Crystal structures of HIV-1 reverse transcriptase complexes with thiocarbamate non-nucleoside inhibitors

Biochemical and Biophysical Research Communications

Volumn 365, Issue 4, 2008, Pages 764-770

  Spallarossa, Andrea ^a   Cesarini, Sara ^a   Ranise, Angelo ^a   Ponassi, Marco ^b   Unge, Torsten ^c   Bolognesi, Martino ^d  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF GENOA   (Italy)

^c UPPSALA UNIVERSITY   (Sweden)

^d UNIVERSITY OF MILAN   (Italy)

Author keywords

HIV 1; Non nucleoside reverse transcriptase inhibitors; Reverse transcriptase; Thiocarbamates; X ray crystallography

Indexed keywords

BROMINE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THIOCARBAMIC ACID; THIOUREA;

ARTICLE; ATOM; CHEMICAL ANALYSIS; CHEMICAL BOND; CRYSTAL STRUCTURE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

BINDING SITES; COMPUTER SIMULATION; CRYSTALLOGRAPHY; ENZYME ACTIVATION; ENZYME INHIBITORS; HIV REVERSE TRANSCRIPTASE; MODELS, CHEMICAL; MODELS, MOLECULAR; NUCLEOSIDES; PROTEIN BINDING; PROTEIN CONFORMATION; THIOCARBAMATES;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 36849047420     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2007.11.036     Document Type: Article

References (30)

