Targeting HIV entry through interaction with envelope glycoprotein 120 (gp120): Synthesis and antiviral evaluation of 1,3,5-triazines with aromatic amino acids

Journal of Medicinal Chemistry

Volumn 54, Issue 15, 2011, Pages 5335-5348

  Lozano, Virginia ^a   Aguado, Leire ^a   Hoorelbeke, Bart ^b   Renders, Marleen ^b   Camarasa, María José ^a   Schols, Dominique ^b   Balzarini, Jan ^b   San Félix, Ana ^a   Pérez Pérez, María Jesús ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; AROMATIC AMINO ACID; CHEMOKINE RECEPTOR CCR5; CHEMOKINE RECEPTOR CXCR4; DIMER; GLYCOPROTEIN GP 120; LECTIN; MONOMER; TRIAZINE;

ANTIVIRAL ACTIVITY; ARTICLE; CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; VIRUS CELL INTERACTION; VIRUS ENTRY; VIRUS ENVELOPE; VIRUS REPLICATION;

ANTI-HIV AGENTS; CELLS, CULTURED; HIV ENVELOPE PROTEIN GP120; HIV-1; HUMANS; LECTINS; RECEPTORS, CCR5; RECEPTORS, CXCR4; SURFACE PLASMON RESONANCE; T-LYMPHOCYTES; TRIAZINES;

EID: 79961237362     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200560r     Document Type: Article

References (42)

