메뉴 건너뛰기




Volumn 50, Issue 2, 2007, Pages 283-293

Dissection of the recognition properties of p38 MAP kinase. Determination of the binding mode of a new pyridinyl-heterocycle inhibitor family

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE; HETEROCYCLIC COMPOUND; MITOGEN ACTIVATED PROTEIN KINASE 14; MITOGEN ACTIVATED PROTEIN KINASE P38; MITOGEN ACTIVATED PROTEIN KINASE P38 INHIBITOR; PYRIDINE DERIVATIVE;

EID: 33846404143     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061073h     Document Type: Article
Times cited : (24)

References (53)
  • 1
    • 0026318171 scopus 로고
    • Inflammatory cytokines: Interleukin-1 and tumor necrosis factor as effector molecules in autoimmune diseases
    • Dinarello, C. A. Inflammatory cytokines: interleukin-1 and tumor necrosis factor as effector molecules in autoimmune diseases. Curr. Opin. Immunol. 1991, 3, 941-948.
    • (1991) Curr. Opin. Immunol , vol.3 , pp. 941-948
    • Dinarello, C.A.1
  • 3
    • 0033168031 scopus 로고    scopus 로고
    • Therapeutic potential and strategies for inhibiting TNF alpha
    • Newton, R. C.; Decicco, C. P. Therapeutic potential and strategies for inhibiting TNF alpha. J. Med. Chem. 1999, 42, 2295-2314.
    • (1999) J. Med. Chem , vol.42 , pp. 2295-2314
    • Newton, R.C.1    Decicco, C.P.2
  • 4
    • 0035689572 scopus 로고    scopus 로고
    • Pugsley, M. K. Etanercept: Immunex. Curr. Opin. Invest. Drugs 2001, 2, 1726.
    • Pugsley, M. K. Etanercept: Immunex. Curr. Opin. Invest. Drugs 2001, 2, 1726.
  • 5
    • 0035037583 scopus 로고    scopus 로고
    • Tumor necrosis factor as a therapeutic target in rheumatoid arthritis and other chronic inflammatory diseases: The clinical experience with infliximab. Remicade
    • Bondeson, J.; Maini, R. N. Tumor necrosis factor as a therapeutic target in rheumatoid arthritis and other chronic inflammatory diseases: The clinical experience with infliximab. Remicade. Int. J. Clin. Pract. 2001, 55, 211.
    • (2001) Int. J. Clin. Pract , vol.55 , pp. 211
    • Bondeson, J.1    Maini, R.N.2
  • 6
    • 0028605318 scopus 로고    scopus 로고
    • Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M. J.; Heys, J. R.; Landvatter, S. W.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature 1994, 372, 739-746.
    • Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M. J.; Heys, J. R.; Landvatter, S. W.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature 1994, 372, 739-746.
  • 7
    • 0142026209 scopus 로고    scopus 로고
    • p38 MAP kinases: Key signalling molecules as therapeutic targets for inflammatory diseases
    • Kumar, S.; Boehm, J.; Lee, J. C. p38 MAP kinases: Key signalling molecules as therapeutic targets for inflammatory diseases. Nat. Rev. Drug Discovery 2003, 2, 717-726.
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 717-726
    • Kumar, S.1    Boehm, J.2    Lee, J.C.3
  • 8
    • 0032862832 scopus 로고    scopus 로고
    • Inhibitors of p38 MAP kinase: Therapeutic intervention in cytokine-mediated diseases
    • Salituro, F. G.; Germann, U. A.; Wilson, K. P.; Bemis, G. W.; Fox, T.; Su, M. S.-S. Inhibitors of p38 MAP kinase: Therapeutic intervention in cytokine-mediated diseases. Curr. Med. Chem. 1999, 6, 807-823.
    • (1999) Curr. Med. Chem , vol.6 , pp. 807-823
    • Salituro, F.G.1    Germann, U.A.2    Wilson, K.P.3    Bemis, G.W.4    Fox, T.5    Su, M.S.-S.6
  • 9
    • 0030954172 scopus 로고    scopus 로고
    • Tong, L.; Pav, S.; White, D. M.; Rogers, S.; Crane, K. M.; Cywin, C. L.; Brown, M. L.; Pargellis, C. A. A highly specific inhibitor of human p38 MAP kinase binds in the ATP binding pocket. Nat. Struct. Biol. 1997, 4, 311-316.
