Novel ferrocenyl-containing N-acetyl-2-pyrazolines inhibit in vitro angiogenesis and human lung cancer growth by interfering with F-actin stress fiber polimeryzation

References

• Aepfelbacher M, Essler M, Huber E, et al. (1997). Bacterial toxins block endothelial wound repair. Evidence that Rho GTPases control cytoskeletal reorganization in migrating endothelial cells. Arterioscler Thromb Vasc Biol 17:1623–9
   PubMed Web of Science ®Google Scholar
• Alderden RA, Mellor HR, Modok S, et al. (2006). Cytotoxic efficacy of an anthraquinone linked platinum anticancer drug. Biochem Pharmacol 71:1136–45
   PubMed Web of Science ®Google Scholar
• Ansari FL, Nazira S, Noureenb H, Mirzab B. (2005). Combinatorial synthesis and antibacterial evaluation of an indexed chalcone library. Chem Biodivers 2:1656–64
   PubMed Web of Science ®Google Scholar
• Banday AH, Mira BP, Lonea IH, et al. (2010). Studies on novel D-ring substituted steroidal pyrazolines as potential anticancer agents. Steroids 75:805–9
   PubMed Web of Science ®Google Scholar
• Bhat TA, Singh RP. (2008). Tumor angiogenesis a potential target in cancer chemoprevention. Food Chem Toxicol 46:1334–45
   PubMed Web of Science ®Google Scholar
• Bijman MNA, van Berkel MPA, van Nieuw Amerongen GP, Boven E. (2008). Interference with actin dynamics is superior to disturbance of microtubule function in the inhibition of human ovarian cancer cell motility. Biochem Pharmacol 76:707–16
   PubMed Web of Science ®Google Scholar
• Bostancioğlu RB, Işik K, Genc H, et al. (2012a). Studies on the cytotoxic, apoptotic, and antitumoral effects of Au(III), Pt(II) complexes of 1,10-phenanthroline on V79 379A and A549 cell lines. J Enzym Inhib Med Chem 27:458–66
   PubMed Web of Science ®Google Scholar
• Bostancioğlu RB, Kürkçüoğlu M, Başer KHC, Koparal AT. (2012b). Assessment of anti-angiogenic and anti-tumoral potentials of Origanum onites L. essential oil. Food Chem Toxicol 50:2002–8
   PubMed Web of Science ®Google Scholar
• Budakoti A, Abid M, Azam A. (2006). Synthesis and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3,5-diphenyl-2-pyrazoline derivatives and their Pd(II) complexes. Eur J Med Chem 41:63–70
   PubMed Web of Science ®Google Scholar
• Chavain N, Biot C. (2010). Organometallic complexes: new tools for chemotherapy. Curr Med Chem 17:2729–45
   PubMed Web of Science ®Google Scholar
• Chen HH, Zhou HJ, Fang X. (2003). Inhibition of human cancer cell line growth and human umbilical vein endothelial cell angiogenesis by artemisinin derivatives in vitro. Pharmacol Res 48:231–6
   PubMed Web of Science ®Google Scholar
• Chou JJ, Li H, Salvesen GS, et al. (1999). Solution structure of BID, an intracellular amplifier of apoptotic signaling. Cell 96:615–24
   PubMed Web of Science ®Google Scholar
• Congiu C, Onnis V, Vesci L, et al. (2010). Synthesis and in vitro antitumor activity of new 4,5-dihydropyrazole derivatives. Bioorgan Med Chem 18:6238–48
   PubMed Web of Science ®Google Scholar
• Csámpai A, Györfi AZ, Túrós Gy. I, Sohar P. (2009). Application of Biginelli reaction to the synthesis of ferrocenylpyrimidones and [3]-ferrocenophane-containing pyrimido[4,5-d]pyrimidinediones. Organomet Chem 694:3667–73
   Web of Science ®Google Scholar
• D’Amore PA, Thompson RW. (1987). Mechanisms of angiogenesis. Annu Rev Physiol 49:453–64
   PubMed Web of Science ®Google Scholar
