4-Aminoquinoline derivatives: Synthesis, in vitro and in vivo antiplasmodial activity against chloroquine-resistant parasites

European Journal of Medicinal Chemistry

Volumn 122, Issue , 2016, Pages 394-407

  Singh, Shailja ^a   Agarwal, Drishti ^a,c   Sharma, Kumkum ^a   Sharma, Manish ^a   Nielsen, Morten A ^b   Alifrangis, Michael ^b   Singh, Ashok K ^a   Gupta, Rinkoo D ^c   Awasthi, Satish K ^a  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c SOUTH ASIAN UNIVERSITY   (India)

Author keywords

4 Aminoquinoline analogues; Amodiaquine; Antimalarial; Chloroquine; Plasmodium berghei; Plasmodium falciparum

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; AMODIAQUINE; ANTIMALARIAL AGENT; CHLOROQUINE; CYCLOGUANIL; PYRIMETHAMINE; 4-AMINOQUINOLINE; AMINOQUINOLINE DERIVATIVE; LACTATE DEHYDROGENASE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIMALARIAL ACTIVITY; ANTIMALARIAL DRUG RESISTANCE; ARTICLE; CONTROLLED STUDY; DRUG DOSE; DRUG POTENTIATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; COST BENEFIT ANALYSIS; DRUG EFFECTS; DRUG RESISTANCE; ENZYMOLOGY; METABOLISM; MOLECULAR DOCKING; PLASMODIUM VIVAX; SYNTHESIS; TUMOR CELL LINE;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; CELL LINE, TUMOR; CHEMISTRY TECHNIQUES, SYNTHETIC; CHLOROQUINE; COST-BENEFIT ANALYSIS; DRUG RESISTANCE; L-LACTATE DEHYDROGENASE; MALE; MICE; MOLECULAR DOCKING SIMULATION; PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84977620891     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2016.06.033     Document Type: Article

References (53)

