[d4U]-Spacer-[HI-236] double-drug inhibitors of HIV-1 reverse-transcriptase

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 13, 2010, Pages 4661-4673

  Younis, Yassir ^a   Hunter, Roger ^a   Muhanji, Clare I ^a   Hale, Ian ^a   Singh, Rajinder ^a   Bailey, Christopher M ^b   Sullivan, Todd J ^b   Anderson, Karen S ^b  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antiviral; d4T; Double drug; HI 236; HIV inhibitors; NNRTI; NRTI; Reverse Transcriptase

Indexed keywords

(D4U) 1 BUTYNYL (HI 236); (D4U) PROPARGYL 1 PEG (HI 236); (D4U) PROPARGYL 2 PEG (HI 236); (D4U) PROPARGYL 4 PEG (HI 236); BENZOIC ACID; NUCLEOSIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHOTRANSFERASE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THIOUREA; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG POTENTIATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; PHOSPHORYLATION; SONOGASHIRA REACTION;

ANTI-HIV AGENTS; BINDING SITES; CELL LINE; COMPUTER SIMULATION; DRUG DESIGN; HIV REVERSE TRANSCRIPTASE; HIV-1; HUMANS; POLYETHYLENE GLYCOLS; PYRIDINES; REVERSE TRANSCRIPTASE INHIBITORS; THIOUREA;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 77954215973     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.05.025     Document Type: Article

References (64)