• D’amato RJ, Loughnan MS, Flynn E, Folkman J. (1994). Thalidomide is an inhibitor of angiogenesis. Proc Natl Acad Sci U S A 91:4082–5
   PubMed Web of Science ®Google Scholar
• Durand PM, Coetzer TL. (2008). Utility of computational methods to identify the apoptosis machinery in unicellular eukaryotes. Bioinform Biol Insights 2:101–17
   PubMedGoogle Scholar
• Fang J, Jin Z, Li Z, Liu W. (2003). Synthesis, structure, and antibacterial activities of novel ferrocenyl-containing 1-phenyl-3-ferrocenyl-4-triazolyl-5-aryl-dihydropyrazole derivatives. J Organomet Chem 674:1–9
   Web of Science ®Google Scholar
• Folkman J. (1971). Tumor angiogenesis: therapeutic applications. New Engl J Med 285:1182–6
   PubMed Web of Science ®Google Scholar
• Folkman J. (1995). Angiogenesis in cancer, vascular, rheumatoid and other disease. Nat Med 1:27–30
   PubMed Web of Science ®Google Scholar
• Gasser G, Metzler-Nolte N. (2012). The potential of organometallic complexes in medicinal chemistry. Curr Opin Chem Biol 16:84–91
   PubMed Web of Science ®Google Scholar
• Gasser G, Ott I, Metzler-Nolte N. (2011). Organometallic anticancer compounds. J Med Chem 54:3–25
   PubMed Web of Science ®Google Scholar
• Griffioen AW, Molema G. (2000). Angiogenesis: potentials for pharmacologic intervention in the treatment of cancer, cardiovascular diseases, and chronic inflammation. Pharmacol Rev 52:237–68
   PubMed Web of Science ®Google Scholar
• Gu Y, Zhang HY, Zhang HJ, et al. (2006). 8-Cloro-adenosine inhibits growth at least partly by interfering with actin polimeryzation in cultured human lung cancer cells. Biochem Pharm 72:541–50
   PubMed Web of Science ®Google Scholar
• Havrylyuk D, Zimenkovsky B, Vasylenko O, et al. (2009). Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity. Eur J Med Chem 44:1396–404
   PubMed Web of Science ®Google Scholar
• Huang L-J, Shih M-L, Chen H-S, et al. (2006). Synthesis of N2-(substituted benzyl)-3-(4-methylphenyl)indazoles as novel anti-angiogenic agents. Bioorg Med Chem 14:528–36
   PubMed Web of Science ®Google Scholar
• Hueso-Falcón I, Giron N, Velasco P, et al. (2010). Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives. Bioorgan Med Chem 18:1724–35
   PubMed Web of Science ®Google Scholar
• Ihde DC. (1992). Chemotherapy of lung cancer. N Engl J Med 327:1434–41
   PubMed Web of Science ®Google Scholar
• Jeong TS, Kim KS, An S, et al. (2004). Novel 3,5-diaryl pyrazolines as human acyl-CoA:cholesterol acyltransferase inhibitors. Bioorg Med Chem Lett 14:2715–17
   PubMed Web of Science ®Google Scholar
• Karadayı N, Turgut Cin G, Demirel S, et al. (2009). 1-Acetyl-5-ferrocenyl-3-phenyl-2-pyrazoline. Acta Cryst Sec E E65:m127–8
   Google Scholar
• Klimova T, Klimova EI, Martinez Garcia M, et al. (2001). Stereoselectivity of formation of polycyclic ferrocenyl-4,5-dihydropyrazoles based on E- and Z-s-cis-α,β-enones. J Organomet Chem 628:107–13
   Web of Science ®Google Scholar
• Koparal AT, Ulus G, Zeytinoğlu M, et al. (2010). Angiogenesis inhibition by a lichen compound olivetoric acid. Phytother Res 24:754–8
   PubMed Web of Science ®Google Scholar
• Krill D, Madden J, Huncik K, Moeller PD. (2010). Induced thyme product prevents VEGF-induced migration in human umbilical vein endothelial cells. Biochem Bioph Res Commun 403:275–81
   PubMed Web of Science ®Google Scholar