1. Volberding, P. A.; Deeks, S. G. Antiretroviral therapy and management of HIV infection Lancet 2010, 376, 49-62
2. Broder, S. Twenty-five years of translational medicine in antiretroviral therapy: promises to keep Sci. Transl. Med. 2010, 2, 39ps33
3. Flexner, C. HIV drug development: the next 25 years Nature Rev. Drug Discovery 2007, 6, 959-966 (Pubitemid 350201786)
4. Balzarini, O. Targeting the glycans of gp120: a novel approach aimed at the Achilles heel of HIV Lancet Infect. Dis. 2005, 5, 726-731
5. Balzarini, J. Targeting the glycans of glycoproteins: a novel paradigm for antiviral therapy Nature Rev. Microbiol. 2007, 5, 583-597 (Pubitemid 47074114)
6. Scanlan, C. N.; Offer, J.; Zitzmann, N.; Dwek, R. A. Exploiting the defensive sugars of HIV-1 for drug and vaccine design Nature 2007, 446, 1038-1045 (Pubitemid 46676066)
7. Balzarini, J. Inhibition of HIV entry by carbohydrate-binding proteins Antiviral Res. 2006, 71, 237-247 (Pubitemid 44223752)
8. Francois, K. O.; Balzarini, J. Potential of carbohydrate-binding agents as therapeutics against enveloped viruses. Med. Res. Rev. 2011, not supplied.
9. Balzarini, J.; Van Laethem, K.; Hatse, S.; Vermeire, K.; De Clercq, E. R.; Peumans, W.; Van Damme, E.; Vandamme, A. M.; Bohlmstedt, A.; Schols, D. Profile of resistance of human immunodeficiency virus to mannose-specific plant lectins J. Virol. 2004, 78, 10617-10627 (Pubitemid 39258388)
10. Balzarini, J.; Van Laethem, K.; Hatse, S.; Froeyen, M.; Peumans, W.; Van Damme, E.; Schols, D. Carbohydrate-binding agents cause deletions of highly conserved glycosylation sites in HIV gp120-A new therapeutic concept to hit the Achilles heel of HIV J. Biol. Chem. 2005, 280, 41005-41014 (Pubitemid 41780596)
11. Balzarini, J.; Van Laethem, K.; Hatse, S.; Froeyen, M.; Van Damme, E.; Bolmstedt, A.; Peumans, W.; De Clercq, E.; Schols, D. Marked depletion of glycosylation sites in HIV-1 gp120 under selection pressure by the mannose-specific plant lectins of Hippeastrum hybrid and Galanthus nivalis Mol. Pharmacol. 2005, 67, 1556-1565 (Pubitemid 40594154)
12. Balzarini, J.; Van Laethem, K.; Peumans, W. J.; Van Damme, E. J. M.; Bolmstedt, A.; Gago, F.; Schols, D. Mutational pathways, resistance profile, and side effects of cyanovirin relative to human immunodeficiency virus type 1 strains with N -glycan deletions in their gp120 envelopes J. Virol. 2006, 80, 8411-8421 (Pubitemid 44384854)
13. Balzarini, J.; Van Laethem, K.; Daelemans, D.; Hatse, S.; Bugatti, A.; Rusnati, M.; Igarashi, Y.; Oki, T.; Schols, D.; Pradimicin, A a carbohydrate-binding nonpeptidic lead compound for treatment of infections with viruses with highly glycosylated envelopes, such as human immunodeficiency virus J. Virol. 2007, 81, 362-373 (Pubitemid 44975175)
14. Huskens, D.; Van Laethem, K.; Vermeire, K.; Balzarini, J.; Schols, D. Resistance of HIV-1 to the broadly HIV-1-neutralizing, anti-carbohydrate antibody 2G12 Virology 2007, 360, 294-304 (Pubitemid 46482610)
15. Balzarini, J.; François, K. O.; Van Laethem, K.; Hoorelbeke, B.; Renders, M.; Auwerx, J.; Liekens, S.; Oki, T.; Igarashi, Y.; Schols, D. Pradimicin S, a highly soluble nonpeptidic small-size carbohydrate-binding antibiotic, is an anti-HIV drug lead for both microbicidal and systemic use Antimicrob. Agents Chemother. 2010, 54, 1425-1435
16. Hoorelbeke, B.; Huskens, D.; Ferir, G.; Francois, K. O.; Takahashi, A.; Van Laethem, K.; Schols, D.; Tanaka, H.; Balzarini, J. Actinohivin, a Broadly Neutralizing Prokaryotic Lectin, Inhibits HIV-1 Infection by Specifically Targeting High-Mannose-Type Glycans on the gp120 Envelope Antimicrob. Agents Chemother. 2010, 54, 3287-3301
17. Reitter, J. N.; Means, R. E.; Desrosiers, R. C. A role for carbohydrates in immune evasion in AIDS Nature Med. 1998, 4, 679-684 (Pubitemid 28274667)
18. Mazik, M.; Konig, A. Recognition properties of an acyclic biphenyl-based receptor toward carbohydrates J. Org. Chem. 2006, 71, 7854-7857 (Pubitemid 44470331)
19. Mazik, M. Design of lectin mimetics ChemBioChem 2008, 9, 1015-1017
20. Mazik, M. Molecular recognition of carbohydrates by acyclic receptors employing noncovalent interactions Chem. Soc. Rev. 2009, 38, 935-956
21. Lis, H.; Sharon, N. Lectins: carbohydrate-specific proteins that mediate cellular recognition Chem. Rev. 1998, 98, 637-674 (Pubitemid 128631438)