1. [1] World Health Organization, World Malaria Report 2012., 2012, World Health Organization, Geneva.
2. [2] World Health Organization, Guidelines for the Treatment of Malaria. 2006, World Health Organization, Geneva http://www.whqlibdoc.who.int/publications/2006/9241546948_eng.pdf.
3. [3] World Health Organization. WHO Global Malaria Programme [ http://www.who.int/malaria/about_us/en/index.html].
4. [4] Wongsrichanalai, C., Sibley, C.H., Clin. Microbiol. Infect. 19 (2013), 908–916.
5. [5] Sáenz, F.E., Mutka, T., Udenze, K., Oduola, A.M., Kyle, D.E., Antimicrob. Agents Chemother. 56 (2012), 94685–94692.
6. [6] Ecker, A., Lehane, A.M., Clain, J., Fidock, D.A., Trends Parasitol. 28 (2012), 504–514.
7. [7] Steck, E.A., The Chemotherapy of Protozoan Diseases. 1971, Walter Reed Army Institute of Medicine.
8. [8] Thomas, F., Erhart, A., D'Alessandro, U., Lancet Infect. Dis. 4 (2004), 235–239.
9. [9] Olliaro, P., Mussano, P., Amodiaquine for treating malaria. Cochrane Database Syst. Rev. CD000016 (2003), 1–70.
10. [10] Winstanley, P.A., Coleman, J.W., Maggs, J.L., Breckenridge, A.M., Park, B.K., Br. J. Clin. Pharmacol. 29 (1990), 479–855.
11. [11] Hawley, S.R., Bray, P.G., Kevin Park, B., Ward, Stephen A., Mol. Biochem. Parasit. 80 (1996), 15–25.
12. [12] Yennawar, H.P., Viswamitra, M.A., Curr. Sci. 61 (1991), 39–43.
13. [13] Clarke, J.B., Neftel, K., Kitteringham, N.R., Park, B.K., Int. Arch. Allergy Appl. Immunol. 95 (1991), 369–375.
14. [14] Delarue-Cochin, S., Paunescu, E., Maes, L., Mouray, E., Sergheraert, C., Grellier, P., Melnyk, P., Eur. J. Med. Chem. 43 (2008), 252–260.
15. [15] Dixit, S.K., Mishra, N., Sharma, M., Singh, S., Agarwal, A., Awasthi, S.K., Bhasin, V.K., Eur. J. Med. Chem. 51 (2012), 52–59.
16. [16] Mishra, N., Arora, P., Kumar, B., Mishra, L.C., Bhattacharya, A., Awasthi, S.K., Bhasin, V.K., Eur. J. Med. Chem. 43 (2008), 1530–1535.
17. [17] Yadav, N., Dixit, S.K., Bhattacharya, A., Mishra, L.C., Sharma, M., Awasthi, S.K., Bhasin, V.K., Chem. Biol. Drug Des. 80 (2012), 340–347.
18. [18] Agarwal, D., Sharma, M., Dixit, S.K., Dutta, R.K., Singh, A.K., Gupta, R.D., Awasthi, S.K., Malar. J., 14, 2015, 48.
19. [19] Singh, S., Sharma, K., Awasthi, S.K., RSC Adv. 5 (2015), 85854–85861.
20. [20] O'Neill, P.M., Harrison, A.C., Storr, R.C., Hawley, S.R., Ward, S.A., Park, B.K., J. Med. Chem. 37 (1994), 1362–1370.
21. [21] O'Neill, P.M., Shone, A.E., Stanford, D., Nixon, G., Asadollahy, E., Park, B.K., Maggs, J.L., Roberts, P., Stocks, P.A., Biagini, G., J. Med. Chem. 52 (2009), 1828–1844.
22. [22] Winstanley, P.A., Coleman, J.W., Maggs, J.L., Breckenridge, A.M., Park, B.K., Br. J. Clin. Pharmacol. 29 (1990), 479–485.
23. [23] O'Neill, P.M., Harrison, A.C., Storr, R.C., Hawley, S.R., Ward, S.A., Park, B.K., J. Med. Chem. 37 (1994), 1362–1370.
24. [24] Abdel-Magid, A.F., Carson, K.G., Harris, B.D., Maryanoff, C.A., Shah, R.D., J. Org. Chem. 61 (1996), 3849–3862.
25. [25] Portela, C., Afonso, C.M., Pinto, M.M., Ramos, M.J., FEBS Lett. 547 (2003), 217–222.
26. [26] Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., Olson, A.J., J. Comput. Chem. 30 (2009), 2785–2791.
27. [27] Aguiar, A.C., Santos Rde, M., Figueiredo, F.J., Cortopassi, W.A., Pimentel, A.S., França, T.C., Meneghetti, M.R., Krettli, A.U., PLoS One, 7, 2012, e37259.
28. [28] Menting, J.G., Tilley, L., Deady, L.W., Ng, K., Simpson, R.J., Cowman, A.F., Foley, M., Mol. Biochem. Parasitol. 88 (1997), 215–224.
