3D-QSAR studies of boron-containing dipeptides as proteasome inhibitors with CoMFA and CoMSIA methods

European Journal of Medicinal Chemistry

Volumn 44, Issue 4, 2009, Pages 1486-1499

  Zhu, Yong Qiang ^a   Lei, Meng ^b   Lu, Ai Jun ^a   Zhao, Xin ^a   Yin, Xiao Jin ^a   Gao, Qing Zhi ^c  

^a Jiangsu Simcere Pharmaceutical Research Institute   (China)

^b NANJING FORESTRY UNIVERSITY   (China)

^c XenoPort Inc   (United States)

Author keywords

3D QSAR; CoMFA; CoMSIA; Dipeptide boronate; Drug design; Proteasome inhibitors

Indexed keywords

BORONIC ACID DERIVATIVE; BORTEZOMIB; HEXESTROL BIS(2 DIETHYLAMINOETHYL) ETHER; MG 264; MG 267; MG 268; MG 270; MG 273; MG 274; MG 282; MG 285; MG 286; MG 287; MG 289; MG 290; MG 291; MG 292; MG 294; MG 295; MG 296; MG 297; MG 298; MG 299; MG 300; MG 301; MG 302; MG 303; MG 306; MG 307; MG 308; MG 309; MG 312; MG 314; MG 315; MG 317; MG 318; MG 324; MG 325; MG 328; MG 329; MG 332; MG 334; MG 336; MG 338; MG 343; MG 346; MG 347; MG 350; MG 351; MG 352; MG 353; MG 356; MG 358; MG 361; MG 368; MG 380; MG 382; MG 383; MG 387; PROTEASOME; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; DRUG BINDING; DRUG CONFORMATION; DRUG DESIGN; DRUG SYNTHESIS; ELECTRICITY; HYDROGEN BOND; HYDROPHOBICITY; PREDICTIVE VALIDITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

BORON; COMPUTER SIMULATION; DIPEPTIDES; DRUG DESIGN; ENZYME INHIBITORS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTEASOME ENDOPEPTIDASE COMPLEX; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 61449124148     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.07.019     Document Type: Article

References (53)

