Inhibition of HIV infection by bicyclams, highly potent and specific CXCR4 antagonists

Molecular Pharmacology

Volumn 57, Issue 5, 2000, Pages 833-839

  De Clercq, Erik ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' [1,4 PHENYLENEBIS(METHYLENE)]BIS(1,4,8,11 TETRAAZACYCLOTETRADECANE); 2,2' [4,4' [(AMINOCARBONYL)AMINO]BIS[N 4' DI(PYRROLE 2 CARBOXAMIDE 1,1' DIMETHYL)] 6,8 NAPHTHALENEDISULFONIC ACID]HEXASODIUM; AMD 2763; AMINO ACID; CHEMOKINE; CHEMOKINE RECEPTOR CXCR4; CYCLAM DERIVATIVE; DEXTRAN SULFATE; DIDANOSINE; DISTAMYCIN A DERIVATIVE; GLYCOPROTEIN GP 120; GLYCOPROTEIN GP 41; JM 2763; MACROPHAGE INFLAMMATORY PROTEIN; MACROPHAGE INFLAMMATORY PROTEIN 1BETA; RANTES; ZIDOVUDINE; ZINTEVIR;

AMINO ACID SEQUENCE; CLINICAL TRIAL; DRUG MECHANISM; DRUG POTENCY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; PRIORITY JOURNAL; SHORT SURVEY; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION;

AMINO ACID SEQUENCE; ANTI-HIV AGENTS; CHEMOKINES, CXC; HETEROCYCLIC COMPOUNDS; HIV INFECTIONS; HIV-1; HUMANS; MOLECULAR SEQUENCE DATA; RECEPTORS, CXCR4; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034062515     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Short Survey

References (39)