1. T.M.L. Souza, D.Q. Rodrigues, V.F. Ferreira, I.P. Marques, F.C. da Costa Santos, A.C. Cunha, M.C.B. Vieira de Souza, I.C. de Palmer Paixao Frugulhetti, D.C. Bou-Habib, and C.F.L. Fontes Curr. HIV Res. 7 2009 327
2. M.D. Marsden, and J.A. Zack J. Antimicrob. Chemother. 63 2009 7
3. Y. Mehellou, and E. De Clercq J. Med. Chem. 53 2010 521
4. P. Zhan, X. Liu, Z. Li, C. Pannecouque, and E. De Clercq Curr. Med. Chem. 16 2009 3903
5. A. Basavapathruni, and K.S. Anderson Curr. Pharm. Des. 12 2006 1857
6. R.G. Nanni, J. Ding, A. Jacobo-Molina, S.H. Hughes, and E. Arnold Perspect. Drug Discovery Des. 1 1993 129
7. S.J. Smerdon, J. Jäger, J. Wang, L.A. Kohlstaedt, A.J. Chirino, J.M. Friedman, P.A. Rice, and T.A. Steitz Proc. Natl. Acad. Sci. U.S.A. 91 1994 3911
8. W.P. Jencks Proc. Natl. Acad. Sci. U.S.A. 78 1981 4046
9. R. Spence, W. Kati, K.S. Anderson, and K.A. Johnson Science 267 1995 988
10. K. Rittinger, G. Divita, and R.S. Goody Proc. Natl. Acad. Sci. U.S.A. 92 1995 8046
11. Z. Gu, Y. Quan, Z. Li, E.J. Arts, and M.A. Wainberg J. Biol. Chem. 270 1995 31046
12. S. Velázquez, R. Alvarez, A. San-Félix, M.L. Jimeno, E. De Clercq, J. Balzarini, and M.-J. Camarasa J. Med. Chem. 38 1995 1641 1649
13. C. Tomassi, A.N. Van Nhien, J. Marco-Contelles, J. Balzarini, C. Pannecouque, E. De Clercq, E. Soriano, and D. Postel Bioorg. Med. Chem. Lett. 18 2008 2277 2281
14. S. Velázquez, V. Tuñón, M.L. Jimeno, C. Chamorro, E. De Clercq, J. Balzarini, and M.-J. Camarasa J. Med. Chem. 42 1999 5188
15. C. Fossey, A.-H. Vu, A. Vidu, I. Zarafu, D. Laduree, S. Schmidt, G. Laumond, and A.-M. Aubertin J. Enzyme Inhib. Med. Chem. 22 2007 591
16. L. Pedersen, P.T. Jørgensen, S. Nielsen, T.H. Hansen, J. Nielsen, and E.B. Pedersen J. Med. Chem. 48 2005 1211
17. S. Velázquez, E. Lobatón, E. De Clercq, D.L. Koontz, J.W. Mellors, J. Balzarini, and M.J. Camarasa J. Med. Chem. 47 2004 3418
18. E. Sugeac, C. Fossey, D. Ladurée, S. Schmidt, G. Laumond, and A.-M. Aubertin J. Enzyme Inhib. Med. Chem. 18 2003 175
19. D. Gavriliu, C. Fossey, A. Ciurea, Z. Delbederi, E. Sugeac, D. Ladurée, S. Schmidt, G. Laumond, and A.M. Aubertin Nucleosides Nucleotides Nucleic Acids 21 2002 505
20. R. Pontikis, V. Dollé, J. Guillaumel, E. Dechaux, R. Note, C.H. Nguyen, M. Legraverend, E. Bisagni, A.M. Aubertin, D.S. Grierson, and C. Monneret J. Med. Chem. 43 2000 1927
21. M. Renoud-Grappin, C. Fossey, G. Fontaine, D. Ladurée, A.M. Aubertin, and A. Kirn Antiviral Chem. Chemother. 9 1998 205
22. C.I. Muhanji, and R. Hunter Curr. Med. Chem. 14 2007 127
23. An interesting variation based on targeting both IN and RT in the form of a non-cleavable portmanteau inhibitor is: Z. Wang, E.M. Bennett, D.J. Wilson, C. Salomon, and R. Vince J. Med. Chem. 50 2007 3416 3419
24. R. Hunter, C.I. Muhanji, I. Hale, C.M. Bailey, A. Basavapathruni, and K.S. Anderson Bioorg. Med. Chem. Lett. 17 2007 2614
25. R. Hunter, Y. Younis, C.-I. Muhanji, T.-L. Curtin, K.J. Naidoo, M. Petersen, C.M. Bailey, A. Basavapathruni, and K.S. Anderson Bioorg. Med. Chem. 16 2008 10270
26. C. Mao, E.A. Sudbeck, T.K. Venkatachalam, and F.M. Uckun Biochem. Pharmacol. 60 2000 1251
27. C. Mao, E.A. Sudbeck, T.K. Venkatachalam, and F.M. Uckun Bioorg. Med. Chem. Lett. 9 1999 1593
28. R. Vig, C. Mao, T.K. Venkatachalam, L. Tuel-Ahlgren, E.A. Sudbeck, and F.M. Uckun Bioorg. Med. Chem. Lett. 8 1998 1461
29. J.L. Ruth, and Y.C. Cheng J. Biol. Chem. 1982 10261
30. J.L. Ruth, and Y.C. Cheng Mol. Pharmacol. 20 1981 415
31. R. Chinchilla, and C. Najera Chem. Rev. 107 2007 874
