Targeting HIV-1 through molecular modeling and docking studies of CXCR4: Leads for therapeutic development

Chemical Biology and Drug Design

Volumn 69, Issue 3, 2007, Pages 191-203

  Singh, Shailza ^a   Malik, B K ^b   Sharma, D K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

^b CSIR INSTITUTE OF GENOMICS AND INTEGRATIVE BIOLOGY   (India)

Author keywords

CXCR4; Docking; Flavonoids; Human immunodeficiency virus; Molecular modeling

Indexed keywords

2 METHOXY 3 METHYL 4,6 DIHYDROXY 5 (3' HYDROXY)CINNAMOYLBENZALDEHYDE; ANTIVIRUS AGENT; BAICALIN; CHALCONE DERIVATIVE; CHEMOKINE RECEPTOR CXCR4; CURCUMIN; FLAVONOID; RHODOPSIN; UNCLASSIFIED DRUG; XANTHOHUMOL;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; COMPUTER MODEL; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG TARGETING; HUMAN IMMUNODEFICIENCY VIRUS 1; INHIBITION KINETICS; MOLECULAR MODEL; PRIORITY JOURNAL; PROTEIN TARGETING; SEQUENCE HOMOLOGY; STRUCTURE ACTIVITY RELATION; VIRUS INACTIVATION;

AMINO ACID SEQUENCE; ANIMALS; ANTI-HIV AGENTS; CATTLE; COMPUTER SIMULATION; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; HIV-1; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN STRUCTURE, SECONDARY; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, CXCR4; SEQUENCE ALIGNMENT;

BOVINAE; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 34247197042     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2007.00478.x     Document Type: Article

References (106)