    • Tong, L.; Pav, S.; White, D. M.; Rogers, S.; Crane, K. M.; Cywin, C. L.; Brown, M. L.; Pargellis, C. A. A highly specific inhibitor of human p38 MAP kinase binds in the ATP binding pocket. Nat. Struct. Biol. 1997, 4, 311-316.
  • 11
    • 0036715931 scopus 로고    scopus 로고
    • Pyridinylimidazole based p38 MAP kinase inhibitors
    • Jackson, P. F.; Bullington, J. L. Pyridinylimidazole based p38 MAP kinase inhibitors. Curr. Topics Med. Chem. 2002, 2, 1011-1020.
    • (2002) Curr. Topics Med. Chem , vol.2 , pp. 1011-1020
    • Jackson, P.F.1    Bullington, J.L.2
  • 12
    • 20244384283 scopus 로고    scopus 로고
    • de Dios, A.; Shih, C.; Lopez de Urald, e. B.; Sánchez, C.; del Prado, M.; Martin Cabrejas, L. M.; Pleite, S.; Blanco-Urgoiti, J.; Lorite, M. J.; Nevill, C. R., Jr.; Bonjouklian, R.; York, J.; Vieth, M.; Wang, Y.; Magnus, N.; Campbell, R. M.; Anderson, B. D.; McCann, D. J.; Giera, D. D.; Lee, P. A.; Schultz, R. M.; Li, L. C.; Johnson, L. M.; Wolos, J. A. Design of potent and selective 2-aminobenzimidazole-based p38alpha MAP kinase inhibitors with excellent in vivo efficacy. J Med. Chem. 2002, 48, 2270-2273.
    • de Dios, A.; Shih, C.; Lopez de Urald, e. B.; Sánchez, C.; del Prado, M.; Martin Cabrejas, L. M.; Pleite, S.; Blanco-Urgoiti, J.; Lorite, M. J.; Nevill, C. R., Jr.; Bonjouklian, R.; York, J.; Vieth, M.; Wang, Y.; Magnus, N.; Campbell, R. M.; Anderson, B. D.; McCann, D. J.; Giera, D. D.; Lee, P. A.; Schultz, R. M.; Li, L. C.; Johnson, L. M.; Wolos, J. A. Design of potent and selective 2-aminobenzimidazole-based p38alpha MAP kinase inhibitors with excellent in vivo efficacy. J Med. Chem. 2002, 48, 2270-2273.
  • 14
    • 0036719870 scopus 로고    scopus 로고
    • The non-heterocycle classes of p38 MAP kinase inhibitors
    • Cirillo, P. F.; Pargellis, C.; Regan, J. The non-heterocycle classes of p38 MAP kinase inhibitors. Curr. Topics Med. Chem. 2002, 2, 1021-1035.
    • (2002) Curr. Topics Med. Chem , vol.2 , pp. 1021-1035
    • Cirillo, P.F.1    Pargellis, C.2    Regan, J.3
  • 15
    • 9744269944 scopus 로고    scopus 로고
    • Leftheris, K.; Ahmed, G.; Chan, R.; Dyckman, A. J.; Hussain, Z.; Ho, K.; Hynes, J., Jr.; Letourneau, J.; Li, W.; Lin, S.; Metzger, A.; Moriarty, K. J.; Riviello, C.; Shimshock, Y.; Wen, J.; Wityak, J.; Wrobleski, S. T.; Wu, H.; Wu, J.; Desai, M.; Gillooly, K. M.; Lin, T. H.; Loo, D.; McIntyre, K. W.; Pitt, S.; Shen, D. R.; Shuster, D. J.; Zhang, R.; Diller, D.; Doweyko, A.; Sack, J.; Baldwin, J.; Banish, J.; Dodd, J.; Henderson, I.; Kanner, S.; Schieven, G. L.; Webb, M. The discovery of orally active triaminotriazine aniline amides as inhibitors of p38 MAP kinase. J. Med. Chem. 2004, 47, 6283-91.
