Thermodynamic optimisation in drug discovery: A case study using carbonic anhydrase inhibitors

ChemMedChem

Volumn 4, Issue 12, 2009, Pages 1985-1989

  Scott, Andrew D ^a   Phillips, Chris ^a   Alex, Alexander ^a   Flocco, Maria ^a   Bent, Andrew ^a   Randall, Amy ^a   O'Brien, Ronan ^b   Damian, Luminita ^b   Jones, Lyn H ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^b GE HEALTHCARE   (United Kingdom)

Author keywords

Carbonic anhydrase; Crystal structures; Drug design; Isothermal titration calorimetry; Thermodynamics

Indexed keywords

BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE INHIBITOR;

ARTICLE; BINDING AFFINITY; CHEMICAL MODEL; CRYSTAL STRUCTURE; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG RESEARCH; ENTHALPY; ENTROPY; HYDROPHILICITY; HYDROPHOBICITY; IMMUNOAFFINITY CHROMATOGRAPHY; ISOTHERMAL TITRATION CALORIMETRY; LIGAND BINDING; PKA; PRIORITY JOURNAL; PROTEIN LIPID INTERACTION; THERMODYNAMICS;

ANIMALS; BENZENE; CALORIMETRY; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CATTLE; CRYSTALLOGRAPHY, X-RAY; DRUG DISCOVERY; HUMANS; PROTEIN BINDING; SERUM ALBUMIN, BOVINE; SULFONAMIDES; THERMODYNAMICS; TITRIMETRY;

EID: 73449087370     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200900386     Document Type: Article

References (24)

1. J. D. Dunitz, Chem. Biol. 1995, 2, 709-712.
2. a) A. J. Ruben, Y. Kiso, E. Freire, Chem. Biol. Drug Des. 2006, 67, 2-4;
3. b) E. Freire, Drug Discovery Today 2008, 13, 869-874.
4. W. H. J. Ward, G. A. Holdgate, Progress in Medicinal Chemistry 2001, 38, 309-376.
5. T. Wiseman, S. Williston, J. F. Brandts, L. N. Lin, Anal. Biochem. 1989, 179, 131-137.
6. TM Isothermal Titration Calorimeter, MicroCal Product Information Sheet, 2008.
7. I. J. Colton, J. D. Carbeck, J. Rao, G. M. Whitesides, Electrophoresis 1998, 19, 367-382.
8. V. M. Krishnamurthy, G. K. Kaufman, A. R. Urbach, I. Gitlin, K. L. Gudiksen, D. B. Weibel, G. M. Whitesides, Chem. Rev. 2008, 108, 946-1051.
9. V. M. Krishnamurthy, B. R. Bohall, C.-Y. Kim, D. T. Moustakas, D. W. Christianson, G. M. Whitesides, Chem. Asian J. 2007, 2, 94-105.
10. A. Hillebrecht, C. T. Supuran, G. Klebe, ChemMedChem 2006, 1, 839-853.
11. V. M. Krishnamurthy, B. R. Bohall, V. Semetey, G. M. Whitesides, J. Am. Chem. Soc. 2006, 128, 5802-5812.
12. D. W. Christianson, C. A. Fierke, Acc. Chem. Res. 1996, 29, 331-339.
13. Both 2-OMe and 2-CN BSA were also analyzed by ITC. However, we were unable to obtain consistent results with these derivatives due to unknown reasons. Further investigations into these compounds are continuing.
14. D. K. Srivastava, K. M. Jude, A. L. Banerjee, M. Haldar, S. Manokaran, J. Kooren, S. Mallik, D. W. Christianson, J. Am. Chem. Soc. 2007, 129, 5528-5537.
15. K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886.
16. P. D. Leeson, B. Springthorpe, Nature Rev. Drug Disc. 2007, 6, 881-890.
17. Personal communication with Dr. Martin Edwards, Pfizer Inc. (La Jolla, USA).
18. A. Velazquez-Campoy, Y. Kiso, E. Freire, Arch. Biochem. Biophys. 2001, 390, 169-175.
19. V. Lafont, A. A. Armstrong, H. Ohtaka, Y. Kiso, L. M. Amzel, E. Freire, Chem. Biol. Drug Des. 2007, 69, 413-422.
20. A. Jain, G. M. Whitesides, R. S. Alexander, D. W. Christianson, J. Med. Chem. 1994, 37, 2100-2105.
21. C. A. Lipinski, Drug Discovery Today Technol. 2004, 1, 337-341.
22. M. M. Hann, A. R. Leach, G. Harper, J. Chem. Inf. Comput. Sci. 2001, 41, 856-864.
23. P. R. Andrews, D. J. Craik, J. L. Martin, J. Med. Chem. 1984, 27, 1648-1657.
24. A. L. Hopkins, C. R. Groom, A. Alex, Drug Discovery Today 2004, 9, 430-431.