• Li W, Chan S, Guo DJ, et al. (2009). Water extract of Rheum officinale Baill. Induces apoptosis in human lung adenocarcinoma A549 and human breast cancer MCF-7 cell lines. J Ethnopharmacol 124:251–6
   PubMed Web of Science ®Google Scholar
• Li Y, Sun W-G, Liu H-K, et al. (2011). γ-Tocotrienol inhibits angiogenesis of human umbilical vein endothelia cell induced by cancer cell. J Nutr Biochem 22:1127–36
   PubMed Web of Science ®Google Scholar
• Liu J, Liu T, Dai H, et al. (2006). Synthesis, structure, and biological activity studies of 2-[(1H-1,2,4-triazol-1-yl)methyl]-1-aryl)-3-ferrocenyl prop-2-en-1-one derivatives. Appl Organomet Chem 20:610–14
   Web of Science ®Google Scholar
• Mazur I, Anhlan D, Mitzner D, et al. (2008). The proapoptotic influenza A virus protein PB1-F2 regulates viral polymerase activity by interaction with the PB1 protein. Cell Microbiol 10:1140–52
   PubMed Web of Science ®Google Scholar
• Moon DO, Kim MO, Nam TJ, et al. (2010). Pectenotoxin-2 induces G2/M phase cell cycle arrest in human breast cancer cells via ATM and Chk1/2-mediated phosphorylation of cdc25C. Oncol Rep 24:271–6
   PubMed Web of Science ®Google Scholar
• Mossman T. (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Met 65:55–63
   PubMed Web of Science ®Google Scholar
• Niu J, Mo Q, Wang H, et al. (2012). Invasion inhibition by a MEK inhibitor correlates with the actin-based cytoskeleton in lung cancer A549 cells. Biochem Biop Res Commun 422:80–8
   PubMed Web of Science ®Google Scholar
• Ornelas C. (2011). Application of ferrocene and its derivatives in cancer research. New J Chem 35:1973–85
   Web of Science ®Google Scholar
• Ouchi N, Kobayashi H, Kiahara S, et al. (2004). Adiponectin stimulates angiogenesis by promoting cross-talk between AMP-activated protein kinase and Akt signaling in endothelial cell. J Biol Chem 279:1304–9
   PubMed Web of Science ®Google Scholar
• Özdemir Z, Kandilci HB, Gümüşel B, et al. (2007a). Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur J Med Chem 42:373–9
   PubMed Web of Science ®Google Scholar
• Özdemir A, Turan-Zitouni G, Kaplancıklı ZA, et al. (2007b). Synthesis of some 4-arylidenamino-4H-1,2,4-triazole-3-thiols and their antituberculosis activity. Eur J Med Chem 42:403–9
   PubMed Web of Science ®Google Scholar
• Pardakhty A, Varshosaz J, Rouholamini A. (2007). In vitro study of polyoxyethylene alkyl ether niosomes for delivery of insulin. Int J Pharm 328:130–41
   PubMed Web of Science ®Google Scholar
• Patra M, Gasser G, Metzler-Nolte N. (2012). Small organometallic compounds as antibacterial agents. Dalton Trans 41:6350–8
   PubMed Web of Science ®Google Scholar
• Raju H, Chandrappa S, Ramakrishna MK, et al. (2010). Synthesis, characterization, and anti-angiogenic effects of novel 5-amino pyrazole derivatives on Ehrlich ascites tumor [EAT] cells in-vivo. J Cancer Ther 1:1–9
   Google Scholar
• Roux C, Biot C. (2012). Ferrocene-based antimalarials. Future Med Chem 4:783–97
   PubMed Web of Science ®Google Scholar
• Rubin LL, Hall DE, Porter S, et al. (1991). A cell culture model of the blood-brain barrier. J Cell Biol 115:1725–35
   PubMed Web of Science ®Google Scholar
• Shaharyar M, Abdullah MM, Bakht MA, Majeed J. (2010). Pyrazoline bearing benzimidazoles: search for anticancer agent. Eur J Med Chem 45:114–19
   PubMed Web of Science ®Google Scholar
