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Volumn 50, Issue 8, 2007, Pages 1865-1875

NMR screening applied to the fragment-based generation of inhibitors of creatine kinase exploiting a new interaction proximate to the ATP binding site

Author keywords

[No Author keywords available]

Indexed keywords

2 FUROIC ACID; ADENOSINE TRIPHOSPHATE; BENZENE DERIVATIVE; CREATINE KINASE; CREATINE KINASE INHIBITOR; ENZYME INHIBITOR; LIGAND; NUCLEOTIDE; UNCLASSIFIED DRUG;

EID: 34247239896     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061460r     Document Type: Article
Times cited : (18)

References (56)
  • 1
    • 1642294294 scopus 로고    scopus 로고
    • Organic chemistry in drug discovery
    • MacCoss, M.; Baillie, T. A. Organic chemistry in drug discovery. Science 2004, 303, 1810-1813.
    • (2004) Science , vol.303 , pp. 1810-1813
    • MacCoss, M.1    Baillie, T.A.2
  • 5
    • 0029836953 scopus 로고    scopus 로고
    • Discovering high-affinity ligands for proteins: SAR by NMR
    • Shuker, S. B.; Hajduk, P. J.; Meadows, R. P.; Fesik, S. W. Discovering high-affinity ligands for proteins: SAR by NMR. Science 1996, 274, 1531-1534.
    • (1996) Science , vol.274 , pp. 1531-1534
    • Shuker, S.B.1    Hajduk, P.J.2    Meadows, R.P.3    Fesik, S.W.4
  • 6
    • 0035438391 scopus 로고    scopus 로고
    • Is there a difference between leads and drugs? A historical perspective
    • Oprea, T. I.; Davis, A. M.; Teague, S. J.; Leeson, P. D. Is there a difference between leads and drugs? A historical perspective. J. Chem. Inf. Comput. Sci. 2001, 41, 1308-1315.
    • (2001) J. Chem. Inf. Comput. Sci , vol.41 , pp. 1308-1315
    • Oprea, T.I.1    Davis, A.M.2    Teague, S.J.3    Leeson, P.D.4
  • 8
    • 1642288258 scopus 로고    scopus 로고
    • Novel inhibitors of DNA gyrase: 3D structure based biased needle screening, hit validation by biophysical methods, and 3D guided optimization. A promising alternative to random screening
    • Boehm, H. J.; Boehringer, M.; Bur, D.; Gmuender, H.; Huber, W.; Klaus, W.; Kostrewa, D.; Kuehne, H.; Luebbers, T.; Meunier-Keller, N.; Mueller, F. Novel inhibitors of DNA gyrase: 3D structure based biased needle screening, hit validation by biophysical methods, and 3D guided optimization. A promising alternative to random screening. J. Med. Chem. 2000, 43, 2664-2674.
    • (2000) J. Med. Chem , vol.43 , pp. 2664-2674
    • Boehm, H.J.1    Boehringer, M.2    Bur, D.3    Gmuender, H.4    Huber, W.5    Klaus, W.6    Kostrewa, D.7    Kuehne, H.8    Luebbers, T.9    Meunier-Keller, N.10    Mueller, F.11
  • 13
    • 0348041598 scopus 로고    scopus 로고
    • Exploring the active site of human factor Xa protein by NMR screening of small molecule probes
    • Fielding, L.; Fletcher, D.; Rutherford, S.; Kaur, J.; Mestres, J. Exploring the active site of human factor Xa protein by NMR screening of small molecule probes. Org. Biomol. Chem. 2003, 1, 4235-4241.
    • (2003) Org. Biomol. Chem , vol.1 , pp. 4235-4241
    • Fielding, L.1    Fletcher, D.2    Rutherford, S.3    Kaur, J.4    Mestres, J.5
  • 14
    • 4344616982 scopus 로고    scopus 로고
    • Targeting apoptosis via chemical design: Inhibition of bid-induced cell death by small organic molecules
    • Becattini, B.; Sareth, S.; Zhai, D.; Crowell, K. J.; Leone, M.; Reed, J. C.; Pellecchia, M. Targeting apoptosis via chemical design: inhibition of bid-induced cell death by small organic molecules. Chem. Biol. 2004, 11, 1107-1117.