1. Barre-Sinoussi J.C., Chermann F., Rey M.T., Nugeyre S., Chamaret J., Gruest C., Dauguest C., Axler-Blin F., Vezinet-Brun C., Rouzioux W., Rozenbaun L., Montagnier M. (1983) Isolation of a T-lymphotropic retrovirus from a patient at risk for acquired immune deficiency syndrome (AIDS). Science;220:868-871.
2. Gallo R.C., Salahuddin S.Z., Popovic M., Shearer G.M., Kaplan M., Haynes B.F., Palker T.J., Redfield R., Oleske J., Saafai B., White G., Foster P., Markham P.D. (1984) Frequent detection and isolation of cytopathic retroviruses (HTLV-III) from patients with AIDS and at risk for AIDS. Science;224:500-503.
3. Balint G.A. (2001) Antiretroviral therapeutic possibilities for human immunodeficiency virus/acquired immunodeficiency syndrome. Pharmacol Ther;89:17-27.
4. Fauci A.S. (2003) HIV and AIDS: 20 years of science. Nat Med;9:839-843.
5. Pomerantz R.J., Horn D.L. (2003) Twenty years of therapy for HIV-1 infection. Nat Med;9:867-873.
6. Carr A. (2003) Toxicity of antiretroviral therapy and implications for drug development. Nat Rev Drug Discov;2:624-634.
7. Duran S., Saves M., Spire B., Cailleton V., Sobel A., Carrieri P., Salmon D., Moatti J.P., Leport C. (2001) Failure to maintain long-term adherence to highly active antiretroviral therapy: the role of lipodystrophy. AIDS;15:2441-2444.
8. Ickovics J.R., Meade C.S. (2002) Adherence to HAART among patients with HIV: breakthroughs and barriers. AIDS Care;14:309-318.
9. Zaitseva M., Peden K., Golding H. (2003) HIV coreceptors: role of structure, post-translational modifications, and internalization in viral-cell fusion and as targets for entry inhibitors. Biochim Biophys Acta;1614:51-61.
10. Murphy P.M. (1994) The molecular biology of leukocyte chemo-attractant receptors. Annu Rev Immunol;12:593-633.
11. Wegner S.A., Ehrenberg P.K., Chang G., Dayhoff D.E., Sleeker A.L., Michael N.L. (1998) Genomic organization and functional characterization of the chemokine receptor CXCR4, a major entry co-receptor for human immunodeficiency virus type 1. J Biol Chem;273:4754-4760.
12. Alkhatib G., Combadiere C., Broder C.C., Feng Y., Kennedy I.E., Murphy I.M., Berger E.A. (1996) CC CKRs-a RANTES, MIP-l-alpha, MIP-l-beta receptor as a fusion cofactor for macrophage-tropic HIV-l. Science;272:1955-1958.
13. Bates P. (1996) Chemokine receptors and HIV-l-an attractive pair. Cell;86:1-3.
14. Berson J.F., Long D., Doranz B.J., Rucker J., Jirik F.R., Doms R.W. (1996) A seven-transmembrane domain receptor involved in fusion and entry of T-cell-tropic human immuno-deficiency virus Type 1 strains. J Virol;70:6288-6295.
15. Choe H., Farzan M., Sun Y., Sullivan N., Rollins B., Ponath P.D., Wu L.J., Mackay C.R., Larosa G., Newman W., Gerard N., Gerard C., Sodroski J. (1996) The beta-chemokine receptors CCR3 and CCR5 facilitate infection by primary HIV-I isolates. Cell;85:1135-1148.
16. Combadiere C., Ahuja S.K., Tiffany H.L., Murphy P.M. (1996) Cloning and functional expression of Cc Ckr5, a human monocyte Cc chemokine receptor selective for Mip-l-alpha, Mip-l-beta, and Rantes. J Leukoc Biol;60:147-152.
17. Deng H., Liu R., Ellmeier W., Choe S., Unutmaz D., Burkhart M., Di Marzio P., Marmon S., Sutton R.E., Hill C.M., Davis C.B., Peiper S.C., Schall T.J., Littman D.R., Landau N.R. (1996) Identification of a major co-receptor for primary isolates of HIV-l. Nature;381:661-666.
18. Dragic T., Litwin V., Allaway G.P., Martin S.R., Huang Y.X., Nagashima K.A., Cayanan C., Maddon P.J., Koup R.A., Moore J.P., Paxton W.A. (1996) HIV-1 entry into Cd4 (+) cells is mediated by the chemokine receptor CC-CKR-5. Nature; 381:667-673.
19. Friedland J.S. (1996) Chemokines in viral disease. Res Virol;147:131-138.
20. Trkola A., Dragic T., Arthos J., Binley J.M., Olson W.C., Allaway G.P., Cheng-Mayer C., Robinson J., Maddon P.J., Moore J.P. (1996) CD4-dependent, antibody-sensitive interactions between HIV-l and its co-receptor CCR-5. Nature;384:184-187.
