Have a personal or library account? Click to login
Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides Cover

Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides

Open Access
|Mar 2019

References

  1. 1. G. Padmanaban and P. N. Rangarajan, Heme metabolism of Plasmodium is a major antimalarial target, Biochem. Biophys. Res. Commun. 268 (2000) 665–668; https://doi.org/10.1006/bbrc.1999.189210.1006/bbrc.1999.189210679261
  2. 2. C. Even, S. Friedman and K. Lamouar, Bipolar disorder after mefloquine treatment, J. Psychiatry Neurosci. 26 (2001) 252–253.
  3. 3. F. de Pilla Varotti, A. C. C. Botelho, A. A. Andrade, R. C. de Paula, E. M. S. Fagundes, A. Valverde, L. M. U. Mayer, J. S. Mendonça, M. V. N. de Souza, N. Boechat and A. U. Krettli, Synthesis, antimalarial activity, and intracellular targets of MEFAS, a new hybrid compound derived from mefloquine and artesunate, Antimicrob. Agents Chemother. 52 (2008) 3868–3874; https://doi.org/10.1128/AAC.00510-0810.1128/AAC.00510-08257309818710907
  4. 4. A. R. Hamann, C. de Kock, P. J. Smith, W. A. L. van Otterlo and M. A. L. Blackie, Synthesis of novel triazole-linked mefloquine derivatives: Biological evaluation against Plasmodium falciparum, Bioorg. Med. Chem. Lett. 24 (2014) 5466–5469; https://doi.org/10.1016/j.bmcl.2014.10.01510.1016/j.bmcl.2014.10.01525455485
  5. 5. N. Sharma, S. Thomas, E. B. Golden, F. M. Hofman, T. C. Chen, N. A. Petasis, A. H. Schönthal and S. G. Louie, Inhibition of autophagy and induction of breast cancer cell death by mefloquine, an antimalarial agent, Cancer Lett. 326 (2012) 143–154; https://doi.org/10.1016/j.canlet.2012.07.02910.1016/j.canlet.2012.07.02922863539
  6. 6. F. A. Rodrigues, I. S. Bomfim, B. C. Cavalcanti, C. Pessoa, R. S. Goncalves, J. L. Wardell, S. M. Wardell and M. V. de Souza, Mefloquine-oxazolidine derivatives: A new class of anticancer agents, Chem. Biol. Drug Des. 83 (2014) 126–131; https://doi.org/10.1111/cbdd.1221010.1111/cbdd.1221023961998
  7. 7. T. Küster, B. Stadelmann, R. Rufener, C. Risch, J. Müller and A. Hemphill, Oral treatments of Echinococcus multilocularis-infected mice with the antimalarial drug mefloquine that potentially interacts with parasite ferritin and cystatin, Int. J. Antimicrob. Agents46 (2015) 546–551; https://doi.org/10.1016/j.ijantimicag.2015.07.01610.1016/j.ijantimicag.2015.07.01626395219
  8. 8. L. E. Bermudez, P. Kolonoski, L. E. Seitz, M. Petrofsky, R. Reynolds, M. Wu and L. S. Young, SRI-286, a thiosemicarbazole, in combination with mefloquine and moxifloxacin for treatment of murine Mycobacterium avium complex disease, Antimicrob. Agents Chemother. 48 (2004) 3556–3558; https://doi.org/10.1128/AAC.48.9.3556-3558.200410.1128/AAC.48.9.3556-3558.200451478815328125
  9. 9. L. Danelishvili, M. Wu, L. S. Young and L. E. Bermudez, Genomic approach to identifying the putative target of and mechanisms of resistance to mefloquine in Mycobacteria, Antimicrob. Agents Chemother. 49 (2005) 3707–3714; https://doi.org/10.1128/AAC.49.9.3707-3714.200510.1128/AAC.49.9.3707-3714.2005119544516127044
  10. 10. R. S. Gonçalves, C. R. Kaiser, M. C. Lourenço, F. A. Bezerra, M. V. de Souza, J. L. Wardell, S. M. Wardell, M. D. Henriques and T. Costa, Mefloquine-oxazolidine derivatives, derived from mefloquine and arenecarbaldehydes: In vitro activity including against the multidrug-resistant tuberculosis strain T113, Bioorg. Med. Chem. 20 (2012) 243–248; https://doi.org/10.1016/j.bmc.2011.11.00610.1016/j.bmc.2011.11.00622142615
