메뉴 건너뛰기




Volumn 49, Issue 23, 2006, Pages 6768-6778

In silico-guided target identification of a scaffold-focused library: 1,3,5-Triazepan-2,6-diones as novel phospholipase A2 inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

1,3,5 TRIAZEPAN 2,6 ONE DERIVATIVE; PHOSPHOLIPASE A2; PHOSPHOLIPASE A2 INHIBITOR; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

EID: 33750712502     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0606589     Document Type: Article
Times cited : (72)

References (61)
  • 6
    • 0033025637 scopus 로고    scopus 로고
    • Chance favors the prepared mind-from serendipity to rational drug design
    • Kubinyi, H. Chance favors the prepared mind-from serendipity to rational drug design. J. Recept. Signal Transduct. Res. 1999, 19, 15-39.
    • (1999) J. Recept. Signal Transduct. Res. , vol.19 , pp. 15-39
    • Kubinyi, H.1
  • 7
    • 1842431386 scopus 로고    scopus 로고
    • Protein tyrosine phosphatases: Strategies for distinguishing proteins in a family containing multiple drug targets and anti-targets
    • Hoffman, B. T.; Nelson, M. R.; Burdick, K.; Baxter, S. M. Protein tyrosine phosphatases: strategies for distinguishing proteins in a family containing multiple drug targets and anti-targets. Curr. Pharm. Des. 2004, 10, 1161-1181.
    • (2004) Curr. Pharm. Des. , vol.10 , pp. 1161-1181
    • Hoffman, B.T.1    Nelson, M.R.2    Burdick, K.3    Baxter, S.M.4
  • 8
    • 0034256065 scopus 로고    scopus 로고
    • The in silico world of virtual libraries
    • Leach, A. R.; Hann, M. M. The in silico world of virtual libraries. Drug Discovery Today 2000, 5, 326-336.
    • (2000) Drug Discovery Today , vol.5 , pp. 326-336
    • Leach, A.R.1    Hann, M.M.2
  • 9
    • 0642347897 scopus 로고    scopus 로고
    • Yeast genomics and proteomics in drug discovery and target validation
    • Parsons, A. B.; Geyer, R.; Hughes, T. R.; Boone, C. Yeast genomics and proteomics in drug discovery and target validation. Prog. Cell Cycle Res. 2003, 5, 159-166.
    • (2003) Prog. Cell Cycle Res. , vol.5 , pp. 159-166
    • Parsons, A.B.1    Geyer, R.2    Hughes, T.R.3    Boone, C.4
  • 12
    • 0032201120 scopus 로고    scopus 로고
    • Bioactive diversity and screening library selection via affinity fingerprinting
    • Dixon, S. L.; Villar, H. O. Bioactive diversity and screening library selection via affinity fingerprinting. J. Chem. Inf. Comput. Sci. 1998, 38, 1192-1203.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 1192-1203
    • Dixon, S.L.1    Villar, H.O.2
  • 13
    • 0001559521 scopus 로고    scopus 로고
    • Flexsim-X: A method for the detection of molecules with similar biological activity
    • Lessei, U. F.; Briem, H. Flexsim-X: a method for the detection of molecules with similar biological activity. J. Chem. Inf. Comput. Sci. 2000, 40, 246-253.
    • (2000) J. Chem. Inf. Comput. Sci. , vol.40 , pp. 246-253
    • Lessei, U.F.1    Briem, H.2
  • 14
    • 26944463088 scopus 로고    scopus 로고
    • Virtual screen for ligands of orphan G protein-coupled receptors
    • Bock, J. R.; Gough, D. A. Virtual screen for ligands of orphan G protein-coupled receptors. J. Chem. Inf. Model. 2005, 45, 1402-1414.