    • (2004) Chem. Biol , vol.11 , pp. 1107-1117
    • Becattini, B.1    Sareth, S.2    Zhai, D.3    Crowell, K.J.4    Leone, M.5    Reed, J.C.6    Pellecchia, M.7
  • 15
    • 0033213957 scopus 로고    scopus 로고
    • Fejzo, J.; Lepre, C. A.; Peng, J. W.; Bemis, G. W.; Ajay;, Murcko, M. A.; Moore, J. M. The SHAPES strategy: an NMR-based approach for lead generation in drug discovery. Chem. Biol. 1999, 6, 755-769.
    • Fejzo, J.; Lepre, C. A.; Peng, J. W.; Bemis, G. W.; Ajay;, Murcko, M. A.; Moore, J. M. The SHAPES strategy: an NMR-based approach for lead generation in drug discovery. Chem. Biol. 1999, 6, 755-769.
  • 17
    • 0034618541 scopus 로고    scopus 로고
    • Privileged molecules for protein binding identified from NMR-based screening
    • Hajduk, P. J.; Bures, M.; Praestgaard, J.; Fesik, S. W. Privileged molecules for protein binding identified from NMR-based screening. J. Med. Chem. 2000, 43, 3443-3447.
    • (2000) J. Med. Chem , vol.43 , pp. 3443-3447
    • Hajduk, P.J.1    Bures, M.2    Praestgaard, J.3    Fesik, S.W.4
  • 18
    • 0035252844 scopus 로고    scopus 로고
    • Library design for NMR-based screening
    • Lepre, C. A. Library design for NMR-based screening. Drug Discovery Today 2001, 6, 133-140.
    • (2001) Drug Discovery Today , vol.6 , pp. 133-140
    • Lepre, C.A.1
  • 19
    • 0029894013 scopus 로고    scopus 로고
    • The properties of known drugs. 1. Molecular frameworks
    • Bemis, G. W.; Murcko, M. A. The properties of known drugs. 1. Molecular frameworks. J. Med. Chem. 1996, 39, 2887-2893.
    • (1996) J. Med. Chem , vol.39 , pp. 2887-2893
    • Bemis, G.W.1    Murcko, M.A.2
  • 20
    • 0033576605 scopus 로고    scopus 로고
    • Properties of known drugs. 2. Side chains
    • Bemis, G. W.; Murcko, M. A. Properties of known drugs. 2. Side chains. J. Med. Chem. 1999, 42, 5095-5099.
    • (1999) J. Med. Chem , vol.42 , pp. 5095-5099
    • Bemis, G.W.1    Murcko, M.A.2
  • 21
    • 15944400625 scopus 로고    scopus 로고
    • Relating structure to mechanism in creatine kinase
    • McLeish, M. J.; Kenyon, G. L. Relating structure to mechanism in creatine kinase. Crit. Rev. Biochem. Mol. Biol. 2005, 40, 1-20.
    • (2005) Crit. Rev. Biochem. Mol. Biol , vol.40 , pp. 1-20
    • McLeish, M.J.1    Kenyon, G.L.2
  • 22
    • 0026585611 scopus 로고
    • Intracellular compartmentation, structure and function of creatine kinase isoenzymes in tissues with high and fluctuating energy demands: The 'phosphocreatine circuit' for cellular energy homeostasis
    • Wallimann, T.; Wyss, M.; Brdiczka, D.; Nicolay, K.; Eppenberger, H. M. Intracellular compartmentation, structure and function of creatine kinase isoenzymes in tissues with high and fluctuating energy demands: the 'phosphocreatine circuit' for cellular energy homeostasis. Biochem. J. 1992, 281 (Part 1), 21-40.