  11. 11. J. Mao, H. Yuan, Y. Wang, B. Wan, D. Pak, R. He and S. G. Franzblau, Synthesis and antituberculosis activity of novel mefloquine-isoxazole carboxylic esters as prodrugs, Bioorg. Med. Chem. Lett. 20 (2010) 1263–1268; https://doi.org/10.1016/j.bmcl.2009.11.10510.1016/j.bmcl.2009.11.10520022500
  12. 12. S. Eswaran, A. V. Adhikari, I. H. Chowdhury, N. K. Pal and K. D. Thomas, New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties, Eur. J. Med. Chem. 45 (2010) 3374–3383; https://doi.org/10.1016/j.ejmech.2010.04.02210.1016/j.ejmech.2010.04.02220537437
  13. 13. G. Džimbeg, B. Zorc, M. Kralj, K. Ester, K. Pavelić, J. Balzarini, E. De Clercq and M. Mintas, The novel primaquine derivatives of N-alkyl, cycloalkyl or aryl urea: synthesis, cytostatic and antiviral activity evaluations, Eur. J. Med. Chem. 43 (2008) 1180–1187; https://doi.org/10.1016/j.ejmech.2007.09.00110.1016/j.ejmech.2007.09.00117961851
  14. 14. M. Šimunović, I. Perković, B. Zorc, K. Ester, M. Kralj, D. Hadjipavlou-Litina and E. Pontiki, Urea and carbamate derivatives of primaquine: synthesis, cytostatic and antioxidant activities, Bioorg. Med. Chem. 17 (2009) 5605–5613; https://doi.org/10.1016/j.bmc.2009.06.03010.1016/j.bmc.2009.06.03019581098
  15. 15. I. Perković, S. Tršinar, J. Žanetić, M. Kralj, I. Martin-Kleiner, J. Balzarini, D. Hadjipavlou-Litina and A. M. Katsori, Novel 1-acyl-4-substituted semicarbazide derivatives of primaquine – synthesis, cytostatic, antiviral and antioxidative studies, J. Enzyme Inhib. Med. Chem. 28 (2013) 601–610; https://doi.org/10.3109/14756366.2012.66336610.3109/14756366.2012.66336622380782
  16. 16. K. Pavić, I. Perković, M. Cindrić, M. Pranjić, I. Martin-Kleiner, M. Kralj, D. Schols, D. Hadjipavlou-Litina, A.-M. Katsori and B. Zorc, Novel semicarbazides and ureas of primaquine with bulky aryl or hydroxyalkyl substituents: Synthesis, cytostatic and antioxidative activity, Eur. J. Med. Chem. 86 (2014) 502–514; https://doi.org/10.1016/j.ejmech.2014.09.01310.1016/j.ejmech.2014.09.01325203780
  17. 17. I. Perković, M. Antunović, I. Marijanović, K. Pavić, K. Ester, M. Kralj, J. Vlainić, I. Kosalec, D. Schols, D. Hadjipavlou-Litina, E. Pontiki and B. Zorc, Novel urea and bis-urea primaquine derivatives with hydroxyphenyl and halogenphenyl substituents: synthesis and biological evaluation, Eur. J. Med. Chem. 124 (2016) 622–636; https://doi.org/10.1016/j.ejmech.2016.08.02110.1016/j.ejmech.2016.08.02127614409
  18. 18. K. Pavić, I. Perković, P. Gilja, F. Kozlina, K. Ester, M. Kralj, D. Schols, D. Hadjipavlou-Litina, E. Pontiki and B. Zorc, Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of amide and acylsemicarbazide type, Molecules21 (2016) 1629–1653; https://doi.org/10.3390/molecules2112162910.3390/molecules21121629627368727916811
  19. 19. K. Pavić, I. Perković, Š. Pospíšilová, M. Machado, D. Fontinha, M. Prudêncio, J. Jampilek, A. Coffey, L. Endersen, H. Rimac and B. Zorc, Primaquine hybrids as promising antimycobacterial and antimalarial agents, Eur. J. Med. Chem. 143 (2018) 769–779; https://doi.org/10.1016/j.ejmech.2017.11.08310.1016/j.ejmech.2017.11.08329220797
  20. 20. J. Vlainić, I. Kosalec, K. Pavić, D. Hadjipavlou-Litina, E. Pontiki and B. Zorc, Insights into biological activity of ureidoamides with primaquine and amino acid moieties, J. Enzyme Inhib. Med. Chem. 33 (2018) 376–382; https://doi.org/10.1080/14756366.2017.142306710.1080/14756366.2017.1423067602103529363364
