Non-nucleoside inhibitors of HIV-1 reverse transcriptase
Tóm tắt
Four years ago it became apparent that an allosteric site on HIV-1 reverse transcriptase was responsible for the enzyme inhibitory activity of a number of structurally diverse organic compounds. These molecules bear little resemblance to the endogenous substrate, deoxynucleotide triphosphates, and through kinetic measurements they were found to be noncompetitive inhibitors. When examined in cell culture, these compounds proved to be potent antiviral agents. Improvements made in the potency and pharmacodynamic properties of the early inhibitors quickly allowed evaluation of several compounds in a clinical setting. From these and other studies came a discouraging profile of rapidly emerging viral resistance. Further work in the field may show that a combination of these and other drugs may be of benefit in combatting AIDS.
Tài liệu tham khảo
Chin, J., Remenyi, M., Morrison, F. and Bulatao, R., World Health Stat. Q., 45 (1992) 220.
Mitsuya, H. and Broder, S., Proc. Natl. Acad. Sci. USA, 83 (1986) 1911.
Mitsuya, H., Weinhold, K.J., Furman, P.A., St Clair, M.H., Lehrman, S.N., Gallo, R.C., Bolognesi, D., Barry, D.W. and Broder, S., Proc. Natl. Acad. Sci. USA, 82 (1985) 7096.
Furman, P.A., Fyfe, J.A., St. Clair, M.H., Weinhold, K., Rideout, J.L., Freeman, G.A., Nusinoff-Lehrman, S., Bolognesi, D., Broder, S., Mitsuya, H. and Barry, D.W., Proc. Natl. Acad. Sci. USA, 83 (1986) 8333.
Richman, D.D., Ann. Rev. Med., 42 (1991) 1731.
Richman, D.D., Fischl, M.A., Grieco, M.H., Gottlieb, M.S., Volberding, P.A., Laskin, O.L., Leedom, J.M., Groopman, J.E., Mildvan, D., Hirsh, M.S., Jackson, G., Durack, D.T. and Nusinoff-Lehrman, S., N. Engl. J. Med., 317 (1987) 192.
Hao, Z., Cooney, D.A., Hartman, N.R., Perno, C.F., Fridland, A., DeVico, A.L., Sangadharan, M.G., Broder, S. and Johns, D.G. Mol. Pharm., 34 (1988) 431.
Saunders, J. and Storer, R., Drug News and Perspectives, 5 (1992) 153.
Tramontano, E. and Cheng, Y-C., Biochem. Pharmacol., 43 (1992) 1371.
DeClerq, E., AIDS Res. Hum. Retroviruses, 8 (1992) 119.
Wu, J.C., Warren, T.C., Adams, J., Proudfoot, J., Skiles, J., Raghavan, P., Perry, C., Potocki, I., Farina, P.R. and Grob, P.M., Biochemistry, 30 (1991) 2022.
Carroll, S.S., Olsen, D.B., Bennett, C.D., Gotlib, L., Graham, D.J., Condra, J.H., Stern, A.M., Schafer, J.A. and Kuo, L.C., J. Biol. Chem., 268 (1993) 276.
Kohlstaedt, L.A., Wang, J., Friedman, J.M., Rice, P.A. and Steitz, T.A., Science, 256 (1992) 1783.
Larder, B.A., Darby, G. and Richman, D.D., Science, 243 (1989) 1731.
Larder, B.A. and Kemp, S.D., Science, 246 (1989) 1155.
Bakhanashvili, M. and Hizi, A., Biochemistry, 31 (1992) 9394.
Nunberg, J.H., Schleif, W.A., Boots, E.J., O'Brien, J.A., Quintero, J.C., Hoffman, J.M., Emini, E.A. and Goldman, M.E., J. Virol., 65 (1991) 4887.
Richman, D., Shih, C-K., Lowy, I., Rose, J., Prodanovich, P., Goff, S. and Griffin, J., Proc. Natl. Acad. Sci. USA, 88, 11 (1991) 241.
Lightfoote, M.M., Coligan, J.E., Folks, T-M., Fauci, A.S., Martin, M.A. and Venkatesan, S., J. Virol., 60 (1986) 771.
