Identification of Novel Inhibitors of Dipeptidylcarboxypeptidase of Leishmania donovani via Ligand-Based Virtual Screening and Biological Evaluation

Chemical Biology and Drug Design

Volumn 79, Issue 2, 2012, Pages 149-156

  Gangwar, Sonali ^a   Baig, Mirza S ^a   Shah, Priyanka ^a   Biswas, Subhashish ^a   Batra, Sanjay ^a   Siddiqi, Mohammad I ^a   Goyal, Neena ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Biological evaluation; Inhibitors; Leishmania Dipeptidylcarboxypeptidase; Leishmaniasis; Molecular docking; Virtual screening

Indexed keywords

DIPEPTIDYL CARBOXYPEPTIDASE;

ARTICLE; DRUG ACTIVITY; DRUG IDENTIFICATION; DRUG SCREENING; DRUG TARGETING; LEISHMANIA DONOVANI; LEISHMANIASIS; PHARMACOPHORE; PRIORITY JOURNAL; SCORING SYSTEM;

ANIMALS; ANTIPARASITIC AGENTS; BINDING SITES; CATALYTIC DOMAIN; COMPUTER SIMULATION; DRUG EVALUATION, PRECLINICAL; ENDOPEPTIDASES; HUMANS; LEISHMANIA DONOVANI; LEISHMANIASIS; LIGANDS; PROTEASE INHIBITORS;

LEISHMANIA DONOVANI; PROTOZOA;

EID: 84855424019     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01262.x     Document Type: Article

References (38)

