Original Article. Study of the cytotoxic/toxic potential of the novel anticancer selenodiazoloquinolone on fibroblast cells and 3D skin model

Jantová, Soňa; Topoľská, Dominika; Janošková, Michaela; Pánik, Miroslav; Milata, Viktor

doi:10.1515/intox-2016-0014

Abstract

The new synthetically prepared quinolone derivative 7-ethyl 9-ethyl-6-oxo-6,9-dihydro[1,2,5]selenadiazolo [3,4-h]quinoline-7-carboxylate (E2h) showed in our previous study cytotoxic effects towards tumor cells and immunomodulatory activities on RAW 264.7 cell line murine macrophages. E2h may have a potential use as a novel chemotherapeutic agent with immunomodulatory properties and the ability to induce apoptotic death of cancer cells. The aim of the present study was to examine the antiproliferative/cytotoxic activities of E2h on human non-cancer fibroblast BHNF-1 cells and reconstructed human epidermis EpiDerm™. Further the effects of E2h on tissue structure and morphology were examined. Cytotoxic/toxic studies showed that selenadiazoloquinolone is not toxic on normal human fibroblast cells BHNF-1 and dimensional skin constructs EpiDerm™. Evaluation of morphological changes in EpiDerm™ showed no change in the construction and morphology of skin tissue treated by E2h compared to control.