Di Marzo Veronese, F., Copeland, T.D., DeVico, A.L., Rahman, R., Oroszlan, S., Gallo, R.C. and Sarngadharan, M.G., Science, 231 (1986) 1289.
Howard, K.J., Frank, K.B., Sim, I.S. and LeGrice, S.F.J., J. Biol. Chem., 266 (1991) 23003.
Garret, M., Romby, P., Jieje, R. and Litvak, S., Nucleic Acids Res., 12 (1984) 2259.
Robert, D., Sallafranque-Andreola, M-L., Border, B., Sarih-Cottin, L., Tarrago-Litvak, L., Graves, P.V., Barr, P.J., Fournier, M. and Litvak, S., FEBS Lett., 277 (1991) 239.
Majumdar, C., Abbotts, J., Broder, S. and Wilson, S.H., J. Biol. Chem., 263 (1988) 15657.
Painter, G.R., Wright, L.L., Hopkins, S. and Furman, P.A., J. Biol. Chem. 266 (1991) 19362.
Huang, P., Farquhar, D. and Plunkett, W., J. Biol. Chem., 265 (1990) 11914.
Goldman, M.E., Nunberg, J.H., O'Brien, J.A., Quintero, J.C., Schleif, W.A., Freun, K.F., Gaul, S.L., Saari, W.S., Wai, J.S., Hoffman, J.M., Anderson, P.S., Hupe, D.J., Emini, E.A. and Stern, A.M., Proc. Natl. Acad. Sci. USA, 88 (1991) 6863.
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. and Sullivan, J.L., Science, 250 (1990) 1411.
Pauwels, R., Andries, K., Desmyter, J., Schols, D., Kukla, M., Breslin, H.J., Raeymaeckers, A., Van Gelder, J., Woestenborghs, R., Heykants, J., Schellekens, K., Janssen, M.A.C., De Clerq, E. and Janssen, P.A.J., Nature, 343 (1990) 470.
Debyser, Z., Pauwels, R., Andries, K., Desmyter, J., Kukla, M., Janssen, P.A.J. and De Clercq, E., Proc. Natl. Acad. Sci. USA, 88 (1991) 1451.
Kukla, M.J., Breslin, H.J., Diamond, C.J., Grous, P.J., Ho, C.Y., Miranda, M., Rodgers, J.D., Shirrill, R.G., De Clerq, E., Pauwels, R., Andries, K., Moens, L.J., Janssen, M.A.C. and Janssen, P.A.J., J. Med. Chem., 34 (1991) 3187.
Debyser, Z., Pauwels, R., Andries, K., Desmyter, J., Engelborghs, Y., Janssen, P.A.J. and De Clerq, E., Mol. Pharm., 41 (1992) 203.
De Lucca, G. and Otto, M.J., Bioorg. and Med. Chem. Lett., 2 (1992) 1639.
Saari, W.S., Hoffman, J.M., Wai, J.S., Fisher, T.E., Rooney, C.S., Smith, A.M., Thomas, C.M., Goldman, M.E., O'Brien, J.A., Nunberg, J.H., Quintero, J.C., Schleif, W.A., Emini, E.A., Stern, A.M. and Anderson, P.S., J. Med. Chem., 34 (1991) 2922.
Saari, W.S., Wai, J.S., Fisher, T.E., Thomas, C.M., Hoffman, J.M., Rooney, C.S., Smith, A.M., Jones, J.H., Bamberger, D.L., Goldman, M.E., O'Brien, J.A., Nunberg, J.H., Quintero, J.C., Schleif, Q.A., Emini, E.A. and Anderson, P.S., J. Med. Chem., 35 (1992) 3792.
Hoffman, J.M., Smith, A.M., Rooney, C.S., Fisher, T.E., Wai, J.S., Thomas, C.M., Bamberger, D.L., Barnes, J.L., Williams, T.M., Jones, J.H., O'Brien, J.A., Goldman, M.E., Nunberg, J.H., Quintero, J.C., Schleif, W.A., Emini, E.A. and Anderson, P.S., J. Med. Chem., 36 (1993) 953
Sardana, V.V., Emini, E.A., Gotlib, L., Graham, D.J., Lineberger, D.W., Long, W.J., Schlabach, A.J., Wolfgang, J.A. and Condra, J.H., J. Biol. Chem., 267 (1992) 17526.
