New macrocyclic amines showing activity as HIV entry inhibitors against wild type and multi-drug resistant viruses

Molecules

Volumn 14, Issue 5, 2009, Pages 1927-1937

  Rusconi, Stefano ^a   Cicero, Mirko Lo ^a   Viganò, Ottavia ^a   Sirianni, Francesca ^a   Bulgheroni, Elisabetta ^a   Ferramosca, Stefania ^a   Bencini, Andrea ^b   Bianchi, Antonio ^b   Ruiz, Lidia ^c   Cabrera, Cecilia ^c   Martinez Picado, Javier ^c   Supuran, Claudiu T ^b   Galii, Massimo ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

^c HOSPITAL UNIVERSITARI GERMANS TRIAS I PUJOL   (Spain)

Author keywords

Co receptors; CXCR4; HIV 1; Macrocyclic polyamines

Indexed keywords

AMINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CHEMOKINE RECEPTOR CXCR4; HETEROCYCLIC COMPOUND; HUMAN IMMUNODEFICIENCY VIRUS FUSION INHIBITOR; PLERIXAFOR; POLYAMINE;

ANTIVIRAL RESISTANCE; CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; DRUG ANTAGONISM; DRUG EFFECT; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; MULTIDRUG RESISTANCE; PHENOTYPE; SYNTHESIS;

AMINES; ANTI-HIV AGENTS; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, VIRAL; HETEROCYCLIC COMPOUNDS; HIV FUSION INHIBITORS; HIV INFECTIONS; HIV-1; HUMANS; MOLECULAR STRUCTURE; PHENOTYPE; POLYAMINES; RECEPTORS, CXCR4;

EID: 67249128864     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14051927     Document Type: Conference Paper

References (36)

