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Volumn 39, Issue 17, 1996, Pages 3291-3299

Paracyclophanes: A novel class of water-soluble inhibitors of HIV proteinase

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; PARACYCLOPHANE DERIVATIVE; PROTEINASE INHIBITOR; SAQUINAVIR; SDZ PRI 053; UNCLASSIFIED DRUG;

EID: 0029785735     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950641i     Document Type: Article
Times cited : (27)

References (31)
  • 1
    • 0028143193 scopus 로고
    • Inhibitors of HIV-1 Proteinase Containing 2-Heterosubstituted 4-Amino-3-hydroxy-5-phenylpentanoic Acid: Synthesis, Enzyme Inhibition, and Antiviral Activity
    • Scholz, D.; Billich, A.; Charpiot, B.; Ettmayer, P.; Lehr, P.; Rosenwirth, B.; Schreiner, E.; Gstach, H. Inhibitors of HIV-1 Proteinase Containing 2-Heterosubstituted 4-Amino-3-hydroxy-5-phenylpentanoic Acid: Synthesis, Enzyme Inhibition, and Antiviral Activity, J. Med. Chem. 1994, 37, 3079-3089.
    • (1994) J. Med. Chem. , vol.37 , pp. 3079-3089
    • Scholz, D.1    Billich, A.2    Charpiot, B.3    Ettmayer, P.4    Lehr, P.5    Rosenwirth, B.6    Schreiner, E.7    Gstach, H.8
  • 2
    • 0014211618 scopus 로고
    • On the Size of the Active Site in Proteases. I. Papain
    • The nomenclature used for describing the individual amino acid residues (P3, P2, P1, P1′, P2′, etc.) of a substrate and the corresponding subsites (S3, S2, S1, S1′, S2′, etc.) of a protease is that of Schechter and Berger: Schechter, I.; Berger, A. On the Size of the Active Site in Proteases. I. Papain. Biochem. Biophys. Res. Commun. 1967, 27, 157-162.
    • (1967) Biochem. Biophys. Res. Commun. , vol.27 , pp. 157-162
    • Schechter, I.1    Berger, A.2
  • 3
    • 0028102546 scopus 로고
    • HIV Proteinase Inhibitors Containing 2-Aminobenzylstatine as a Novel Scissile Bond Replacement: Biochemical and Pharmacological Characterization
    • Billich, A.; Charpiot, B.; Fricker, G.; Gstach, H.; Lehr, P.; Peichl, P.; Scholz, D.; Rosenwirth, B. HIV Proteinase Inhibitors Containing 2-Aminobenzylstatine as a Novel Scissile Bond Replacement: Biochemical and Pharmacological Characterization. Antivir. Res. 1994, 25, 215-233.
    • (1994) Antivir. Res. , vol.25 , pp. 215-233
    • Billich, A.1    Charpiot, B.2    Fricker, G.3    Gstach, H.4    Lehr, P.5    Peichl, P.6    Scholz, D.7    Rosenwirth, B.8
  • 5
    • 0029944321 scopus 로고    scopus 로고
    • Inhibitors of HIV-I Protease Containing 2-Aminobenzyl Substituted 4-Amino-3-hydroxy-5-phenylpentanoic Acid (AHPPA): Synthesis, Activity, and Oral Bioavailability
    • (b) Lehr, P.; Billich, A.; Charpiot, B.; Gstach, H.; Ettmayer, P.; Scholz, D.; Rosenwirth, B. Inhibitors of HIV-I Protease Containing 2-Aminobenzyl Substituted 4-Amino-3-hydroxy-5-phenylpentanoic Acid (AHPPA): Synthesis, Activity, and Oral Bioavailability. J. Med. Chem. 1996, 39, 2060-2067.
