Piperonal ciprofloxacin hydrazone induces growth arrest and apoptosis of human hepatocarcinoma SMMC-7721 cells

Acta Pharmacologica Sinica

Volumn 33, Issue 2, 2012, Pages 271-278

  Shi, Zhen Yu ^a   Li, Yong Qiang ^a   Kang, Yu Hua ^a   Hu, Guo Qiang ^a   Huang Fu, Chao Shen ^a   Deng, Jin Bo ^a   Bin, Liu ^a  

^a HENAN UNIVERSITY   (China)

Author keywords

anticancer drug; apoptosis; breast adenocarcinoma cells; colon adenocarcinoma cells; fluoroquinolone; hepatocarcinoma cells; mitochondrial membrane potential; piperonal ciprofloxacin hydrazone; topoisomerase II

Indexed keywords

4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL; CASPASE 3; CASPASE 8; CASPASE 9; CYTOCHROME C; DNA; DNA FRAGMENT; DNA TOPOISOMERASE (ATP HYDROLYSING); PIPERONAL CIPROFLOXACIN HYDRAZONE; PLASMID DNA; PROTEIN BAX; PROTEIN BCL 2; PROTEIN P53; QNT 4; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

AGAR GEL ELECTROPHORESIS; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL PROLIFERATION; CELL STRAIN HCT 8; CELL STRAIN MCF 7; CELL STRAIN SMMC 7721; CONTROLLED STUDY; CYTOSOL; CYTOTOXICITY; DNA FRAGMENTATION; DNA STRAND BREAKAGE; DRUG EFFECT; ENZYME ACTIVITY; FLUORESCENCE; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; IC 50; LIVER CELL CARCINOMA; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRION; NICK END LABELING; PROTEIN CLEAVAGE; PROTEIN EXPRESSION; WESTERN BLOTTING;

ADENOCARCINOMA; ANTINEOPLASTIC AGENTS; APOPTOSIS; BREAST NEOPLASMS; CARCINOMA, HEPATOCELLULAR; CELL LINE, TUMOR; CELL PROLIFERATION; CIPROFLOXACIN; COLONIC NEOPLASMS; DNA TOPOISOMERASES, TYPE II; FEMALE; HUMANS; HYDRAZONES; LIVER NEOPLASMS; MEMBRANE POTENTIAL, MITOCHONDRIAL;

EID: 84863163376     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1038/aps.2011.158     Document Type: Article

References (34)