• Top S, Dauer B, Vaissermann J, Jaouen G. (1997). Facile route to ferrocifen, 1-[4-(2-dimethylaminoethoxy)]-1-(phenyl-2-ferrocenyl-but-1-ene), first organometallic analogue of tamoxifen, by the McMurry reaction. J Organomet Chem 541:355–61
   Web of Science ®Google Scholar
• Top S, Tang J, Vessieres A, et al. (1996). Ferrocenyl hydroxytamoxifen: a prototype for a new range of oestradiol receptor site-directed cytotoxics. Chem Commun 82:955–6
   Google Scholar
• Top S, Vessieres A, Cabestaing C, et al. (2001). Studies on organometallic selective estrogen receptor modulators. (SERMs) Dual activity in the hydroxy-ferrocifen series. J Organomet Chem 637:500–6
   Web of Science ®Google Scholar
• Top S, Vessieres A, Leclercq G, et al. (2003). Synthesis, biochemical properties and molecular modelling studies of organometallic specific estrogen receptor modulators (SERMs), the ferrocifens and hydroxyferrocifens: evidence for an antiproliferative effect of hydroxyferrocifens on both hormone-dependent and hormone-independent breast cancer cell lines. J Chem Eur 9:5223–36
   PubMed Web of Science ®Google Scholar
• Tsai AC, Pan SL, Liao CH, et al. (2010). Moscatilin, a bibenzyl derivative from the India orchid Dendrobrium loddigesii, suppresses tumor angiogenesis and growth in vitro and in vivo. Cancer Lett 292:163–70
   PubMed Web of Science ®Google Scholar
• Turgut Cin G, Demirel S, Karadayı N, Büyükgüngör O. (2008). 1-Acetyl-5-ferrocenyl-3-phenyl-2-pyrazoline. Acta Cryst Sec E E64:m514–5
   Google Scholar
• Turgut Cin G, Demirel S, Çakıcı A. (2011). Synthesis of novel ferrocenyl-containing pyrazolo[4,3-c]quinolines. J Organomet Chem 696:613–21
   Web of Science ®Google Scholar
• Turgut Cin G, Demirel S, Çakıcı A, et al. (2012). Synthesis, crystal structure and thermal properties of N-acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline and N-acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline. J Chem Crystallogr 42:372–80
   Web of Science ®Google Scholar
• van Zandwijk N, Giaccone G. (1996). Treatment of metastatic non-small cell lung cancer. Curr Opin Oncol 8:120–5
   PubMedGoogle Scholar
• Wu X, Tiekink ER, Kostetski I, et al. (2006). Antiplasmodial activity of ferrocenyl chalcones: investigations into the role of ferrocene. Eur J Pharm Sci 17:175–87
   Google Scholar
• Xie YS, Pan X-H, Zhao B-X, et al. (2008). Synthesis, structure characterization, and preliminary biological evaluation of novel 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-α]pyrazin-4(5H)-one derivatives. J Organomet Chem 693:1367–74
   Web of Science ®Google Scholar
• Xie Y-S, Zhao H-L, Su H, et al. (2010). Synthesis, single-crystal characterization, and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-α]pyrazin-4(5H)-one derivatives. Eur J Med Chem 45:210–8
   PubMed Web of Science ®Google Scholar
• Zora M, Görmen M. (2007). Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1-chlorovinyl)ferrocene with hydrazines. J Organomet Chem 692:5026–32
   Web of Science ®Google Scholar
• Zora M, Velioğlu Ö. (2008). Synthesis of ferrocenyl quinolines. J Organomet Chem 693:2159–62
   Web of Science ®Google Scholar
• Zsoldos-Mády V, Csámpai A, Szabó R, et al. (2006). Synthesis, structure, and in vitro antitumor activity of some glycoside derivatives of ferrocenyl-chalcones and ferrocenyl-pyrazolines. Chem Med Chem 1:1119–25
   Google Scholar