    • (1996) J. Med. Chem. , vol.39 , pp. 2060-2067
    • Lehr, P.1    Billich, A.2    Charpiot, B.3    Gstach, H.4    Ettmayer, P.5    Scholz, D.6    Rosenwirth, B.7
  • 7
    • 0027405931 scopus 로고
    • Symmetry-based Inhibitors of HIV Protease. Structure-Activity Studies of Acylated 2,4-Diamino-1,5-diphenyl-3-hydroxypentane and 2,5-Diamino-1,6-diphenylhexane-3,4-diol
    • Kempf, D. J.; Codacovi, L.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Saldivar, A.; Vasavanonda, S.; Marsh, K. C.; Bryant, P.; Sham, H. L. Symmetry-based Inhibitors of HIV Protease. Structure-Activity Studies of Acylated 2,4-Diamino-1,5-diphenyl-3-hydroxypentane and 2,5-Diamino-1,6-diphenylhexane-3,4-diol. J. Med. Chem. 1993, 36, 320-330.
    • (1993) J. Med. Chem. , vol.36 , pp. 320-330
    • Kempf, D.J.1    Codacovi, L.2    Wang, X.C.3    Kohlbrenner, W.E.4    Wideburg, N.E.5    Saldivar, A.6    Vasavanonda, S.7    Marsh, K.C.8    Bryant, P.9    Sham, H.L.10
  • 8
    • 0028231995 scopus 로고
    • Protein Binding of Human Immunodeficiency Virus Protease Inhibitor KNI-272 and Alteration of its in Vitro Antiretroviral Activity in the Presence of High Concentrations of Proteins
    • Kageyama, S.; Anderson, B. D.; Hoesterey, B. L.; Hayashi, H.; Kiso, Y.; Flora, K. P.; Mitsuya, H. Protein Binding of Human Immunodeficiency Virus Protease Inhibitor KNI-272 and Alteration of its in Vitro Antiretroviral Activity in the Presence of High Concentrations of Proteins. Antimicrob. Agents Chemother. 1994, 38, 1107-1111.
    • (1994) Antimicrob. Agents Chemother. , vol.38 , pp. 1107-1111
    • Kageyama, S.1    Anderson, B.D.2    Hoesterey, B.L.3    Hayashi, H.4    Kiso, Y.5    Flora, K.P.6    Mitsuya, H.7
  • 9
    • 0028591825 scopus 로고
    • A Bioactive Fullerene Peptide
    • Toniolo, C.; Bianco, A.; Maggini, M.; Scorrano, G.; Prato, M.; Marastoni, M.; Tomatis, R.; Spisani, S.; Palu, G.; Blair, E. D. A Bioactive Fullerene Peptide. J. Med. Chem. 1994, 37, 4558-4562. Brinekworth, R.; Woon, T.; Fairlie, D. Inhibition of HIV-1 Proteinase by non-Peptide Carboxylates. Biochem Biophys. Res. Commun. 1991, 176, 241-246. DesJarlais, R.; Seibel, G.; Kuntz, I.; Furth, P.; Alvarez, J.; Ortiz de Montellano, P.; DeCamp, D.; Babe, L.; Craik, C.; Structure Based Design of Nonpeptide Inhibitors Specific for the Human Immunodeficieny Virus 1 Protease. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 6644-6648.
    • (1994) J. Med. Chem. , vol.37 , pp. 4558-4562
    • Toniolo, C.1    Bianco, A.2    Maggini, M.3    Scorrano, G.4    Prato, M.5    Marastoni, M.6    Tomatis, R.7    Spisani, S.8    Palu, G.9    Blair, E.D.10
  • 10
    • 0025848484 scopus 로고
    • Inhibition of HIV-1 Proteinase by non-Peptide Carboxylates
    • Toniolo, C.; Bianco, A.; Maggini, M.; Scorrano, G.; Prato, M.; Marastoni, M.; Tomatis, R.; Spisani, S.; Palu, G.; Blair, E. D. A Bioactive Fullerene Peptide. J. Med. Chem. 1994, 37, 4558-4562. Brinekworth, R.; Woon, T.; Fairlie, D. Inhibition of HIV-1 Proteinase by non-Peptide Carboxylates. Biochem Biophys. Res. Commun. 1991, 176, 241-246. DesJarlais, R.; Seibel, G.; Kuntz, I.; Furth, P.; Alvarez, J.; Ortiz de Montellano, P.; DeCamp, D.; Babe, L.; Craik, C.; Structure Based Design of Nonpeptide Inhibitors Specific for the Human Immunodeficieny Virus 1 Protease. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 6644-6648.