1. UNAIDS/WHO. AIDS Epidemic Update: December 2008; http://www.unaids.org.
2. Graves, M.C.; Lim, J.J.; Heimer, E.P., Kramer, R.A. An 11-kDa form of human immunodeficiency virus protease expressed in Escherichia coli is sufficient for enzymatic activity. Proc. Natl. Acad. Sci. USA 1988, 85, 2449-2453.
3. 3.Drake,S.M.NNRTIs-anewclassofdrugsforHIV.J.Antimicr.Chemother.2000,45, 417-420.(Pubitemid30199132)
4. 4. De Clercq, E. New approaches toward anti-HIV chemotherapy. J. Med. Chem. 2005, 48, 1297-1313. (Pubitemid 40364540)
5. 5. Barbaro, G.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. Highly active antiretroviral therapy: current state of the art, new agents and their pharmacological interactions useful for improving therapeutic outcome. Curr. Pharm. Des. 2005, 11, 1805-1843. (Pubitemid 40668138)
6. 6. Grabar, S.; Pradier, C.; Le Corfec, E.; Lancar, R.; Allavena, C.; Bentata, M.; Berlureau, P.; Dupont, C.; Fabbro-Peray, P.; Poizot-Martin, I.; Costagliola, D. Factors associated with clinical and virological failure in patients receiving a triple therapy including a protease inhibitor. AIDS 2000, 14, 141-149. (Pubitemid 30116439)
7. 7. Citterio, P.; Rusconi, S. Novel inhibitors of the early steps of the HIV-1 life cycle. Exp. Opin. Invest. Drugs 2007, 16, 11-23. (Pubitemid 44964163)
8. 8. Berger, E.A.; Murphy, P.M.; Farber, J.M. Chemokine receptors as HIV-1 coreceptors: roles in viral entry, tropism, and disease. Annu. Rev. Immunol. 1999, 17, 657-700. (Pubitemid 29241137)
9. 9. Cocchi, F.; De Vico, A.L.; Garzino-Demo A.; Cara, A.; Gallo, R.C.; Lusso, P. The V3 domain of the HIV-1 gp120 envelope glycoprotein is critical for chemokine-mediated blockade of infection. Nat. Med. 1996, 2, 1244-1247. (Pubitemid 26375410)
10. 10. Donzella, G.A.; Schols, D.; Lin, S.W.; Este, J.A.; Nagashima, K.A.; Maddon, P.J.; Allaway, G.P.; Sakmar, T.P.; Henson, G.; De Clercq, E.; Moore, J.P. AMD3100, a small molecule inhibitor of HIV-1 entry via the CXCR4 co-receptor. Nat. Med. 1998, 4, 72-77. (Pubitemid 28133082)
11. 11. Hendrix, C.W.; Collier, A.C.; Lederman, M.M.; Schols, D.; Pollard, R.B.; Brown, S.; Jackson, J.B.; Coombs, R.W.; Glesby, M.J.; Flexner, C.W.; Bridger, G.J.; Badel, K.; MacFarland, R.T.; Henson, G.W.; Calandra, G.; the AMD 3100 HIV Study Group. Safety, pharmacokinetics, and antiviral activity of AMD3100, a selective CXCR4 receptor inhibitor, in HIV-1 infection. J. Acquir. Defic. Syndr. 2004, 37, 1253-1262. (Pubitemid 39281506)
12. 12. Hatse, S.; Princen, K.; Bridger, G.; De Clercq, E.; Schols, D. Chemokine receptor inhibition by AMD3100 is strictly confined to CXCR4. FEBS Lett. 2002, 527, 255-262. (Pubitemid 35253875)
13. 13. Fricker, S.P.; Anastassov, V.; Cox, J.; Darkes, M.C.; Grujic, O.; Idzan, S.R.; Labrecque, J.; Lau, G.; Mosi, R.M.; Nelson, K.L.; Qin, L.; Santucci, Z.; Wong, R.S.Y. Characterization of the molecular pharmacology of AMD3100: a specific antagonist of the G-protein coupled chemokine receptor, CXCR4. Biochem. Pharmacol. 2006, 72, 588-596. (Pubitemid 44163295)
14. 14. Mastrolorenzo, A.; Scozzafava, A.; Supuran, C.T. Small molecule antagonists of chemokine receptors as emerging anti-HIV agents. Expert Opin. Ther. Pat. 2001, 11, 1245-1252. (Pubitemid 32707658)
15. 15. Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. Non-peptidic chemokine receptors antagonists as emerging anti-HIV agents. J. Enz. Inhib. Med. Chem. 2002, 17, 69-76. (Pubitemid 34855323)
16. 16. Rusconi, S.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. New advances in HIV entry inhibitors development. Curr. Drug Targets - Infect. Dis. 2004, 4, 339-355. (Pubitemid 39534768)
17. 17. Rusconi, S.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. An update in the development of HIV entry inhibitors. Curr. Top. Med. Chem. 2007, 7, 1273-1289. (Pubitemid 47317047)
18. Flicker, S.P. A novel CXCR4 antagonist for hematopoietic stem cell mobilization. Expert Opin. Investig. Drugs 2008, 17, 1749-1760.
19. 19. Hatse, S.; Princen, K.; De Clercq, E.; Rosenkilde, M.M.; Schwartz, T.W.; Hernandez-Abad, P.E.; Skerlj, R.T.; Bridger, G.J.; Schols, D. AMD3465, a monomacrocyclic CXCR4 antagonist and potent HIV entry inhibitor. Biochem. Pharmacol. 2005, 70, 752-761. (Pubitemid 41058710)