    • (1992) Biochem. J , vol.281 , Issue.PART 1 , pp. 21-40
    • Wallimann, T.1    Wyss, M.2    Brdiczka, D.3    Nicolay, K.4    Eppenberger, H.M.5
  • 23
    • 0033935979 scopus 로고    scopus 로고
    • Creatine and creatinine metabolism
    • Wyss, M.; Kaddurah-Daouk, R. Creatine and creatinine metabolism. Physiol. Rev. 2000, 80, 1107-1213.
    • (2000) Physiol. Rev , vol.80 , pp. 1107-1213
    • Wyss, M.1    Kaddurah-Daouk, R.2
  • 24
    • 0037800382 scopus 로고    scopus 로고
    • Screening of substrate analogs as potential enzyme inhibitors for the arginine kinase of Trypanosoma cruzi
    • Pereira, C. A.; Alonso, G. D.; Ivaldi, S.; Bouvier, L. A.; Torres, H. N.; Flawia, M. M. Screening of substrate analogs as potential enzyme inhibitors for the arginine kinase of Trypanosoma cruzi. J. Eukaryotic Microbiol. 2003, 50, 132-134.
    • (2003) J. Eukaryotic Microbiol , vol.50 , pp. 132-134
    • Pereira, C.A.1    Alonso, G.D.2    Ivaldi, S.3    Bouvier, L.A.4    Torres, H.N.5    Flawia, M.M.6
  • 25
    • 0030695481 scopus 로고    scopus 로고
    • N-dibenzylphospho-N′-3-(2,6-dichlorophenyl)propyl-guanidine is a bisubstrate-analog for creatine kinase
    • Min, K. L.; Steghens, J. P.; Henry, R.; Doutheau, A.; Collombel, C. N-dibenzylphospho-N′-3-(2,6-dichlorophenyl)propyl-guanidine is a bisubstrate-analog for creatine kinase. Biochim. Biophys. Acta 1997, 1342, 83-89.
    • (1997) Biochim. Biophys. Acta , vol.1342 , pp. 83-89
    • Min, K.L.1    Steghens, J.P.2    Henry, R.3    Doutheau, A.4    Collombel, C.5
  • 26
    • 79960698472 scopus 로고
    • Water suppression that works - Excitation sculpting using arbitrary wave-forms and pulsed-field gradients
    • Hwang, T. L.; Shaka, A. J. Water suppression that works - Excitation sculpting using arbitrary wave-forms and pulsed-field gradients. J. Magn. Reson., A 1995, 112, 275-279.
    • (1995) J. Magn. Reson., A , vol.112 , pp. 275-279
    • Hwang, T.L.1    Shaka, A.J.2
  • 27
    • 0035692794 scopus 로고    scopus 로고
    • WaterLOGSY as a method for primary NMR screening: Practical aspects and range of applicability
    • Dalvit, C.; Fogliatto, G.; Stewart, A.; Veronesi, M.; Stockman, B. WaterLOGSY as a method for primary NMR screening: practical aspects and range of applicability. J. Biomol. NMR 2001, 21, 349-359.
    • (2001) J. Biomol. NMR , vol.21 , pp. 349-359
    • Dalvit, C.1    Fogliatto, G.2    Stewart, A.3    Veronesi, M.4    Stockman, B.5
  • 28
    • 20444446596 scopus 로고    scopus 로고
    • Determination of protein-ligand binding affinity by NMR: Observations from serum albumin model systems
    • Fielding, L.; Rutherford, S.; Fletcher, D. Determination of protein-ligand binding affinity by NMR: observations from serum albumin model systems. Magn. Reson. Chem. 2005, 43, 463-470.
    • (2005) Magn. Reson. Chem , vol.43 , pp. 463-470
    • Fielding, L.1    Rutherford, S.2    Fletcher, D.3
  • 29
    • 0019407381 scopus 로고
    • On the attribution and additivity of binding energies
    • Jencks, W. P. On the attribution and additivity of binding energies. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 4046-4050.