1. De Clercq E. New developments in anti-HIV chemotherapy. Curr. Med. Chem. 8 (2001) 1543-1572
2. Palella F.J., Delaney K.M., Moorman A.C., Loveless M.O., Fuhrer J., Satten G.A., Aschman D.J., and Holmberg S.D. Declining morbidity and mortality among patients with advanced human immunodeficiency virus infection. HIV outpatient study investigators. N. Engl. J. Med. 338 (1998) 853-860
3. De Clercq E. Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future. Chem. Biodivers. 1 (2004) 44-64
4. Sarafianos S.G., Das K., Hughes S.H., and Arnold E. Taking aim at a moving target: designing drugs to inhibit drug-resistant HIV-1 reverse transcriptases. Curr. Opin. Struct. Biol. 14 (2004) 716-730
5. Das K., Clark A.D.J., Lewi P.J., Heeres J., de Jonge M.R., Koymans L.M.H., M Vinkers H., Daeyaert F., Ludovici D.W., Kukla M.J., et al. Roles of conformational and positional adaptability in structure-based design of TMC125-R165335 (Etravirine) and related non-nucleoside reverse transcriptase inhibitors that are highly potent and effective against wild-type and drug-resistant HIV-1 variants. J. Med. Chem. 47 (2004) 2550-2560
6. Esnouf R., Ren J., Ross C., Jones Y., Stammers D., and Stuart D.I. Mechanism of Inhibition of HIV-1 Reverse Transcriptase by Non-nucleoside Inhibitors. Nat. Struct. Biol. 2 (1995) 303-308
7. Hsiou Y., Ding J., Das K., Clark A.D.J., Hughes S.H., and Arnold E. Structure of unliganded HIV-1 reverse transcriptase at 2.7 Å resolution: implications of conformational changes for polymerization and inhibition mechanisms. Structure 4 (1996) 853-860
8. Spallarossa R.A., Cesarini S., Bondavalli F., Schenone S., Bruno O., Menozzi G., Fossa P., Mosti L., La Colla M., et al. Structure-based design, parallel synthesis, structure-activity relationship, and molecular modeling studies of thiocarbamates, new potent non-nucleoside HIV-1 reverse transcriptase inhibitor isosteres of phenethylthiazolylthiourea derivatives. J. Med. Chem. 48 (2005) 3858-3873
9. Bell F.W., Cantrell A.S., Hogberg M., Jaskunas S.R., Johansson N.G., Jordan C.L., Kinnick M.D., Lind P., Morin J.M.J., Noreen R., et al. PETT compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure-activity relationship studies of PETT analogs. J. Med. Chem. 38 (1995) 4929-4936
10. Cantrell A.S., Engelhardt P., Hogberg M., Jaskunas S.R., Johansson N.G., Jordan C.L., Kangasmetsa J., Kinnick M.D., Lind P., Morin J.M.J., et al. Phenethylthiazolylthiourea (PETT) compounds as a new class of HIV-1 reverse transcriptase inhibitors. 2. Synthesis and further structure-activity relationship studies of PETT analogs. J. Med. Chem. 39 (1996) 4261-4274
11. Ludovici D.W., De Corte B.L., Kukla M.J., Ye H., Ho C.Y., Lichtenstein M.A., Kavash R.W., Andries K., de Bethune M.P., Azijn H., et al. Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues. Bioorg. Med. Chem. Lett. 11 (2001) 2235-2239
12. McMahon J.B., Buckheit R.W.J., Gulakowski R.J., Currens M.J., Vistica D.T., Shoemaker R.H., Stinson S.F., Russell J.D., Bader J.P., Narayanan V.L., et al. Biological and biochemical anti-human immunodeficiency virus activity of UC 38, a new non-nucleoside reverse transcriptase inhibitor. J. Pharmacol. Exp. Ther. 276 (1996) 298-305
13. Artico M. Non-nucleoside anti-HIV-1 reverse transcriptase inhibitors (NNRTIs): a chemical survey from lead compounds to selected drugs for clinical trials. Farmaco 51 (1996) 305-331
14. Auffinger P., Hays F.A., Westhof E., and Ho P.S. Halogen bonds in biological molecules. Proc. Natl. Acad. Sci. USA 101 (2004) 16789-16794
15. Lindberg J., Sigurosson S., Lowgren S., Andersson H.O., Sahlberg C., Noreen R., Fridborg K., Zhang H., and Unge T. Structural basis for the inhibitory efficacy of efavirenz (DMP-266), MSC194 and PNU142721 towards the HIV-1 RT K103N mutant. Eur. J. Biochem. 269 (2002) 1670-1677 and references therein
16. Z. Otwinowski, Proceedings of the CCP4 Study Weekend. Data Collection and Processing; L. Sawyer, N. Isaacs & S. Bailey (Ed.), Warrington: Daresbury Laboratory, 1993, pp. 56-62.
17. Otwinowski Z., and Minor W. Processing of X-ray diffraction data collection in oscillation mode. Methods Enzymol. 276 (1997) 307-326
18. nr4, C.C. & P. The CCp4 suite: programs for protein crystallography, Acta Cryst. D50 (1994) 760-763.
19. Hogberg M., Sahlberg C., Engelhardt P., Noreen R., Kangasmetsa J., Johansson N.G., Oberg B., Vrang L., Zhang H., Sahlberg B.L., et al. Urea-PETT compounds as a new class of HIV-1 reverse transcriptase inhibitors. 3. Synthesis and further structure-activity relationship studies of PETT analogues. J. Med. Chem. 42 (1999) 4150-4160
20. Murshudov G.N., Vagin A.A., and Dodson E.J. Refinement of macromolecular structures by the maximum-likelihood method. Acta Cryst. D53 (1997) 240-255
21. Kleywegt G.J., and Brunger A.T. Checking your imagination: applications of the free R. value. Structure 4 (1996) 897-904
22. Jones T.A., Zou J.-Y., Cowan S.W., and Kjeldgaard M. Improved methods for the building of protein models in electron density maps and the location of errors in these models. Acta Cryst. A47 (1991) 110-119
23. Potterton E., McNicholas S., Krissinel E., Cowtan K., and Noble M. The CCP4 molecular-graphics project. Acta Cryst. D58 (2002) 1955-1957
24. Kraulis P.J. MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures. J. Appl. Crystallogr. 24 (1991) 946-950
25. Esnouf R.M. An extensively modified version of MolScript that includes greatly enhanced coloring capabilities. J. Mol. Graph. Model. 15 (1997) 132-134
26. Hopkins A.L., Ren J., Esnouf R.M., Willcox B.E., Jones E.Y., Ross C., Miyasaka T., Walker R.T., Tanaka H., Stammers D.K., and Stuart D.I. Complexes of HIV-1 reverse transcriptase with inhibitors of the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors. J. Med. Chem. 39 (1996) 1589-1600
27. Pauwels R. New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections. Curr. Opin. Pharmacol. 4 (2004) 437-446
28. Kuntz I.D. Structure-based strategies for drug design and discovery. Science 257 (1992) 1078-1082
29. Ren J., Diprose J., Warren J., Esnouf R.M., Bird L.E., Ikemizu S., Slater M., Milton J., Balzarini J., Stuart D.I., and Stammers D.K. Phenylethylthiazolylthiourea (PETT) non-nucleoside inhibitors of HIV-1 and HIV-2 reverse transcriptases. Structural and biochemical analyses. J. Biol. Chem. 275 (2000) 5633-5639
30. Ren J., Esnouf R.M., Hopkins A.L., Warren J., Balzarini J., Stuart D.I., and Stammers D.K. Crystal structures of HIV-1 reverse transcriptase in complex with carboxanilide derivatives. Biochemistry 37 (1998) 14394-14403