    • (2005) J. Chem. Inf. Model. , vol.45 , pp. 1402-1414
    • Bock, J.R.1    Gough, D.A.2
  • 15
    • 33646251585 scopus 로고    scopus 로고
    • Chemometric analysis of ligand receptor complementarity: Identifying complementary ligands based on receptor information (CoLiBRI)
    • Oloff, S.; Zhang, S.; Sukumar, N.; Breneman, C.; Tropsha, A. Chemometric Analysis of Ligand Receptor Complementarity: Identifying Complementary Ligands Based on Receptor Information (CoLiBRI). J. Chem. Inf. Model. 2006, 46, 844-851.
    • (2006) J. Chem. Inf. Model. , vol.46 , pp. 844-851
    • Oloff, S.1    Zhang, S.2    Sukumar, N.3    Breneman, C.4    Tropsha, A.5
  • 17
    • 10044268555 scopus 로고    scopus 로고
    • Comparing ligand interactions with multiple receptors via serial docking
    • Fernandes, M. X.; Kairys, V.; Gilson, M. K. Comparing ligand interactions with multiple receptors via serial docking. J. Chem. Inf. Comput. Sci. 2004, 44, 1961-1970.
    • (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 1961-1970
    • Fernandes, M.X.1    Kairys, V.2    Gilson, M.K.3
  • 18
    • 0035217619 scopus 로고    scopus 로고
    • Prediction of potential toxicity and side effect protein targets of a small molecule by a ligand-protein inverse docking approach
    • Chen, Y. Z.; Ung, C. Y. Prediction of potential toxicity and side effect protein targets of a small molecule by a ligand-protein inverse docking approach. J. Mol. Graph. Model. 2001, 20, 199-218.
    • (2001) J. Mol. Graph. Model. , vol.20 , pp. 199-218
    • Chen, Y.Z.1    Ung, C.Y.2
  • 19
    • 0035342428 scopus 로고    scopus 로고
    • Ligand-protein inverse docking and its potential use in the computer search of protein targets of a small molecule
    • Chen, Y. Z.; Zhi, D. G. Ligand-protein inverse docking and its potential use in the computer search of protein targets of a small molecule. Proteins 2001, 43, 217-226.
    • (2001) Proteins , vol.43 , pp. 217-226
    • Chen, Y.Z.1    Zhi, D.G.2
  • 20
    • 1542286205 scopus 로고    scopus 로고
    • Recovering the true targets of specific ligands by virtual screening of the protein data bank
    • Paul, N.; Kellenberger, E.; Bret, G.; Muller, P.; Rognan, D. Recovering the true targets of specific ligands by virtual screening of the protein data bank. Proteins 2004, 54, 671-680.
    • (2004) Proteins , vol.54 , pp. 671-680
    • Paul, N.1    Kellenberger, E.2    Bret, G.3    Muller, P.4    Rognan, D.5
  • 22
    • 0031370977 scopus 로고    scopus 로고
    • LIGSITE: Automatic and efficient detection of potential small molecule-binding sites in proteins
    • 389
    • Hendlich, M.; Rippmann, F.; Barnickel, G. LIGSITE: automatic and efficient detection of potential small molecule-binding sites in proteins. J. Mol. Graph. Model. 1997, 15, 359-363, 389.
    • (1997) J. Mol. Graph. Model. , vol.15 , pp. 359-363
    • Hendlich, M.1    Rippmann, F.2    Barnickel, G.3
  • 23
    • 21044444449 scopus 로고    scopus 로고
    • Pocketome via comprehensive identification and classification of ligand binding envelopes
    • An, J.; Totrov, M.; Abagyan, R. Pocketome via comprehensive identification and classification of ligand binding envelopes. Mol. Cell. Proteomics 2005, 4, 752-761.
    • (2005) Mol. Cell. Proteomics , vol.4 , pp. 752-761
    • An, J.1    Totrov, M.2    Abagyan, R.3
  • 25
    • 33646254603 scopus 로고    scopus 로고
    • A searchable database for comparing protein-ligand binding sites for the analysis of structure-function relationships
    • Gold, N. D.; Jackson, R. M. A searchable database for comparing protein-ligand binding sites for the analysis of structure-function relationships. J. Chem. Inf. Model. 2006, 46, 736-742.