1. Hershko A. Trends Biochem. Sci. 21 (1996) 445-449
2. Etlinger J.D., and Goldberg A.L. Proc. Natl. Acad. Sci. U.S.A. 74 (1977) 54-58
3. Goldberg A.L. Nature (London) 426 (2003) 895-899
4. Rock K.L., Gramm C.F., Rothstein L., Clark K., Stein R., Dick L., Hwang D., and Goldberg A.L. Cell 78 (1994) 761-771
5. Craiu A., Gaczynska M., Akopian T., Gramm C.F., Fenteany G., Goldberg A.L., and Rock K.L. J. Biol. Chem. 272 (1997) 13437-13445
6. Rock K.L., and Goldberg A.L. Annu. Rev. Immunol. 17 (1999) 739-779
7. Mitch W.E., and Goldberg A.L. N. Engl. J. Med. 335 (1996) 1897-1905
8. Murakami Y., Matsufuji S., Kameji T., Hayashi S., Igarashi K., Tamura T., Tanaka K., and Ichihara A. Nature (London) 360 (1992) 597-599
9. Turner G.C., Du F., and Varshavsky A. Nature (London) 405 (2000) 579-583
10. Naidoo N., Song W., Hunter-Ensor M., and Sehgal A. Science 285 (1999) 1737-1741
11. Chain D.G., Schwartz J.H., and Hegde A.N. Mol. Neurobiol. 20 (1999) 125-142
12. Alves-Rodrigues A., Gregori L., and Figueiredo-Pereira M.E. Trends Neurosci. 21 (1998) 516-520
13. Sakamoto K.M. Mol. Genet. Metab. 77 (2002) 44-56
14. Sun J.Z., Nam S., Lee C.S., Li B.Y., Coppola D., Hamilton A.D., Dou Q.P., and Sebti S.M. Cancer Res. 61 (2001) 1280-1284
15. Keck S., Nitsch R., Grune T., and Ullrich O. J. Neurochem. 85 (2003) 115-122
16. Rodgers K.J., and Dean R.T. Int. J. Biochem. Cell Biol. 35 (2003) 716-727
17. Willis W.S., and Patterson C. J. Mol. Cell. Cardiol. 41 (2006) 567-579
18. Zolk O., Schenke C., and Sarikas A. Cardiovasc. Res. 70 (2006) 410-421
19. Arrigo A.P., Tanaka K., Goldberg A.L., and Welch W.J. Nature (London) 331 (1988) 192-194
20. Coux O., Tanaka K., and Goldberg A.L. Annu. Rev. Biochem. 65 (1996) 801-847
21. Löwe J., Stock D., Jap B., Zwickl P., Baumeister W., and Huber R. Science 268 (1995) 533-539
22. Groll M., Ditzel L., Löwe J., Stock D., Bochtler M.B., and Huber R. Nature (London) 386 (1997) 463-471
23. Brannigan J.A., Dodson G., Duggleby H.J., Moody P.C., Smith J.L., Tomchick D.R., and Murzin A.G. Nature (London) 378 (1995) 416-419
24. Schubert U., Anton L.C., Gibbs J., Norbury C.C., Yewdell J.W., and Bennink J.R. Nature (London) 404 (2000) 770-774
25. Larsen C.N., and Finley D. Cell 91 (1997) 431-434
26. Baumeister W., Walz J., Zühl F., and Seemüller E. Cell 92 (1998) 367-380
27. Delcros J.G., Baudy Floc'h M., Prigent C., and Arlot-Bonnemains Y. Curr. Med. Chem. 10 (2003) 479-503
28. Richardson P.G., Sonneveld P., Schuster M.W., Irwin D., Stadtmauer E.A., Facon T., Harousseau J.L., Ben-Yehu D., Lonial S., and Goldschmidt H. N. Engl. J. Med. 352 (2005) 2487-2498
29. Adams J. Trends Mol. Med. 8 Suppl. (2002) S49-S54
30. Adams J., Palombella V.J., Sausville E.A., Johnson J., Destree A., Lazarus D.D., Maas J., Pien C.S., Prakash S., and Elliott P.J. Cancer Res. 59 (1999) 2615-2622
31. Pham L., Tamayo A., Lo P., Yoshimura L., and Ford R.J. Blood 98 (2001) 465a
32. Groll M., Berkers C.R., Ploegh H.L., and Ovaa H. Structure 14 (2006) 451-456
33. Adams J., Behnke M., Chen S.W., Cruickshank A.A., Dick L.R., Grenie L., Klunder J.M., Ma Y.T., Plamondon L., and Stein R.L. Bioorg. Med. Chem. Lett. 8 (1998) 333-338
34. Adams J. Drug Discov. Today 8 (2003) 307-315
35. Zhu Y.Q., Pei J.F., Liu Z.M., Lai L.H., Cui J.R., and Li R.T. Bioorg. Med. Chem. 14 (2006) 1483-1496
36. Kubinyi H. Drug Discov. Today 2 (1997) 457-467
37. Cramer III R.D., Patterson D.E., and Bunce J.D. J. Am. Chem. Soc. 110 (1988) 5959-5967
38. Klebe G., Abraham U., and Mietzner T. J. Med. Chem. 37 (1994) 4130-4146
39. Endo Y., Iijima T., Yaguchi K., Kawachi E., Inoue N., Kagechika H., Kubo A., and Itai A. Bioorg. Med. Chem. Lett. 11 (2001) 1307-1311
40. Endo Y., Iijima T., Yamakoshi Y., Fukasawa H., Miyaura C., Inada M., Kubu A., and Itai A. Chem. Biol. 8 (2001) 341-355
41. Endo Y., Yaguchi K., Tsuji M., Yamaguchi K., and Shudo K. Chem. Pharm. Bull. 47 (1999) 699-701
42. Endo Y., Yoshimi T., Kimura K., and Itai A. Bioorg. Med. Chem. Lett. 9 (1999) 2561-2564
43. Tsuji M., Koiso Y., Takahashi H., Hashimoto Y., and Endo Y. Biol. Pharm. Bull. 23 (2000) 513-516
44. Tao P., and Lai L.H. J. Comput.-Aided Mol. Des. 15 (2001) 429-446
45. J. Adams, Y.T. Ma, R. Stein, M. Baevsky, L. Grenier, L. Plamonda, PCT Int. Appl., WO 1996013266, 1995.
46. Johnsamuel J., Byun Y., Jones T.P., Endo Y., and Tjarks W. J. Organomet. Chem. 680 (2003) 223-231
47. Johnsamuel J., Byun Y., Jones T.P., Endo Y., and Tjarks W. Bioorg. Med. Chem. Lett. 13 (2003) 3213-3216
48. Sybyl Theory Manual (1988), Tripos Associates Inc., 1699 South Hanley Road, St. Louis, MO
49. Sybyl Molecular Spreadsheet Manual (1988), Tripos Associates Inc., 1699 South Hanley Road, St. Louis, MO
50. Sybyl Tutorial Manual (1988), Tripos Associates Inc., 1699 South Hanley Road, St. Louis, MO
51. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902-3909
52. Gasteiger J., and Marsili M. Tetrahedron 36 (1980) 3219-3228
53. Böhm M., Stürzebecher J., and Klebe G. J. Med. Chem. 42 (1999) 458-477