    • Leftheris, K.; Ahmed, G.; Chan, R.; Dyckman, A. J.; Hussain, Z.; Ho, K.; Hynes, J., Jr.; Letourneau, J.; Li, W.; Lin, S.; Metzger, A.; Moriarty, K. J.; Riviello, C.; Shimshock, Y.; Wen, J.; Wityak, J.; Wrobleski, S. T.; Wu, H.; Wu, J.; Desai, M.; Gillooly, K. M.; Lin, T. H.; Loo, D.; McIntyre, K. W.; Pitt, S.; Shen, D. R.; Shuster, D. J.; Zhang, R.; Diller, D.; Doweyko, A.; Sack, J.; Baldwin, J.; Banish, J.; Dodd, J.; Henderson, I.; Kanner, S.; Schieven, G. L.; Webb, M. The discovery of orally active triaminotriazine aniline amides as inhibitors of p38 MAP kinase. J. Med. Chem. 2004, 47, 6283-91.
  • 18
    • 33846440041 scopus 로고    scopus 로고
    • Pyrazolopyridine Derivatives
    • International Patent Application WO 2004076450
    • Almansa, C.; Virgili, M. Pyrazolopyridine Derivatives. International Patent Application WO 2004076450.
    • Almansa, C.1    Virgili, M.2
  • 19
    • 33846450573 scopus 로고    scopus 로고
    • All IC50s referenced in the paper were determined by Upstate Ltd. (ATP concentration of 100 μM in an enzyme competitive inhibition assay).
    • All IC50s referenced in the paper were determined by Upstate Ltd. (ATP concentration of 100 μM in an enzyme competitive inhibition assay).
  • 20
    • 7044239742 scopus 로고
    • Free energy calculations: Applications to chemical and biochemical phenomena
    • Kollman, P. A. Free energy calculations: Applications to chemical and biochemical phenomena. Chem. Rev. 1993, 93, 2395-2417.
    • (1993) Chem. Rev , vol.93 , pp. 2395-2417
    • Kollman, P.A.1
  • 21
    • 1642357706 scopus 로고    scopus 로고
    • The many roles of computation in drug discovery
    • Jorgensen, W. L. The many roles of computation in drug discovery. Science 2004, 303, 1813-1818.
    • (2004) Science , vol.303 , pp. 1813-1818
    • Jorgensen, W.L.1
  • 22
    • 0035846166 scopus 로고    scopus 로고
    • Are free energy calculations useful in practice? A comparison with rapid scoring functions for the p38 MAP kinase proteins system
    • Pearlman, D. A.; Charifson, P. S. Are free energy calculations useful in practice? A comparison with rapid scoring functions for the p38 MAP kinase proteins system. J. Med. Chem. 2001, 44, 3417-3423.
    • (2001) J. Med. Chem , vol.44 , pp. 3417-3423
    • Pearlman, D.A.1    Charifson, P.S.2
  • 23
    • 0035576327 scopus 로고    scopus 로고
    • Classical Molecular Interaction Potentials: Improved Setup Procedure in Molecular Dynamics Simulations of Proteins
    • Gelpí, J. L.; Kalko, S. G.; Barril, X.; Cirera, J.; de la Cruz, X.; Luque, F. J.; Orozco, M. Classical Molecular Interaction Potentials: Improved Setup Procedure in Molecular Dynamics Simulations of Proteins. Proteins 2001, 45, 428.
    • (2001) Proteins , vol.45 , pp. 428
    • Gelpí, J.L.1    Kalko, S.G.2    Barril, X.3    Cirera, J.4    de la Cruz, X.5    Luque, F.J.6    Orozco, M.7
  • 26
    • 3042524904 scopus 로고    scopus 로고
    • Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges. J. Chem. Phys. 1993, 97, 10269-10280.
    • Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges. J. Chem. Phys. 1993, 97, 10269-10280.
  • 28
    • 84986533234 scopus 로고
    • A new strategy for the evaluation of force parameters from quantum mechanical computations
    • Aleman, C.; Canela, E. I.; Franco, R.; Orozco, M. A new strategy for the evaluation of force parameters from quantum mechanical computations. J. Comput. Chem. 1991, 12, 664-674.
