The role of hydrophobic properties of chemicals in promoting allosteric reactions

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 11, 2005, Pages 3737-3762

  Mekapati, Suresh B ^a   Kurup, Alka ^a   Verma, Rajeshwar P ^a   Hansch, Corwin ^a  

^a POMONA COLLEGE   (United States)

Author keywords

Allosteric reaction; Hydrophobicity; Quantitative structure activity relationship (QSAR)

Indexed keywords

5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; 6 (2,4 DIFLUOROPHENYLTHIO) 5 METHANESULFONAMIDO 1 INDANONE; ADRENALIN; BRIMONIDINE; CLONIDINE; DICLOFENAC; EPININE; FLURBIPROFEN; INDOMETACIN; KETOPROFEN; KETOROLAC; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; NAPROXEN; NORADRENALIN; NORFENEFRINE; OXEDRINE; OXYMETAZOLINE; PHENYLEPHRINE; PIPERAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; PIROXICAM; PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SC 57125; SULFAMONOMETHOXINE; SULINDAC SULFIDE; TENOXICAM; THIAZOLE DERIVATIVE; TOLAZOLINE; TOLMETIN; UNINDEXED DRUG;

ALLOSTERISM; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYDROPHOBICITY; MATHEMATICAL MODEL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 18144420870     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.03.025     Document Type: Article

References (58)

