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Volumn 54, Issue 8, 2011, Pages 3081-3085

On a possible neutral charge state for the catalytic dyad in β-secretase when bound to hydroxyethylene transition state analogue inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ASPARTIC ACID; BETA SECRETASE 1; BETA SECRETASE INHIBITOR; ETHYLENE DERIVATIVE; HYDROXYETHYLENE DERIVATIVE; OM00 3; OM99 2; UNCLASSIFIED DRUG;

EID: 79955385829     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101568y     Document Type: Article
Times cited : (14)

References (29)
  • 1
    • 0033600274 scopus 로고    scopus 로고
    • Translating cell biology into therapeutic advances in Alzheimer's disease
    • Selkoe, D. J. Translating cell biology into therapeutic advances in Alzheimer's disease Nature 1999, 399, A23-A31
    • (1999) Nature , vol.399
    • Selkoe, D.J.1
  • 2
    • 34447256355 scopus 로고    scopus 로고
    • The search for drug leads targeted to the β-secretase: An example of the roles of computer assisted approaches in drug discovery
    • DOI 10.2174/156802607780906708
    • Villaverde, M. C.; González-Louro, L.; Sussman, F. The Search for Drug Leads Targeted to the β-Secretase: An Example of the Roles of Computer Assisted Approaches in Drug Discovery Curr. Top. Med. Chem. 2007, 7, 980-990 (Pubitemid 47040526)
    • (2007) Current Topics in Medicinal Chemistry , vol.7 , Issue.10 , pp. 980-990
    • Villaverde, M.C.1    Gonzalez-Louro, L.2    Sussman, F.3
  • 4
    • 62249167406 scopus 로고    scopus 로고
    • Boom in the Development of Non-peptidic β-Secretase (BACE1) Inhibitors for the Treatment of Alzheimer's Disease
    • Silvestri, R. Boom in the Development of Non-peptidic β-Secretase (BACE1) Inhibitors for the Treatment of Alzheimer's Disease Med. Res. Rev. 2009, 29, 295-338
    • (2009) Med. Res. Rev. , vol.29 , pp. 295-338
    • Silvestri, R.1
  • 5
    • 46749092486 scopus 로고    scopus 로고
    • β-Secretase as a Therapeutic Target for Alzheimer's Disease
    • DOI 10.1016/j.nurt.2008.05.007, PII S1933721308000974
    • Ghosh, A. K.; Gemma, S.; Tang, J. β-Secretase as a Therapeutic Target for Alzheimer's Disease Neurotherapeutics 2008, 5, 399-408 (Pubitemid 351952491)
    • (2008) Neurotherapeutics , vol.5 , Issue.3 , pp. 399-408
    • Ghosh, A.K.1    Gemma, S.2    Tang, J.3
  • 6
    • 65249101192 scopus 로고    scopus 로고
    • Harnessing Nature's Insight: Design of Aspartyl Protease Inhibitors from Treatment of Drug-Resistant HIV to Alzheimer's Disease
    • Ghosh, A. K. Harnessing Nature's Insight: Design of Aspartyl Protease Inhibitors from Treatment of Drug-Resistant HIV to Alzheimer's Disease J. Med. Chem. 2009, 52, 2163-2176
    • (2009) J. Med. Chem. , vol.52 , pp. 2163-2176
    • Ghosh, A.K.1
  • 7
    • 20144369541 scopus 로고    scopus 로고
    • Virtual screening for β-secretase (BACE1) inhibitors reveals the importance of protonation states at Asp32 and Asp228
    • DOI 10.1021/jm049133b
    • Polgár, T.; Keserü, G. M. Virtual Screening for β-Secretase (BACE1) Inhibitors Reveals the Importance of Protonation States at Asp32 and Asp228 J. Med. Chem. 2005, 48, 3749-3755 (Pubitemid 40776849)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.11 , pp. 3749-3755
    • Polgar, T.1    Keseru, G.M.2
  • 8
    • 0347694970 scopus 로고    scopus 로고
    • Determination of the Active Site Protonation State of β-Secretase from Molecular Dynamics Simulation and Docking Experiment: Implications for Structure-Based Inhibitor Design
    • DOI 10.1021/ja0304493
    • Park, H.; Lee, S. Determination of the Active Site Protonation State of β-Secretase from Molecular Dynamics Simulation and Docking Experiment: Implications for Structure-Based Inhibitor Design J. Am. Chem. Soc. 2003, 125, 16416-16422 (Pubitemid 38020666)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.52 , pp. 16416-16422