    • (1991) J. Comput. Chem , vol.12 , pp. 664-674
    • Aleman, C.1    Canela, E.I.2    Franco, R.3    Orozco, M.4
  • 29
    • 33846459913 scopus 로고    scopus 로고
    • The hydrated systems were subjected to 4000 cycles of energy minimization of water hydrogens; (ii) 4000 cycles of energy minimization of all water molecules; (iii) 2000 cycles of energy minimization of the entire system except the protein; (iv) 2000 cycles of energy minimization of waters, counterions, inhibitor, and all residues lining the ATP binding site (group 1), i.e., residues 27-89, 102-120, 129-190, 193-194, 200-202, 204-209, 211-213, 215-216, 221, 228, and 318-331. The optimized systems were thermalized by increasing the temperature from 150 to 300 K in four steps during 50 ps. They were then equilibrated for 100 ps at constant temperature (T = 300 K). Water, inhibitor, counterions, and all the residues in group 1 were allowed to move during the trajectories.
    • The hydrated systems were subjected to 4000 cycles of energy minimization of water hydrogens; (ii) 4000 cycles of energy minimization of all water molecules; (iii) 2000 cycles of energy minimization of the entire system except the protein; (iv) 2000 cycles of energy minimization of waters, counterions, inhibitor, and all residues lining the ATP binding site (group 1), i.e., residues 27-89, 102-120, 129-190, 193-194, 200-202, 204-209, 211-213, 215-216, 221, 228, and 318-331. The optimized systems were thermalized by increasing the temperature from 150 to 300 K in four steps during 50 ps. They were then equilibrated for 100 ps at constant temperature (T = 300 K). Water, inhibitor, counterions, and all the residues in group 1 were allowed to move during the trajectories.
  • 30
    • 33646940952 scopus 로고
    • Numerical integration of the Cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes
    • Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. Numerical integration of the Cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes. J. Comput. Phys. 1977, 23, 327-341.
    • (1977) J. Comput. Phys , vol.23 , pp. 327-341
    • Ryckaert, J.P.1    Ciccotti, G.2    Berendsen, H.J.C.3
  • 31
    • 33846441155 scopus 로고    scopus 로고
    • Geometries were optimised at the HF/6-31.G* level, and energy was computed at the MP2/6-311++G(d) and MP4/6-31G(d) level for the unsubstituted bicycle (see Figure 2). In the case of compound 13, the ONIOM procedure was applied (ref 32), representing the central bicycle as the higher layer at the MP4/6-31G* level and the rest of the molecule at the HF/6-31G* level (see Figure 2).
    • Geometries were optimised at the HF/6-31.G* level, and energy was computed at the MP2/6-311++G(d) and MP4/6-31G(d) level for the unsubstituted bicycle (see Figure 2). In the case of compound 13, the ONIOM procedure was applied (ref 32), representing the central bicycle as the higher layer at the MP4/6-31G* level and the rest of the molecule at the HF/6-31G* level (see Figure 2).
  • 32
    • 0033515394 scopus 로고    scopus 로고
    • A new ONIOM implementation in Gaussian 98. Part I. The calculation of energies, gradients, vibrational frequencies and electric field derivatives
    • Dapprich, S.; Komaromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J. A new ONIOM implementation in Gaussian 98. Part I. The calculation of energies, gradients, vibrational frequencies and electric field derivatives. THEOCHEM 1999, 461, 1-21.
    • (1999) THEOCHEM , vol.461 , pp. 1-21
    • Dapprich, S.1    Komaromi, I.2    Byun, K.S.3    Morokuma, K.4    Frisch, M.J.5
  • 33
    • 0000878441 scopus 로고
    • Theoretical study of the tautomerism and protonation of 7-aminopyrazolopyrimidine in the gas phase and in aqueous solution
    • Orozco, M.; Luque, J. L. Theoretical study of the tautomerism and protonation of 7-aminopyrazolopyrimidine in the gas phase and in aqueous solution. J. Am. Chem. Soc. 1995, 117, 1378-1386.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 1378-1386
    • Orozco, M.1    Luque, J.L.2
  • 34
    • 0025016995 scopus 로고
    • Ab initio study of the protonation and the tautomerism of the 7-aminopyrazolopyrimidine molecule
    • Orozco, M.; Canela, E. I.; Mallol, J.; Lluis, C.; Franco, R. Ab initio study of the protonation and the tautomerism of the 7-aminopyrazolopyrimidine molecule. J. Org. Chem. 1990, 55, 753-756.