21. He J., Chen Y., Farzan M., Choe H., Ohagen A., Gartner S., Busciglio J., Yang X., Hofmann W., Newman W., Mackay C.R., Sodroski J., Gabuzda D. (1997) CCR3 and CCR5 are coreceptors for HIV-l infection of microglia. Nature;385:645-649.
22. Cooley L.A., Lewin S.R. (2003) HIV-1 cell entry and advances in viral entry inhibitor therapy. J Clin Virol;26:121-132.
23. Jiang S., Debnath A.K. (2000) Development of HIV entry inhibitors targeted to the coiled coil regions of gp41. Biochem Biophys Res Commun;269:641-646.
24. Jiang S., Zhao Q., Debnath A.K. (2002) Peptide and non-peptide HIV fusion inhibitors. Curr Pharm Des;8:563-580.
25. Jiang S., Lu H., Liu S., Zhao Q., He Y., Debnath A.K. (2004) N-substituted pyrrole derivatives as novel human immunodeficiency virus type 1 entry inhibitors that interfere with the gp41 six-helix bundle formation and block virus fusion. Antimicrob Agents Chemother;48:4349-4359.
26. Jiang S., Siddiqui P., Liu S. (2004) Blocking viral entry: a complimentary strategy for HIV therapy. Drug Discov Today: Ther Strateg;1:497-503.
27. Kwong P.D., Wyatt R., Robinson J., Sweet R.W., Sodroski J., Hendrickson W.A. (1998) Structure of an HIV gp120 envelope glycoprotein in complex with the CD4 receptor and a neutralizing human antibody. Nature;393:648-659.
28. Wyatt R., Kwong P.D., Desjardins E., Sweet R.W., Robinson J., Hendrickson W.A., Sodroski J.G. (1998) The antigenic structure of the HIV gp120 envelope glycoprotein. Nature; 393:705-711.
29. Sullivan N., Sun Y., Sattentau Q., Thali M., Wu D., Denisova G., Gershoni J., Robinson J., Moore J., Sodroski J. (1998) CD4-induced conformational changes in the human immunodeficiency virus type 1 gp120 glycoprotein: consequences for virus entry and neutralization. J Virol;72:4694-4703.
30. Neffe A.T., Meyer B. (2004) A peptidomimetic HIV-entry inhibitor directed against the CD4 binding site of the viral glycoprotein gp120. Angew Chem, Int Ed Engl;43:2937-2940.
31. Omura S., Tanaka H., Matsuzaki K., Ikeda H., Masuma R. (1993) Isochromophilones I and II, novel inhibitors against gp120-CD4 binding from Penicillium sp. J Antibiot (Tokyo);46:1908-1911.
32. Dey B., Lerner D.L., Lusso P., Boyd M.R., Elder J.H., Berger E.A. (2000) Multiple antiviral activities of cyanovirin-N: blocking of human immunodeficiency virus type 1 gp120 interaction with CD4 and coreceptor and inhibition of diverse enveloped viruses. J Virol;74:4562-4569.
33. Tamamura H., Ishihara T., Otaka A., Murakami T., Ibuka T., Waki M., Matsumoto A., Yamamoto N., Fujii N. (1996) Analysis of the interaction of an anti-HIV peptide, T22 ([Tyr5, 12, Lys7]-polyphemusin II), with gp120 and CD4 by surface plasmon resonance. Biochim Biophys Acta;1298:37-44.
34. Tamamura H., Otaka A., Murakami T., Ishihara T., Ibuka T., Waki M., Matsumoto A., Yamamoto N., Fujii N. (1996) Interaction of an anti-HIV peptide, T22, with gp120 and CD4. Biochem Biophys Res Commun;219:555-559.
35. Vermeire K., Princen K., Hatse S., De Clercq E., Dey K., Bell T.W., Schols D. (2004) CADA, a novel CD4-targeted HIV inhibitor, is synergistic with various anti-HIV drugs in vitro. AIDS;18:2115-2125.
36. Bewley C.A., Ray S., Cohen F., Collins S.K., Overman L.E. (2004) Inhibition of HIV-1 envelope-mediated fusion by synthetic batzelladine analogues. J Nat Prod;67:1319-1324.
37. Okamoto M., Fujiwara M., Kodama E., Yamamoto O., Shigeta S., Mitsuya H., Konno K., Yokota T., Baba M. (1999) Inhibition of human immunodeficiency virus replication by RD6-Y664, a novel benzylhydroxylamine derivative. Antiviral Chem Chemother; 10:71-77.
38. Matsuzaki K., Tahara H., Inokoshi J., Tanaka H., Masuma R., Omura S. (1998) New brominated and halogen-less derivatives and structureactivity relationship of azaphilones inhibiting gp120-CD4 binding. J Antibiot (Tokyo);51:1004-1011.
39. Sun X.L., Takayanagi H., Matsuzaki K., Tanaka H., Furuhata K., Omura S. (1996) Synthesis and inhibitory activities of isochromophilone analogues against gp120-CD4 binding. J Antibiot (Tokyo);49:689-692.