    • (1981) Proc. Natl. Acad. Sci. U.S.A , vol.78 , pp. 4046-4050
    • Jencks, W.P.1
  • 30
    • 0035025191 scopus 로고    scopus 로고
    • DOCK 4.0: Search strategies for automated molecular docking of flexible molecule databases
    • Ewing, T. J.; Makino, S.; Skillman, A. G.; Kuntz, I. D. DOCK 4.0: search strategies for automated molecular docking of flexible molecule databases. J. Comput.-Aided Mol. Des. 2001, 15, 411-428.
    • (2001) J. Comput.-Aided Mol. Des , vol.15 , pp. 411-428
    • Ewing, T.J.1    Makino, S.2    Skillman, A.G.3    Kuntz, I.D.4
  • 31
    • 0031848225 scopus 로고    scopus 로고
    • Structural changes of creatine kinase upon substrate binding
    • Forstner, M.; Kriechbaum, M.; Laggner, P.; Wallimann, T. Structural changes of creatine kinase upon substrate binding. Biophys. J. 1998, 75, 1016-1023.
    • (1998) Biophys. J , vol.75 , pp. 1016-1023
    • Forstner, M.1    Kriechbaum, M.2    Laggner, P.3    Wallimann, T.4
  • 32
    • 0037180313 scopus 로고    scopus 로고
    • The 2.1 A structure of Torpedo californica creatine kinase complexed with the ADP-Mg(2+)-NO(3)(-)-creatine transition-state analogue complex
    • Lahiri, S. D.; Wang, P. F.; Babbitt, P. C.; McLeish, M. J.; Kenyon, G. L.; Allen, K. N. The 2.1 A structure of Torpedo californica creatine kinase complexed with the ADP-Mg(2+)-NO(3)(-)-creatine transition-state analogue complex. Biochemistry 2002, 41, 13861-13867.
    • (2002) Biochemistry , vol.41 , pp. 13861-13867
    • Lahiri, S.D.1    Wang, P.F.2    Babbitt, P.C.3    McLeish, M.J.4    Kenyon, G.L.5    Allen, K.N.6
  • 33
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 2001, 46, 3-26.
    • (2001) Adv. Drug Delivery Rev , vol.46 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 34
    • 0030880683 scopus 로고    scopus 로고
    • Convenient preparations of t-butyl esters and ethers from t-butanol
    • Wright, S. W.; Hageman, D. L.; Wright, A. S.; McClure, L. D. Convenient preparations of t-butyl esters and ethers from t-butanol. Tetrahedron Lett. 1997, 38, 7345-7348.
    • (1997) Tetrahedron Lett , vol.38 , pp. 7345-7348
    • Wright, S.W.1    Hageman, D.L.2    Wright, A.S.3    McClure, L.D.4
  • 36
    • 33646731783 scopus 로고    scopus 로고
    • Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group
    • Jung, J. H.; Rim, J. A.; Han, W. S.; Lee, S. J.; Lee, Y. J.; Cho, E. J.; Kim, J. S.; Ji, Q.; Shimizu, T. Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group. Org. Biomol. Chem. 2006, 4, 2033-2038.
    • (2006) Org. Biomol. Chem , vol.4 , pp. 2033-2038
    • Jung, J.H.1    Rim, J.A.2    Han, W.S.3    Lee, S.J.4    Lee, Y.J.5    Cho, E.J.6    Kim, J.S.7    Ji, Q.8    Shimizu, T.9
  • 37
    • 0017396929 scopus 로고    scopus 로고
    • Byran, D. B.; Hall, R. F.; Holden, K. G.; Huffman, W. F.; Gleason, J. G. Nuclear analogues of beta-lactam antibiotics. 2 The total synthesis of 8-oxo-4-thia-z-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids. J. Am. Chem. Soc. 1977, 99, 2353-2355.
