Discovery of safe and orally effective 4-aminoquinaldine analogues as apoptotic inducers with activity against experimental visceral leishmaniasis

Antimicrobial Agents and Chemotherapy

Volumn 56, Issue 1, 2012, Pages 432-445

  Palit, Partha ^a,b   Hazra, Abhijit ^a   Maity, Arindam ^a   Vijayan, R S K ^a   Manoharan, Prabu ^a   Banerjee, Sukdeb ^a   Mondal, Nirup B ^a   Ghoshal, Nanda ^a   Ali, Nahid ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b Dr B C Roy College of Pharmacy and Allied Health Sciences   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 DIMETHYLAMINO PHENYL) 3 (2 METHYLQUINOLIN 4 YLAMINO)PROPAN 2 ONE; 2 (2 METHYLQUINOLIN 4 YLAMINO)N 4 TOLYLACETAMIDE; 2 (2 METHYLQUINOLIN 4 YLAMINO)N PHENYLACETAMIDE; 2 [(2 METHYLQUINOLIN 4 YL)(2 MORPHOLIN 4 YL 2 OXO ETHYL)AMINO] 1 MORPHOLIN 4 YL ETHANONE; 4 AMINOQUINALDINE DERIVATIVE; 4 METHYL N(2 METHYLQUINOLIN 4 YL)BENZAMIDE; ANTILEISHMANIAL AGENT; ANTIMONY GLUCONATE; DIHYDROFOLATE REDUCTASE; GLUTATHIONE; MILTEFOSINE; N (2,3 DICHLORO PHENYL) 2 (2 METHYLQUINOLIN 4 YLAMINO)ACETAMIDE; N (2,5 DICHLORO PHENYL) 2 (2 METHYLQUINOLIN 4 YLAMINO)ACETAMIDE; N CYCLOHEXYL 2 [CYCLOHEXYLCARBAMOYLMETHYL(2 METHYLQUINOLIN 4 YL)AMINO]ACETAMIDE; N(2 CHLORO PHENYL) 2 (2 METHYLQUINOLIN 4 YLAMINO)ACETAMIDE; N(2,4 DICHLORO PHENYL) 2 (2 METHYLQUINOLIN 4 YLAMINO)ACETAMIDE; N(4 METHOXY PHENYL) 2 (2 METHYLQUINOLIN 4 YLAMINO)ACETAMIDE; N(4 METHYLPHENYL) 3 (2 METHYLQUINOLIN 4 YLAMINO)PROPIONAMIDE; PROTEINASE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

AMASTIGOTE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; APOPTOSIS; ARTICLE; CONTROLLED STUDY; DNA FRAGMENTATION; DRUG EFFICACY; DRUG MECHANISM; DRUG PENETRATION; DRUG SAFETY; ENZYME ACTIVATION; ENZYME INHIBITION; LEISHMANIA DONOVANI; LIPID PEROXIDATION; MITOCHONDRIAL MEMBRANE POTENTIAL; MOLECULAR DOCKING; MOUSE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROMASTIGOTE; UPREGULATION; VISCERAL LEISHMANIASIS;

ADMINISTRATION, ORAL; AMINOQUINOLINES; ANIMALS; ANTIMONY SODIUM GLUCONATE; ANTIPROTOZOAL AGENTS; APOPTOSIS; DNA FRAGMENTATION; DRUG RESISTANCE; GLUTATHIONE; INHIBITORY CONCENTRATION 50; INJECTIONS, INTRAPERITONEAL; LEISHMANIA DONOVANI; LEISHMANIASIS, VISCERAL; LIPID PEROXIDATION; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICE; MICE, INBRED BALB C; PROTOZOAN PROTEINS; QUINALDINES; REACTIVE OXYGEN SPECIES; TETRAHYDROFOLATE DEHYDROGENASE;

EID: 84455192504     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00700-11     Document Type: Article

References (61)