    • (1991) Biochem Biophys. Res. Commun. , vol.176 , pp. 241-246
    • Brinekworth, R.1    Woon, T.2    Fairlie, D.3
  • 11
    • 0025054246 scopus 로고
    • Structure Based Design of Nonpeptide Inhibitors Specific for the Human Immunodeficieny Virus 1 Protease
    • Toniolo, C.; Bianco, A.; Maggini, M.; Scorrano, G.; Prato, M.; Marastoni, M.; Tomatis, R.; Spisani, S.; Palu, G.; Blair, E. D. A Bioactive Fullerene Peptide. J. Med. Chem. 1994, 37, 4558-4562. Brinekworth, R.; Woon, T.; Fairlie, D. Inhibition of HIV-1 Proteinase by non-Peptide Carboxylates. Biochem Biophys. Res. Commun. 1991, 176, 241-246. DesJarlais, R.; Seibel, G.; Kuntz, I.; Furth, P.; Alvarez, J.; Ortiz de Montellano, P.; DeCamp, D.; Babe, L.; Craik, C.; Structure Based Design of Nonpeptide Inhibitors Specific for the Human Immunodeficieny Virus 1 Protease. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 6644-6648.
    • (1990) Proc. Natl. Acad. Sci. U.S.A. , vol.87 , pp. 6644-6648
    • DesJarlais, R.1    Seibel, G.2    Kuntz, I.3    Furth, P.4    Alvarez, J.5    Ortiz De Montellano, P.6    DeCamp, D.7    Babe, L.8    Craik, C.9
  • 12
    • 0026487085 scopus 로고
    • Highly Potent, Orally Active Diester Macrocyclic Human Renin Inhibitors
    • Weber, A. E.; Steiner, M. G.; Krieter, P. A.; Colletti, A. E.; Tata, J. R.; Halgren, T. A.; Ball, R. G.; Doyle, J. J.; Schorn, T. W.; Stearns, R. A. Highly Potent, Orally Active Diester Macrocyclic Human Renin Inhibitors. J. Med. Chem. 1992, 35, 3755-73. Reily, M. D.; Thanabal, V.; Lunney, E. A.; Repine, J. T.; Humblet, C. C.; Wagner, G. Design, Synthesis and Solution Structure of a Renin Inhibitor. Structural Constraints from NOE, and Homonuclear and Heteronuclear Coupling Constants Combined with Distance Geometry Calculations. FEBS Lett. 1992, 302, 97-103. Weber, A. E.; Halgren, T. A.; Doyle, J. J.; Lynch, R. J.; Siegl, P. K.; Parsons, W. H; Greenlee, W. J.; Patchett, A. A. Design and Synthesis of P2-P1′-linked Macrocyclic Human Renin Inhibitors. J. Med. Chem. 1991, 34, 2692-2701. Fesik, S. W.; Bolis, G.; Sham, H. L.; Olejniczak, E. T. Structure Refinement of a Cyclic Peptide from Two-Dimensional NMR Data and Molecular Modeling. Biochemistry 1987, 26, 1851-1859.