40. Notka F., Meier G., Wagner R. (2004) Concerted inhibitory activities of Phyllanthus amarus on HIV replication in vitro and ex vivo. Antiviral Res;64:93-102.
41. Walker J.E., Saraste M. (1996) Membrane protein structure. Curr Opin Struct Biol;6:457-459.
42. Mitsuya H., Weinhold K.J., Furman P.A., St Clair M.H., Nusinoff-Lehrman S., Gallo R.C., Bolognesi D., Barry D.W., Broder S. (1985) 3′-Azido- 3′-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III: lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci U S A;82:7096-7100.
43. Fischl M.A., Richman D.D., Grieco M.H., Gottlieb M.S., Volberding P.A., Laskin O.L., Leedon J.M., Groopman J.E., Mildvan D., Schooley R.T., Jackson G.G., Durack D.T., Phil D., King D., the AZT Collaborative Working Group (1987) The efficacy of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex: a double-blind, placebo-controlled trial. N Engl J Med;317:185-191.
44. Browne M.J., Mayer K.H., Chafee S.B.D., Dudley M.N., Posner M.R., Steinberg S.M., Graham K.K. et al. (1993) 2′, 3′-Didehydro-3′- deoxythymidine (d4T) in patients with AIDS or AIDS-related complex: a phase I trial. J Infect Dis;167:21-29.
45. Yarchoan R., Weinhold K.J., Lyerly H.K., Gelmann E., Blum R.M., Shearer G.M., Mitsuya H. et al. (1986) Administration of 3′-azido-3′- deoxythymidine, an inhibitor of HTLVIII: LAV replication, to patients with AIDS or AIDS-related complex. Lancet; 1:575-580.
46. Yarchoan R., Perno C.F., Thomas R.V., Klecker R.W., Allain J.P., Wills R.J., McAtee N. et al. (1988) Phase I studies of 2′,3′- dideoxycytidine in severe human immunodeficiency virus infection as a single agent and alternating with zidovudine (AZT). Lancet;1:76-81.
47. Richman D.D., Fischl M.A., Grieco M.H., Gottlieb M.S., Volberding P.A., Lskin O.L., Leedom J.M., Groopman J.E., Mildvan D., Hirsch M.S., Jackson G.G., Durack D.T., Phil D., Nusinoff-Lehrman S., the AZT Collaborative Working Group (1987) The toxicity of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex. N Engl J Med;317:192-197.
48. Larder B.A., Darby G., Richman D.D. (1989) HIV with reduced sensitivity to zidovudine (AZT) isolated during prolonged therapy. Science;243:1731-1734.
49. 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., Sullivan J.L. (1990) Inhibition of HIV-1 replication by a nonnucleoside reverse transcriptase inhibitor. Science;250:1411-1413.
50. Pauwels R., Andries K., Desmyter J., Schols D., Kukla M.J., Breslin H.J., Raeymaeckers A., Van Gelder J., Woestenborghs R., Heykants J., Schellekens K., Janssen M.A.C., De Clercq E., Janssen P.A.J. (1990) Potent and selective inhibition of HIV-1 replication in vitro by a novel series of TIBO derivatives. Nature;343:470-474.
51. De Clercq E. (1995) Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J Med Chem;38:2491-2517.
52. De Clercq E. (1995) Antiviral therapy for human immunodeficiency virus infections. Clin Microbiol Rev;8:200-239.
53. Moore J.P., Doms R.W. (2003) The entry of entry inhibitors: a fusion of science and medicine. Proc Natl Acad Sci U S A;100:10598-10602.
54. Lin P.F., Blair W., Wang T., Spicer T., Guo Q., Zhou N., Gong Y.F. et al. (2003) A small molecule HIV-1 inhibitor that targets the HIV-1 envelope and inhibits CD4 receptor binding. Proc Natl Acad Sci U S A;100:11013-11018.
55. De Clercq E. (2003) The bicyclam AMD3100 story. Nat Rev Drug Discov;2:581-587.
56. Dando T.M., Perry C.M. (2003) Enfuvirtide. Drugs;63:2755-2766.
57. LaBonte J., Lebbos J., Kirkpatrick P. (2003) Enfuvirtide. Nat Rev Drug Discov;2:345-346.
58. Charloteaux B., Lorin A., Crowet J.M., Stroobant V., Lins L., Thomas A., Brasseur R. (2006) The N-terminal 12 residue long peptide of HIV gp41 is the minimal peptide sufficient to induce significant T-cell-like membrane destabilization in vitro. J Mol Biol;359:597-609.
59. Xie L., Zhao C.H., Zhou T., Chen H.F., Fan B.T., Chen X.H., Ma J.Z., Li J.Y., Bao Z.Y., Lo Z., Yu D., Lee K.H. (2005) Molecular modeling, design, synthesis, and biological evaluation of novel 3′,4′-dicamphanoyl-(+) -cis-khellactone (DCK) analogs as potent anti-HIV agents. Bioorg Med Chem;13:6435-6449.
