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Chloroquine Urea Derivatives: Synthesis and Antitumor Activity in Vitro Cover

Chloroquine Urea Derivatives: Synthesis and Antitumor Activity in Vitro

Open Access
|Oct 2018

References

  1. 1. T. L. Lemke, D. A. Williams, V. F. Roche and S. W. Zito, Foye’s Principles of Medicinal Chemistry, 6th ed., Wolters Kluwer (Health)/Lippincott Williams & Wilkins, Philadelphia 2008.
  2. 2. E. Hempelmann, Hemozoin biocrystallization in Plasmodium falciparum and the antimalarial activity of crystallization inhibitors, Parasitol. Res. 100 (2007) 671-676; https://doi.org/10.1007/s00436-006-0313-x10.1007/s00436-006-0313-x17111179
  3. 3. C. Verbaanderd, H. Maes, M. B. Schaaf, V. P. Sukhatme, P. Pantziarka, V. Sukhatme, P. Agostinis and G. Bouche, Repurposing drugs in oncology (ReDO) - chloroquine and hydroxychloroquine as anti-cancer agents, eCancer 11 (2017) Article ID 781; https://doi.org/10.3332/ecancer.2017.78110.3332/ecancer.2017.781571803029225688
  4. 4. H. Monma, Y. Iida, T. Moritani, T. Okimoto, R. Tanino, Y. Tajima and M. Harada, Chloroquine augments TRAIL-induced apoptosis and induces G2/M phase arrest in human pancreatic cancer cells, PLoS One 13 (2018) Article ID e0193990; https://doi.org/10.1371/journal.pone.019399010.1371/journal.pone.0193990584181129513749
  5. 5. V. R. Solomon and H. Lee, Chloroquine and its analogs: A new promise of an old drug for effective and safe cancer therapies, Eur. J. Pharmacol. 625 (2009) 220-233; https://doi.org/10.1016/j.ejphar.2009.06.06310.1016/j.ejphar.2009.06.06319836374
  6. 6. A. K. Abdel- Aziz, S. Shouman, E. El-Demerdash, M. Elgendy and A. B. Abdel-Naim, Chloroquine as a promising adjuvant chemotherapy together with sunitinib, Sci. Proc. 1 (2014) Article ID e384;https://doi.org/10.14800/sp.38410.14800/sp.384
  7. 7. F. Liu, Y. Shang and S-Z. Chen, Chloroquine potentiates the anti-cancer effect of lidamycin on non-small cell lung cancer cells in vitro, Acta Pharmacol. Sin. 35 ( 2014) 6 45-652; https://doi.org/10.1038/aps.2014.310.1038/aps.2014.3481403824727941
  8. 8. A. R. Choi, J. H. Kim, Y. H. Woo, H. S. Kim and S. Yoon, Anti-malarial drugs primaquine and chloroquine have different sensitization effects with anti-mitotic drugs in resistant cancer cells, Anticancer Res. 36 (2016) 1641-1648.10.21873/anticanres.11171
  9. 9. A. Ganguli, D. Choudhury, S. Datta, S. Bhattacharya and G. Chakrabarti, Inhibition of autophagy by chloroquine potentiates synergistically anti-cancer property of artemisinin by promoting ROS dependent apoptosis, Biochimie 107 (2014) 338-349; https://doi.org/10.1016/j.biochi.2014.10.00110.1016/j.biochi.2014.10.00125308836
  10. 10. L. Liu, C. Han, H. Yu, W. Zhu, H. Cui, L. Zheng, C. Zhang and L. Yue, Chloroquine inhibits cell growth in human A549 lung cancer cells by blocking autophagy and inducing mitochondrialmediated apoptosis, Oncol. Rep. 39 (2018) 2807-2816; https://doi.org/10.3892/or.2018.636310.3892/or.2018.636329658606
  11. 11. F. Wang, J. Tang, P. Li, S. Si, H. Yu, X. Yang, J. Tao, Q. Lv, M. Gu, H. Yang and Z. Wang, Chloroquine enhances the radiosensitivity of bladder cancer cells by inhibiting autophagy and activating apoptosis, Cell. Physiol. Biochem. 45 (2018) 54-66; https://doi.org/10.1159/00048622210.1159/00048622229316551
  12. 12. J. M. Mulcahy Levy, S. Zahedi, A. M. Griesinger, A. Morin, K. D. Davies, D. L. Aisner, B. K. Kleinschmidt- DeMasters, B. E. Fitzwalter, M. L. Goodall, J. Thorburn, V. Amani, A. M. Donson, D. K. Birks, D. M. Mirsky, T. C. Hankinson, M. H. Handler, A. L. Green, R. Vibhakar, N. K. Foreman and A. Thorburn, Autophagy inhibition overcomes multiple mechanisms of resistance to BRAF inhibition in brain tumors, eLife 6 (2017) Article ID e19671; https://doi.org/10.7554/eLife.19671.00110.7554/eLife.19671.001
  13. 13. T. Kimura, Y. Takabatake, A. Takahashi and Y. Isaka, Chloroquine in cancer therapy: A doubleedged sword of autophagy, Cancer Res. 73 (2013) 3-7; https://doi.org/10.1158/0008-547210.1158/0008-5472.CAN-12-2464
  14. 14. S. Edaye, D. Tazoo, D. Scott Bohle and E. Georges, 3-Halo chloroquine derivatives overcome Plasmodium falciparum chloroquine resistance transporter-mediated drug resistance in P. falciparum, Antimicrob. Agents Chemother. 59 (2015) 7891-7893; https://doi.org/10.1128/AAC.01139-1510.1128/AAC.01139-15464915626438496