References

Adams M, Mahringer A, Kunert O, Fricker G, Efferth T, Bauer R. (2007). Cytotoxicity and p-glycoprotein modulating eff ects of quinolones and indoloquinazolines from the Chinese herb Evodia rutaecarpa. Planta Med 73: 1554-1557.
Search in Google Scholar Back to article
Asoh K, Kohchi M, Hyoudoh I, Ohtsuka T, Masubuchi M, Kawasaki K, Ebiike H, Shiratori Y, Fukami T, Kondoh O, Tsukaguchi T, Ishii N, Aoki Y, Shimma N, Sakaitani M. (2009). Synthesis and structure-activity relationships of novel benzofuran farnesyltransferase inhibitors. Bioorg Med Chem Lett 19: 1753-1757.
Search in Google Scholar Back to article
Azema J, Guidetti B, Dewelle J, Le Calve B, Mijatovic T, Korolyov A, Vaysse J, Malet-Martino M, Martino R, Kiss R. (2009). 7-((4-Substituted)piperazin-1-yl) derivatives of ciprofl oxacin: Synthesis and in vitro biological evaluation as potential antitumor agents. Bioorg Med Chem 17: 5396-5407.
Search in Google Scholar Back to article
Barbieriková Z, Bella M, Lietava J, Dvoranová D, Staško A, Füzik T, Milata V, Jantová S, Brezová V. (2011a). Spectroscopic characterization and photoinduced processes of 4-oxoquinoline derivatives. J Photochem Photobiol A: Chemistry 224: 123-134.10.1016/j.jphotochem.2011.09.015
Search in Google Scholar Back to article
Barbierikova Z, Bella M, Kučerák J, Milata V, Jantová S, Dvoranová D, Veselá M, Staško A, Brezová V. (2011b). Photoinduced Superoxide Radical Anion and Singlet Oxygen Generation in the Presence of Novel Selenadiazoloquinolones (An EPR Study). Photochem Photobiol 87: 32-44.10.1111/j.1751-1097.2010.00832.x21073477
Search in Google Scholar Back to article
Barbieriková Z, Bella, M, Sekeráková Ľ, Lietava J, Bobeničová M, Dvoranová D, Milata V, Sádecká J, Mercheková D, Topoľská D, Heizer T, Hudec R, Czimerová A, Jantová S, Brezová V. (2013). Spectroscopic characterization, photoinduced processes and cytotoxic properties of substituted N-ethyl selenadiazoloquinolones. J Phys Org Chem 26: 565-574.
Search in Google Scholar Back to article
Bella M, Milata V. (2014). Synthesis of 9-ethyl[1,2,5]selenadiazolo[3,4-h]quinolones by the application of modifi ed Gould-Jacobs reaction to N-ethyl-2,1,3-benzoselenadiazol-4-amine. Arcivoc (v), 181-198.
Search in Google Scholar Back to article
Dalhoff A, (2005). Immunomodulatory activities of fl uoroquinolones. Infection 33: 55-70. Dalhoff A, Shalit I. (2003). Immunomodulatory eff ects of quinolones. Lancet Infect. Dis. 3: 359-371.
Search in Google Scholar Back to article
Darque A, Dumetre A, Hutter S, Casano G, Robin M, Pannecouque C, Azas N. (2009). Synthesis and biological evaluation of new heterocyclic quinolinones as anti-parasite and anti-HIV drug candidates. Bioorg Med Chem Lett 19: 5962-5964.
Search in Google Scholar Back to article
Drlica K, Zhao X. (1997). DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev 61: 377-392.
Search in Google Scholar Back to article
Drygin D, Siddiqui-Jain A, O’Brien S, Schwaebe M, Lin A, Bliesath J, Ho C, Proffi tt C, Trent K, Whitten J, Lim J, Von Hoff D, Anderes K, Rice W. (2009). Anticancer activity of CX-3543: a direct inhibitor of rRNA biogenesis. Cancer Res 69: 7653-7661.
Search in Google Scholar Back to article
Foroumadi A, Emami S, Rajabalian S, Badinloo M, Mohammadhosseini N, Shafiee A. (2009). N-Substituted piperazinyl quinolones as potential cytotoxic agents: structure-activity relationships study. Biomed Pharmacother 63: 216-220.
Search in Google Scholar Back to article
George S, Pili R. (2013). Tasquinimod: a novel angiogenesis inhibitor-development in prostate cancer. Curr Oncol Rep 15: 65-68.
Search in Google Scholar Back to article
Golub A, Yakovenko O, Bdzhola V, Sapelkin V, Zien P, Yarmoluk S. (2006). Evaluation of 3-carboxy-4(1H)-quinolones as inhibitors of human protein kinase CK2. J Med Chem 49: 6443-6450.
Search in Google Scholar Back to article
Hadjeri M, Peiller E, Beney C, Deka N, Lawson M, Dumontet C, Boumendjel A, (2004). Antimitotic activity of 5-hydroxy-7-methoxy-2-phenyl-4-quinolones. J Med Chem 47: 4964-4970.
Search in Google Scholar Back to article
Huang L, Hsieh M, Teng C, Lee K, Kuo S. (1998). Synthesis and antiplatelet activity of phenyl quinolones. Bioorg Med Chem 6: 1657-1662.
Search in Google Scholar Back to article
Chang Y, Yang J, Kuo S, Chung J. (2009). Induction of mitotic arrest and apoptosis by a novel synthetic quinolone analogue, CWC-8, via intrinsic and extrinsic apoptotic pathways in human osteogenic sarcoma U-2 OS cells. Anticancer Res 29: 3139-3148.
Search in Google Scholar Back to article
Chou L., Yang J, Huang L, Wu H, Lu C, Chiang J, Chen K, Kuo S, Chung J. (2009). The synthesized 2-(2-fl uorophenyl)-6,7-methylenedioxyquinolin-4-one (CHM-1) promoted G2/M arrest through inhibition of CDK1 and induced apoptosis through the mitochondrial-dependent pathway in CT-26 murine colorectal adenocarcinoma cells. J Gastroenterol 44: 1055-1063.
Search in Google Scholar Back to article
Chung DT, Tsai CY, Chen SJ, Chang LW, King CHR, Hsu CH, Chiu KM, Tan HC, Chang YT, Hsu MC. (2010). Multiple-dose safety, tolerability, and pharmacokinetics of oral nemonoxacin (TG-873870) in healthy volunteers. Antimicrobiol Agents Chemother 54: 411-417.