    • (1990) J. Org. Chem , vol.55 , pp. 753-756
    • Orozco, M.1    Canela, E.I.2    Mallol, J.3    Lluis, C.4    Franco, R.5
  • 35
    • 0035425603 scopus 로고    scopus 로고
    • Solvation in octanol: Parametrization of the continuum MST model
    • Curutchet, C.; Orozco, M.; Luque, F. J. Solvation in octanol: Parametrization of the continuum MST model. J. Comput. Chem. 2001, 22, 1180-1193.
    • (2001) J. Comput. Chem , vol.22 , pp. 1180-1193
    • Curutchet, C.1    Orozco, M.2    Luque, F.J.3
  • 36
    • 84962432699 scopus 로고
    • Aproximate evaluations of the electrostatic free energy and internal energy changes in solution processes
    • Miertus, S.; Tomasi, J. Aproximate evaluations of the electrostatic free energy and internal energy changes in solution processes. Chem. Phys. 1982, 65, 239-245.
    • (1982) Chem. Phys , vol.65 , pp. 239-245
    • Miertus, S.1    Tomasi, J.2
  • 37
    • 33846433057 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Jr, Stratmann, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Baboul, A. G, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B, Chen, W, Wong, M. W, Andres, J. L, Gonzalez, C, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 98, rev. A.7, Gaussian, Inc, Pittsburgh, PA, 1998
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, rev. A.7.; Gaussian, Inc.: Pittsburgh, PA, 1998.
  • 38
    • 33846442308 scopus 로고    scopus 로고
    • Peterson, M.; Poirier, R. MonsterGauss; Department of Biochemistry, University of Toronto: Toronto, Canada: version modified by Cammi, R. and Tomasi, J., 1987, and by Luque, F. J. and Orozco, M., 2004.
    • Peterson, M.; Poirier, R. MonsterGauss; Department of Biochemistry, University of Toronto: Toronto, Canada: version modified by Cammi, R. and Tomasi, J., 1987, and by Luque, F. J. and Orozco, M., 2004.
  • 40
    • 0242500887 scopus 로고    scopus 로고
    • Theoretical studies of the inhibition mechanism of cyclooxygenase-2. Is there a unique recognition site?
    • Soliva, R.; Almansa, C.; Kalco, S. G.; Luque, F. J.; Orozco, M. Theoretical studies of the inhibition mechanism of cyclooxygenase-2. Is there a unique recognition site? J. Med. Chem. 2003, 46, 1372-82.
    • (2003) J. Med. Chem , vol.46 , pp. 1372-1382
    • Soliva, R.1    Almansa, C.2    Kalco, S.G.3    Luque, F.J.4    Orozco, M.5
  • 41
    • 0026332547 scopus 로고
    • Electrostatic effects in proteins: Comparison of dielectric and charge models
    • Mehler, E. L.; Solmajer, T. Electrostatic effects in proteins: Comparison of dielectric and charge models. Protein Eng. 1991, 4, 903-910.
    • (1991) Protein Eng , vol.4 , pp. 903-910
    • Mehler, E.L.1    Solmajer, T.2
  • 42
    • 33846438132 scopus 로고    scopus 로고
    • The dehydration particle is a simple cubic particle (1 Å3 in this work) which is assumed to remove water in its environment. The desolvation penalty is then determined by integrating the solvation density as computed by the SEDO version of the Poisson-Boltzmann method see ref 43
    • 3 in this work) which is assumed to remove water in its environment. The desolvation penalty is then determined by integrating the solvation density as computed by the SEDO version of the Poisson-Boltzmann method (see ref 43).
  • 43
    • 0035314043 scopus 로고    scopus 로고
    • Solvation energy density occlusion approximation for evaluation of desolvation penalties in biomolecular interactions
    • Arora, N.; Bashford, D. Solvation energy density occlusion approximation for evaluation of desolvation penalties in biomolecular interactions. Proteins 2001, 43, 12-27.