  15. 15. S-J. Yeo, D-X. Liu, H. S. Kim and H. Park, Anti-malarial effect of novel chloroquine derivatives as agents for the treatment of malaria, Malaria J. 16 (2017) Article ID 80 (9 pages); https://doi.org/10.1186/s12936-017-1725-z10.1186/s12936-017-1725-z531621328212631
  16. 16. O. M. Yvette, S. F. Malan, D. Taylor, E. Kapp and J. Joubert, Adamantane amine-linked chloroquinoline derivatives as chloroquine resistance modulating agents in Plasmodium falciparum, Bioorg. Med. Chem. Lett. 28 (2018) 1287-1291; https://doi.org/10.1016/j.bmcl.2018.03.02610.1016/j.bmcl.2018.03.02629559277
  17. 17. E. A. Hall, J. E. Ramsey, Z. Peng, D. Hayrapetyan, V. Shkepu, B. O’Rourke, W. Geiger, K. Lam and C. F. Verschraegen, Novel organometallic chloroquine derivative inhibits tumor growth, J. Cell.Biochem. (2018) (in press); https://doi.org/10.1002/jcb.2678710.1002/jcb.2678729575007
  18. 18. C. Teixeira, N. Vale, B. Pérez, A. Gomes, J. R. Gomes, P. Gomes, “Recycling” classical drugs for malaria, Chem. Rev. 114 (2014) 11164-11220; https://doi.org/10.1021/cr500123g10.1021/cr500123g25329927
  19. 19. V. R. Solomon, C. Hu and H. Lee, Design and synthesis of chloroquine analogs with anti-breast cancer property, Eur. J. Med. Chem. 45 (2010) 3916-3923; https://doi.org/10.1016/j.ejmech.2010.05.04610.1016/j.ejmech.2010.05.04620561720
  20. 20. B. C. Pérez, I. Fernandes, N. Mateus, C. Teixeira and P. Gomes, Recycling antimalarial leads for cancer: Antiproliferative properties of N-cinnamoyl chloroquine analogues, Bioorg. Med. Chem. Lett. 23 (2013) 6769-6772; https://doi.org/10.1016/j.bmcl.2013.10.02510.1016/j.bmcl.2013.10.02524184076
  21. 21. M. Quiliano, A. Pabón, E. Moles, L. Bonilla-Ramirez, I. Fabing, K. Y. Fong, D. A. Nieto-Aco, D. W. Wright, J. C. Pizarro, A. Vettorazzi, A. López de Cerain, E. Deharo, X. Fernández-Busquets, G. Garavito, I. Aldana and S. Galiano, Structure-activity relationship of new antimalarial 1-aryl- 3-susbtituted propanol derivatives: Synthesis, preliminary toxicity profiling, parasite life cycle stage studies, target exploration, and targeted delivery, Eur. J. Med. Chem. 152 (2018) 489-514;https://doi.org/10.1016/j.ejmech.2018.04.03810.1016/j.ejmech.2018.04.03829754074
  22. 22. F. M. Ferguson and N. S. Gray, Kinase inhibitors: the road ahead, Nature Rev. Drug Discov. 17 (2018) 353-377; https://doi.org/10.1038/nrd.2018.2110.1038/nrd.2018.2129545548
  23. 23. V. Reddy, Organofluorine Compounds in Biology and Medicine, 1st ed., Elsevier, Amsterdam 2015.10.1016/B978-0-444-53748-5.00001-0
  24. 24. B. Meunier, A. Robert, O. Dechy-Cabaret and F. Benoit-Vical, Dual Molecules Containing a Peroxide Derivative, Synthesis and Therapeutic Applications thereof, U. S. Pat. 20040038957A1, 26 Feb 2004.
  25. 25. I. Kalčić, M. Zovko, M. Jadrijević-Mladar Takač, B. Zorc and I. Butula, Synthesis and reactions of some azolecarboxylic acid derivatives, Croat. Chem. Acta 76 (2003) 217-228.
  26. 26. Z. Rajić, D. Hadjipavlou-Litina, E. Pontiki, M. Kralj, L. Šuman and B. Zorc, The novel ketoprofen amides - Synthesis and biological evaluation as antioxidants, lipoxygenase inhibitors and cytostatic agents, Chem. Biol. Drug. Des. 75 (2010) 641-652; https://doi.org/10.1111/j.1747-0285.2010.00963.x10.1111/j.1747-0285.2010.00963.x20337784
  27. 27. L. Uzelac, Đ. Škalamera, K. Mlinarić-Majerski, N. Basarić and M. Kralj, Selective photocytotoxicity of anthrols on cancer stem-like cells: the effect of quinone methides or reactive oxygen species, Eur. J. Med. Chem. 137 (2017) 558-574; https://doi.org/10.1016/j.ejmech.2017.05.06310.1016/j.ejmech.2017.05.06328633106
  28. 28. Chemicalize, 2017, ChemAxon Ltd., Budapest, Hungary; available from https://chemicalize.com/
DOI: https://doi.org/10.2478/acph-2018-0039 | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075
Language: English
Page range: 471 - 483
Submitted on: Sep 11, 2018
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Accepted on: Sep 14, 2018
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Published on: Oct 3, 2018
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year
Related subjects:

© 2018 Kristina Pavić, Zrinka Rajić, Zvonimir Mlinarić, Lidija Uzelac, Marijeta Kralj, Branka Zorc, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.