    • (2006) J. Chem. Inf. Model. , vol.46 , pp. 736-742
    • Gold, N.D.1    Jackson, R.M.2
  • 27
    • 0036406643 scopus 로고    scopus 로고
    • A new method to detect related function among proteins independent of sequence and fold homology
    • Schmitt, S.; Kuhn, D.; Klebe, G. A new method to detect related function among proteins independent of sequence and fold homology. J. Mol. Biol. 2002, 323, 387-406.
    • (2002) J. Mol. Biol. , vol.323 , pp. 387-406
    • Schmitt, S.1    Kuhn, D.2    Klebe, G.3
  • 28
    • 33644876699 scopus 로고    scopus 로고
    • SitesBase: A database for structure-based protein-ligand binding site comparisons
    • Gold, N. D.; Jackson, R. M. SitesBase: a database for structure-based protein-ligand binding site comparisons. Nucleic Acids Res. 2006, 34, D231-234.
    • (2006) Nucleic Acids Res. , vol.34
    • Gold, N.D.1    Jackson, R.M.2
  • 30
    • 4544367743 scopus 로고    scopus 로고
    • Comparative evaluation of eight docking tools for docking and virtual screening accuracy
    • Kellenberger, E.; Rodrigo, J.; Muller, P.; Rognan, D. Comparative evaluation of eight docking tools for docking and virtual screening accuracy. Proteins 2004, 57, 225-242.
    • (2004) Proteins , vol.57 , pp. 225-242
    • Kellenberger, E.1    Rodrigo, J.2    Muller, P.3    Rognan, D.4
  • 31
    • 33751010274 scopus 로고    scopus 로고
    • The sc-PDB database is available at
    • The sc-PDB database is available at http://bioinfo-pharma.u-strasbg.fr/ sc-PDB.
  • 33
    • 0000845126 scopus 로고
    • We use a nomenclature based on the amino acid three letter code to describe 1,3,5-triazepan-2,6-diones. Accordingly, heterocycles prepared from the dipeptide sequence Boc-Xaa-Xbb-OH will be denoted cyclo(Xaa-gXbb-CO). g = gem, refers to the 2-alkyl gem-diamino-derivative of the corresponding amino acid according to the nomenclature proposed by Goodman et al. (Acc. Chem. Res. 1993, 26, 266-273).
    • (1993) Acc. Chem. Res. , vol.26 , pp. 266-273
    • Goodman1
  • 35
    • 0000440533 scopus 로고
    • A new acid-labile anchor group for the solid-phase synthesis of C-terminal peptide amides by the Fmoc method
    • Sieber, P. A new acid-labile anchor group for the solid-phase synthesis of C-terminal peptide amides by the Fmoc method. Tetrahedron Lett. 1987, 28, 2107-2110.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 2107-2110
    • Sieber, P.1
  • 36
    • 0037047328 scopus 로고    scopus 로고
    • Crystal structure of human group X secreted phospholipase A2. Electrostatically neutral interfacial surface targets zwitterionic membranes
    • Pan, Y. H.; Yu, B. Z.; Singer, A. G.; Ghomashchi, F.; Lambeau, G.; Gelb, M. H.; Jain, M. K.; Bahnson, B. J. Crystal structure of human group X secreted phospholipase A2. Electrostatically neutral interfacial surface targets zwitterionic membranes. J. Biol. Chem. 2002, 277, 29086-29093.