    • (2001) Proteins , vol.43 , pp. 12-27
    • Arora, N.1    Bashford, D.2
  • 45
    • 0042915882 scopus 로고    scopus 로고
    • The structure of JNK3 in complex with small molecule inhibitors: Structural basis for potency and selectivity
    • Scapin, G.; Patel, S. B.; Lisnock, J.; Becker, J. W.; LoGrasso, P. V. The structure of JNK3 in complex with small molecule inhibitors: Structural basis for potency and selectivity. Chem. Biol. 2003, 10, 705-712.
    • (2003) Chem. Biol , vol.10 , pp. 705-712
    • Scapin, G.1    Patel, S.B.2    Lisnock, J.3    Becker, J.W.4    LoGrasso, P.V.5
  • 46
    • 0030015253 scopus 로고    scopus 로고
    • Tautomerism and protonation of guanine and cytosine. Implications in the formation of triplex DNA
    • Colominas, C.; Luque, F. J.; Orozco, M. Tautomerism and protonation of guanine and cytosine. Implications in the formation of triplex DNA. J. Am. Chem. Soc. 1996, 118, 6811-6821.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 6811-6821
    • Colominas, C.1    Luque, F.J.2    Orozco, M.3
  • 47
    • 84962432615 scopus 로고    scopus 로고
    • Correlated ab initio study of nucleic acid bases and their tautomers in the gas phase and aqueous solition.1. Cytosine
    • Trygubenko, S. A.; Bogdan, T. V.; Sponer, J.; Rueda, M.; Orozco, M.; Luque, F. J.; Slavíek, P.; Hobza, P. Correlated ab initio study of nucleic acid bases and their tautomers in the gas phase and aqueous solition.1. Cytosine. Phys. Chem Chem. Phys. 2002, 4, 4192-4203.
    • (2002) Phys. Chem Chem. Phys , vol.4 , pp. 4192-4203
    • Trygubenko, S.A.1    Bogdan, T.V.2    Sponer, J.3    Rueda, M.4    Orozco, M.5    Luque, F.J.6    Slavíek, P.7    Hobza, P.8
  • 48
    • 84961978175 scopus 로고    scopus 로고
    • Theoretical study of alkyl-PI and aryl-PI interactions. Reconciling theory and experiment
    • (a) Ribas, J.; Cubero, E.; Luque, F. J.; Orozco, M. Theoretical study of alkyl-PI and aryl-PI interactions. Reconciling theory and experiment. J. Org. Chem. 2002, 67, 7057-7065.
    • (2002) J. Org. Chem , vol.67 , pp. 7057-7065
    • Ribas, J.1    Cubero, E.2    Luque, F.J.3    Orozco, M.4
  • 49
    • 0034703739 scopus 로고    scopus 로고
    • Origin of the attraction and directionality of the NH/PI interaction: Comparison with the OH/PI and CH/PI interactions
    • (b) Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. Origin of the attraction and directionality of the NH/PI interaction: Comparison with the OH/PI and CH/PI interactions. J. Am. Chem. Soc. 2000, 122, 11450.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 11450
    • Tsuzuki, S.1    Honda, K.2    Uchimaru, T.3    Mikami, M.4    Tanabe, K.5
  • 50
    • 10744227768 scopus 로고    scopus 로고
    • Acquisition of sensitivity of stress-activated protein kinases to the p38 inhibitor, SB203580, by alteration of one or more amino acids within the ATP binding pocket
    • Gum, R. J.; McLaughlin, M. M.; Kumar, S.; Wang, Z.; Bower, M. J.; Lee, J. C.; Adams, J. L.; Livi, G. P.; Goldsmith, E. J.; Young, P. R. Acquisition of sensitivity of stress-activated protein kinases to the p38 inhibitor, SB203580, by alteration of one or more amino acids within the ATP binding pocket. J. Biol. Chem. 1998, 273, 15605-15610.
    • (1998) J. Biol. Chem , vol.273 , pp. 15605-15610
    • Gum, R.J.1    McLaughlin, M.M.2    Kumar, S.3    Wang, Z.4    Bower, M.J.5    Lee, J.C.6    Adams, J.L.7    Livi, G.P.8    Goldsmith, E.J.9    Young, P.R.10
  • 52
    • 85056023389 scopus 로고    scopus 로고
    • B).
    • B).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.