1. Bolon MK. The newer fluoroquinolones. Infect Dis Clin North Am 2009; 23: 1027-51.
2. Bax BD, Chan PF, Eggleston DS, Fosberry A, Gentry DR, Gorrec F, et al. Type IIA topoisomerase inhibition by a new class of antibacterial agents. Nature 2010; 466: 935-40.
3. Rajabalian S, Foroumadi A, Shafee A, Emami S. Functionalized N-(2-oxyiminoethyl) piperazinyl quinolones as new cytotoxic agents. J Pharm Pharm Sci 2007; 10: 153-8.
4. Yamashita Y, Ashizawa T, Morimoto M, Hosomi J, Nakano H. Antitumor quinolones with mammalian topoisomerase II mediated DNA cleavage activity. Cancer Res 1992; 52: 2818-22.
5. Kamat AM, DeHaven JI, Lamm DL. Quinolone antibiotics: a potential adjunct to intravesical chemotherapy for bladder cancer. Urology 1999; 54: 56-61. (Pubitemid 29323333)
6. Koziel R, Szczepanowska J, Magalska A, Piwocka K, Duszynski J, Zablocki K. Ciprofoxacin inhibits proliferation and promotes generation of aneuploidy in Jurkat cells. J Physiol Pharmacol 2010; 61: 233-9.
7. Hawtin RE, Stockett DE, Byl JA, McDowell RS, Nguyen T, Arkin MR, et al. Voreloxin is an anticancer quino lone derivative that intercalates DNA and poisons topoisomerase II. PLoS One 2010; 5: e10186.
8. Foroumadi A, Emami S, Rajabalian S, Badinloo M, Mohammadhosseini N, Shafee A. N-Substituted piperazinyl quinolones as potential cyto-toxic agents: structure-activity relationships study. Biomed Phar-macother 2009; 63: 16-20.
9. Chang YH, Hsu MH, Wang SH, Huang LJ, Qian K, Morris-Natschke SL, et al. Design and synthesis of 2-(3-benzo[b]thienyl)-6,7-methylene-dioxyquinolin-4-one analogues as potent anti tumor agents that inhibit tubulin assembly. J Med Chem 2009; 52: 4883-91.
10. You QD, Li ZY, Huang CH, Yang Q, Wang XJ, Guo QL, et al. Discovery of a novel series of quinolone and naphthyridine derivatives as potential topo isomerase I inhibitors by scaffold modification. J Med Chem 2009; 52: 5649-61.
11. Hu GQ, Wu XK, Wang X, Zhang ZQ, Xie SQ, Huang WL, et al. Synthesis and antitumor activity of C3 heterocyclic-substituted fuoro quinolone derivatives (I): ciprofloxacin aminothiodiazole Schiff-bases. Acta Pharm Sin 2008, 43: 1112-5.
12. Kumar D, Sundaree S, Johnson EO, Shah K. An effcient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents. Bioorg Med Chem Lett 2009; 19: 4492-4.
13. Robinson MJ, Martin BA, Gootz TD, McGuirk PR, Moynihan M, Sutcliffe JA, et al. Effects of quinolone derivatives on eukaryotic topoi some-rase II. A novel mechanism for enhancement of enzyme-medi ated DNA cleavage. J Biol Chem 1991; 266: 14585-92. (Pubitemid 21907543)
14. Pommier Y, Leo E, Zhang H, Marchand C. DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chem Biol 2010; 17: 421-33.
15. Efthimiadou EK, Thomadaki H, Sanakis Y, Raptopoulou CP, Katsaros N, Scorilas A, et al. Structure and biological properties of the copper (II) complex with the quinolone antibacterial drug N-pro-pyl-norfoxacin and 2,2′-bipyridine. J Inorg Biochem 2007; 101: 64-73. (Pubitemid 44895351)
16. DoganKoruznjak J, Slade N, Zamola B, Pavelić K, Karminski-Zamola G. Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno (3′,2′:4,5) thieno (2,3-c) quinolones. Chem Pharm Bull 2002; 50: 656-60. (Pubitemid 41694937)
17. Hammonds TR, Foster SR, Maxwell A. Increased sensitivity to quino-lone antibacterials can be engineered in human topoisomerase II alpha by selective mutagenesis. J Mol Biol 2000; 300: 481-91.
18. Kamat AM, De Haven JI, Lamm DL. A potential adjunct to intravesical chemotherapy for bladder cancer. Urology 1999; 54: 56-61. (Pubitemid 29323333)
19. Elsea SH, Osheroff N, Nitiss JL. Cytotoxicity of quinolones toward eukaryotic cells. Identification of topoisomerase II as the primary cellular target for the quinolone CP-115, 953 in yeast. J Biol Chem 1992; 267: 13150-3.
20. Nitiss JL. Targeting DNA topoisomerase II in cancer chemotherapy. Nat Rev Cancer 2009; 9: 338-50.
21. Elsea SH, McGuirk PR, Gootz TD, Moynihan M, Osheroff N. Drug features that contribute to the activity of quinolones against mammalian topoisomerase II and cultured cells: correlation between enhancement of enzyme-mediated DNA cleavage in vitro and cytotoxic potential. Antimicrob Agents Chemother 1993; 37: 2179-86. (Pubitemid 23298208)
22. Yogeeswari P, Sriram D, Kavya R, Tiwari S. Synthesis and in-vitro cyto toxicity evaluation of gatifoxacin Mannich bases. Biomed Phar-macother 2005; 59: 501-10. (Pubitemid 41642949)
23. Hammonds TR, Foster SR, Maxwell A. Increased sensitivity to quino-lone antibacterials can be engineered in human topoisomerase II alpha by selective mutagenesis. J Mol Biol 2000; 300: 481-91.
24. Sheng Z, Cao X, Peng S, Wang C, Li Q, Wang Y, et al. Ofoxacin induces apoptosis in microencapsulated juvenile rabbit chondrocytes by caspase-8 dependent mitochondrial pathway. Toxicol Appl Pharmacol 2008; 226: 119-27. (Pubitemid 350297341)
25. Smart DJ, Halicka HD, Traganos F, Darzynkiewicz Z, Williams GM. Ciprofoxacin induced G2 arrest and apoptosis in TK6 lymphoblastoid cells is not dependent on DNA double-strand break formation. Cancer Biol Ther 2008; 7: 113-9. (Pubitemid 351590463)
26. Andera L. Signaling activated by the death receptors of the TNFR family. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub 2009; 153: 173-80.
27. Ott M, Norberg E, Zhivotovsky B. Mitochondrial targeting of tBid/Bax: a role for the TOM complex? Cell Death Differ 2009; 16: 1075-82.
28. Xie CY, Zhu H, Lin LP, Miao ZH, Geng MY, Cai YJ, et al. MFTZ-1, an actinomycetes subspecies derived antitumor macrolide, functions as a novel topoisomerase II poison. Mol Cancer Ther 2007; 6: 3059-70. (Pubitemid 350206784)
29. Chen YC, Lu PH, Pan SL, Teng CM, Kuo SC, Lin TP, et al. Quinolone analogue inhibits tubulin polymerization and induces apoptosis via Cdk1-involved signaling pathways. Biochem Pharmacol 2007; 74: 10-9.
30. Hsu SC, Yang JS, Kuo CL, Lo C, Lin JP, Hsia TC, et al. Novel quinolone CHM-1 induces apoptosis and inhibits metastasis in a human ostero-genic sarcoma cell line. J Orthop Res 2009; 27: 1637-44.
31. Patil JB, Kim J, Jayaprakasha GK. Berberine induces apoptosis in breast cancer cells (MCF-7) through mitochondrial-dependent pathway. Eur J Pharmacol 2010; 645: 70-8.
32. Chang YH, Yang JS, Kuo SC, Chung JG. 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 2009; 29: 3139-48.
33. Herold C, Ocker M, Ganslmayer M, Gerauer H, Hahn EG, Schuppan D. Cipro foxacin induces apoptosis and inhibits proliferation of human colo rectal carcinoma cells. Br J Cancer 2002; 86: 443-8. (Pubitemid 34185131)
34. Wang SW, Pan SL, Huang YC, Guh JH, Chiang PC, Huang DY, et al. CHM-1, a novel synthetic quinolone with potent and selective anti-mitotic antitumor activity against human hepatocellular carcinoma in vitro and in vivo. Mol Cancer Ther 2008; 7: 350-60.