    • (2002) J. Biol. Chem. , vol.277 , pp. 29086-29093
    • Pan, Y.H.1    Yu, B.Z.2    Singer, A.G.3    Ghomashchi, F.4    Lambeau, G.5    Gelb, M.H.6    Jain, M.K.7    Bahnson, B.J.8
  • 37
    • 0025788172 scopus 로고
    • Interfacial catalysis by phospholipase A2: Dissociation constants for calcium, substrate, products, and competitive inhibitors
    • Jain, M. K.; Yu, B. Z.; Rogers, J.: Ranadive, G. N.; Berg, O. G. Interfacial catalysis by phospholipase A2: dissociation constants for calcium, substrate, products, and competitive inhibitors. Biochemistry 1991, 30, 7306-7317.
    • (1991) Biochemistry , vol.30 , pp. 7306-7317
    • Jain, M.K.1    Yu, B.Z.2    Rogers, J.3    Ranadive, G.N.4    Berg, O.G.5
  • 38
    • 0015952137 scopus 로고
    • Histidine at the active site of phospholipase A2
    • Volwerk, J. J.; Pieterson, W. A.; de Haas, G. H. Histidine at the active site of phospholipase A2. Biochemistry 1974, 13, 1446-1454.
    • (1974) Biochemistry , vol.13 , pp. 1446-1454
    • Volwerk, J.J.1    Pieterson, W.A.2    De Haas, G.H.3
  • 39
    • 0028832557 scopus 로고
    • Multifunctional activity of the extracellular domain of the M-type (180 kDa) membrane receptor for secretory phospholipases A2
    • Ancian, P.; Lambeau, G.; Lazdunski, M. Multifunctional activity of the extracellular domain of the M-type (180 kDa) membrane receptor for secretory phospholipases A2. Biochemistry 1995, 34, 13146-13151.
    • (1995) Biochemistry , vol.34 , pp. 13146-13151
    • Ancian, P.1    Lambeau, G.2    Lazdunski, M.3
  • 41
    • 1542613782 scopus 로고    scopus 로고
    • Inhibition of the complete set of mammalian secreted phospholipases A(2) by indole analogues: A structure-guided study
    • Smart, B. P.; Pan, Y. H.; Weeks, A. K.; Bollinger, J. G.; Bahnson, B. J. et al. Inhibition of the complete set of mammalian secreted phospholipases A(2) by indole analogues: a structure-guided study. Bioorg. Med. Chem. 2004, 12, 1737-1749.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 1737-1749
    • Smart, B.P.1    Pan, Y.H.2    Weeks, A.K.3    Bollinger, J.G.4    Bahnson, B.J.5
  • 46
    • 0346962971 scopus 로고    scopus 로고
    • Structural interaction fingerprint (SIFt): A novel method for analyzing three-dimensional protein-ligand binding interactions
    • Deng, Z.; Chuaqui, C.; Singh, J. Structural interaction fingerprint (SIFt): a novel method for analyzing three-dimensional protein-ligand binding interactions. J. Med. Chem. 2004, 47, 337-344.
    • (2004) J. Med. Chem. , vol.47 , pp. 337-344
    • Deng, Z.1    Chuaqui, C.2    Singh, J.3
  • 47
    • 1942453243 scopus 로고    scopus 로고
    • Ligand efficiency: A useful metric for lead selection
    • Hopkins, A. L.; Groom, C. R.; Alex, A. Ligand efficiency: a useful metric for lead selection. Drug Discovery Today 2004, 9, 430-431.
    • (2004) Drug Discovery Today , vol.9 , pp. 430-431
    • Hopkins, A.L.1    Groom, C.R.2    Alex, A.3
  • 49
  • 50
    • 0043123204 scopus 로고    scopus 로고
    • Phospholipase A2 expression in tumours: A target for therapeutic intervention?
    • Laye, J. P.; Gill, J. H. Phospholipase A2 expression in tumours: a target for therapeutic intervention? Drug Discovery Today 2003, 8, 710-716.
    • (2003) Drug Discovery Today , vol.8 , pp. 710-716
    • Laye, J.P.1    Gill, J.H.2
  • 51
    • 27944472180 scopus 로고    scopus 로고
    • Inhibitors of secretory phospholipase A2 group IIA
    • Reid, R. C. Inhibitors of secretory phospholipase A2 group IIA. Curr. Med. Chem. 2005, 12, 3011-3026.