  21. 21. J. Levatić, K. Pavić, I. Perković, L. Uzelac, K. Ester, M. Kralj, M. Kaiser, M. Rottmann, F. Supek and B. Zorc, Machine learning prioritizes synthesis of primaquine ureidoamides with high antimalarial activity and attenuated cytotoxicity, Eur. J. Med. Chem. 146 (2018) 651–667; https://doi.org/10.1016/j.ejmech.2018.01.06210.1016/j.ejmech.2018.01.06229407988
  22. 22. M. Beus, Z. Rajić, D. Maysinger, Z. Mlinarić, M. Antunović, I. Marijanović, D. Fontinha, M. Prudêncio, J. Held, S. Olgen and B. Zorc, SAHAquines, novel hybrids based on SAHA and primaquine motifs, as potential anticancer and antiplasmodial agents, ChemistryOpen7 (2018) 624–638; https://doi.org/10.1002/open.20180011710.1002/open.201800117610443330151334
  23. 23. Z. Rajić, M. Beus, H. Michnova, J. Vlainić, L. Persoons, I. Kosalec, J. Jampilek, D. Schols, T. Keser and B. Zorc, Asymmetric primaquine and halogenaniline fumardiamides as novel biologically active Michael acceptors, Molecules23 (2018) Article ID 1724 (18 pages); https://doi.org/10.3390/molecules2307172410.3390/molecules23071724610058230011922
  24. 24. I. Zhang, M. Beus, U. Stochaj, P. U. Le, B. Zorc, Z. Rajić, K. Petrecca and D. Maysinger, Inhibition of glioblastoma cell proliferation, invasion, and mechanism of action of a novel hydroxamic acid hybrid molecule, Cell Death Discov. 4 (2018) Article ID 41; https://doi.org/10.1038/s41420-018-0103-010.1038/s41420-018-0103-0615828830302275
  25. 25. A. M. Mendes, I. S. Albuquerque, M. Machado, J. Pissarra, P. Meireles and M. Prudêncio, Inhibition of Plasmodium liver infection by ivermectin, Antimicrob. Agents Chemother. 61 (2017) e02005-16; https://doi.org/10.1128/AAC.02005-1610.1128/AAC.02005-16527874227895022
  26. 26. J. Held, T. Gebru, M. Kalesse, R. Jansen, K. Gerth, R. Müller and B. Mordmüller, Antimalarial activity of the myxobacterial macrolide chlorotonil A, Antimicrob. Agents Chemother. 58(2014) 6378–6384; https://doi.org/10.1128/AAC.03326-1410.1128/AAC.03326-14424938225114138
  27. 27. H. Noedl, J. Bronnert, K. Yingyuen, B. Attlmayr, H. Kollaritsch and M. Fukuda, Simple histidinerich protein 2 double-site sandwich enzyme-linked immunosorbent assay for use in malaria drug sensitivity testing, Antimicrob. Agents Chemother. 49 (2005) 3575–3577; https://doi.org/10.1128/AAC.49.8.3575-3577.200510.1128/AAC.49.8.3575-3577.2005119622316048989
  28. 28. R Core Team, 2015, R: A language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, Austria; https://www.R-project.org/; last access December 15, 2018
  29. 29. E. Borenfreund and J. A. Puerner, A simple quantitative procedure using monolayer cultures for cytotoxicity assays (HTD/NR-90), J. Tissue Culture Method9 (1985) 7–9; https://doi.org/10.1007/BF0166603810.1007/BF01666038
  30. 30. Chemicalize, 2017, ChemAxon Ltd., Budapest, Hungary; https://chemicalize.com; last access November 28, 2018
  31. 31. SwissADME Programs, Swiss Institute of Bioinformatics, Lausanne, Switerland; http://www.swissadme.ch; last access November 28, 2018
DOI: https://doi.org/10.2478/acph-2019-0019 | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075
Language: English
Page range: 233 - 248
Accepted on: Feb 14, 2019
Published on: Mar 28, 2019
Published by: Croatian Pharmaceutical Society
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year
Related subjects:

© 2019 Maja Beus, Diana Fontinha, Jana Held, Zrinka Rajić, Miguel Prudêncio, Branka Zorc, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.