1. Afrin F, Ali N. 1997. Adjuvanticity and protective immunity elicited by Leishmania donovani antigens encapsulated in positively charged liposomes. Infect. Immun. 65:2371-2377. (Pubitemid 27237322)
2. Ameisen JC. 2002. On the origin, evolution, and nature of programmed cell death: a timeline of four billion years. Cell Death Differ. 9:367-393. (Pubitemid 34822817)
3. Backus HH, et al. 2003. Thymidylate synthase inhibition triggers apoptosis via caspases-8 and -9 in both wild-type and mutant p53 colon cancer cell lines. Eur. J. Cancer 39:1310-1317. (Pubitemid 36579205)
4. Banki K, Hutter E, Gonchoroff NJ, Perl A. 1999. Elevation of mitochondrial transmembrane potential and reactive oxygen intermediate levels are early events and occur independently from activation of caspases in Fas signaling. J. Immunol. 162:1466-1479. (Pubitemid 29307019)
5. Berman JD, King M, Edwards N. 1989. Antileishmanial activities of 2,4-diaminoquinazoline putative dihydrofolate reductase inhibitors. Antimicrob. Agents Chemother. 33:1860-1863. (Pubitemid 19266244)
6. Bermudez R, Dagger F, D'Aquino JA, Benaim G, Dawidowicz K. 1997. Characterization of mitochondrial electron-transfer in Leishmania mexicana. Mol. Biochem. Parasitol. 90:43-54. (Pubitemid 28044376)
7. Chakrabarti G, et al. 1999. Indolylquinoline derivatives are cytotoxic to Leishmania donovani promastigotes and amastigotes in vitro and are effective in treating murine visceral leishmaniasis. J. Antimicrob. Chemother. 43:359-366. (Pubitemid 29121875)
8. Chappuis F, et al. 2007. Visceral leishmaniasis: what are the needs for diagnosis, treatment and control? Nat. Rev. 5:873-882. (Pubitemid 47578388)
9. Chowdhury AR, et al. 2003. Dihydrobetulinic acid induces apoptosis in Leishmania donovani by targeting DNA topoisomerase I and II: implications in antileishmanial therapy. Mol. Med. 9:26-36. (Pubitemid 36667689)
10. Croft SL, Seifert K, Yardley V. 2006. Current scenario of drug development for leishmaniasis. Indian J. Med. Res. 123:399-410. (Pubitemid 43905578)
11. Das M, Mukherjee SB, Shaha C. 2001. Hydrogen peroxide induces apoptosis-like death in Leishmania donovani promastigotes. J. Cell Sci. 114:2461-2469. (Pubitemid 32684800)
12. Das R, Roy A, Dutta N, Majumder HK. 2008. Reactive oxygen species and imbalance of calcium homeostasis to curcumin induced programmed cell death in Leishmania donovani. Apoptosis 13:867-882.
13. Davis AJ, Kedzierski L. 2005. Recent advances in antileishmanial drug development. Curr. Opin. Investig. Drugs 6:163-169. (Pubitemid 43072954)
14. Deb I, et al. 2009. Synthesis and characterizations of novel quinoline derivatives having mixed ligand activities at the kappa and mu receptors: potential therapeutic efficacy against morphine dependence. Bioorg. Med. Chem. 17:5782-5790.
15. Dey T, Anam K, Afrin F, Ali N. 2000. Antileishmanial activities of stearylamine-bearing liposomes. Antimicrob. Agents Chemother. 44: 1739-1742. (Pubitemid 30340831)
16. Dubar F, Khalife J, Brocard J, Dive D, Biot C. 2008. Ferroquine, an ingenious antimalarial drug: thoughts on the mechanism of action. Molecules 13:2900-2907.
17. Duranteau J, Chandel NS, Kulisz A, Shao Z, Schumacker PT. 1998. Intracellular signaling by reactive oxygen species during hypoxia in cardiomyocytes. J. Biol. Chem. 273:11619-11624. (Pubitemid 28272061)
18. Fairlamb AH, Cerami A. 1992. Metabolism and functions of trypanothione in the Kinetoplastida. Annu. Rev. Microbiol. 46:695-729.
19. Galvao LO, et al. 2000. Therapeutic trial in experimental tegumentary leishmaniasis caused by Leishmania (Leishmania) amazonensis. A comparative study between mefloquine and aminosidine. Rev. Soc. Bras. Med. Trop. 33:377-382. (Pubitemid 30604785)
