocycl Chem 2014;51:E294–302.
   Web of Science ®Google Scholar
• Caruso A, Lancelot JC, El-Kashef H, et al. A rapid and versatile synthesis of novel pyrimido[5,4-b]carbazoles. Tetrahedron 2009;65:10400–5.
   Web of Science ®Google Scholar
• Rizza P, Pellegrino M, Caruso A, et al. 3-(Dipropylamino)-5-hydroxybenzofuro[2,3-f]quinazolin-1(2H)-one (DPA-HBFQ-1) plays an inhibitory role on breast cancer cell growth and progression. Eur J Med Chem 2016;107:275–87.
   PubMed Web of Science ®Google Scholar
• Saturnino C, Caruso A, Longo P, et al. Crystallographic study and biological evaluation of 1,4-dimethyl-N-alkylcarbazoles. Curr Top Med Chem 2015;15:973–9.
   PubMed Web of Science ®Google Scholar
• Galsky MD, Hahn NM, Wong B, et al. Phase 2 trial of the topoisomerase II inhibitor, amrubicin, as second-line therapy in patients with metastatic urothelial carcinoma. Cancer Chemother Pharmacol 2015;76:1259–65.
   PubMed Web of Science ®Google Scholar
• Yao BL, Mai YW, Chen SB, et al. Design, synthesis and biological evaluation of novel 7-alkylamino substituted benzo[a]phenazin derivatives as dual topoisomerase I/II inhibitors. Eur J Med Chem 2015;92:540–53.
   PubMed Web of Science ®Google Scholar
• Andre V, Boissart C, Lechevrel M, et al. Mutagenicity of nitro- and amino-substituted carbazoles in Salmonella typhimurium. I. Monosubstituted derivatives of 9H-carbazole. Mutat Res 1993;299:63–73.
   PubMed Web of Science ®Google Scholar
• Saturnino C, Palladino C, Napoli M, et al. Synthesis and biological evaluation of new N-alkylcarbazole derivatives as STAT3 inhibitors: preliminary study. Eur J Med Chem 2013;60:112–9.
   PubMed Web of Science ®Google Scholar
• Sopkova-de Oliveira Santos J, Caruso A, Lohier JF, et al. 9-Ethyl-1,4-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole and 6-bromo-9-ethyl-1,4-dimethyl-9H-carbazole. Acta Crystallogr C 2008;64:o453–5.
   PubMedGoogle Scholar
• Lohier JF, Caruso A, Sopkova-de Oliveira Santos J, et al. tert-Butyl 6-bromo-1,4-dimethyl-9H-carbazole-9-carboxyl-ate. Acta Crystallogr Sect E Struct Rep Online 2010;66:o1971–2.
   PubMedGoogle Scholar
• Paesano N, Marzocco S, Vicidomini C, et al. Synthesis and biological evaluation of 3-benzyl-1-methyl- and 1-methyl-3-phenyl-isothioureas as potential inhibitors of iNOS. Bioorg Med Chem Lett 2005;15:539–43.
   PubMed Web of Science ®Google Scholar
• Carocci A, Catalano A, Bruno C, et al. N-(Phenoxyalkyl)amides as MT(1) and MT(2) ligands: antioxidant properties and inhibition of Ca(2+)/CaM-dependent kinase II. Bioorg Med Chem 2013;21:847–51.
   PubMed Web of Science ®Google Scholar
• Sirignano E, Saturnino C, Botta A, et al. Synthesis, characterization and cytotoxic activity on breast cancer cells of new half-titanocene derivatives. Bioorg Med Chem Lett 2013;23:3458–62.
   PubMed Web of Science ®Google Scholar
• Sala M, Chimento A, Saturnino C, et al. Synthesis and cytotoxic activity evaluation of 2,3-thiazolidin-4-one derivatives on human breast cancer cell lines. Bioorg Med Chem Lett 2013;23:4990–5.
   PubMed Web of Science ®Google Scholar
• Chimento A, Saturnino C, Iacopetta D, et al. Inhibition of human topoisomerase I and II and anti-proliferative effects on MCF-7 cells by new titanocene complexes. Bioorg Med Chem 2015;23:7302–12.
   PubMed Web of Science ®Google Scholar
• Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248–54.
   PubMed Web of Science ®Google Scholar
• Iacopetta D, Grande F, Caruso A, et al. New insights for the use of quercetin analogs in cancer treatment. Future Med Chem 2017;9:2011–28.
