Molecular docking and 3D-quantitative structure activity relationship analyses of peptidyl vinyl sulfones: Plasmodium Falciparum cysteine proteases inhibitors

Journal of Computer-Aided Molecular Design

Volumn 25, Issue 8, 2011, Pages 763-775

  Teixeira, Cátia ^a,b   Gomes, José R B ^a,c   Couesnon, Thierry ^c   Gomes, Paula ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

^c UNIVERSITÉ PARIS DIDEROT   (France)

Author keywords

CoMFA; CoMSIA; Docking; Falcipain 2; Malaria; Peptidyl vinyl sulfone

Indexed keywords

ALIGNMENT; AMINO ACIDS; BIOACTIVITY; COMPUTATIONAL CHEMISTRY; CRYSTAL STRUCTURE; DOCKING; ENZYME ACTIVITY; HYDROPHOBICITY; LIGANDS; MOLECULAR GRAPHICS;

COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE-MOLECULAR-SIMILARITY-INDICES ANALYSIS; CYSTEINE PROTEASE INHIBITORS; DOCKING; FALCIPAIN-2; HYDROPHOBICS; MALARIA; PEPTIDYL VINYL SULPHONE; PLASMODIUM FALCIPARUM; VINYL SULFONES;

ELECTROSTATICS;

ANTIMALARIAL AGENT; CYSTEINE PROTEINASE INHIBITOR; FALCIPAIN 2; PEPTIDYL VINYL SULFONE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; BINDING AFFINITY; BINDING SITE; BIOLOGICAL ACTIVITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CONFORMATION; ENZYME ACTIVE SITE; ENZYME INHIBITION; HYDROGEN BOND; HYDROPHOBICITY; IC 50; MOLECULAR DOCKING; NONHUMAN; PHYSICAL CHEMISTRY; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATIC ELECTRICITY;

EID: 80055072036     PISSN: 0920654X     EISSN: 15734951     Source Type: Journal    
DOI: 10.1007/s10822-011-9459-4     Document Type: Article

References (32)

1. Das MK, Lumb V, Mittra P, Singh SS, Dash AP, Sharma YD (2010) J Antimicrob Chemother 65(6):1258
2. Martin RE, Kirk K (2004) Mol Biol Evol 21(10):1938
3. Wiesner J, Ortmann R, Jomaa H, Schlitzer M (2003) Angewandte Chemie 42(43):5274
4. Sachs J, Malaney P (2002) Nature 415(6872):680
5. Gardner MJ, Hall N, Fung E, White O, Berriman M, Hyman RW, Carlton JM, Pain A, Nelson KE, Bowman S, Paulsen IT, James K, Eisen JA, Rutherford K, Salzberg SL, Craig A, Kyes S, Chan MS, Nene V, Shallom SJ, Suh B, Peterson J, Angiuoli S, Pertea M, Allen J, Selengut J, Haft D, Mather MW, Vaidya AB, Martin DM, Fairlamb AH, Fraunholz MJ, Roos DS, Ralph SA, McFadden GI, Cummings LM, Subramanian GM, Mungall C, Venter JC, Carucci DJ, Hoffman SL, Newbold C, Davis RW, Fraser CM, Barrell B (2002) Nature 419(6906):498
6. Padmanaban G (2003) Adv Biochem Eng/Biotechnol 84:123
7. Teixeira C, Gomes JR, Gomes P (2011) Curr Med Chem 18(10):1555
8. Rosenthal PJ, Sijwali PS, Singh A, Shenai BR (2002) Curr Pharm Des 8(18):1659
9. Rosenthal PJ (2004) Int J Parasitol 34(13-14):1489
10. Subramanian S, Hardt M, Choe Y, Niles RK, Johansen EB, Legac J, Gut J, Kerr ID, Craik CS, Rosenthal PJ (2009) PloS one 4(4):e5156
11. Batra S, Sabnis YA, Rosenthal PJ, Avery MA (2003) Bioorg Med Chem 11(10):2293
12. Rosenthal PJ, Olson JE, Lee GK, Palmer JT, Klaus JL, Rasnick D (1996) Antimicrob Agents Chemother 40(7):1600
13. Singh A, Rosenthal PJ (2001) Antimicrob Agents Chemother 45(3):949
14. Ettari R, Bova F, Zappala M, Grasso S, Micale N (2010) Med Res Rev 30(1):136
15. Olson JE, Lee GK, Semenov A, Rosenthal PJ (1999) Bioorg Med Chem 7(4):633
16. Shenai BR, Lee BJ, Alvarez-Hernandez A, Chong PY, Emal CD, Neitz RJ, Roush WR, Rosenthal PJ (2003) Antimicrob Agents Chemother 47(1):154
17. MarvinSketch 5.2.2, 2009, ChemAxon (http://www.chemaxon. com)
18. Sybyl X 1.3, Tripos Software, St. Louis, USA
19. Jones G, Willett P, Glen RC (1995) J Mol Biol 245(1):43
20. Jones G, Willett P, Glen RC, Leach AR, Taylor R (1997) J Mol Biol 267(3):727
21. Kerr ID, Lee JH, Pandey KC, Harrison A, Sajid M, Rosenthal PJ, Brinen LS (2009) J Med Chem 52(3):852
22. Case DA, Darden TA, Cheatham TE, Simmerling CLI, Wang J, Duke RE, Luo R, Crowley M, Walker RC, Zhang W, Merz KM, Wang B, Hayik S, Roitberg A, Seabra G, Kolossváry KF, Wong KF, Paesani F, Vanicek F, Wu X, Brozell SR, Steinbrecher T, Gohlke H, Yang L, Tan C, Mongan J, Hornak V, Cui G, Mathews DH, Seetin MG, Sagui C, Babin V, Kollman PA (2008) AMBER
23. University of California, San Francisco
24. Duan Y, Wu C, Chowdhury S, Lee MC, Xiong G, Zhang W, Yang R, Cieplak P, Luo R, Lee T, Caldwell J, Wang J, Kollman P (2003) J Comput Chem 24(16):1999
25. Kerr ID, Lee JH, Farady CJ, Marion R, Rickert M, Sajid M, Pandey KC, Caffrey CR, Legac J, Hansell E, McKerrow JH, Craik CS, Rosenthal PJ, Brinen LS (2009) J Biol Chem 284(38): 25697
26. Holm L, Park J (2000) Bioinformatics 16(6):566
27. Perkins R, Fang H, Tong W, Welsh WJ (2003) Environ Toxicol Chem/SETAC 22(8):1666
28. Golbraikh A, Tropsha A (2002) J Mol Graph Model 20(4):269
29. Saxena AK, Prathipati P (2003) SAR QSAR Environ Res 14(5-6):433
30. Gramatica P (2004) Evaluation of different statistical approaches for the validation of quantitative structure-activity relationships. Final report for JRC Contract ECVA-CCR.496576-Z. European Chemicals Bureau, Joint Research Centre, European Commission, Ispra, Italy
31. Bohm M, Sturzebecher J, Klebe G (1999) J Med Chem 42(3):458
32. Mittal RR, McKinnon RA, Sorich MJ (2008) J Mol Model 14(1):59