20. Gamcsik MP, et al. 2001. Dual role of glutathione in modulating camptothecin activity: depletion potentiates activity, but conjugation enhances the stability of the topoisomerase I-DNA cleavage complex. Mol. Cancer Ther. 1:11-20.
21. Hidalgo IT, et al. 1989. Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 96:736-749.
22. Ian HG. 2002. Inhibitors of dihydrofolate reductase in Leishmania and trypanosomes. Biochim. Biophys. Acta 1587:249-257.
23. Jha TK, et al. 1999. Miltefosine, an oral agent, for the treatment of Indian visceral leishmaniasis. N. Engl. J. Med. 341:1795-1800.
24. Johnson JV, Rauchman BS, Baccanari DP, Roth B. 1989. 2,4-Diamino- 5-benzylpyrimidines and analogues as antibacterial agents. 12. 1,2- Dihydroquinolylmethyl analogues with high activity and specificity for bacterial dihydrofolate reductase. J. Med. Chem. 32:1942-1949. (Pubitemid 19204384)
25. Khabnadideh S, et al. 2005. Design, synthesis and evaluation of 2,4- diaminoquinazolines as inhibitors of trypanosomal and leishmanial dihydrofolate reductase. Bioorg. Med. Chem. 13:2637-2649. (Pubitemid 40341666)
26. Knighton DR, et al. 1994. Structure of and kinetic channelling in bifunctional dihydrofolate reductase-thymidylate synthase. Nat. Struct. Biol. 1:186-194. (Pubitemid 24974835)
27. Kono Y. 1978. Generation of superoxide radical during autoxidation of hydroxylamine and an assay for superoxide dismutase. Arch. Biochem. Biophys. 186:189-195. (Pubitemid 8290500)
28. Kwok JB, Tattersall MH. 1992. DNA fragmentation, dATP pool elevation and potentiation of antifolate cytotoxicity in L1210 cells by hypoxanthine. Br. J. Cancer 65:503-508.
29. Lee N, et al. 2002. Programmed cell death in the unicellular protozoan parasite Leishmania. Cell Death Differ. 9:53-64. (Pubitemid 34071993)
30. Loiseau PM, et al. 2011. In vitro activities of new 2-substituted quinolines against Leishmania donovani. Antimicrob. Agents Chemother. 55:1777-1780.
31. Lopez-Martin C, Perez-Victoria JM, Carvalho L, Castanys S, Gamarro F. 2008. Sitamaquine sensitivity in Leishmania species is not mediated by drug accumulation in acidocalcisomes. Antimicrob. Agents Chemother. 52:4030-4036.
32. Maganti L, Manoharan P, Ghoshal N. 2010. Probing the structure of Leishmania donovani chagasi DHFR-TS: comparative protein modeling and protein-ligand interaction studies. J. Mol. Model. 16:1539-1547.
33. Majumder S, Dey SN, Chowdhury R, Dutta C, Das J. 1988. Intracellular development of cholerphage Φ 149 under permissive and nonpermissive conditions: an electron microscopic study. Intervirology 29:27-38.
34. Mishra BB, Singh RK, Srivastava A, Tripathi VJ, Tiwari VK. 2009. Fighting against Leishmaniasis: search of alkaloids as future true potential anti-leishmanial agents. Mini Rev. Med. Chem. 9:107-123.
35. Mishra J, Saxena A, Singh S. 2007. Chemotherapy of leishmaniasis: past, present and future. Curr. Med. Chem. 14:1153-1169. (Pubitemid 46679457)
36. Mosmann T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65:55-63. (Pubitemid 14203433)
37. Nakayama H, et al. 2005. Efficacy of orally administered 2-substituted quinolines in experimental murine cutaneous and visceral leishmaniases. Antimicrob. Agents Chemother. 49:4950-4956. (Pubitemid 41778905)
38. Nare B, Hardy LW, Beverley SM. 1997. The roles of pteridine reductase 1 and dihydrofolate reductase-thymidylate synthase in pteridine metabolism in the protozoan parasite Leishmania major. J. Biol. Chem. 272:13883-13891. (Pubitemid 27224830)
39. Naumann K. 2000. Influence of chlorine substituents on biological activity of chemicals: a review. Pest Manag. Sci. 56:3-21. (Pubitemid 30123413)
40. Navarro-Peran E, et al. 2005. The antifolate activity of tea catechins. Cancer Res. 65:2059-2064. (Pubitemid 40490108)