    • (1992) J. Med. Chem. , vol.35 , pp. 3755-3773
    • Weber, A.E.1    Steiner, M.G.2    Krieter, P.A.3    Colletti, A.E.4    Tata, J.R.5    Halgren, T.A.6    Ball, R.G.7    Doyle, J.J.8    Schorn, T.W.9    Stearns, R.A.10
  • 13
    • 0026590494 scopus 로고
    • Design, Synthesis and Solution Structure of a Renin Inhibitor. Structural Constraints from NOE, and Homonuclear and Heteronuclear Coupling Constants Combined with Distance Geometry Calculations
    • Weber, A. E.; Steiner, M. G.; Krieter, P. A.; Colletti, A. E.; Tata, J. R.; Halgren, T. A.; Ball, R. G.; Doyle, J. J.; Schorn, T. W.; Stearns, R. A. Highly Potent, Orally Active Diester Macrocyclic Human Renin Inhibitors. J. Med. Chem. 1992, 35, 3755-73. Reily, M. D.; Thanabal, V.; Lunney, E. A.; Repine, J. T.; Humblet, C. C.; Wagner, G. Design, Synthesis and Solution Structure of a Renin Inhibitor. Structural Constraints from NOE, and Homonuclear and Heteronuclear Coupling Constants Combined with Distance Geometry Calculations. FEBS Lett. 1992, 302, 97-103. Weber, A. E.; Halgren, T. A.; Doyle, J. J.; Lynch, R. J.; Siegl, P. K.; Parsons, W. H; Greenlee, W. J.; Patchett, A. A. Design and Synthesis of P2-P1′-linked Macrocyclic Human Renin Inhibitors. J. Med. Chem. 1991, 34, 2692-2701. Fesik, S. W.; Bolis, G.; Sham, H. L.; Olejniczak, E. T. Structure Refinement of a Cyclic Peptide from Two-Dimensional NMR Data and Molecular Modeling. Biochemistry 1987, 26, 1851-1859.
    • (1992) FEBS Lett. , vol.302 , pp. 97-103
    • Reily, M.D.1    Thanabal, V.2    Lunney, E.A.3    Repine, J.T.4    Humblet, C.C.5    Wagner, G.6
  • 14
    • 0025925104 scopus 로고
    • Design and Synthesis of P2-P1′-linked Macrocyclic Human Renin Inhibitors
    • Weber, A. E.; Steiner, M. G.; Krieter, P. A.; Colletti, A. E.; Tata, J. R.; Halgren, T. A.; Ball, R. G.; Doyle, J. J.; Schorn, T. W.; Stearns, R. A. Highly Potent, Orally Active Diester Macrocyclic Human Renin Inhibitors. J. Med. Chem. 1992, 35, 3755-73. Reily, M. D.; Thanabal, V.; Lunney, E. A.; Repine, J. T.; Humblet, C. C.; Wagner, G. Design, Synthesis and Solution Structure of a Renin Inhibitor. Structural Constraints from NOE, and Homonuclear and Heteronuclear Coupling Constants Combined with Distance Geometry Calculations. FEBS Lett. 1992, 302, 97-103. Weber, A. E.; Halgren, T. A.; Doyle, J. J.; Lynch, R. J.; Siegl, P. K.; Parsons, W. H; Greenlee, W. J.; Patchett, A. A. Design and Synthesis of P2-P1′-linked Macrocyclic Human Renin Inhibitors. J. Med. Chem. 1991, 34, 2692-2701. Fesik, S. W.; Bolis, G.; Sham, H. L.; Olejniczak, E. T. Structure Refinement of a Cyclic Peptide from Two-Dimensional NMR Data and Molecular Modeling. Biochemistry 1987, 26, 1851-1859.