    • Park, H.1    Lee, S.2
  • 9
    • 4744338363 scopus 로고    scopus 로고
    • Modeling the protonation states of the catalytic aspartates in β-secretase
    • DOI 10.1021/jm049817j
    • Rajamani, R.; Reynolds, C. H. Modeling the Protonation States of the Catalytic Aspartates in β-Secretase J. Med. Chem. 2004, 47, 5159-5166 (Pubitemid 39314913)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.21 , pp. 5159-5166
    • Rajamani, R.1    Reynolds, C.H.2
  • 10
    • 33751504561 scopus 로고    scopus 로고
    • Assigning the Protonation States of Key Aspartates in β-Secretase Using QM/MM X-ray Structure Refinement
    • Yu, N.; Hayik, S. A.; Wang, B.; Liao, N.; Reynolds, C. H.; Merz, K. M., Jr. Assigning the Protonation States of Key Aspartates in β-Secretase Using QM/MM X-ray Structure Refinement J. Chem. Theory Comput. 2006, 2, 1057-1069
    • (2006) J. Chem. Theory Comput. , vol.2 , pp. 1057-1069
    • Yu, N.1    Hayik, S.A.2    Wang, B.3    Liao, N.4    Reynolds, C.H.5    Merz Jr., K.M.6
  • 12
    • 0001557694 scopus 로고
    • Preparation of some bromodeoxyaldonic acids
    • Bock, K.; Lundt, I.; Pedersen, C. Preparation of some bromodeoxyaldonic acids Carbohydr. Res. 1979, 68, 313-319
    • (1979) Carbohydr. Res. , vol.68 , pp. 313-319
    • Bock, K.1    Lundt, I.2    Pedersen, C.3
  • 13
    • 0013538592 scopus 로고
    • Preparation of some 2,3-Dideoxylactones by an Unusual Catalytic Hydrogenolysis
    • Lundt, I.; Pedersen, C. Preparation of some 2,3-Dideoxylactones by an Unusual Catalytic Hydrogenolysis Synthesis 1986, 1052-1054
    • (1986) Synthesis , pp. 1052-1054
    • Lundt, I.1    Pedersen, C.2
  • 15
    • 0026331003 scopus 로고
    • An Efficient Synthesis of Hydroxyethylene Dipeptide Isosteres: The Core Unit of Potent HIV-1 Protease Inhibitors
    • Ghosh, A. K.; McKee, S. P.; Thomson, W. J. An Efficient Synthesis of Hydroxyethylene Dipeptide Isosteres: The Core Unit of Potent HIV-1 Protease Inhibitors J. Org. Chem. 1991, 56, 6500-6503
    • (1991) J. Org. Chem. , vol.56 , pp. 6500-6503
    • Ghosh, A.K.1    McKee, S.P.2    Thomson, W.J.3
  • 16
    • 0026713746 scopus 로고
    • A Stereoselective Method for the Preparation of HIV-1 Protease Inhibitors Based on the Lewis Acid Mediated Reaction of Allylsilanes and N -Boc-α-amino Aldehydes
    • D'Aniello, F.; Taddei, M. A Stereoselective Method for the Preparation of HIV-1 Protease Inhibitors Based on the Lewis Acid Mediated Reaction of Allylsilanes and N -Boc-α-amino Aldehydes J. Org. Chem. 1992, 57, 5247-5250
    • (1992) J. Org. Chem. , vol.57 , pp. 5247-5250
    • D'Aniello, F.1    Taddei, M.2
  • 17
    • 0032566021 scopus 로고    scopus 로고
    • Ring-closing metathesis strategy to unsaturated γ- and δ-lactones: Synthesis of hydroxyethylene isostere for protease inhibitors
    • DOI 10.1016/S0040-4039(98)00887-9, PII S0040403998008879
    • Ghosh, A. K.; Cappiello, J.; Shin, D. Ring-closing metathesis strategy to unsaturated γ- and δ-lactones: synthesis of hydroxyethylene isostere for protease inhibitors Tetrahedron Lett. 1998, 39, 4651-4654 (Pubitemid 28267013)
    • (1998) Tetrahedron Letters , vol.39 , Issue.26 , pp. 4651-4654
    • Ghosh, A.K.1    Cappiello, J.2    Shin, D.3
  • 18
    • 0014211618 scopus 로고
    • On the size of the active site in proteases. I. Papain
    • 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
  • 19
    • 0035964269 scopus 로고    scopus 로고
    • Subsite specificity of memapsin 2 (β-secretase): Implications for inhibitor design
    • DOI 10.1021/bi015546s
    • Turner, R. T., III; Koelsch, G.; Hong, L.; Castenheira, P.; Ghosh, A.; Tang, J. Subsite Specificity of Memapsin 2 (β-Secretase): Implications for Inhibitor Design Biochemistry 2001, 40, 10001-10006 (Pubitemid 32800106)
    • (2001) Biochemistry , vol.40 , Issue.34 , pp. 10001-10006