1. C. Hansch, R. Garg, and A. Kurup Bioorg. Med. Chem. 9 2001 283
2. R. Garg, A. Kurup, S.B. Mekapati, and C. Hansch Bioorg. Med. Chem. 11 2003 621
3. C. Hansch, D. Hoekman, A. Leo, D. Weininger, and C.D. Selassie Chem. Rev. 102 2002 783
4. C. Hansch, R. Garg, A. Kurup, and S.B. Mekapati Bioorg. Med. Chem. 11 2003 2075
5. R. Garg, A. Kurup, and C. Hansch Bioorg. Med. Chem. 9 2001 3161
6. S.B. Mekapati, and C. Hansch Bioorg. Med. Chem. 9 2001 3225
7. D.E. Koshland Jr. Proc. Natl. Acad. Sci. U.S.A. 44 1958 98
8. J. Monod, J.P. Changeux, and F. Jacob J. Mol. Biol. 6 1963 306
9. M.G. Perutz Mechanisms of Cooperativity and Allosteric Regulation in Proteins 1990 Cambridge University Press Cambridge
10. J.-P. Changeux, and S.J. Edelstein Neuron 21 1998 959
11. C. Hansch, and A. Leo Exploring QSAR. Fundamentals and Applications in Chemistry and Biology 1995 American Chemical Society Washington, DC
12. C. Hansch, A. Leo, and D. Hoekman Exploring QSAR. Hydrophobic, Electronic and Steric Constants 1995 American Chemical Society Washington, DC
13. C. Fotsch, J.D. Sonnenberg, N. Chen, C. Hale, W. Karbon, and M.H. Norman J. Med. Chem. 44 2001 2344
14. G. Dannhardt, and W. Kiefer Eur. J. Med. Chem. 36 2001 109
15. D.V. Santi, and P.V. Danenberg Biochemistry 10 1971 4813
16. K. Horakova, L. Drobnica, P. Nemec, A. Antos, and P. Kristian Neoplasma 15 1968 169
17. S.M. Sami, R.T. Dorr, D.S. Alberts, A.M. Solyom, and W.A. Remers J. Med. Chem. 43 2000 3067
18. E.W. Brooke, S.G. Davies, A.W. Mulvaney, M. Okada, F. Pompeo, E. Sim, R.J. Vickers, and I.M. Westwood Bioorg. Med. Chem. Lett. 13 2003 2527
19. A.A.F. Wasfy, and A.A. Aly Folia Microbiol. 48 2003 51
20. J. Witherington, V. Bordas, D. Haigh, D.M.B. Hickey, R.J. Ife, A.D. Rawlings, B.P. Slingsby, D.G. Smith, and R.W. Ward Bioorg. Med. Chem. Lett. 13 2003 1581
21. G. Dannhardt, W. Kiefer, G. Kramer, S. Maehrlein, U. Nowe, and B. Fiebich Eur. J. Med. Chem. 35 2000 499
22. S.M. Sondhi, M. Johar, N. Singh, R. Shukla, R. Raghubir, and S.G. Dastidar Indian J. Chem. 41B 2002 2659
23. A. Kolczewski, G. Adam, A.M. Cesura, F. Jenck, M. Hennig, T. Oberhauser, S.M. Poli, F. Rossler, S. Rover, J. Wichmann, and F.M. Dautzenberg J. Med. Chem. 46 2003 255
24. T. Goslinski, B. Golankiewicz, E. De Clercq, and J. Balzarini J. Med. Chem. 45 2002 5052
25. N. Micale, M. Zappala, S. Grasso, G. Puja, G. De Sarro, G. Ferreri, A. De Sarro, L. Toma, and C. De Micheli J. Med. Chem. 45 2002 4433
26. Y. Hamada, H. Tokuhara, A. Masuyama, M. Nojima, H.-S. Kim, K. Ono, N. Ogura, and Y. Wataya J. Med. Chem. 45 2002 1374
27. A. Scozzafava, F. Briganti, and C.T. Supuran Rev. Roum. Chim. 44 1999 895
28. B.G. Szczepankiewicz, G. Liu, H.-S. Jae, A.S. Tasker, I.W. Gunawardana, T.W. Von Gelderm, S.L. Gwaltney II, J.R. Wu-Wong, L. Gehrke, W.J. Chiou, R.B. Credo, J.D. Alder, M.A. Nukkala, N.A. Zielinski, K. Jarvis, K.W. Mollison, D.J. Frost, J.L. Bauch, Y.H. Hui, A.K. Claiborne, Q. Li, and S.H. Rosenberg J. Med. Chem. 44 2001 4416
29. K. Kiriyama, K. Iwaya, S. Kagabu, and K. Nishimura J. Pestic. Sci. 26 2001 55
30. C.T. Supuran, M.A. Ilies, and A. Scozzafava Eur. J. Med. Chem. 33 1998 739
31. J. Pernak, J. Rogoza, and I. Mirska Eur. J. Med. Chem. 36 2001 313
32. W.-N. Tian, D.D. Miller, and R.C. Deth J. Pharmacol. Exp. Ther. 292 2000 664