29. [29] Read, J., Wilkinson, K., Tranter, R., Sessions, R., Brady, R., J. Biol. Chem. 274 (1999), 10213–10218.
30. [30] Dorn, A., Vippagunta, S.R., Matile, H., Jaquet, C., Vennerstrom, J.L., Ridley, R.G., Biochem. Pharmacol. 55 (1998), 727–736.
31. [31](a) Solomon, V.R., Puri, S.K., Srivastava, K., Katti, S.B., Bioorg. Med. Chem. 13 (2005), 2157–2165.
32. [31](b) Ismail, F.M.D., DAscombe, M.J., CArr, P., North, S.E., J. Pharm. Pharmacol. 48 (1996), 841–850.
33. [31](c) de Souza, M.V.N., Pais, K.C., Kaiser, C.R., Peralta, M.A., de L. Ferreira, M., Lourenco, M.C.S., Biorg. Med. Chem. 17 (2009), 1474–1480.
34. [32](a) Ressurreicao, A.S., Goncalves, D., Sitoe, A.R., Albuquerque, I.S., Gut, J., Gois, A., Goncalves, L.M., Bronze, M.R., Hanscheid, T., Biagini, G.A., Rosenthal, P.J., Prudencio, M., O'Neill, P., Mota, M.M., Lopes, F., Moreira, R., J. Med. Chem. 56 (2013), 7679–7690.
35. [32](b) Motiwala, H.F., Kumar, R., Chakraborti, A.K., Aust. J. Chem. 60 (2007), 369–374.
36. [33](a) Kumar, D., Khan, S.I., Tekwani, B.L., Ponnan, Prija, Rawat, D.S., Eur. J. Med. Chem. 89 (2015), 490–502.
37. [33](b) Mwande Maguene, G., Lekana-Douki, J., Mouray, E., Bousquet, T., Grellier, P., Pellegrini, S., Samba Toure Ndouo, F., Lebibi, J., Pelinski, L., Eur. J. Med. Chem. 90 (2015), 519–525.
38. [33](c) Vandekerckhove, S., Van Herreweghe, S., Willems, J., Danneels, B., Desmet, T., de Kock, C., Smith, P.J., Chibale, K., Dhooghe, M., Eur. J. Med. Chem. 92 (2015), 91–102.
39. [33](d) Jones, R.A., Panda, S.S., Dennis Hall, C., Eur. J. Med. Chem. 97 (2015), 335–355.
40. [33](e) Medapi, B., Suryadevara, P., Renuka, J., Padma Sridevi, J., Yogeeswari, P., Sriram, D., Eur. J. Med. Chem. 103 (2015), 1–16.
41. [33](f) Pandey, S., Agarwal, P., Srivastava, K., RajaKumar, S., Puri, S.K., Verma, P., Saxena, J.K., Sharma, A., Lal, J., Chauhan, P.M.S., Eur. J. Med. Chem. 66 (2013), 69–81.
42. [34](a) Abdel-Magid, A.F., Mayano, C.A., Carson, K.G., Tetrahedron Lett. 31 (1990), 5595–5598.
43. [34](b) Opsenica, I.M., Tot, Miklos, Gomba, Laura, Nuss, Jonathan E., Sciotti, R.J., Bavari, Sina, Burnett, J.C., Solaja, B.A., J. Med. Chem. 56 (2013), 5860–5871.
44. [34](c) Wenzel, N.I., Chavain, N., Wang, Y., Friebolin, W., Maes, L., Pradines, B., Lanzer, M., Yardley, V., Brun, R., Herold-Mende, O.C., Biot, C., Toth, K., Davioud-Charve, E., J. Med. Chem. 53 (2010), 3214–3226.
45. [35] Jensen, S., Omarsdottir, S., Bwalya, A.G., Nielsen, M.A., Tasdemir, D., Olafsdottir, E.F., Phytomedicine 19 (2012), 1191–1195.
46. [36] Ryley, J.F., Peters, W., Ann. Trop. Med. Parasitol. 84 (1970), 209–222.
47. [37] Peters, W., Exp. Parasitol. 17 (1965), 80–89.
48. [38] Van Meerloo, J., Kaspers, G.J., Cloos, J., Methods Mol. Biol. 731 (2011), 237–245.
49. [39] MarvinSketch [ http://www.chemaxon.com/marvin/sketch/index.jsp].
50. [40] Frisch, A., Gaussian 09W Reference. 2009, Gaussian, Inc., Wallingford, CT.
51. [41] Morris, G.M., Huey, R., Olson, A.J., Using AutoDock for ligand-receptor docking. Curr. Protoc. Bioinform., 8, 2008 unit 14.1–8.14.
52. [42] Berman, H.M., Battistuz, T., Bhat, T.N., Bluhm, W.F., Bourne, P.E., Burkhardt, K., Feng, Z., Gilliland, G.L., Iype, L., Jain, S., Fagan, P., Marvin, J., Padilla, D., Ravichandran, V., Schneider, B., Thanki, N., Weissig, H., Westbrook, J.D., Zardecki, C., Acta Crystallogr. D. Biol. Crystallogr. 58 (2002), 899–907.
53. [43] Aguiar, A.C., Santos, Rde. M., Figueiredo, F.J., Cortopassi, W.A., Pimentel, A.S., França, T.C., Meneghetti, M.R., Krettli, A.U., PLoS One, 7, 2012, e37259.