    • (1991) J. Med. Chem. , vol.34 , pp. 2692-2701
    • Weber, A.E.1    Halgren, T.A.2    Doyle, J.J.3    Lynch, R.J.4    Siegl, P.K.5    Parsons, W.H.6    Greenlee, W.J.7    Patchett, A.A.8
  • 15
    • 0023647099 scopus 로고
    • Structure Refinement of a Cyclic Peptide from Two-Dimensional NMR Data and Molecular Modeling
    • Weber, A. E.; Steiner, M. G.; Krieter, P. A.; Colletti, A. E.; Tata, J. R.; Halgren, T. A.; Ball, R. G.; Doyle, J. J.; Schorn, T. W.; Stearns, R. A. Highly Potent, Orally Active Diester Macrocyclic Human Renin Inhibitors. J. Med. Chem. 1992, 35, 3755-73. Reily, M. D.; Thanabal, V.; Lunney, E. A.; Repine, J. T.; Humblet, C. C.; Wagner, G. Design, Synthesis and Solution Structure of a Renin Inhibitor. Structural Constraints from NOE, and Homonuclear and Heteronuclear Coupling Constants Combined with Distance Geometry Calculations. FEBS Lett. 1992, 302, 97-103. Weber, A. E.; Halgren, T. A.; Doyle, J. J.; Lynch, R. J.; Siegl, P. K.; Parsons, W. H; Greenlee, W. J.; Patchett, A. A. Design and Synthesis of P2-P1′-linked Macrocyclic Human Renin Inhibitors. J. Med. Chem. 1991, 34, 2692-2701. Fesik, S. W.; Bolis, G.; Sham, H. L.; Olejniczak, E. T. Structure Refinement of a Cyclic Peptide from Two-Dimensional NMR Data and Molecular Modeling. Biochemistry 1987, 26, 1851-1859.
    • (1987) Biochemistry , vol.26 , pp. 1851-1859
    • Fesik, S.W.1    Bolis, G.2    Sham, H.L.3    Olejniczak, E.T.4
  • 16
    • 0028020289 scopus 로고
    • Design, Synthesis, and Conformational Analysis of a Novel Macrocyclic HIV-Protease Inhibitor
    • Podlogar, B. L.; Fair, R. A.; Friedrich, D.; Tarnus, C.; Huber E. W.; Cregge, R. J.; Schiriin, D. Design, Synthesis, and Conformational Analysis of a Novel Macrocyclic HIV-Protease Inhibitor. J. Med. Chem. 1994, 37, 3684-3692. Smith, R. A.; Coles, P. J.; Chen, J. J.; Robinson, V. J.; Macdonald, I. D.; Carriere, J.; Krantz, A. Design, Synthesis, and Activity of Conformationally-Constrained Macrocyclic Peptide-Based Inhibitors of HIV Protease. Bioorg. Med. Chem. Lett. 1994, 4, 2217-2222.
    • (1994) J. Med. Chem. , vol.37 , pp. 3684-3692
    • Podlogar, B.L.1    Fair, R.A.2    Friedrich, D.3    Tarnus, C.4    Huber, E.W.5    Cregge, R.J.6    Schiriin, D.7
  • 17
    • 0028096657 scopus 로고
    • Design, Synthesis, and Activity of Conformationally-Constrained Macrocyclic Peptide-Based Inhibitors of HIV Protease
    • Podlogar, B. L.; Fair, R. A.; Friedrich, D.; Tarnus, C.; Huber E. W.; Cregge, R. J.; Schiriin, D. Design, Synthesis, and Conformational Analysis of a Novel Macrocyclic HIV-Protease Inhibitor. J. Med. Chem. 1994, 37, 3684-3692. Smith, R. A.; Coles, P. J.; Chen, J. J.; Robinson, V. J.; Macdonald, I. D.; Carriere, J.; Krantz, A. Design, Synthesis, and Activity of Conformationally-Constrained Macrocyclic Peptide-Based Inhibitors of HIV Protease. Bioorg. Med. Chem. Lett. 1994, 4, 2217-2222.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2217-2222
    • Smith, R.A.1    Coles, P.J.2    Chen, J.J.3    Robinson, V.J.4    Macdonald, I.D.5    Carriere, J.6    Krantz, A.7
  • 18
    • 0028841007 scopus 로고
    • 3D Qantitative Structure-Activity Relationships of Human Immunodeficiency Virus Type-1 Proteinase Inhibitors: Comparative Molecular Field Analysis of 2 Heterosubstituted Staline Derivatives - Implications for the Design of Novel Inhibitors
    • For full details of the docking experiments see: Krömer, R. T.; Ettmayer, P.; Hecht, P. 3D Qantitative Structure-Activity Relationships of Human Immunodeficiency Virus Type-1 Proteinase Inhibitors: Comparative Molecular Field Analysis of 2 Heterosubstituted Staline Derivatives - Implications for the Design of Novel Inhibitors. J. Med. Chem. 1995, 38, 4917-4928.