Search in Google Scholar Back to article
Jantová S, Letašiová S, Koňariková K, Milata V, Brezová V. (2010). Eff ect of new synthetically prepared quinolone ethyl-1,4-dihydro-8-nitro-4-oxoquinoline-3-carboxylate on human leukemia cell line HL-60 without/with presence of UVA irradiation. Acta Chimica Slovaca 3: 51-72.
Search in Google Scholar Back to article
Jantová S, Koňariková K, Letašiová S, Paulovičová E, Milata V, Brezová V. (2011). Photochemical and phototoxic properties of ethyl 1,4-dihydro-8- nitro-4-oxoquinoline-3-carboxylate, a new quinolone derivative. J Photochem Photobiol B - Biology 102: 77-91.
Search in Google Scholar Back to article
Jantová S, Mrvová N, Hudec R, Sedlák J, Pánik M, Milata V. (2016a) Pro-apoptotic eff ect of new quinolone 7- ethyl 9-ethyl-6-oxo-6,9-dihydro[1,2,5] selenadiazolo[3,4-h]quinoline-7-carboxylate on cervical cancer cell line HeLa alone/with UVA irradiation. Toxicol in Vitro 33: 35-44.10.1016/j.tiv.2016.02.01226916084
Search in Google Scholar Back to article
Jantová S, Paulovičová E, Paulovičová L, Topoľská D, Pánik M, Milata V. (2016b) The eff ects of novel selenadiazoloquinolone derivative on cancer cell proliferation, apoptosis and immunomodulatory activities. Cell Biol Toxicol [Accepted in Press].
Search in Google Scholar Back to article
Khodursky A, Zechiedrich E, Cozzarelli N. (1995). Topoisomerase IV is a target of quinolones in Escherichia coli. Proc Nat Acad Sci USA 92: 11801-11805.
Search in Google Scholar Back to article
Letašiová S, Jantová S, Čipák Ľ, Múčková M. (2006). Berberine-antiproliferative activity in vitro and induction of apoptosis/necrosis of the U937 and B16 cells. Cancer Lett 239: 254-262.
Search in Google Scholar Back to article
Medeiros B, Landau H, Morrow M, Lockerbie R, Pitts T, Eckhardt S. (2007). The farnesyl transferase inhibitor, tipifarnib, is a potent inhibitor of the MDR1 gene product, P-glycoprotein, and demonstrates signifi cant cytotoxic synergism against human leukemia cell lines. Leukemia 21(4): 739-46.
Search in Google Scholar Back to article
Meyer E, Schwab F, Gastmeier P, Ruden H, Heininger A. (2007). Antifungal use in intensive care units. J Antimicrobiol Chemother 60: 619-624.
Search in Google Scholar Back to article
Oriel J. (1989). Use of quinolones in chlamydial infection. Rev Infect Dis 11: S1273-S1276.
Search in Google Scholar Back to article
Riesbeck K. (2002). Immunomodulating activity of quinolones: review. J Chemother 14: 3-12.
Search in Google Scholar Back to article
Santos F, Abreu P, Castro H, Paixão I, Cirne-Santos C, Giongo V, Barbosa J, Simonetti B, Garrido V, Bou-Habib D, Silva D, Batalha P, Temerozo J, Souza T, Nogueira C, Cunha A, Rodrigues C, Ferreira V, de Souza M. (2009). Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives. Bioorg Med Chem 17: 5476-5481.
Search in Google Scholar Back to article
Sharma PC, Jain A, Jain S. (2009). Fluoroquinolone antibacterials: a review on chemistry, microbiology and therapeutic prospects. Acta Pol Pharm 66: 587-604.
Search in Google Scholar Back to article
Sheng Z, Cao X, Peng S, Wang C, Li Q, Wang Y, Liu M. (2008). Ofl oxacin induces apoptosis in microencapsulated juvenile rabbit chondrocytes by caspase-8-dependent mitochondrial pathway. Toxicol Appl Pharmacol 226: 119-127.
Search in Google Scholar Back to article
Sokolova G, Kunichan AD, Lazareva YV. (2009). Levofl oxacin (Tavanic) in complex therapy of tuberculosis. Antibiot Khimioter 54: 31-37.
Search in Google Scholar Back to article
Tawfik AF, Shoeb HA, Bishop SJ, Al-Shammary FJ, Shbl AM. (1990). Infl uence of new quinolones on normal immune capabilities. J Chemother 2: 300-3005.
Search in Google Scholar Back to article
Vinayaka AC, Sadashiva MP, Wu X, Biryukov SS, Stoute JA, Rangappa KS, Gowda DC. (2014). Facile synthesis of antimalarial odiazoloquinolone on fi - broblasts and skin model 1,2-disubstituted 4-quinolones from 1,3-bisarylmonothio-1,3-diketones. Org Biomol Chem 12: 8555-8561.
Search in Google Scholar Back to article
Xia Y, Yang Z, Xia P, Hackl T, Hamel E, Mauger A, Wu J, Lee K. (2001). Antitumoragents. 211. Fluorinated 2-phenyl-4-quinolone derivatives as antimitotic antitumor agents. J Med Chem 44: 3932-3936.
Search in Google Scholar Back to article
Xiao ZP, Li HQ, Shi L, Lv PC, Song ZC, Zhu HL. (2008). Synthesis, antiproliferative activity, and structure-activity relationships of 3-aryl-1H-quinolin-4- ones. Chem Med Chem 3: 1077-1082.
Search in Google Scholar Back to article
Yamashita Y, Ashizawa T, Morimoto M, Hosomi J, Nakano H. (1992). Antitumor quinolones with mammalian topoisomerase II mediated DNA cleavage activity. Cancer Res 52: 2818-2822.
Search in Google Scholar Back to article
You Q, Li Z, Huang C, Yang Q, Wang X, Guo Q, Chen X, He X, Li T, Chern J. (2009). Discovery of a novel series of quinolone and naphthyridine derivatives as potential topoisomerase I inhibitors by Scaff old modifi cation. J Med Chem 52: 5649-5661.
Search in Google Scholar Back to article

Original Article. Study of the cytotoxic/toxic potential of the novel anticancer selenodiazoloquinolone on fibroblast cells and 3D skin model

Abstract

Paradigm

My account