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1-(7-Chloroquinolin-4-yl)-2-[(1H-pyrrol-2-yl)methylene]hydrazine: a potent compound against cancer

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Abstract

Heteroaromatic derivatives (3a–f) have been synthesized and evaluated for their activity against four cancer cell lines. Among the studied compounds, 1-(7-Chloroquinolin-4-yl)-2-[(1H-pyrrol-2-yl)methylene]hydrazine (3e) exhibited an excellent cytotoxic activity against the referred lines, and especially on melanoma cells (MDAMB-435). In this case, compound 3e is four times more active than the standard substance Doxorubicin. Together with other results from our group, 7-chloro-4-quinolinylhydrazones derived from chloroquine could be considered a relevant finding toward the rational design of new leads for antitumor compounds.

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References

  • Ahmed SA, Gogal RM Jr, Walsh JE (1994) A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes: An alternative to [3H]thymidine incorporation assay. J Immunol Methods 170:211–224

    Article  PubMed  CAS  Google Scholar 

  • Augustijns P, Geusens P, Verbeke N (1992) Chloroquine levels in blood during chronic treatment of patients with rheumatoid arthritis. Eur J Clin Pharmacol 42:429–433

    PubMed  CAS  Google Scholar 

  • Chuandong F, Wang W, Zhao B, Zhang S, Miao J (2006) Chloroquine inhibits cell growth and induces cell death in A549 lung cancer cells. Bioorg Med Chem 14:3218–3222. doi:10.1016/j.bmc.2005.12.035

    Article  Google Scholar 

  • Fattorusso C, Campiani G, Kukreja G, Persico M, Butini S, Romano MP, Altarelli M, Ros S, Brindisi M, Savini L, Novellino E, Nacci V, Fattorusso E, Parapini S, Basilico N, Taramelli D, Yardley V, Croft S, Borriello M, Gemma S (2008) Design, synthesis, and structure-activity relationship studies of 4-quinolinyl- and 9-acrydinylhydrazones as potent antimalarial agents. J Med Chem 51:1333–1343. doi:10.1021/jm7012375

    Article  PubMed  CAS  Google Scholar 

  • Ferreira ML, Gonçalves RSB, Cardoso LNF, Kaiser CR, Candéa ALP, Henriques MGO, Lourenço MCS, Bezerra FAFM, Souza MVN (2010) Synthesis and antitubercular activity of heteroaromatic isonicotinoyl and 7-chloro-4-quinolinyl hydrazone derivatives. TheScientificWorldJOURNAL 10:1347–1355. doi:10.1100/tsw.2010.124

    Article  CAS  Google Scholar 

  • Foley M, Tilley L (1998) Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents. Pharmacol Ther 79:55–87. doi:10.1016/S0163-7258(98)00012-6

    Article  PubMed  CAS  Google Scholar 

  • Font M, Monge A, Ruiz I, Heras B (1997) Structure-activity relationships in quinoline Reissert derivatives with HIV-1 reverse transcriptase inhibitory activity. Drug Des Discov 14:259–272

    PubMed  CAS  Google Scholar 

  • Kaminsky D, Meltzer RI (1968) Quinolone antibacterial agents: Oxolinic acid and related compounds. J Med Chem 11:160–163. doi:10.1021/jm00307a041

    Article  PubMed  CAS  Google Scholar 

  • Kim EL, Wüstenberg R, Rübsam A, Schmitz-Salue C, Warnecke G, Bücker EM, Pettkus N, Speidel D, Rohde V, Schulz-Schaeffer W, Deppert W, Giese A (2010) Chloroquine activates the p53 pathway and induces apoptosis in human glioma cells. Neuro Oncol 12:389–400

    Article  PubMed  CAS  Google Scholar 

  • Krause W, Jordan A, Scholz R, Jimenez JLM (2005) Iodinated nitroimidazoles as radiosensitizers. Anticancer Res 25:2145–2151

    PubMed  CAS  Google Scholar 

  • Montenegro RC, Lotufo LV, Moraes MO, Pessoa CO, Rodrigues FAR, Bispo MLF, Cardoso LNF, Kaiser CR, Souza MVN (2011) Synthesis and antitumoral evaluation of 7-chloro-4-quinolinylhydrazones derivatives. Med Chem 7:599–604

    Article  PubMed  CAS  Google Scholar 

  • Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Podeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski J (2006) Antifungal properties of new series of quinoline derivatives. Bioorg Med Chem 14:3592–3598. doi:10.1016/j.bmc.2006.01.016

    Article  PubMed  CAS  Google Scholar 

  • Savarino A, Di Trani L, Donatelli I, Cauda R, Cassone A (2006) New insights into the antiviral effects of chloroquine. Lancet Infect Dis 6:67–69

    Article  PubMed  Google Scholar 

  • Sharma P, Sharma JD (2001) In vitro hemolysis of human erythrocytes—by plant extracts with antiplasmodial activity. J Ethnopharmacol 74:239–243

    Article  PubMed  CAS  Google Scholar 

  • Sloboda AE, Powell D, Poletto JF, Pickett WC, Gibbons JJJr, Bell DH, Oronsky AL, Kerwar SS (1991) Antiinflammatory and antiarthritic properties of a substituted quinoline carboxylic acid: CL 306, 293. J Rheumatol 18:855–860

    PubMed  CAS  Google Scholar 

  • Warshakoon NC, Sheville J, Bhatt RT, Ji W, Mendez-Andino JL, Meyers KM, Kim N, Wos JA, Mitchell C, Paris JL, Pinney BB, Reizes O, Hu XE (2006) Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents. Bioorg Med Chem Lett 16:5207–5211

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Instituto de Tecnologia em Fármacos-Far Manguinhos, Fundação Oswaldo Cruz, Rua Sizenando Nabuco, 100, Manguinhos, Rio de Janeiro, RJ, 21041-250, Brazil

    Marcelle de Lima Ferreira Bispo, Camila Cataldi de Alcantara & Marcus Vinícius Nora de Souza

  2. Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, CP 68563, Rio de Janeiro, RJ, 21945-970, Brazil

    Marcelle de Lima Ferreira Bispo & Carlos Roland Kaiser

  3. Laboratório de Oncologia Experimental, Universidade Federal do Ceará, Fortaleza, CE, Brazil

    Letícia Veras Lotufo, Manoel Odorico de Moraes, Cláudia do Ó. Pessoa & Felipe Augusto Rocha Rodrigues

  4. Laboratório de Genética Humana e Médica, Universidade Federal do Pará, Belém, PA, Brazil

    Raquel Carvalho Montenegro

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  1. Raquel Carvalho Montenegro
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  2. Letícia Veras Lotufo
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  3. Manoel Odorico de Moraes
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  4. Cláudia do Ó. Pessoa
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  5. Felipe Augusto Rocha Rodrigues
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  6. Marcelle de Lima Ferreira Bispo
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  7. Camila Cataldi de Alcantara
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  8. Carlos Roland Kaiser
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  9. Marcus Vinícius Nora de Souza
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Correspondence to Marcus Vinícius Nora de Souza.

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Montenegro, R.C., Lotufo, L.V., de Moraes, M.O. et al. 1-(7-Chloroquinolin-4-yl)-2-[(1H-pyrrol-2-yl)methylene]hydrazine: a potent compound against cancer. Med Chem Res 21, 3615–3619 (2012). https://doi.org/10.1007/s00044-011-9894-8

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  • DOI: https://doi.org/10.1007/s00044-011-9894-8

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