Novel pharmacophore-based methods reveal gossypol as a reverse transcriptase inhibitor

Journal of Molecular Graphics and Modelling

Volumn 21, Issue 5, 2003, Pages 365-373

  Keller, Paul A ^a   Birch, Chris ^c   Leach, Scott P ^a   Tyssen, David ^c   Griffith, Renate ^a,b  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b UNIVERSITY OF NEWCASTLE   (Australia)

^c VICTORIAN INFECTIOUS DISEASES REFERENCE LABORATORY   (Australia)

Author keywords

Database searching; Gossypol; Pharmacophores; Reverse transcriptase

Indexed keywords

ENZYME INHIBITION; FILTRATION;

PHARMACOPHORES;

MOLECULAR GRAPHICS;

ANTIVIRUS AGENT; GOSSYPOL DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; DATA BASE; DRUG SCREENING; ENZYME INHIBITION; PHARMACOPHORE; PRIORITY JOURNAL;

DATABASES, FACTUAL; GOSSYPOL; HIV-1 REVERSE TRANSCRIPTASE; HUMANS; MOLECULAR STRUCTURE; NEVIRAPINE; REVERSE TRANSCRIPTASE INHIBITORS; SOFTWARE;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0346034671     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1093-3263(02)00183-3     Document Type: Article

References (19)

1. Gussio R., Pattabiraman N., Kellog G.E., Zaharerevitz D.W. Use of 3D QSAR methodology for data mining the National Cancer Institute repository of small molecules: application to HIV-1 reverse transcriptase inhibition. Methods. 14:1998;255-263.
2. Hopfinger A.J., Wang S., Tokarski J.S., Jin B., Albuquerque M., Madhav P.J., Duraiswami C. Construction of 3D-QSAR models using the 4D-QSAR analysis formalism. J. Am. Chem. Soc. 119:1997;10509-10524.
3. Gussio R., Pattabiraman N., Zaharerevitz D.W., Kellog G.E., Igor A., Rice W.G., Schaeffer C., Erickson J.W., Burt S.K. All-atom models for the non-nucleoside binding site of HIV-1 reverse transcriptase complexed with inhibitors: a 3D QSAR approach. J. Med. Chem. 39:1996;1645-1650.
4. Mestres J., Rohrer D.C., Maggiora G.M. A molecular field-based similarity study of non-nucleoside HIV-1 reverse transcriptase inhibitors. J. Comput. Aided Mol. Des. 13:1999;79-93.
5. Mestres J., Rohrer D.C., Maggiora G.M. MIMIC: a molecular-field matching program. Exploiting applicability of molecular similarity approaches. J. Comput. Chem. 18:1997;934-954.
6. Tronchet J.M.J., Grigorov M., Dolatshahi N., Moriaud F., Weber J. A QSAR Study confirming the heterogeneity of the HEPT derivative series regarding their interaction with HIV reverse transcriptase. Eur. J. Med. Chem. 32:1997;279-299.
7. Jager J., Smerdon S.J., Wang J., Boisvert D.C., Steitz T.A. Comparison of three different crystal forms shows HIV-1 reverse transcriptase displays an internal swivel motion. Structure. 2:1994;869-876.
8. Catalyst, version 4.0, Molecular Simulations, Inc. (now Accelrys), San Diego, CA, USA, 1998 (and accompanying documentation).
9. P.W. Sprague, R. Hoffmann, Catalyst pharmacophore models and their utility as queries for searching 3D databases, in: H. van der Waterbeemd, B. Testa, G. Folkers (Eds.), Computer-Assisted Lead Finding and Optimization: Current Tools for Medicinal Chemistry, VHCA Wiley-VCH, Weinheim, Germany, 1997, pp. 225-240.
10. Ding J., Das K., Tantillo C., Zhang W., Clark A.D., Jessen S., Lu X., Hsiou Y., Jacobomolina A., Andries K., Pauwels R., Moereels H., Koymans L., Janssen P.A.J., Smith R.H., Koepke M.K., Michejda C.J., Hughes S.H., Arnold E. Structure of HIV-1 reverse transcriptase in a complex with the non-nucleoside inhibitor α-APA R 95845 at 2.8 Å resolution. Structure. 3:1995;365-379.
11. Kelly T.A., Proudfoot J.R., McNeil D.W., Patel U.R., David E., Hargrave K.D., Grob P.M., Cardozo M., Agarwal A., Adams J. Novel non-nucleoside inhibitors of human immunodeficiency virus Type 1 reverse transcriptase. 5. 4-Substituted and 2,4-disubstituted analogs of nevirapine. J. Med. Chem. 38:1995;4839-4847.
12. De Clercq E. HIV-1-specific RT inhibitors: highly selective inhibitors of human immunodeficiency virus Type 1 that are specifically targeted at the viral reverse transcriptase. Med. Res. Rev. 13:1993;229-258.
13. Ho W., Kukla M.J., Breslin H.J., Ludovici D.W., Grous P.P., Diamond C.J., Miranda M., Rodgers J.D., Ho C.Y., De Clercq E., Pauwels R., Andries K., Janssen M.A.C., Janssen P.A.J. Synthesis and anti-HIV-1 activity of 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-one (TIBO) derivatives. 4. J. Med. Chem. 38:1995;794-802.
14. Keller P.A., Leach S.P., Luu T.T.T., Titmuss S.J., Griffith R. Development of computational and graphical tools for analysis of movement and flexibility in large molecules. J. Mol. Graphics Model. 18:2000;235-241. (and references cited therein).
15. Titmuss S.J., Keller P.A., Griffith R. Docking experiments in the flexible non-nucleoside inhibitor binding pocket of HIV-1 reverse transcriptase. Bioorg. Med. Chem. 7:1999;1163-1170.
16. Casimiro-Garcia A., Micklatcher M., Turpin J.A., Stup T.L., Watson K., Buckheit R.W., Cushman M. Novel modifications in the alkenyldiarylmethane (ADAM) series of non-nucleoside reverse transcriptase inhibitors. J. Med. Chem. 42:1999;4861-4874. (and references sited therein).
17. Lin T.S., Schinazi R., Griffith B.P., August E.M., Eriksson B.F.H., Zheng D.K., Huang L., Prusoff W.H. Selective inhibition of human immunodeficiency virus Type 1 replication by the (-) but not the (+) enantiomer of gossypol. Antimicrob. Agents Chemother. 33:1989;2149-2151.
18. Royer R.E., Mills R.G., Younf S.A., Vander Jagt D.L. Comparison of the antiviral activities of 3′-azido-3′-deoxythymidine (AZT) and gossylic iminolactone (GIL) against clinical isolates of HIV-1. Pharmacol. Res. 31:1995;49-52.
19. McMahon J.B., Currens M.J., Gulakowski R.J., Buckheit R.W., Lackmansmith C., Hallock Y.F., Boyd M.R. Michellamine B, a novel plant alkaloid, inhibits human immunodeficiency virus-induced cell killing by at least two distinct mechanisms. Antimicrob. Agents Chemother. 39:1995;484-488.