41. Nwaka S, Hudson A. 2006. Innovative lead discovery strategies for tropical diseases. Nat. Rev. Drug Discov. 5:941-955. (Pubitemid 44660607)
42. Pal S, Ravindran R, Ali N. 2004. Combination therapy using sodium antimony gluconate in stearylamine-bearing liposomes against established and chronic Leishmania donovani infection in BALB/c mice. Antimicrob. Agents Chemother. 48:3591-3593. (Pubitemid 39129369)
43. Pecoul B. 2004. New drugs for neglected diseases: from pipeline to patients. PLoS Med. 1:e6.
44. Peters GJ, et al. 2000. Molecular downstream events and induction of thymidylate synthase in mutant and wild-type p53 colon cancer cell lines after treatment with 5-fluorouracil and the thymidylate synthase inhibitor raltitrexed. Eur. J. Cancer 36:916-924. (Pubitemid 30214143)
45. Peters W. 1981. The treatment of kala-azar - new approaches to an old problem. Indian J. Med. Res. 73(Suppl):1-18. (Pubitemid 11083495)
46. Renslo AR, McKerrow JH. 2006. Drug discovery and development for neglected parasitic diseases. Nat. Chem. Biol. 2:701-710. (Pubitemid 44764212)
47. Rodenhuis S, Kremer JM, Bertino JR. 1987. Increase of dihydrofolate reductase in peripheral blood lymphocytes of rheumatoid arthritis patients treated with low-dose oral methotrexate. Arthritis Rheum. 30:369-374. (Pubitemid 17080772)
48. Sahu NP, et al. 2002. Synthesis of a novel quinoline derivative,2-(2- methylquinolin-4-ylamino)-N-phenylacetamide - a potential antileishmanial agent. Bioorg. Med. Chem. 10:1687-1693. (Pubitemid 34286361)
49. Savioli L, et al. 2006. Response from Savioli and colleagues from the Department of Neglected Tropical Diseases, World Health Organization. PLoS Med. 3:e283.
50. Schlegel RA, Williamson P. 2001. Phosphatidylserine, a death knell. Cell Death Differ. 8:551-563. (Pubitemid 32586592)
51. Schurigt U, et al. 2010. Aziridine-2,3-dicarboxylate-based cysteine cathepsin inhibitors induce cell death in Leishmania major associated with accumulation of debris in autophagy-related lysosome-like vacuoles. Antimicrob. Agents Chemother. 54:5028 -5041.
52. Sen N, et al. 2004. Camptothecin induced mitochondrial dysfunction leading to programmed cell death in unicellular hemoflagellate Leishmania donovani. Cell Death Differ. 11:924-936. (Pubitemid 39139751)
53. Shargel L, Wu-Pong S, Yu ABC. 2005. Applied biopharmaceutics & pharmacokinetics. Appleton & Lange Reviews/McGraw-Hill, Medical Publishing Division, New York, NY.
54. Shimasaki H. 1994. Assay of fluorescent lipid peroxidation products. Methods Enzymol. 233:338-346.
55. Tempone AG, et al. 2005. Synthesis and antileishmanial activities of novel 3-substituted quinolines. Antimicrob. Agents Chemother. 49: 1076-1080. (Pubitemid 40327726)
56. Vijayan RS, Prabu M, Mascarenhas NM, Ghoshal N. 2009. Hybrid structure-based virtual screening protocol for the identification of novel BACE1 inhibitors. J. Chem. Infect. Model. 49:647-657.
57. West JA, et al. 2000. Heterogeneity of Clara cell glutathione. A possible basis for differences in cellular responses to pulmonary cytotoxicants. Am. J. Respir. Cell Mol. Biol. 23:27-36. (Pubitemid 30597092)
58. World Health Organization. 1999. Tropical disease research: progress in international research, 1997-1998. World Health Organization, Geneva Switzerland.
59. World Health Organization. 2010. Leishmaniasis: burden of disease. World Health Organization, Geneva, Switzerland. http://www.who.int/leishmaniasis/ burden/en.
60. Yardley V, Gamarro F, Croft SL. 2010. Antileishmanial and antitrypanosomal activities of the 8-aminoquinoline tafenoquine. Antimicrob. Agents Chemother. 54:5356-5358.
61. Zuccotto F, Martin AC, Laskowski RA, Thornton JM, Gilbert IH. 1998. Dihydrofolate reductase: a potential drug target in trypanosomes and leishmania. J. Comput. Aided Mol. Des. 12:241-257. (Pubitemid 128510954)