1. Arakaki R, Tamamura H, Premanathan M, Kanbara K, Ramanan S, Mochizuki K, Baba M, Fujii N and Nakashima H (1999) T134, a small-molecule CXCR4 inhibitor, has no cross-drug resistance with AMD3100, a CXCR4 antagonist with a different structure. J Virol 73:1719-1723.
2. Berson JF, Long D, Doranz BJ, Rucker J, Jirik FR and Doms RW (1996) A seven-transmembrane domain receptor involved in fusion and entry of T-cell-tropic human immunodeficiency virus type 1 strains. J Virol 70:6288-6295.
3. Blanco J, Barretina J, Henson G, Bridger G, De Clercq E, Clotet B and Esté JA (20001 The CXCR4 antagonist AMD3100 efficiently inhibits cell-surface-expressed human immunodeficiency virus type 1 envelope-induced apoptosis. Antimicrob Agents Chemother 44:51-56.
4. Bridger GJ, Skerlj RT, Padmanabhan S, Martellucci SA, Henson GW, Abrams MJ, Joao HC, Witvrouw M, De Vreese K, Pauwels R and De Clercq E (1996) Synthesis and structure-activity relationships of phenylenebis(methylene)-linked bistetraaza-macrocycles that inhibit human immunodeficiency virus replication. 2. Effect of heteroaromatic linkers on the activity of bicyclams. J Med Chem 39:109-119.
5. Bridger GJ, Skerlj RT, Padmanabhan S, Martellucci SA, Henson GW, Struyf S, Witvrouw M, Schols D and De Clercq E (1999) Synthesis and structure-activity relationships of phenylenebis (methylene)-linked bis-azamacrocycles that inhibit HIV-1 and HIV-2 replication by antagonism of the chemokine receptor CXCR4. J Med Chem 42:3971-3981.
6. Bridger GJ, Skerlj RT, Thornton D, Padmanabhan S, Martellucci SA, Henson GW, Abrams MJ, Yamamoto N, De Vreese K, Pauwels R and De Clercq E (1995) Synthesis and structure-activity relationships of phenylenebis(methylene)-linked bis-tetraazamacrocycles that inhibit HIV replication. Effects of macrocyclic ring size and substituents on the aromatic linker. J Med Chem 38:366-378.
7. Cammack N (1999) Human immunodeficiency virus type 1 entry and chemokine receptors: A new therapeutic target. Antiviral Chem Chemother 10:53-62.
8. Daelemans D, Schols D, Witvrouw M, Pannecouque C, Hatse S, Van Dooren S, Hamy F, Klimkait T, De Clercq E and Vandamme A-M (2000) A second target for the peptoid Tat/Transactivation response element inhibitor CGP64222: Inhibition of human immunodeficiency virus replication by blocking CXC-chemokine receptor 4-mediated virus entry. Mol Pharmacol 57:116-124.
9. Datema R, Rabin L, Hincenbergs M, Moreno MB, Warren S, Linquist V, Rosenwirth B, Seifert J and McCune JM (1996) Antiviral efficacy in vivo of the anti-human immunodeficiency virus bicyclam SDZ SID 791 (JM 3100), an inhibitor of infectious cell entry. Antimicrob Agents Chemother 40:750-754.
10. Dealwis C, Fernandez EJ, Thompson DA, Simon RJ, Siani MA and Lolis E (1998) Crystal structure of chemically synthesized [N33A] stromal cell-derived factor 1α, a potent ligand for the HIV-1 "fusin" coreceptor. Proc Natl Acad Sci USA 95:6941-6946.
11. De Clercq E (1992) Human immunodeficiency virus inhibitors targeted at virus-cell fusion and/or viral uncoating. Int J Immunother 8:115-123.
12. De Clercq E (1995) Antiviral therapy for human immunodeficiency virus infections. Clin Microbiol Rev 8:200-239.
13. De Clercq E, Yamamoto N, Pauwels R, Baba M, Schols D, Nakashima H, Balzarini J, Debyser Z, Murrer BA, Schwartz D, Thornton D, Bridger G, Flicker S, Henson G, Abrams M and Picker D (1992) Potent and selective inhibition of human immunodeficiency virus (HIV)-1 and HIV-2 replication by a class of bicyclams interacting with a viral uncoating event. Proc Natl Acad Sci USA 89:5286-5290.
14. De Clercq E, Yamamoto N, Pauwels R, Balzarini J, Witvrouw M, De Vreese K, Debyser Z, Rosenwirth B, Peichl P, Datema R, Thornton D, Skerlj R, Gaul F, Padmanabhan S, Bridger G, Henson G and Abrams M (1994) Highly potent and selective inhibition of human immunodeficiency virus by the bicyclam derivative JM3100. Antimicrob Agents Chemother 38:668-674.
15. Dessolin J, Galea P, Vlieghe P, Chermann J-M and Kraus J-L 11999) New bicyclam-AZT conjugates: Design, synthesis, anti-HIV evaluation, and their interaction with CXCR-4 coreceptor. J Med Chem 42:229-241.
16. De Vreese K, Kofler-Mongold V, Leutgeb C, Weber V, Vermeire K, Schacht S, Anne J, De Clercq E, Datema R and Werner G (1996a) The molecular target of bicyclams, potent inhibitors of human immunodeficiency virus replication. J Virol 70:689-696.
17. De Vreese K, Reymen D, Griffin P, Steinkasserer A, Werner G, Bridger GJ, Esté J, James W, Henson GW, Desmyter J, Anné J and De Clercq E (1996b) The bicyclams, a new class of potent human immunodeficiency virus inhibitors, block viral entry after binding. Antiviral Res 29:209-219.
18. De Vreese K, Van Nerum I, Vermeire K, Anne J and De Clercq E (1997) Sensitivity of human immunodeficiency virus to bicyclam derivatives is influenced by the three-dimensional structure of gp120. Antimicrob Agents Chemother 41:2616-2620.