Saag, M.S., Emini, E.A., Laskin, O.L., Douglas, J., Lapidus, W.I., Schleif, W.A., Whitley, R.J., Byrnes, V.W., Kappes, J.C., Anderson, K.W., Massari, F.E. and Shaw, G.M., New Engl. J. Med., in press.
Wai, J.S., Williams, T.M., Bamberger, D.L., Fisher, T.E., Hoffman, J.M., Hudcosky, R.J., MacTough, S.C., Rooney, C.S., Saari, W.S., Thomas, C.M., Goldman, M.E., O'Brien, J.A., Emini, E.A., Nunberg, J.H., Quintero, J.C., Schleif, W.A. and Anderson, P.S., J. Med. Chem., 36 (1993) 249.
Hargrave, K.D., Proudfoot, J.R., Grozinger, K.D., Cullen, E., Kapadia, S.R., Patel, U.R., Fuchs, V.U., Mauldin, S.C., Vitous, J., Behnke, M.L., Klunder, J.M., Pal, K., Skiles, J.W., McNeil, D.W., Rose, J.M., Chow, G.C., Skoog, M.T., Wu, J.C., Schmidt, G., Engel, W.W., Eberlein, W.G., Saboe, T.D., Campbell, S.J., Rosenthal, A.S. and Adams, J., J. Med. Chem., 34 (1991) 2231.
Klunder, J.M., Hargrave, K.D., West, M., Cullen, E., Pal, K., Behnke, M.L., Kapadia, S.R., McNeil, D.W., Wu, J.C. and Adams, J., J. Med. Chem., 35 (1992) 1887.
Cohen, K.A., Hopkins, J., Ingraham, R.H., Pargellis, C., Wu, J.C., Pallidino, D.E.H., Kinkade, P., Warren, T.C., Rogers, S., Adams, J., Farina, P.R. and Grob, P.M., J. Biol. Chem., 266 (1991) 670.
Terrett, N.K., Bojanic, D., Merson, J.R. and Stephenson, P.T., Bioorg. and Med. Chem. Lett., 2 (1992) 1745.
Romero, D.L., Busso, M., Tan, C.-K., Reusser, F., Palmer, J.R., Poppe, S.M., Aristoff, P.A., Downey, K.M., So, A.G., Resnick, L. and Tarpley, W.G., Proc. Natl. Acad. Sci. USA, 88 (1991) 8806.
Romero, D.L., Thomas, R.C., Morge, R.A., Poel, T.J., Hosley, M.J., Palmer, J.R., Aristoff, P.A., Johnson, P.D., Reusser, F., Althaus, I.W. and Tarpley, W.G., 204th American Chemical Society National Meeting. Washington, 1991 [abstr.].
Dueweke, T.J., Kezdy, F.J., Waszak, G.A., Deibel Jr., M.R. and Tarpley, W.G., J. Biol. Chem., 267 (1992) 27.
Vasudevachari, M.B., Battista, C., Lane, H.C., Psallidopoulos, M.C., Zhao, B., Cook, J., Palmer, J.R., Romero, D.L., Tarpley, W.G. and Salzman, N.P., Virology, 190 (1992) 269.
Miyasaka, T., Tanaka, H., Baba, M., Hayakawa, H., Walker, R.T., Balzarini, J. and De Clerq, E., J. Med. Chem., 32 (1989) 2507.
Debyser, Z., Vandamme, A-M., Pauels, R., Baba, M., Desmyter, J. and DeClerq, E., J. Biol. Chem., 267, 11 (1992) 769.
Baba, M., DeClerq, E., Tanaka, H., Ubasawa, M., Takashima, H.T., Sekiya, K., Nitta, I., Umezu, K., Nakashima, H., Mori, S., Shigeta, S., Walker, R.T. and Miyasaka, T., Proc. Natl. Acad. Sci. USA, 88 (1991) 2356.