   PubMed Web of Science ®Google Scholar
• Iacopetta D, Lappano R, Cappello AR, et al. SLC37A1 gene expression is up-regulated by epidermal growth factor in breast cancer cells. Breast Cancer Res Treat 2010;122:755–64.
   PubMed Web of Science ®Google Scholar
• Iacopetta D, Mariconda A, Saturnino C, et al. Novel Au and Ag carbene complexes exert anti-tumor effects triggering the ROS-dependent intrinsic apoptotic pathway. ChemMedChem 2017;12:2054–65.
   PubMed Web of Science ®Google Scholar
• Sanchez-Linares I, Perez-Sanchez H, Cecilia JM, Garcia JM. High-throughput parallel blind virtual screening using BINDSURF. BMC Bioinformatics 2012;13(Suppl 14):S13.
   PubMed Web of Science ®Google Scholar
• Pettersen EF, Goddard TD, Huang CC, et al. UCSF Chimera – a visualization system for exploratory research and analysis. J Comput Chem 2004;25:1605–12.
   PubMed Web of Science ®Google Scholar
• Monnot M, Mauffret O, Simon V, et al. DNA-drug recognition and effects on topoisomerase II-mediated cytotoxicity. A three-mode binding model for ellipticine derivatives. J Biol Chem 1991;266:1820–9.
   PubMed Web of Science ®Google Scholar
• Froelich-Ammon SJ, Patchan MW, Osheroff N, Thompson RB. Topoisomerase II binds to ellipticine in the absence or presence of DNA. Characterization of enzyme–drug interactions by fluorescence spectroscopy. J Biol Chem 1995;270:14998–5004.
   PubMed Web of Science ®Google Scholar
• Kizek R, Adam V, Hrabeta J, et al. Anthracyclines and ellipticines as DNA-damaging anticancer drugs: recent advances. Pharmacol. Ther 2012;133:26–39.
   PubMed Web of Science ®Google Scholar
• de Murcia JM, Niedergang C, Trucco C, et al. Requirement of poly(ADP-ribose) polymerase in recovery from DNA damage in mice and in cells. Proc Natl Acad Sci USA 1997;94:7303–7.
   PubMed Web of Science ®Google Scholar
• D'Amours D, Desnoyers S, D'Silva I, Poirier GG. Poly(ADP-ribosyl)ation reactions in the regulation of nuclear functions. Biochem J 1999;342: 249–68.
   PubMed Web of Science ®Google Scholar
• Kaufmann SH, Desnoyers S, Ottaviano Y, et al. Specific proteolytic cleavage of poly(ADP-ribose) polymerase: an early marker of chemotherapy-induced apoptosis. Cancer Res 1993;53:3976–85.
   PubMed Web of Science ®Google Scholar
• Soldani C, Scovassi AI. Poly(ADP-ribose) polymerase-1 cleavage during apoptosis: an update. Apoptosis 2002;7:321–8.
   PubMed Web of Science ®Google Scholar
• Elmore S. Apoptosis: a review of programmed cell death. Toxicol Pathol 2007;35:495–516.
   PubMed Web of Science ®Google Scholar
• Ouyang L, Shi Z, Zhao S, et al. Programmed cell death pathways in cancer: a review of apoptosis, autophagy and programmed necrosis. Cell Prolif 2012;45:487–98.
   PubMed Web of Science ®Google Scholar
• Cullen SP, Martin SJ. Caspase activation pathways: some recent progress. Cell Death Differ 2009;16:935–8.
   PubMed Web of Science ®Google Scholar
• Kadam CY, Abhang SA. Apoptosis markers in breast cancer therapy. Adv Clin Chem 2016;74:143–93.
   PubMed Web of Science ®Google Scholar
• Suen DF, Norris KL, Youle RJ. Mitochondrial dynamics and apoptosis. Genes Dev 2008;22:1577–90.
   PubMed Web of Science ®Google Scholar
• Torre LA, Bray F, Siegel RL, et al. Global cancer statistics, 2012. CA Cancer J Clin 2015;65:87–108.
   PubMed Web of Science ®Google Scholar
• Siegel RL, Miller KD, Jemal A. Cancer statistics, 2016. CA Cancer J Clin 2016;66:7–30.
   PubMed Web of Science ®Google Scholar