    • Turner III, R.T.1    Koelsch, G.2    Hong, L.3    Castenheira, P.4    Ghosh, A.5    Tang, J.6
  • 21
    • 0034613320 scopus 로고    scopus 로고
    • Structure of the Protease Domain of Memapsin 2 (β-Secretase) Complexed with Inhibitor
    • Hong, L.; Koelsch, G.; Lin, X.; Wu, S.; Terzyan, S.; Ghosh, A. K.; Zhang, X. C.; Tang, J. Structure of the Protease Domain of Memapsin 2 (β-Secretase) Complexed with Inhibitor Science 2000, 290, 150-153
    • (2000) Science , vol.290 , pp. 150-153
    • Hong, L.1    Koelsch, G.2    Lin, X.3    Wu, S.4    Terzyan, S.5    Ghosh, A.K.6    Zhang, X.C.7    Tang, J.8
  • 22
    • 55549111898 scopus 로고    scopus 로고
    • A fast and accurate computational approach to protein ionization
    • Spassov, V. Z.; Yan, L. A fast and accurate computational approach to protein ionization Protein Sci. 2008, 17, 1955-1970
    • (2008) Protein Sci. , vol.17 , pp. 1955-1970
    • Spassov, V.Z.1    Yan, L.2
  • 23
    • 0032898499 scopus 로고    scopus 로고
    • Thermodynamic linkage between the binding of protons and inhibitors to HIV-1 protease
    • Trylska, J.; Antosiewicz, J.; Geller, M.; Hodge, C. N.; Klabe, R. M.; Head, M. S.; Gilson, M. K. Thermodynamic linkage between the binding of protons and inhibitors to HIV-1 protease Protein Sci. 1999, 8, 180-195 (Pubitemid 29035531)
    • (1999) Protein Science , vol.8 , Issue.1 , pp. 180-195
    • Trylska, J.1    Antosiewicz, J.2    Geller, M.3    Hodge, N.4    Klabe, R.M.5    Head, M.S.6    Gilson, M.K.7
  • 25
    • 2442606719 scopus 로고    scopus 로고
    • The Low Barrier Hydrogen Bond (LBHB) Proposal Revisited: The Case of the Asp • His Pair in Serine Proteases
    • DOI 10.1002/prot.20096
    • Schutz, C. N.; Warshel, A. The Low Barrier Hydrogen Bond (LBHB) Proposal Revisited: The Case of the Asp•••His Pair in Serine Proteases Proteins 2004, 44, 711-723 (Pubitemid 38620094)
    • (2004) Proteins: Structure, Function and Genetics , vol.55 , Issue.3 , pp. 711-723
    • Schutz, C.N.1    Warshel, A.2
  • 26
    • 0025829331 scopus 로고
    • Structure at 2.5 Å Resolution of Chemically Synthesized Human Immunodeficiency Virus Type 1 Protease Complexed with a Hydroxyethylene-Based Inhibitor
    • Jaskólski, M.; Tomaselli, A. G.; Sawyer, T. K.; Staples, D. G.; Heinrikson, R. L.; Schneider, J.; Kent, S. B. H.; Wlodawer, A. Structure at 2.5 Å Resolution of Chemically Synthesized Human Immunodeficiency Virus Type 1 Protease Complexed with a Hydroxyethylene-Based Inhibitor Biochemistry 1991, 30, 1600-1609
    • (1991) Biochemistry , vol.30 , pp. 1600-1609
    • Jaskólski, M.1    Tomaselli, A.G.2    Sawyer, T.K.3    Staples, D.G.4    Heinrikson, R.L.5    Schneider, J.6    Kent, S.B.H.7    Wlodawer, A.8
  • 27
    • 0028040716 scopus 로고
    • A low-barrier hydrogen bond in the catalytic triad of serine proteases
    • Frey, P. A.; Whitt, S. A.; Tobin, J. B. A low-barrier hydrogen bond in the catalytic triad of serine proteases Science 1994, 264, 1927-1930 (Pubitemid 24245638)
    • (1994) Science , vol.264 , Issue.5167 , pp. 1927-1930
    • Frey, P.A.1    Whitt, S.A.2    Tobin, J.B.3
  • 28
    • 33846189019 scopus 로고    scopus 로고
    • δ1 Hydrogen Bond in Unbound HIV Protease: A QM/MM Characterization
    • δ1 Hydrogen Bond in Unbound HIV Protease: A QM/MM Characterization J. Chem. Theory Comput. 2006, 2, 1675-1684
    • (2006) J. Chem. Theory Comput. , vol.2 , pp. 1675-1684
    • Porter, M.A.1    Molina, P.A.2
  • 29
    • 33644557736 scopus 로고    scopus 로고
    • Binding of Phosphinate and Phosphonate Inhibitors to Aspartic Proteases: A First-Principles Study
    • Vidossich., P.; Carloni, P. Binding of Phosphinate and Phosphonate Inhibitors to Aspartic Proteases: A First-Principles Study J. Phys. Chem. B 2006, 110, 1437-1442
    • (2006) J. Phys. Chem. B , vol.110 , pp. 1437-1442
    • Vidossich, P.1    Carloni, P.2


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