Structure of HIV-1 nonnucleoside reverse transcriptase inhibitors derivatives of N-benzyl-benzimidazole with different substituents in position 4

Journal of Molecular Structure

Volumn 963, Issue 2-3, 2010, Pages 188-193

  Ziółkowska, Natasza E ^a   Michejda, Christopher J ^b   Bujacz, Grzegorz D ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

AIDS; Crystal structure; Drug design; HIV 1; Reverse transcriptase inhibitor

Indexed keywords

BENZIMIDAZOLES; BIOLOGICAL ACTIVITIES; DRUG DESIGN; DRUG RESISTANCE; GLOBAL EXPANSION; HIV-1 REVERSE TRANSCRIPTASE; NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURAL DATA;

DISEASES; DRUG THERAPY; ENZYME INHIBITION; VIRUSES;

CRYSTAL STRUCTURE;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 73449148997     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2009.10.034     Document Type: Article

References (32)

1. Kohlstaedt L.A., Wang J., Friedman J.M., Rice P.A., and Steitz T.A. Science 256 (1992) 1783
2. Yarchoan R., Klecker R.W., Weinhold K.J., Markham P.D., Lyerly H.K., Durack D.T., Gelmann E., Lehrman S.N., Blum R.M., Barry D.W., Shearer G.M., Fischl M.A., Mitsuya H., Gallo R.C., and Collins J.M. Lancet 1 (1986) 575
3. Huttner A.C., Kaufmann G.R., Battegay M., Weber R., and Opravil M. AIDS 21 (2007) 939
4. Yarchoan R., Perno C.F., Thomas R.V., Klecker R.W., Allain J.P., Wills R.J., McAtee N., Fischl M.A., Dubinsky R., McNeely M.C., Mitsuya H., Pluda J.M., Lawley T.J., Leuther M., Safai B., Collins J.M., Myers C.E., and Broder S. Lancet 331 (1988) 76
5. Jeffries D.J. J. Antimicrob. Chemother. Suppl. A (1989) 29
6. Yarchoan R., Mitsuya H., Thomas R.V., Pluda J.M., Hartman N.R., Perno C.F., Marczyk K.S., Allain J.P., Johns D.G., and Broder S. Science 245 (1989) 412
7. Blanco J.L., Biglia A., Lazzari de E., Mallolas J., Martinez E., Pumarola T., Larrousse M., Milinkovic A., Leon A., Lonca M., Laguno M., and Gatell J.M. AIDS 20 (2006) 1891
8. August E.M., Marongiu M.E., Lin T.S., and Prusoff W.H. Biochem. Pharmacol. 37 (1988) 4419
9. Hill A., Ruxrungtham K., Hanvanich M., Katlama C., Wolf E., Soriano V., Milinkovic A., Gatell J., and Ribera E. Expert Opin. Pharmacother. 8 (2007) 679
10. Merluzzi V.J., Hargrave K.D., Labadia M., Grozinger K., Skoog M., Wu J.C., Shih C.K., Eckner K., Hattox S., Adams J., Rosenthal A.S., Faanes R., Eckner R.J., Koup R.A., and Sullivan J.L. Science 250 (1990) 1411
11. Wu J.C., Warren T.C., Adams J., Proudfoot J., Skiles J., Raghavan P., Perry C., Potocki I., Farina P.R., and Grob P.M. Biochemistry 30 (1991) 2022
12. Maggiolo F. Expert Opin. Pharmacother. 8 (2007) 1137
13. Young S.D., Britcher S.F., Tran L.O., Payne L.S., Lumma W.C., Lyle T.A., Huff J.R., Anderson P.S., Olsen D.B., Carroll S.S., Pettibone D.J., O'Brien J.A., Ball R.G., Balani S.K., Lin J.H., Chen I.-W., Schleif W.A., Sardana V.V., Long W.J., Byrnes V.W., and Emini E.A. Antimicrob. Agents Chemother. 39 (1995) 2602
14. Scott L.J., and Perry C.M. Drugs 60 (2000) 1411
15. Tran J.Q., Gerber J.G., and Kerr B.M. Clin. Pharmacokinet. 40 (2001) 207
16. Tantillo C., Ding J., Jacobo-Molina A., Nanni R.G., Boyer P.L., Huges S.H., Pauwels R., Aries K., Jansen P.A.J., and Arnold E. J. Mol. Biol. 243 (1994) 369
17. Ding J., Das K., Moereels H., Koymans L., Andries K., Jansen P.A.J., Huges S.H., and Arnold E. Nat. Struct. Biol. 2 (1995) 407
18. Smith M.B.K., Rouzer C.A., Taneyhill L.A., Smith N.A., Huges S.H., Boyer P.L., Jansen P.A.J., Moereels H., Koymans L., Arnold E., Ding J., Das K., Zhang W., Michejda C.J., and Smith R.H. Protein Sci. 4 (1995) 2203
19. Frenz B.A. SDP - Structure Determination Package (1984), Enraf-Nonius, Delft, Holland
20. North A.C.T., Philips D.C., and Mathews F.S. Acta Cryst. A24 (1968) 351
21. G. M. Sheldrick, G.M. Kruger, R. Goddard, SHELXS-86, Crystallographic Computing 5, Oxford, 1985.
22. Sheldrick G.M. Acta Cryst. A64 (2008) 112
23. Sheldrick, G.M. SHELXL-93, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1993.
24. Vickovic J. J. Appl. Cryst. 21 (1988) 987
25. Chimirri A., Grasso S., Monforte A.M., Monforte P., and Zappala M. Il Farmaco 46 (1991) 817
26. Chimirri A., Grasso S., Monforte A.M., Monforte P., and Zappala M. Il Farmaco 46 (1991) 925
27. Roth T., Morningstar M.L., Boyer P.L., Huges S.H., Buckheit R.W., and Michejda C.J. J. Med. Chem. 40 (1997) 4199
28. Morningstar M.L., Roth T., Farnsworth D.W., Smith M.K., Watson K., Buckheit Jr. R.W., Das K., Zhang W., Arnold E., Julias J.G., Hughes S.H., and Michejda C.J. J. Med Chem. 50 (2007) 4003
29. Siemens Analytical Xray Inst. XP - Interactive Molecular Grafics, 1992.
30. W.L. DeLano, The PyMOL Molecular Graphics System (2002) DeLano Scientific, San Carlos, CA, USA. Available from: http://www.pymol.org.
31. Emsley P., and Cowtan K. Acta Cryst. D60 (2004) 2126
32. Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK (fax +44 1223 336033), Available from: http://www.ccdc.cam.ac.uk/.