19. Donzella GA, Schols D, Lin SW, Esté JA, Nagashima KA, Maddon PJ, Allaway GP, Sakmar TP, Henson G, De Clercq E and Moore JP (1998) AMD3100, a small molecule inhibitor of HIV-1 entry via the CXCR4 co-receptor. Nat Med 4:72-77.
20. Doranz BJ, Grovit-Ferbas K, Sharron MP, Mao S-H, Goetz MB, Daar ES, Doras RW and O'Brien WA ( 1997) A small-molecule inhibitor directed against the chemokine receptor CXCE4 prevents its use as an HIV-1 coreceptor. J Exp Med 186:1395-1400.
21. Egberink HF, De Clercq E, Van Vliet ALW, Balzarini J, Bridger GJ, Henson G, Horzinek MC and Schols D (1999) Bicyclams, selective antagonists of the human chemokine receptor CXCR4, potently inhibit feline immunodeficiency virus replication. J Virol 73:6346-6352.
22. Esté JA, Cabrera C, De Clercq E, Struyf S, Van Damme J, Bridger G, Skerlj RT, Abrams MJ, Henson G, Gutierrez A, Clotet B and Schols D (1999a) Activity of different bicyclam derivatives against human immunodeficiency virus depends on their interaction with the CXCR4 chemokine receptor. Mol Pharmacol 55:67-73.
23. Esté JA, De Vreese K, Witvrouw M, Schmit J-C, Vandamme A-M, Anne J, Desmyter J, Henson GW, Bridger G and De Clercq E (1996) Antiviral activity of the bicyclam derivative JM3100 against drug-resistant strains of human immunodeficiency virus type 1. Antiviral Res 29:297-307.
24. Esté JA, Schols D, Cabrera C, Blanco J, Gutierrez A, Bridger G, Henson G., Clotet B and De Clercq E (1999b) Shift of clinical human immunodeficiency virus type 1 isolates from X4 to R5 and prevention of emergence of the syncytium-inducing phenotype by blockade of CXCR4. J Virol 73:5577-5585.
25. Hendrix C, Flexner C, MacFarland R, Giandomenico C, Schweitzer and Henson G (1999) Chemokine CXCR-4 receptor blocker, AMD-3100: Clinical and pre-clinical studies of pharmacokinetics and safety. Abstracts of the 6th Conference on Retroviruses and Opportunistic Infections; 1999 Jan 31-Feb 4; Chicago, IL; no. 610.
26. Howard OMZ, Oppenheim JJ, Hollingshead MG, Covey JM, Bigelow J, McCormack JJ, Buckheit RW Jr, Clanton DJ, Turpin JA and Rice WG (1998) Inhibition of in vitro and in vivo HIV replication by a distamycin analogue that interferes with chemokine receptor function: A candidate for chemotherapeutic and microbicidal application. J Med Chem 41:2184-2193.
27. Joao HC, De Vreese K, Pauwels R, De Clercq E, Henson GW and Bridger GJ (1995) Quantitative structural activity relationship study of bis-tetraazacyclic compounds. A novel series of HIV-1 and HIV-2 inhibitors. J Med Chem 38:3865-3873.
28. Labrosse B, Brelot A, Heveker N, Sol N, Schols D, De Clercq E and Alizon M ( 1998) Determinants for sensitivity of human immunodeficiency virus coreceptor CXCR4 to the bicyclam AMD3100. J Virol 72:6381-6388.
29. Luster AD (1998) Chemokines - chemotactic cytokines that mediate inflammation. N Engl J Med 338:436-445.
30. Murakami T, Nakajima T, Koyanagi Y, Tachibana K, Fujii N, Tamamura H, Yoshida N, Waki M, Matsumoto A, Yoshie O, Kishimoto T, Yamamoto N and Nagasawa T (1997) A small molecule CXCR4 inhibitor that blocks T cell line-tropic HIV-1 infection. J Exp Med 186:1389-1393.
31. Proudfoot AEI, Wells TNC and Clapham PR (1999) Chemokine receptors-future therapeutic targets for HIV? Biochem Pharmacol 57:451-463.
32. Schols D and De Clercq E (1998) The simian immunodeficiency virus mnd(GB-1) strain uses CXCR4, not CCR5, as coreceptor for entry in human cells. J Gen Virol 79:2203-2205.
33. Schols D, Esté JA, Cabrera C and De Clercq E (1998) T-Cell-line-tropic human immunodeficiency virus type 1 that is made resistant to stromal cell-derived factor Ia contains mutations in the envelope gp120 but does not show a switch in coreceptor use. J Virol 72:4032-4037.
34. Schols D, Esté JA, Henson G and De Clercq E (1997a) Bicyclams, a class of potent anti-HIV agents, are targeted at the HIV coreceptor fusin/CXCR-4. Antiviral Res 35:147-156.
35. Schols D, Struyf S, Van Damme J, Esté JA, Henson G and De Clercq E (1997b) Inhibition of T-tropic HIV strains by selective antagonization of the chemokine receptor CXCR4. J Exp Med 186:1383-1388.
36. Simmons G, Reeves JD, McKnight A, Dejucq N, Hibbits S, Power CA, Aarons E, Schols D, De Clercq E, Proudfoot AEI and Clapham PR 11998) CXCR4 as a functional coreceptor for human immunodeficiency virus type 1 infection of primary macrophages. J Virol 72:8453-8457.
37. 7]-polyphemusin II). Bioorg Med Chem 6:231-238.
38. Yi Y, Isaacs SN, Williams DA, Frank I, Schols D, De Clercq E, Kolson DL and Collman RG ( 1999) Role of CXCR4 in cell-cell fusion and infection of monocyte-derived macrophages by primary human immunodeficiency virus type 1 (HIV-1) strains: Two distinct mechanisms of HIV-1 dual tropism. J Virol 73:7117-7125.
39. Zhang Y-J and Moore JP (1999) Will multiple coreceptors need to be targeted by inhibitors of human immunodeficiency virus type 1 entry? J Virol 73:3443-3448.