1. Alvar J., Yactayo S., Bern C. (2006) Leishmaniasis and poverty. Trends Parasitol;22:552-557.
2. Guerin P.J., Olliaro P., Sundar S., Boelaert M., Croft S.L., Desjeux P., Wasunna M.K., Bryceson A.D. (2002) Visceral leishmaniasis: current status of control, diagnosis, and treatment, and a proposed research and development agenda. Lancet Infect Dis;2:494-501.
3. Rijal S., Chappuis F., Singh R., Bovier P.A., Acharya P., Karki B.M., Das M.L., Desjeux P., Loutan L., Koirala S. (2003) Treatment of visceral leishmaniasis in south-eastern Nepal: decreasing efficacy of sodium stibogluconate and need for a policy to limit further decline. Trans R Soc Trop Med Hyg;97:350-354.
4. Berman J. (2005) Clinical status of agents being developed for leishmaniasis. Expert Opin Investig Drugs;14:1337-1346.
5. Sundar S., Chatterjee M. (2006) Visceral leishmaniasis - current therapeutic modalities. Indian J Med Res;123:345-352.
6. Sundar S., More D.K., Singh M.K., Singh V.P., Sharma S., Makharia A. (2000) Failure of pentavalent antimony in visceral leishmaniasis in India: report from the center of Indian epidemic. Clin Infect Dis;31:1104-1106.
7. Ashutosh, Gupta S., Ramesh, Sundar S., Goyal N. (2005) Use of Leishmania donovani field isolates expressing the luciferase reporter gene in in vitro drug screening. Antimicrob Agents Chemother;49:3776-3783.
8. Goyal N., Duncan R., Selvapandiyan A., Debrabant A., Baig M.S., Nakhasi H.L. (2006) Cloning and characterization of angiotensin converting enzyme related dipeptidylcarboxypeptidase from Leishmania donovani. Mol Biochem Parasitol;145:147-157.
9. Yaron A., Mlynar D., Berger A. (1972) A dipeptidocarboxypeptidase from E. coli. Biochem Biophys Res Commun;47:897-902.
10. Skeggs L.T., Kahn J.R., Shumway N.P. (1956) The purification of hypertension II. J Exp Med;103:295-301.
11. Deutch C.E., Soffer R.L. (1978) Escherichia coli mutant defective in dipeptidyl carboxypeptidase. Proc Natl Acad Sci USA;75:5998-6001.
12. Henrich B., Becker S., Schroeder U., Plapp R. (1993) dcp gene of Escherichia coli: cloning, sequencing, transcript mapping, and characterization of the gene product. J Bacteriol;175:7290-7300.
13. Soffer R.L. (1976) Angiotensin-converting enzyme and the regulation of vasoactive peptides. Annu Rev Biochem;45:73-94.
14. Rainey P.M., Spithill T.W., McMahon-Pratt D., Pan A.A. (1991) Biochemical and molecular characterization of L. pifanoi amastigotes in continous axenic culture. Mol Biochem Parasitol;49:111-118.
15. Andrade Ribeirode A.S., Santero M.M., de Melo M.N., Mares-Guia M. (1998) Leishmania (Leishmania) amazonensis: purification and enzymatic characterization of soluble serine oligopeptidase. Exp Parasitol;89:153-160.
16. Morty R.E., Morehead J. (2002) Cloning and characterization of leucylaminopeptidase from three pathogenic Leishmania species. J Biol Chem;277:26057-26065.
17. Baig M.S., Kumar A., Siddiqi M.I., Goyal N. (2010) Characterization of dipeptidylcarboxypeptidase of Leishmania donovani: a molecular model for structure based design of antileishmanials. J Comput Aided Mol Des;24:77-87.
18. Gasteiger J., Marsili M. (1980) Iterative partial equalization of orbital electronegativity - rapid access to atomic charges. Tetrahedron;36:3219-3228.
19. Rarey M., Kramer B., Lengauer T., Klebe G. (1996) A fast flexible docking method using an incremental construction algorithm. J Mol Biol;261:470-489.
20. Jones G., Willett P., Glen R.C., Leach A.R., Taylor R. (1997) Development and validation of a genetic algorithm for flexible docking. J Mol Biol;267:727-748.
21. Muegge I., Martin Y.C. (1999) A general and fast scoring function for protein-ligand interactions: a simplified potential approach. J Med Chem;42:791-804.
22. Ewing T.J.A., Kuntz I.D. (1997) Critical evaluation of search algorithms used in automated molecular docking. J Comput Chem;18:1175-1189.
23. Eldridge M.D., Murray C.W., Auton T.R., Paolini G.V., Mee R.P. (1997) Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J Comput Aided Mol Des;11:425-445.
24. Pettersen E.F., Goddard T.D., Huang C.C., Couch G.S., Greenblatt D.M., Meng E.C., Ferrin E.C. (2004) UCSF Chimera - a visualization system for exploratory research and analysis. J Comput Chem;25:1605-1612.
25. Mills J.E., Dean P.M. (1996) Three-dimensional hydrogen-bond geometry and probability information from a crystal survey. J Comput Aided Mol Des;10:607-622.
26. Laemmli U.K. (1970) Cleavage of structrural proteins during the assembly of the head of bacteriphage T4. Nature;227:680-685.
27. Cushman D.W., Cheung H.S. (1971) Spectrophotometric assay and properties of the angiotensin-converting enzyme of rabbit lung. Biochem Pharmacol;20:1637-1648.
28. Bradford M.M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem;72:248-254.
29. Baig M.S., Gangwar S., Goyal N. (2011) Biochemical characterization of dipeptidylcarboxypeptidae of Leishmania donovani. Cell Mol Biol;57:54-61.
30. Jones G., Willett P., Glen R.C. (1995) A genetic algorithm for flexible molecular overlay and pharmacophore elucidation. J Comput Aided Mol Des;9:532-549.
31. Abagyan R., Totrov M. (2001) High-throughput docking for lead generation. Curr Opin Chem Biol;5:375-382.
32. Bissantz C., Folkers G., Rognan D. (2000) Protein-based virtual screening of chemical databases. 1. Evaluation of different docking/scoring combinations. J Med Chem;43:4759-4767.
33. Agarwal H., Kumar A., Bal N.C., Siddiqi M.I., Arora A. (2007) Ligand based virtual screening and biological evaluation of inhibition of chorismate mutase (Rv1885c) from Mycobacterium tuberculosis H37Rv. Bioorg Med Chem Lett;17:3053-3058.
34. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev;46:3-26.
35. Kramer B., Rarey M., Lengauer T. (1999) Evaluation of the FLEXX incremental construction algorithm for protein-ligand docking. Proteins;37:228-241.
36. Kuntz I.D., Chen K., Sharp K.A., Kollman P.A. (1999) The maximal affinity of ligands. Proc Natl Acad Sci USA;96:9997-10002.
37. Batra S., Bhaduri A.P., Joshi B.S., Roy R., Khanna A.K., Chander R. (2001) Syntheses and biological evaluation of Alkanediamines as antioxidant and hypolipidemic agents. Bioorg Med Chem;9:3093-3099.
38. Batra S., Roy A.K., Patra A., Bhaduri A.P., Surin W.R., Raghavan S.A.V., Sharma P., Kapoor K., Dikshit M. (2004) Baylis-Hillman reaction assisted parallel synthesis of 3, 5-disubstituted isoxazoles and their in vivo bioevaluation as antithrombotic agents. Bioorg Med Chem;12:2059-2077.