    • (2005) Curr. Med. Chem. , vol.12 , pp. 3011-3026
    • Reid, R.C.1
  • 52
    • 23444442916 scopus 로고    scopus 로고
    • Secretory phospholipase A2 enzymes in atherogenesis
    • Webb, N. R. Secretory phospholipase A2 enzymes in atherogenesis. Curr. Opin. Lipidot. 2005, 16, 341-344.
    • (2005) Curr. Opin. Lipidot. , vol.16 , pp. 341-344
    • Webb, N.R.1
  • 53
    • 27644566534 scopus 로고    scopus 로고
    • Secretory phospholipases A2 in inflammatory and allergic diseases: Not just enzymes
    • Triggiani, M.; Granata, F.; Giannattasio, G.; Marone, G. Secretory phospholipases A2 in inflammatory and allergic diseases: not just enzymes. J. Allergy Clin. Immunol. 2005, 116, 1000-1006.
    • (2005) J. Allergy Clin. Immunol. , vol.116 , pp. 1000-1006
    • Triggiani, M.1    Granata, F.2    Giannattasio, G.3    Marone, G.4
  • 54
    • 16244389350 scopus 로고    scopus 로고
    • Phospholipase A2 inhibitors as potential anti-inflammatory agents
    • Meyer, M. C.; Rastogi, P.; Beckett, C. S.; McHowat, J. Phospholipase A2 inhibitors as potential anti-inflammatory agents. Curr. Pharm. Des. 2005, 11, 1301-1312.
    • (2005) Curr. Pharm. Des. , vol.11 , pp. 1301-1312
    • Meyer, M.C.1    Rastogi, P.2    Beckett, C.S.3    McHowat, J.4
  • 56
    • 33646748549 scopus 로고    scopus 로고
    • The first potent inhibitor of Mammalian group X secreted phospholipase A2: Elucidation of sites for enhanced binding
    • Smart, B. P.; Oslund, R. C.; Walsh, L. A.; Gelb, M. H. The first potent inhibitor of Mammalian group X secreted phospholipase A2: elucidation of sites for enhanced binding. J. Med. Chem. 2006, 49, 2858-2860.
    • (2006) J. Med. Chem. , vol.49 , pp. 2858-2860
    • Smart, B.P.1    Oslund, R.C.2    Walsh, L.A.3    Gelb, M.H.4
  • 57
    • 16644387827 scopus 로고    scopus 로고
    • Hot topics in phospholipase A2 field
    • Murakami, M. Hot topics in phospholipase A2 field. Biol. Pharm. Bull. 2004, 27, 1179-1182.
    • (2004) Biol. Pharm. Bull. , vol.27 , pp. 1179-1182
    • Murakami, M.1
  • 58
    • 7044237564 scopus 로고    scopus 로고
    • Secretory phospholipase A2
    • Murakami, M.; Kudo, I. Secretory phospholipase A2. Biol. Pharm. Bull. 2004, 27, 1158-1164.
    • (2004) Biol. Pharm. Bull. , vol.27 , pp. 1158-1164
    • Murakami, M.1    Kudo, I.2
  • 59
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Wilett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
    • (1997) J. Mol. Biol. , vol.267 , pp. 727-748
    • Jones, G.1    Wilett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 60
    • 9944237693 scopus 로고    scopus 로고
    • Tripos Assoc., Inc.: St. Louis, MO
    • SYBYL 6.91, Tripos Assoc., Inc.: St. Louis, MO.
    • SYBYL 6.91
  • 61
    • 0033963089 scopus 로고    scopus 로고
    • The ENZYME database in 2000
    • Bairoch, A. The ENZYME database in 2000. Nucleic Acids Res 2000, 28, 304-305.
    • (2000) Nucleic Acids Res , vol.28 , pp. 304-305
    • Bairoch, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.