Tanaka, H., Baba, M., Hayakawa, H., Sakamaki, T., Miyasaka, T., Ubasawa, M., Takashima, H., Sekiya, K., Nitta, I., Shigeta, S., Walker, R.T., Balzarini, J. and DeClerq, E., J. Med. Chem., 34 (1991) 349.
Tanaka, H., Baba, M., Ubasawa, M., Takashima, H., Sekiya, K., Nitta, I., Shigeta, S., Walker, R.T., DeClerq, E. and Miyasaka, T., J. Med. Chem., 34 (1991) 1394.
Tanaka, H., Takashima, H., Ubasawa, M., Sekiya, K., Nitta, I., Baba, M., Shigeta, S., Walker, R.T., DeClerq, E. and Miyasaka, T., J. Med. Chem., 35 (1992) 4713.
Baba, M., Debyser, Z., Shigeta, S. and DeClerq, E., Drugs Future, 17 (1992) 891.
Balzarini, J., Perez-Perez, M-J., San-Felix, A., Schols, D., Perno, C-F., Vandamme, A-M., Camarasa, M-J. and DeClerq, E., Proc. Natl. Acad. Sci. USA, 89 (1992) 4392.
Balzarini, J., Perez-Perez, M-J., San-Felix, A., Camarasa, M-J., Bathurst, I.C., Barr, P.J. and DeClerq, E., J. Biol. Chem., 267 (1992) 11831.
Van Daele, G.H., Verdonck, M.G., Bosmans, J-P. and Janssen, P.A., International Patent Application WO 92/00952: to Janssen Pharmaceutica N.V., 22 January 1992.
Pauwels, R., Andries, K., Schols, D., Van Deele, J., Debyser, Z., Janssen, M.A.C., Desmyter, J., DeClerq, E. and Janssen, P.A., VIII International Conference on AIDS, Amsterdam, 1992.
Koenig, B., Leser, U., Mertens, A., Shafer, W. and Poll, T. International Patent Application WO 92/16207: to Boehringer Mannheim GmbH, 1 October 1992.
Mases, G., Immendoefer, U., Leser, U., Pfalf, E., Goody, R. and Koenig, B. VIII International Conference on AIDS, Amsterdam, 1992.
Williams, T.M., Ciccarone, T.M., MacTough, S.C., Rooney, C.S., Balani, S.K., Condra, J.H., Emini, E.A., Goldman, M.E., Greenlee, W.J., O'Brien, J.A., Sardana, V.V., Schleif, W.A., Theoharides, A.D. and Anderson, P.S., J. Med. Chem., 36 (1993) 1291.
Larder, B.A., Darby, G. and Richman, D.D., Science, 243 (1989) 1731.
Japour, A.J., Chatis, P.A., Eigenrauch, H.A. and Crumpaker, C.S., Proc. Natl. Acad. Sci. USA, 88 (1991) 3092.
Larder, B.A., Coates, K.E. and Kemp, S.D., J. Virol., 65 (1991) 5232.
St. Clair, M.H., Marin, J.L., Tudor-Williams, G., Bach, M.C., Vavro, C.L., King, D.M., Kellam, P., Kemp, S.D. and Larder, B.A., Science, 263 (1991) 1557.
Mellors, J.W., Im, G-J., Tramontano, E., Winkler, S.R., Medina, D.J., Dutschman, G.E., Bazmi, H.Z., Piras, G., Gonzalez, C.J. and Cheng, Y-C., Mol. Pharm., 43 (1993) 11.
Shih, C-K., Rose, J.M., Hansen, G.L., Wu, J.C., Bacolla, A. and Griffin, J.A., Proc. Natl. Acad. Sci. USA, 88 (1991) 9878.
Richman, D., Rosenthal, A.S., Skoog, M., Eckner, R.J., Chou, T-C., Sabo, J.P. and Merluzzi, V.J., Antimicrob. Agents Chemother., 35 (1991) 305.
Larder, B.A., Antimicrob. Agents Chemother., 36 (1992) 2664.
Chow, Y.-K., Hirsh, M.S., Merrill, D.P., Bechtel, L.J., Eron, J.J., Kaplan, J.C., D'Aquila, R.T., Nature, 361 (1993) 650.