60. Bonini C., Chiummiento L., De Bonis M., Funicello M., Lupattelli P., Suanno G., Bertib F., Campaner P. (2005) Synthesis, biological activity and modelling studies of two novel anti-HIV PR inhibitors with a thiophene containing hydroxyethylamino core. Tetrahedron;61:6580-6589.
61. Das K., Lewi P.J., Hughes S.H., Arnold E. (2005) Crystallography and the design of anti-AIDS drugs: conformational flexibility and positional adaptability are important in the design of nonnucleoside HIV-1 reverse transcriptase inhibitors. Prog Biophys Mol Biol;88:209-231.
62. Lam P.Y.S., Jadhav P.K., Eyermann C.J., Hodge C.N., Ru Y., Bacheler L.T., Meek O.M.J., Rayner M.M. (1994) Rational design of potent, bio-available, non-peptide cyclic ureas as HIV-1 protease inhibitors. Science;263:380-384.
63. Ax A., Schaal W., Vrang L., Samuelsson B., Hallberg A., Karlen A. (2005) Cyclic sulfamide HIV-1 protease inhibitors, with sidechains spanning from P2/P2' to P1/P1'. Bioorg Med Chem;13:755-764.
64. Wang H.K., Xia Y., Yang Z.Y., Morris-Natschke S.L., Lee K.H. (1998) Recent advances in the discovery and development of flavonoids and their analogues as antitumor and anti-HIV. In: Manthey J.A., Buslig B.S., editors. Advances in Experimental Medicine and Biology. New York: Plenum Press;p. 438.
65. Ono K., Nakane H. (1990) Mechanisms of inhibition of various cellular DNA and RNA polymerases by several flavonoids. J Biochem;108:609-613.
66. Sharma D.K. (2006) Bioprospecting for drug research and functional foods for the prevention of diseases - role of flavonoids in drug development. J Sci Ind Res;65:391-401.
67. Wilson E.O. (2003) What is nature worth. Span;44:23-29.
68. Sharma D.K. (2006) Pharmacological properties of flavonoids including flavonolignans - integration of petrocrops with drug development from plants. J Sci Ind Res;65:477-484.
69. Sharma D.K., Hall I.H. (1991) Hypolipidemic,anti-inflammatory and antineoplasmic and cytotoxicity of flavanolignans isolated from Hydnocarpus wightiana seeds. J Nat Prod;54:1298-1302.
70. Bairoch A., Apweiler R. (2000) The SWISS-PROT protein sequence database and its supplement TrEMBL in 2000. Nucleic Acids Res;28:45-48.
71. Palczewski K., Kumasaka T., Hori T., Behnke C.A., Motoshima H., Fox B.A., Le Trong I., Teller D.C., Okada T., Stenkamp R.E., Yamamoto M., Miyano M. (2000) Crystal structure of rhodopsin: a G protein-coupled receptor. Science;289:739-745.
72. Guex N., Peitsch M.C. (1997) SWISS-MODEL and Swiss-Pdb Viewer: an environment for comparative protein modeling. Electrophoresis; 18:2714-2723.
73. Kelley L.A., MacCallum R.M., Sternberg M.J.E. (2000) Enhanced. Genome annotation using structural profiles in the program 3D-PSSM. J Mol Biol;299:499-520.
74. Jones D.T. (1999) Protein secondary structure prediction based on position-specific scoring matrices. J Mol Biol;292:195-202.
75. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., Bourne P.E. (2000) The Protein Data Bank. Nucleic Acids Res;28:235-242.
76. Sali A., Blundell T.L. (1993) Comparative protein modeling by satisfaction of spatial restraints. J Mol Biol;234:779-815.
77. Laskowski R.A., MacArthur M.W., Moss D.S., Thornton J.M. (1993) PROCHECK: a program to check the stereochemical quality of protein structures. J Appl Cryst;26:283-291.
78. Berendsen H.J., van der Spoel D., van Drunen R. (1995) GROMACS: a message-passing parallel molecular dynamics implementation. Comput Phys Commun;91:43-56.
79. Lindahl E., Hess B., van der Spoel D. (2001) Gromacs 3.0: a package for molecular simulation and trajectory analysis. J Mol Med;7:306-317.
80. van der Spoel D., van Buuren A.R., Apol E., Meulenhoff P.J., Tieleman D.P., Sijbers A.L., Hess B., Feenstra K.A., Lindahl E., van Drunen R., Berendsen H.J.C. (2001) Gromacs User Manual, Version 3.0. Nijenborgh, AG Groningen, the Netherlands. Available at: http://www.gromacs.org [accessed on 9 December 2006].