20. Rusconi, S.; Merrill, D.P.; La Seta Catamancio, S.; Citterio, P.; Bulgheroni, E.; Croce, F.; Chou, T.C.; Yang, O.O.; Herrmann, S.H.; Galli, M.; Hirsch, M.S. In vitro inhibition of HIV-1 by Met-SDF-1β alone or in combination with antiretroviral agents. Antiviral Ther. 2000, 5, 199-204.
21. 21. Tremblay, C.L.; Giguel, F.; Kollman, C.; Guan, Y.; Chou, T.C.; Baroudy, B.M.; Hirsch, M.S. Anti-human immunodeficiency virus interactions of SCH-C (SCH 351125), a CCR5 antagonist, with other antiretroviral agents in vitro. Antimicrob. Agents Chemother. 2002, 46, 1336-1339. (Pubitemid 34415311)
22. 22. Tremblay, C.L.; Giguel, F.; Guan, Y.; Chou, T.C.; Takashima, K.; Hirsch. M.S. TAK-220, a novel small-molecule CCR5 antagonist, has favorable anti-human immunodeficiency virus interactions with other antiretrovirals in vitro. Antimicrob. Agents Chemother. 2005, 49, 3483-3485. (Pubitemid 41060599)
23. 23. Zhang, X.Q.; Sorensen, M.; Fung, M.; Schooley, R.T. Synergistic in vitro antiretroviral activity of a humanized monoclonal anti-CD4 antibody (TNX-355) and enfuvirtide (T-20). Antimicrob. Agents Chemother. 2006, 50, 2231-2233. (Pubitemid 43807552)
24. Bazzicalupi, C.; Bencini A.; Fusi, V.; Giorgi, C.; Paoletti, P.; Valtancoli, B. Lead complexation by novel phenanthroline-containing macrocycles. J. Chem. Soc., Dalton Trans. 1999, 393-399.
25. Bazzicalupi, C.; Bencini, A.; Ciattini, S.; Giorgi, C.; Masotti, A.; Paoletti, P.; Valtancoli, B.; Navon, N.; Meyerstein, D. Copper-(II) and -(I) co-ordination by hexa-amine ligands of different rigidities. A thermodynamic, structural and electrochemical investigation. J. Chem. Soc. Dalton Trara. 2000, 2383-2391.
26. 26.Bazzicalupi,C.;Bellusci,A.;Bencini,A.;Berni,E.;Bianchi,A.;Ciattini,S. ;Giorgi,C.;Valtancoli,B.Anewdipyridine-containingcryptandforbothprotonandCu(II) encapsulation.Asolutionandsolidstatestudy.J.Chem.Soc.DaltonTrans.2002,2151-2157. (Pubitemid35188406)
27. 27.Bencini,A.;Bianchi,A.;Lodeiro,C.;Masotti,A.;Parola,J.A.;Melo,J.S. ;Pina,F.;Valtancoli,B.Anovelfluorescentchemosensorexhibitingexciplexemission. AnexampleofanelementarymolecularmachinedrivenbypHandbylight.Chem.Commun.2000, 1639-1640.(Pubitemid30700654)
28. Chandler, C.J.; Deady, L.W.; Reiss, J.A. Synthesis of some 2,9-disubstituted-1,10-phenanthrolines. J. Heterocycl. Chem. 1981, 18, 599-605
29. Bencini, A.; Burguete, M.I.; Garcia-España, E.; Luis, S.V.; Miravet, J.F.; Soriano, C. An Efficient Synthesis of Polyaza[n]paracyclophanes. J. Org. Chem. 1993, 58, 4749-4753.
30. Motekaitis, RJ.; Martell, A.E.; Murase, I. Cascade halide binding by multiprotonated 7,19,30-trioxa-1,4,10,13,16,22,27,33octaazabicyclo[11.11.11] pentatriacontane (BISTREN) and copper(II) BISTREN cryptates. Inorg. Chem. 1986, 25, 938-944
31. Arago, J.; Bencini, A.; Bianchi, A.; Garcia-España, E.; Micheloni, M.; Paoletti, P.; Ramirez, J.A.; Paoli, P. Interaction of "Long" Open-Chain Polyazaalkanes with Hydrogen and Copper(II) Ions. Inorg. Chem. 1991, 30, 1843-1847.
32. 2O. Inorg. Chem. 1990, 29, 3282-3286.
33. 33.Björndal,Å.;Deng,H.;Jansson,M.;Fiore,J.R.;Colognesi,C. ;Karlsson,A.;Albert,J.;Scarlatti,G.;Littman,D.R.;Fenyö,E.M. Coreceptorusageofprimaryhumanimmunodeficiencyvirustype1isolatesvariesaccording- biologicalphenotype.J.Virol.1997,71,7478-7487.(Pubitemid27391688)
34. 34. Rusconi, S.; La Seta Catamancio, S.; Citterio, P.; Bulgheroni, E.; Croce, F.; Herrmann, S.H.; Offord, R.E.; Galli, M.; Hirsch, M.S. Combinations of CCR5 and CXCR4 inhibitors in therapy of human immunodeficiency virus type 1 infection: in vitro studies of mixed virus infections. J. Virol. 2000, 74, 9328-9332. (Pubitemid 30759638)
35. Chou, T.C.; Talalay, P. Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors. Adv. Enzyme Regul. 1984, 22, 27-55.
36. Chou, T.C. The median-effect principle and the combination index for quantitation of synergism and antagonism. In Synergism and Antagonism in Chemotherapy; Chou, T.C., Rideout, D.C., Eds.; Academic Press, Inc.: San Diego, CA, USA, 1991; pp. 61-102.