    • Byran, D. B.; Hall, R. F.; Holden, K. G.; Huffman, W. F.; Gleason, J. G. Nuclear analogues of beta-lactam antibiotics. 2 The total synthesis of 8-oxo-4-thia-z-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids. J. Am. Chem. Soc. 1977, 99, 2353-2355.
  • 39
    • 0034622590 scopus 로고    scopus 로고
    • Magnesium-adenosine diphosphate binding sites in wild-type creatine kinase and in mutants: Role of aromatic residues probed by Raman and infrared spectroscopies
    • Hagemann, H.; Marcillat, O.; Buchet, R.; Vial, C. Magnesium-adenosine diphosphate binding sites in wild-type creatine kinase and in mutants: Role of aromatic residues probed by Raman and infrared spectroscopies. Biochemistry 2000, 39, 9251-9256.
    • (2000) Biochemistry , vol.39 , pp. 9251-9256
    • Hagemann, H.1    Marcillat, O.2    Buchet, R.3    Vial, C.4
  • 43
    • 0034923647 scopus 로고    scopus 로고
    • Nuclear magnetic resonance-based approaches for lead generation in drug discovery
    • Peng, J. W.; Lepre, C. A.; Fejzo, J.; Abdul-Manan, N.; Moore, J. M. Nuclear magnetic resonance-based approaches for lead generation in drug discovery. Methods Enzymol. 2001, 338, 202-230.
    • (2001) Methods Enzymol , vol.338 , pp. 202-230
    • Peng, J.W.1    Lepre, C.A.2    Fejzo, J.3    Abdul-Manan, N.4    Moore, J.M.5
  • 44
    • 0029585123 scopus 로고
    • Atom/fragment contribution method for estimating octanol-water partition coefficients
    • Meylan, W. M.; Howard, P. H. Atom/fragment contribution method for estimating octanol-water partition coefficients. J. Pharm. Sci. 1995, 84, 83-92.
    • (1995) J. Pharm. Sci , vol.84 , pp. 83-92
    • Meylan, W.M.1    Howard, P.H.2
  • 45
    • 0033789206 scopus 로고    scopus 로고
    • Identification of compounds with binding affinity to proteins via magnetization transfer from bulk water
    • Dalvit, C.; Pevarello, P.; Tato, M.; Veronesi, M.; Vulpetti, A.; Sundstrom, M. Identification of compounds with binding affinity to proteins via magnetization transfer from bulk water. J. Biomol. NMR 2000, 18, 65-68.
    • (2000) J. Biomol. NMR , vol.18 , pp. 65-68
    • Dalvit, C.1    Pevarello, P.2    Tato, M.3    Veronesi, M.4    Vulpetti, A.5    Sundstrom, M.6
  • 46
    • 0033553844 scopus 로고    scopus 로고
    • Characterization of ligand binding by saturation transfer difference NMR spectroscopy
    • Mayer, M.; Meyer, B. Characterization of ligand binding by saturation transfer difference NMR spectroscopy. Angew. Chem., Int. Ed. 1999, 38, 1784-1788.
    • (1999) Angew. Chem., Int. Ed , vol.38 , pp. 1784-1788
    • Mayer, M.1    Meyer, B.2
  • 47
    • 0034823890 scopus 로고    scopus 로고
    • Group epitope mapping by saturation transfer difference NMR to identify segments of a ligand in direct contact with a protein receptor
    • Mayer, M.; Meyer, B. Group epitope mapping by saturation transfer difference NMR to identify segments of a ligand in direct contact with a protein receptor. J. Am. Chem. Soc. 2001, 123, 6108-6117.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 6108-6117
    • Mayer, M.1    Meyer, B.2
  • 48
    • 33746885488 scopus 로고    scopus 로고
    • Probing hot spots at protein-ligand binding sites: A fragment-based approach using biophysical methods
    • Ciulli, A.; Williams, G.; Smith, A. G.; Blundell, T. L.; Abell, C. Probing hot spots at protein-ligand binding sites: A fragment-based approach using biophysical methods. J. Med. Chem. 2006, 49, 4992-5000.