81. van der Spoel D., van Buuren A.R., Tieleman D.P., Berendsen H.J. (1996) Molecular dynamics simulations of peptides from BPTI: a closer look at amide-aromatic interactions. J Biomol NMR;8:229-238.
82. van Gunsteren W.F., Berendsen H.J. (1987) Gromos-87 Manual. Biomos BV, Nijenborgh, Groningen, the Netherlands.
83. Humphrey W., Dalke A., Schulten K. (1996) VMD: visual molecular dynamics. J Mol Graph;14:33-38.
84. Moore P.B., Zhong Q., Husslein T., Klein M.L. (1998) The entry of entry inhibitors: a fusion of science and medicine. FEBS Lett;431:143-148.
85. Zhong Q., Husslein T., Moore P.B., Newns D.M., Pattnaik P., Klein M.L. (1998) The M2 channel of influenza A virus: a molecular dynamics study. FEBS Lett;434:265-271.
86. Zhong Q., Jiang Q., Moore P.B., Newns D.M., Klein M.L. (1998) Molecular dynamical simulation of synthetic four-helix bundle ion channel protein. Biophys J;74:3-10.
87. + channel. Biochemistry; 38:8599-8604.
88. Guidoni L., Torre V., Carloni P. (2000) Water and potassium dynamics inside the KcsA K+ channel. FEBS Lett;477:37-42.
89. Ng T.B., Huang B., Fong W.P., Yeung H.W. (1997) Anti-human immunodeficiency virus (anti-HIV) natural products with special emphasis on HIV reverse transcriptase inhibitors. Life Sci;61:933-949.
90. Vlietinck A.J., De Bruyne T., Apers S., Pieters L.A. (1998) Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection. Planta Med;64:97-109.
91. Xie L., Takeuchi Y., Cosentino M., Lee K.H. (1999) Anti-AIDS agents: 37. Synthesis and structure-activity relationships of (3′R, 4′R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents. J Med Chem;42:2662-2672.
92. Kubo M., Matsuda H., Tanaka M., Kimura Y., Okuda H., Higashino M., Tani T., Namba K., Arichi S. (1984) Studies on Scutellariae radix: VII. Anti-arthritic and anti-inflammatory actions of methanolic extract and flavonoid components from Scutellariae radix. Chem Pharm Bull;32:2724-2729.
93. Huang X., Tu C.H.L., Zhang L.X., Dai J.R., Jin Y.D. (1986) Huang Qin. In: Huang X., editor. Immunopharmacology. Shanghai: Shanghai Science and Technology Press;p. 159-160.
94. Li B.Q., Fu T., Dongyan Y., Mikovits J.A., Ruscetti F.W., Wang J.M. (2000) Flavonoid baicalin inhibits HIV-1 infection at the level of viral entry. Biochem Biophys Res Commun;276:534-538.
95. Matthee G., Wright A.D., Konig G.M. (1999) HIV reverse transcriptase inhibitors of natural origin. Planta Med;65:493-506.
96. Pardee A.B., Li J., Crumpacker C., Zang L. (1994) US Patent US933470, WO9404139, pp. 1-31.
97. Fesen M.R., Pommier Y., Leteurtre F., Hiroguchi S., Yung J., Kohn K.W. (1994) Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. Biochem Pharmacol;48:595-608.
98. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., Olson A.J. (1998) Autodock 3.0. J Comput Chem;19:1639-1662.
99. Altschul S.F., Thomas L.M., Alejandro A.S., Jinghui Z., Zheng Z., Webb M., David J.L. (1997) Gapped BLAST and PSI BLAST: a new generation of protein database search programs. Nucleic Acids Res;25:3389-3402.
100. Sanchez R., Sali A. (1999) Comparative protein structure modeling in genomics. J Comput Phys;151:388-401.
101. Cordes F.S., Bright N., Sansom M.S.P. (2002) Proline-induced distortions of transmembrane helices. J Mol Biol;323:951-960.
102. Kuntz I.D., Chen K., Sharp K.A., Kollman P.A. (1999) The maximal affinity of ligands. Proc Natl Acad Sci U S A;96:9997-10002.
103. Souza J. Jr, de Almeida Santos R.H., Ferreira M.M.C., Molfetta F.A., Camargo A.J., Honorio K.M., da Silva A.B.F. (2003) A quantum chemical and statistical study of flavonoid compounds (flavones) with anti-HIV activity. Eur J Med Chem;38:929-938.
104. Wu J.H., Wang X.H., Yi Y.H., Lee K.H. (2003) Anti-AIDS agents: 54. A potent anti-HIV chalcone and flavonoids from genus Desmos. Bioorg Med Chem Lett;13:1813-1815.
105. Singh A., Latombe J., Brutlag D. A Motion Planning Approach to Flexible Ligand Binding. Available at: http://cmgm.stanford.edu/~brutlag/Abstracts/ singh98.html
106. Koradi R., Billeter M., Wuthrich K. (1996) MOLMOL: a program for display and analysis of macromolecular structures. J Mol Graph;14:51-55.