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Research Paper

Insights into biological activity of ureidoamides with primaquine and amino acid moieties

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Pages 376-382 | Received 08 Nov 2017, Accepted 27 Dec 2017, Published online: 24 Jan 2018

References

  • Primaquine – FDA prescribing information, side effects and uses. [internet]. 2017. Sanofi-Aventis U.S. LLC. Available from: https://www.drugs.com/pro/primaquine.html, [last accessed 9 Jan 2018].
  • van Huijsduijnen RH, Guy RK, Chibale K, et al. Anticancer properties of distinct antimalarial drug classes. PLoS One 2013;8:e82962.
  • Liu F, Shang Y, Chen SZ. Chloroquine potentiates the anti-cancer effect of lidamycin on non-small cell lung cancer cells in vitro. Acta Pharmacol Sin 2014;35:645–52.
  • Das AK. Anticancer effect of antimalarial artemisinin compounds. Ann Med Health Sci Res 2015;5:93–102.
  • Pascolo S. Time to use a dose of chloroquine as an adjuvant to anti-cancer chemotherapies. Eur J Pharmacol 2016;771:139–44.
  • Lin YC, Lin JF, Wen SI, et al. Chloroquine and hydroxychloroquine inhibit bladder cancer cell growth by targeting basal autophagy and enhancing apoptosis. Kaohsiung J Med Sci 2017;33:215–23.
  • Džimbeg G, Zorc B, Kralj M, et al. The novel primaquine derivatives of N-alkyl, cycloalkyl or aryl urea: synthesis, cytostatic and antiviral activity evaluations. Eur. J Med Chem 2008;43:1180–7.
  • Šimunović M, Perković I, Zorc B, et al. Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities. Bioorg Med Chem 2009;17:5605–13.
  • Perković I, Tršinar S, Žanetić J, et al. Novel 1-acyl-4-substituted semicarbazide derivatives of primaquine − synthesis, cytostatic, antiviral and antioxidative studies. J Enzyme Inhib Med Chem 2013;28:601–10.
  • Pavić K, Perković I, Cindrić M, et al. Novel semicarbazides and ureas of primaquine with bulky aryl or hydroxyalkyl substituents: synthesis, cytostatic and antioxidative activity. Eur J Med Chem 2014;86:502–14.
  • Perković I, Antunović M, Marijanović I, et al. Novel urea and bis-urea primaquine derivatives with hydroxyphenyl and halogenphenyl substituents: synthesis and biological evaluation. Eur J Med Chem 2016;124:622–36.
  • Pavić K, Perković I, Gilja P, et al. Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type. Molecules 2016;21:1629–53.
  • Pavić K, Perković I, Pospíšilová Š, et al. Primaquine hybrids as promising antimycobacterial and antimalarial agents. Eur J Med Chem 2018;143:769–79
  • Pavić K, Supek F, Levatić J, et al. QSAR based synthesis of novel primaquine ureidoamides. In: 25th Croatian Meeting of Chemists and Chemical Engineers; 19–22 Apr 2017; Poreč, Croatia.
  • Van Acker H, Van Dijck P, Coenye T. Molecular mechanisms of antimicrobial tolerance and resistance in bacterial and fungal biofilms. Trends Microbiol 2014;22:326–33.
  • Hobley L, Harkins C, MacPhee CE, Stanley-Wall NR. Giving structure to the biofilm matrix: an overview of individual strategies and emerging common themes. FEMS Microbiol Rev 2015;39:649–69.
  • Bjarnsholt T. The role of bacterial biofilms in chronic infections. APMIS Suppl 2013;136:1–51.
  • Uppuluri P, Chaturvedi AK, Srinivasan A, et al. Dispersion as an important step in the Candida albicans biofilm developmental cycle. PLoS Pathog 2010;6:e1000828.
  • Rabin N, Zheng Y, Opoku-Temeng C, et al. Agents that inhibit bacterial biofilm formation. Future Med Chem 2015;7:647–71.
  • European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society for Clinical Microbiology and Infectious Diseases (ESCMID). EUCAST Discussion Document E. Dis 5.1: determination of minimum inhibitory concentrations (MICs) of antibacterial agents by broth dilution, Clin. Microbiol. Infec. 2003, 9 (insert), 1.
  • Luzina EL, Popov AV. Synthesis, evaluation of anticancer activity and COMPARE analysis of N-bis(tri fluoromethyl)alkyl-N’-substituted ureas with pharmacophoric moieties. Eur J Med Chem 2012;53:364–73.
  • Chemicalize. ChemAxon Ltd. 2017. Available from: http://www.chemicalize.org
  • Donlan RM, Costerton JW. Biofilms: survival mechanisms of clinically relevant microorganisms. Clin Microbiol Rev 2002;15:167–93.
  • Frirdich E, Whitfield C. Lipopolysaccharide inner core oligosaccharide structure and outer membrane stability in human pathogens belonging to the Enterobacteriaceae. J Endotoxin Res 2005;11:133–44.
  • Bowman ZS, Morrow JD, Jollow DJ, McMillan DC. Primaquine-induced hemolytic anemia: role of membrane lipid peroxidation and cytoskeletal protein alterations in the hemotoxicity of 5-hydroxyprimaquine. J Pharmacol Exp Ther 2005;314:838–45.
  • Basso LG, Rodrigues RZ, Naal RMZG, Costa-Filho AJ. Effects of the antimalarial drug primaquine on the dynamic structure of lipid model membranes. Biochim Biophys Acta 2011;1808:55–64.
  • Branda SS, Vik S, Friedman L, Kolter R. Biofilms: the matrix revisited. Trends Microbiol 2005;13:20–6.
  • Laleve A, Vallieres C, Golinelli-Cohen MP, et al. The antimalarial drug primaquine targets Fe-S cluster proteins and yeast respiratory growth. Redox Biol 2016;7:21–9.
  • Cuéllar-Cruz M, López-Romero E, Villagómez-Castro JC, Ruiz-Baca E. Candida species: new insights into biofilm formation. Future Microbiol 2012;7:755–71.
  • Hiebsch RR, Raub TJ, Wattenberg BW. Primaquine blocks transport by inhibiting the formation of functional transport vesicles. Studies in a cell-free assay of protein transport through the Golgi apparatus. J Biol Chem 1991;266:20323–8.
  • Vale N, Moreira R, Gomes P. Primaquine revisited six decades after its discovery. Eur J Med Chem 2009;44:937–53.
  • Pergola C, Werz O. 5-Lipoxygenase inhibitors: a review of recent developments and patents. Expert Opin Ther Pat 2010;20:355–75.