    • (2006) J. Med. Chem , vol.49 , pp. 4992-5000
    • Ciulli, A.1    Williams, G.2    Smith, A.G.3    Blundell, T.L.4    Abell, C.5
  • 49
    • 0037030693 scopus 로고    scopus 로고
    • NMR-based screening with competition water-ligand observed via gradient spectroscopy experiments: Detection of high-affinity ligands
    • Dalvit, C.; Fasolini, M.; Flocco, M.; Knapp, S.; Pevarello, P.; Veronesi, M. NMR-based screening with competition water-ligand observed via gradient spectroscopy experiments: Detection of high-affinity ligands. J. Med. Chem. 2002, 45, 2610-2614.
    • (2002) J. Med. Chem , vol.45 , pp. 2610-2614
    • Dalvit, C.1    Fasolini, M.2    Flocco, M.3    Knapp, S.4    Pevarello, P.5    Veronesi, M.6
  • 50
    • 0032515099 scopus 로고    scopus 로고
    • Crystal structure of rabbit muscle creatine kinase
    • Rao, J. K.; Bujacz, G.; Wlodawer, A. Crystal structure of rabbit muscle creatine kinase. FEBS Lett. 1998, 439, 133-137.
    • (1998) FEBS Lett , vol.439 , pp. 133-137
    • Rao, J.K.1    Bujacz, G.2    Wlodawer, A.3
  • 51
    • 0027136282 scopus 로고
    • Comparative protein modelling by satisfaction of spatial restraints
    • Sali, A.; Blundell, T. L. Comparative protein modelling by satisfaction of spatial restraints. J. Mol. Biol. 1993, 234, 779-815.
    • (1993) J. Mol. Biol , vol.234 , pp. 779-815
    • Sali, A.1    Blundell, T.L.2
  • 52
    • 0033810049 scopus 로고    scopus 로고
    • Modeling of loops in protein structures
    • Fiser, A.; Do, R. K.; Sali, A. Modeling of loops in protein structures. Protein Sci. 2000, 9, 1753-1773.
    • (2000) Protein Sci , vol.9 , pp. 1753-1773
    • Fiser, A.1    Do, R.K.2    Sali, A.3
  • 54
    • 0033576680 scopus 로고    scopus 로고
    • Consensus scoring: A method for obtaining improved hit rates from docking databases of three-dimensional structures into proteins
    • Charifson, P. S.; Corkery, J. J.; Murcko, M. A.; Walters, W. P. Consensus scoring: A method for obtaining improved hit rates from docking databases of three-dimensional structures into proteins. J. Med. Chem. 1999, 42, 5100-5109.
    • (1999) J. Med. Chem , vol.42 , pp. 5100-5109
    • Charifson, P.S.1    Corkery, J.J.2    Murcko, M.A.3    Walters, W.P.4
  • 55
    • 0034645763 scopus 로고    scopus 로고
    • Knowledge-based scoring function to predict protein-ligand interactions
    • Gohlke, H.; Hendlich, M.; Klebe, G. Knowledge-based scoring function to predict protein-ligand interactions. J. Mol. Biol. 2000, 295, 337-356.
    • (2000) J. Mol. Biol , vol.295 , pp. 337-356
    • Gohlke, H.1    Hendlich, M.2    Klebe, G.3
  • 56
    • 0019821048 scopus 로고
    • Heart mitochondrial creatine kinase solubilization. Effect of mitochondrial swelling and SH group reagents
    • Font, B.; Vial, C.; Goldschmidt, D.; Eichenberger, D.; Gautheron, D. C. Heart mitochondrial creatine kinase solubilization. Effect of mitochondrial swelling and SH group reagents. Arch. Biochem. Biophys. 1981, 212, 195-203.
    • (1981) Arch. Biochem. Biophys , vol.212 , pp. 195-203
    • Font, B.1    Vial, C.2    Goldschmidt, D.3    Eichenberger, D.4    Gautheron, D.C.5


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