32. R. Pauwels Curr. Opin. Pharmacol. 4 2004 437
33. R.A. Glennon, S.M. Liebowitz, D. Leming-Doot, and J.A. Rosecrans J. Med. Chem. 23 1980 990
34. B.C. Chen, S.L. Quinlan, J.G. Ried, and R.H. Spector Tetrahedron Lett. 39 1998 729
35. B.C. Chen, S.L. Quinlan, D.R. Stark, G. Reid, V.H. Audia, J.G. George, E. Eisenreich, S.P. Brundidge, S. Racha, and R.H. Spector Tetrahedron Lett. 36 1995 7957
36. J.F. Codington, I.L. Doerr, and J.J. Fox J. Org. Chem. 29 1964 558
37. J.F. Codington, R. Fecher, and J.J. Fox J. Am. Chem. Soc. 82 1960 2794
38. J. Sheng, A.E.A. Hassan, and Z. Huang J. Org. Chem. 73 2008 3725
39. J.E. Starrett Jr., D.R. Tortolani, D.C. Baker, M.T. Omar, A.K. Hebbler, J.A. Wos, J.C. Martin, and M.M. Mansuri Nucleosides Nucleotides 9 1990 885
40. M.M. Mansuri, J.E. Starrett Jr., J.A. Wos, D.R. Tortolani, P.R. Brodfuehrer, H.G. Howell, and J.C. Martin J. Org. Chem. 54 1989 4780
41. J. Asakura, and M.J. Robins J. Org. Chem. 55 1990 4928 4933
42. M.J. Robins, and P.J. Barr J. Org. Chem. 48 1983 1854
43. F.W. Hobbs Jr. J. Org. Chem. 54 1989 3420
44. G. Crisp, and B.L. Flynn J. Org. Chem. 58 1993 6614
45. L.A. Agrofolio, I. Gillaizeau, and Y. Saito Chem. Rev. 103 2003 1875
46. M.R. Kelleher, C. McGuigan, O. Bidet, A. Carangio, H. Weldon, G. Andrei, R. Snoeck, E. De Clercq, and J. Balzarini Nucleosides Nucleotides Nucleic Acids 24 2005 643
47. F.W. Bell, A.S. Cantrell, M. Högberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordan, M.D. Kinnick, P. Lind, J.M. Morin Jr., R. Noréen, B. Öberg, J.A. Palkowitz, C.A. Parrish, P. Pranc, C. Sahlberg, R.J. Ternansky, R.T. Vasileff, L. Vrang, S.J. West, H. Zhang, and X.-X. Zhou J. Med. Chem. 38 1995 4929
48. M.J. Robins, R.S. Vinayak, and S.G. Wood Tetrahedron Lett. 31 1990 3731
49. N. Olivi, P. Spruyt, J.-F. Peyrat, M. Alami, and J.-D. Brion Tetrahedron Lett. 45 2004 2607
50. C. Meier Eur. J. Org. Chem. 2006 1081
51. J. Balzarini, A. Karlsson, S. Aquaro, C.-F. Perno, D. Cahard, L. Naesens, E. De Clercq, and C. McGuigan Proc. Natl. Acad. Sci. U.S.A. 93 1996 7295
52. A.Q. Siddiqui, C. Ballatore, C. McGuigan, E. De Clercq, and J. Balzarini J. Med. Chem. 42 1999 393
53. C. McGuigan, R. Pathirana, J. Balzarini, and E. De Clercq J. Med. Chem. 36 1993 1048
54. Y. Mehellou, J. Balzarini, and C. McGuigan Org. Biomol. Chem. 7 2009 2548
55. Y. Mehellou, C. McGuigan, A. Brancale, and J. Balzarini Bioorg. Med. Chem. Lett. 17 2007 3666
56. C. McGuigan, H.W. Tsang, D. Cahard, K. Turner, S. Velazquez, A. Salgado, L. Bidois, L. Naesens, E. De Clercq, and J. Balzarini Antiviral Res. 35 1997 195
57. C. Pannecouque, D. Daelemans, and E. De Clercq Nat. Protocols 3 2008 427
58. A. Ciurea, C. Fossey, D. Gavriliu, Z. Delbederi, E. Sugeac, D. Ladurée, S. Schmidt, G. Laumond, and A.M. Aubertin J. Enzyme Inhib. 19 2004 511
59. B.-L. Deng, T.L. Hartman, R.W. Buckheit Jr., C. Pannecouque, E. De Clercq, P.E. Fanwick, and M. Cushman J. Med. Chem. 48 2005 6140
60. T. Haertle, C.J. Carrera, D.B. Wasson, L.C. Sowers, D.D. Richmann, and D.A. Carson J. Biol. Chem. 263 1988 5870
61. S. Harada, Y. Koyanagi, and N. Yamamoto Science 229 1985 563
62. M. Popovic, E. Read-Connole, and R. Gallo Lancet 2 1984 1472
63. M. Popovic, M.G. Sarngadharan, E. Read, and R.C. Gallo Science 224 1984 497
64. L. Ratner, W. Haseltine, R. Patarca, K.J. Livak, B. Starcich, S.F. Josephs, E.R. Doran, J.A. Rafalski, E.A. Whitehorn, K. Baumeister, L. Ivanoff, S.R. Petteway Jr., M.L. Pearson, J.A. Lautenberger, T.S. Papas, J. Ghrayab, N.T. Chang, R.C. Gallo, and F. Wong-Stall Nature 313 1985 277