    • (1995) J. Med. Chem. , vol.38 , pp. 4917-4928
    • Krömer, R.T.1    Ettmayer, P.2    Hecht, P.3
  • 19
    • 10144233931 scopus 로고    scopus 로고
    • note
    • The structures were minimized in a two-step procedure: (A) using the standard Tripos Force Field without electrostatics applying the Powell minimization technique. The convergence criteria were set to be an energy change of <0.05 kcal/mol in two consecutive steps; (B) the resulting structure was minimized under the same conditions in the protease environment (brook-haven: 4HVP without inhibitor) which was defined as completely rigid. Distance constraints corresponding to a set of hydrogen bonds between inhibitor and protein were applied as described in footnote 11. If the conformation of the modeled structure displayed unfavorable interactions or did not fulfill the distance constrain requirements to a large extent, the starting conformation was manually modified and the new conformer was subjected again to minimization procedures A and B.
  • 20
    • 0027278829 scopus 로고
    • A Practical Synthesis of Fibrinogen Receptor Antagonist MK-383. Selective Functionalisation of (S)-Tyrosine
    • The phenolic O-alkylation was done in analogy to: Chung, J. Y. L.; Zhao, D.; Hughes, D. L.; Grabowski, E. J. J. A Practical Synthesis of Fibrinogen Receptor Antagonist MK-383. Selective Functionalisation of (S)-Tyrosine. Tetrahedron 1993, 49, 5767-5776.
    • (1993) Tetrahedron , vol.49 , pp. 5767-5776
    • Chung, J.Y.L.1    Zhao, D.2    Hughes, D.L.3    Grabowski, E.J.J.4
  • 22
    • 0027948458 scopus 로고
    • Update on a Proteinase Inhibitor
    • Vella, S. Update on a Proteinase Inhibitor. AIDS 1994, 8 (suppl 3), S25-S29.
    • (1994) AIDS , vol.8 , Issue.3 SUPPL.
    • Vella, S.1
  • 23
    • 10144247705 scopus 로고    scopus 로고
    • Quinoline Carboxylic Acid Amides. CIBA U.S.P: 2798873 (1953)
    • Kobler, A.; Malter, M. Quinoline Carboxylic Acid Amides. CIBA U.S.P: 2798873 (1953).
    • Kobler, A.1    Malter, M.2
  • 24
    • 0025278878 scopus 로고
    • Purification, Assay and Kinetic Features of HIV-1 proteinase
    • Billich, A.; Hammerschmid, F.; Winkler, G. Purification, Assay and Kinetic Features of HIV-1 proteinase. Biol. Chem. Hoppe-Seyler 1990, 371, 265-272.
    • (1990) Biol. Chem. Hoppe-Seyler , vol.371 , pp. 265-272
    • Billich, A.1    Hammerschmid, F.2    Winkler, G.3
  • 28
    • 0024464323 scopus 로고
    • Characterization of an HIV-2 Related Virus with a Smaller Sized Extracellular Envelope Glycoprotein
    • Rey, M. A.; Krust, B.; Laurent, A. G.; Guetard, D.; Montagnier, L.; Hovanessian, A. G. Characterization of an HIV-2 Related Virus with a Smaller Sized Extracellular Envelope Glycoprotein. Virology 1989, 173, 258-267.
    • (1989) Virology , vol.173 , pp. 258-267
    • Rey, M.A.1    Krust, B.2    Laurent, A.G.3    Guetard, D.4    Montagnier, L.5    Hovanessian, A.G.6


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