22. Harata, K.; Muraki, M. Crystal structures of Urtica dioica agglutinin and its complex with tri- N -acetylchitotriose J. Mol. Biol. 2000, 297, 673-681
23. Feinberg, H.; Mitchell, D. A.; Drickamer, K.; Weis, W. I. Structural basis for selective recognition of oligosaccharides by DC-SIGN and DC-SIGNR Science 2001, 294, 2163-2166 (Pubitemid 33150672)
24. Botos, I.; Wlodawer, A. Proteins that bind high-mannose sugars of the HIV envelope Prog. Biophys. Mol. Biol. 2005, 88, 233-282 (Pubitemid 39568612)
25. Jin, S.; Cheng, Y. F.; Reid, S.; Li, M. Y.; Wang, B. H. Carbohydrate recognition by boronolectins, small molecules, and lectins Med. Res. Rev. 2010, 30, 171-257
26. Díaz-Ortiz, A.; Elguero, J.; de la Hoz, A.; Jiménez, A.; Moreno, A.; Moreno, S.; Sánchez-Migallón, A. Microwave-assisted synthesis and dynamic behaviour of N -2, N -4, N -6-tris(1 H -pyrazolyl)-1,3,5-triazine-2,4,6-triamines QSAR Comb. Sci. 2005, 24, 649-659 (Pubitemid 41074333)
27. Lozano, V.; Hernández, R.; Mijangos, C.; Pérez- Pérez, M. J. A novel organogelator incorporating tert -butyl esters of asparagines Org. Biomol. Chem. 2009, 7, 364-369
28. Bookser, B. C.; Zhu, S. R. Solid phase extraction purification of carboxylic acid products from 96-well format solution phase synthesis with DOWEX 1 × 8-400 formate anion exchange resin J. Comb. Chem. 2001, 3, 205-215 (Pubitemid 33614506)
29. Wallace, K. J.; Hanes, R.; Anslyn, E.; Morey, J.; Kilway, K. V.; Siegel, J. Preparation of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene from two versatile 1,3,5-tri(halosubstituted) 2,4,6-triethylbenzene derivatives Synthesis 2005, 2080-2083 (Pubitemid 41138650)
30. Liu, J.; Bartesaghi, A.; Borgnia, M. J.; Sapiro, G.; Subramaniam, S. Molecular architecture of native HIV-1 gp120 trimers Nature 2008, 455, 109-113
31. Hennrich, G.; Anslyn, E. V. 1,3,5-2,4,6-functionalized, facially segregated benzenes-exploitation of sterically predisposed systems in supramolecular chemistry Chem.-Eur. J. 2002, 8, 2219-2224
32. Buckheit, R. W.; Roberson, J. L.; Lackmansmith, C.; Wyatt, J. R.; Vickers, T. A.; Ecker, D. J. Potent and specific inhibition of HIV envelope-mediated cell-fusion and virus binding by G-quartet-forming oligonucleotide (ISIS 5320) AIDS Res. Hum. Retroviruses 1994, 10, 1497-1506 (Pubitemid 24382202)
33. Andrei, G.; De Clercq, E.; Snoeck, R. Novel inhibitors of human CMV Curr. Opin. Invest. Drugs 2008, 9, 132-145 (Pubitemid 351206372)
34. Biron, K. K. Antiviral drugs for cytomegalovirus diseases Antiviral Res. 2006, 71, 154-163 (Pubitemid 44223768)
35. Grillone, L. R.; Lanz, R. Fomivirsen Drugs Today 2001, 37, 245-255 (Pubitemid 32506283)
36. Ghosh, T.; Chattopadhyay, K.; Marschall, M.; Karmakar, P.; Mandal, P.; Ray, B. Focus on antivirally active sulfated polysaccharides: From structure-activity analysis to clinical evaluation Glycobiology 2009, 19, 2-15
37. Pirrone, V.; Wigdahl, B.; Krebs, F. C. The rise and fall of polyanionic inhibitors of the human immunodeficiency virus type 1 Antiviral Res. 2011, 90, 168-182
38. Van Damme, L.; Govinden, R.; Mirembe, F. M.; Guedou, F.; Solomon, S.; Becker, M. L.; Pradeep, B. S.; Krishnan, A. K.; Alary, M.; Pande, B.; Ramjee, G.; Deese, J.; Crucitti, T.; Taylor, D.; Grp, C. S. S. Lack of effectiveness of cellulose sulfate gel for the prevention of vaginal HIV transmission N. Engl. J. Med. 2008, 359, 463-472
39. Huskens, D.; Vermeire, K.; Profy, A. T.; Schols, D. The candidate sulfonated microbicide, PRO 2000, has potential multiple mechanisms of action against HIV-1 Antiviral Res. 2009, 84, 38-47
40. McCormack, S.; Ramjee, G.; Kamali, A.; Rees, H.; Crook, A. M.; Gafos, M.; Jentsch, U.; Pool, R.; Chisembele, M.; Kapiga, S.; Mutemwa, R.; Vallely, A.; Palanee, T.; Sookrajh, Y.; Lacey, C. J.; Darbyshire, J.; Grosskurth, H.; Profy, A.; Nunn, A.; Hayes, R.; Weber, J. PRO2000 vaginal gel for prevention of HIV-1 infection (Microbicides Development Programme 301): a phase 3, randomised, double-blind, parallel-group trial Lancet 2010, 376, 1329-1337
41. Fletcher, P. S.; Wallace, G. S.; Mesquita, P. M. M.; Shattock, R. J. Candidate polyanion microbicides inhibit HIV-1 infection and dissemination pathways in human cervical explants Retrovirology 2006, 3, 46
42. Johnsson, B.; Lofas, S.; Lindquist, G. Immobilization of proteins to a carboxymethyldextran-modified gold surface for biospecific interaction analysis in surface plasmon resonance sensors Anal. Biochem. 1991, 198, 268-277