33. K. Fox, G.-P. Zauke, and W. Butte Ecotoxicol. Environ. Safety 28 1994 99
34. J.I. Levin, M.T. Du, J.F. Dijoseph, L.M. Killar, A. Sung, T. Walter, M.A. Sharr, C.E. Roth, F.J. Moy, R. Powers, G. Jin, R. Cowling, and J.S. Skotnicki Bioorg. Med. Chem. Lett. 11 2001 235
35. H. Nogami, T. Nagai, and S. Wada Chem. Pharm. Bull. 18 1970 348
36. F. Markwardt, J. Drawert, and P. Walsmann Biochem. Pharmacol. 23 1974 2247
37. Doyle, P.; Fujita, T.; Fukuto, T. R. In Proc. 5th International Congress Pest. Chem. Japan; 1982; Vol. 1, p 203
38. H.H. Pertz, H.-C. Milhahn, and E. Eich J. Med. Chem. 42 1999 659
39. T. Otzen, E.G. Wempe, B. Kunz, R. Bartels, G. Lehwarkyvetot, W. Hansel, K.-J. Sharper, and J.K. Seydel J. Med. Chem. 47 2004 2401
40. M. Rosini, A. Antonello, A. Cavalli, M.L. Bolognesi, A. Minarini, G. Marucci, E. Poggesi, A. Leonardi, and C. Melchiorre J. Med. Chem. 46 2003 4895
41. G. Rastelli, S. Pacchioni, W. Sirawaraporn, R. Sirawaraporn, M.D. Parenti, and A.M. Ferrari J. Med. Chem. 46 2003 2834
42. I.T. Forbes, D.G. Cooper, E.K. Dodds, S.E. Douglas, A.D. Gribble, R.J. Ife, A.P. Lightfoot, M. Meeson, L.P. Campbell, T. Coleman, G.J. Riley, and D.R. Thomas Bioorg. Med. Chem. Lett. 13 2003 1055
43. M.A. El-Sherbeny Arzneim.-Forsch. 50 II 2000 848
44. M. Patel, L.T. Bacheler, M.M. Rayner, B.C. Cordova, R.M. Klabe, E.-V. Susan, and S.P. Seitz Bioorg. Med. Chem. Lett. 8 1998 823
45. G. Sabbioni Chem. Res. Toxicol. 7 1994 267
46. P.I. Reisberg, and J.S. Olson J. Biol. Chem. 255 1980 4144
47. D.X. Wang, H. Booth, N. Lerner-Marmorosh, T.S. Osdene, and L.G. Abood Drug Dev. Res. 45 1998 10
48. T. Dahlgren, R.L. Dean, L.A. Gharat, A.M. Johansson, G. Lambert, H.B. Li, D.L. Nelson, Y. Yang, and A.R. Martin Bioorg. Med. Chem. Lett. 5 1995 2963
49. P.R. Carlier, M.M.-C. Lo, P.C.-K. Lo, E. Richelson, M. Tatsumi, I.J. Reynolds, and T.A. Sharma Bioorg. Med. Chem. Lett. 8 1998 487
50. H. Annaoura, K. Nakanishi, M. Uesugi, A. Fukunaga, S. Imajo, A. Miyajima, Y. Tamura-Horikawa, and S. Tamura Bioorg. Med. Chem. 10 2002 371
51. G. Phillips, W.J. Guilford, B.O. Buckman, D.D. Davey, K.A. Eagen, S. Koovakkat, A. Liang, M. McCarrick, R. Mohan, H.P. Ng, M. Pinkerton, B. Subramanyam, E. Ho, L. Trinh, M. Whitlow, S. Wu, W. Xu, and M.M. Morrissey J. Med. Chem. 45 2002 2484
52. M. Pedro, F. Cerqueira, M.E. Sousa, M.S.J. Nasciemento, and M. Pinto Bioorg. Med. Chem. 10 2002 3725
53. X. Li, S. Chu, V.A. Feher, M. Khalili, Z. Nie, S. Margosiak, V. Nikulin, J. Levin, K.G. Sprankle, M.E. Tedder, R. Almassy, K. Appelt, and K.M. Yager J. Med. Chem. 46 2003 5663
54. W.-T. Li, D.-R. Hwang, C.-P. Chen, C.-W. Shen, C.-L. Huang, T.-W. Chen, C.-H. Lin, Y.-L. Chang, Y.-Y. Chang, Y.-K. Lo, H.-Y. Tseng, C.-C. Lin, J.-S. Song, H.-C. Chen, S.-J. Chen, S.-H. Wu, and C.-T. Chen J. Med. Chem. 46 2003 1706
55. K. Nishimura, M. Ohaka, and T. Fujita Pestic. Biochem. Physiol. 28 1987 257
56. M. Tobe, Y. Isobe, H. Tomizawa, T. Nagasaki, F. Obara, M. Matsumoto, and H. Hayashi Chem. Pharm. Bull. 50 2002 1073
57. L. Zhi, C.M. Tegley, B. Pio, J.P. Edwards, M. Motamedi, T.K. Jones, K.B. Marschke, D.E. Mais, B. Risek, and W.T. Schrader J. Med. Chem. 46 2003 4104
58. B. Buttelmann, A. Alanine, A. Bourson, R. Gill, M.-P. Heitz, V. Mutel, E. Pinard, G. Trube, and R. Wyler Bioorg. Med. Chem. Lett. 13 2003 1759