Thermodynamic characterization of allosteric glycogen phosphorylase inhibitors

Biochemistry

Volumn 47, Issue 16, 2008, Pages 4683-4691

  Anderka, Oliver ^a   Loenze, Petra ^a   Klabunde, Thomas ^a   Dreyer, Matthias K ^a   Defossa, Elisabeth ^a   Wendt, K Ulrich ^a   Schmoll, Dieter ^a  

^a SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOSTERIC GLYCOGEN PHOSPHORYLASE INHIBITORS; ENZYME ASSAY; PHYSIOLOGICAL ACTIVATORS;

BIOASSAY; GLUCOSE; MEDICAL PROBLEMS; OPTIMIZATION; PATIENT TREATMENT; THERMODYNAMICS;

ENZYME INHIBITION;

ADENOSINE PHOSPHATE; AVE 2865; AVE 5688; AVE 9423; ENZYME INHIBITOR; GLYCOGEN PHOSPHORYLASE; GLYCOGEN PHOSPHORYLASE INHIBITOR; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ALLOSTERISM; ARTICLE; BINDING AFFINITY; BINDING SITE; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENTHALPY; ENTROPY; ISOTHERMAL TITRATION CALORIMETRY; NON INSULIN DEPENDENT DIABETES MELLITUS; PRIORITY JOURNAL; THERMODYNAMICS;

ALLOSTERIC REGULATION; ANIMALS; BUFFERS; CALORIMETRY; ENZYME INHIBITORS; GLUCOSE; GLYCOGEN PHOSPHORYLASE; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; RABBITS; TEMPERATURE; THERMODYNAMICS; TITRIMETRY;

EID: 42349106956     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi702397d     Document Type: Article

References (37)

1. Lefebvre, P. J., and Scheen, A. J. (1999) Glucose metabolism and the postprandial state. Eur. J. Clin. Invest. 29 (Suppl. 2), 1-6.
2. Roden, M., and Bernroider, E. (2003) Hepatic glucose metabolism in humans: Its role in health and disease. Best Pract. Res., Clin. Endocrinol. Metab. 17, 365-383.
3. Henke, B. R., and Sparks, S. M. (2006) Glycogen Phosphorylase inhibitors. Mini-Rev. Med. Chem. 6, 845-857.
4. Lee, W. N., Guo, P., Lim, S., Bassilian, S., Lee, S. T., Boren, J., Cascante, M., Go, V. L., and Boros, L. G. (2004) Metabolic sensitivity of pancreatic tumour cell apoptosis to glycogen phosphorylase inhibitor treatment. Br. J. Cancer 91, 2094-2100.
5. Schnier, J. B., Nishi, K., Monks, A., Gorin, F. A., and Bradbury, E. M. (2003) Inhibition of glycogen Phosphorylase (GP) by CP-91,149 induces growth inhibition correlating with brain GP expression. Biochem. Biophys. Res. Commun. 309, 126-134.
6. Schnier, J. B., Nishi, K., Gumerlock, P. H., Gorin, F. A., and Bradbury, E. M. (2005) Glycogen synthesis correlates with androgen-dependent growth arrest in prostate cancer. BMC Urol. 5, 6.
7. Johnson, L. N. (1992) Glycogen Phosphorylase: Control by phosphorylation and allosteric effectors. FASEB J. 6, 2274-2282.
8. Klabunde, T., Wendt, K. U., Kadereit, D., Brachvogel, V., Burger, H. J., Herling, A. W., Oikonomakos, N. G., Kosmopoulou, M. N., Schmoll, D., Sarubbi, E., von Roedern, E., Schoenafinger, K., and Defossa, E. (2005) Acyl ureas as human liver glycogen phosphorylase inhibitors for the treatment of type 2 diabetes. J. Med. Chem. 48, 6178-6193.
9. Oikonomakos, N. G., Kosmopoulou, M. N., Chrysina, E. D., Leonidas, D. D., Kostas, I. D., Wendt, K. U., Klabunde, T., and Defossa, E. (2005) Crystallographic studies on acyl ureas, a new class of glycogen phosphorylase inhibitors, as potential antidiabetic drugs. Protein Sci. 14, 1760-1771.
10. Defossa, E., Kadereit, D., Schoenafinger, K., Klabunde, T., Burger, H. J., Herling, A. W., Wendt, K. U., von Roedern, E., Ehnsen, A., and Rieke-Zapp, J. (2003) Preparation of 4-(benzoylureido)-benzoic acids as antidiabetics. WO2003084922, example 49.
11. Schoenafinger, K., Defossa, E., Kadereit, D., von Roedern, E., Klabunde, T., Burger, H. J., Herling, A. W., and Wendt, K. U. (2004) Preparation of heterocyclylbenzoylureas for treating type 2 diabetes. WO2004007455, example 16.
12. Defossa, E., Kadereit, D., Ruf, S., Klabunde, T., Schmoll, D., Herling, A. W., and Wendt, K. U. (2005) 7-Phenylamino-4-quinolone-3-carboxylic acid derivatives, methods for production and use thereof as medicaments. WO2005073229, example 325.
13. Rath, V. L., Ammirati, M., LeMotte, P. K., Fennell, K. F., Mansour, M. N., Danley, D. E., Hynes, T. R., Schulte, G. K., Wasilko, D. J., and Pandit, J. (2000) Activation of human liver glycogen phosphorylase by alteration of the secondary structure and packing of the catalytic core. Mol Cell 6, 139-148.
14. Kastenschmidt, L. L., Kastenschmidt, J., and Helmreich, E. (1968) Subunit interactions and their relationship to the allosteric properties of rabbit skeletal muscle phosphorylase b. Biochemistry 7, 3590-3608.
15. Murphy, K. P., and Freire, E. (1992) Thermodynamics of structural stability and cooperative folding behavior in proteins. Adv. Protein Chem. 43, 313-361.
16. Xie, D., and Freire, E. (1994) Molecular basis of cooperativity in protein folding. V. Thermodynamic and structural conditions for the stabilization of compact denatured states. Proteins 19, 291-301.
17. Segel, I. H. (1993) Enzyme Kinetics, Wiley, New York.
18. Sprang, S. R., Goldsmith, E. J., Fletterick, R. J., Withers, S. G., and Madsen, N. B. (1982) Catalytic site of glycogen phosphorylase: Structure of the T state and specificity for α-D-glucose. Biochemistry 21, 5364-5371.
19. Spolar, R. S., Livingstone, J. R., and Record, M. T., Jr. (1992) Use of liquid hydrocarbon and amide transfer data to estimate contributions to thermodynamic functions of protein folding from the removal of nonpolar and polar surface from water. Biochemistry 31, 3947-3955.
20. Gomez, J., Hilser, V. J., Xie, D., and Freire, E. (1995) The heat capacity of proteins. Proteins 22, 404-412.
21. Spolar, R. S., and Record, M. T., Jr. (1994) Coupling of local folding to site-specific binding of proteins to DNA. Science 263, 777-784.
22. Guzman-Casado, M., Sanchez-Ruiz, J. M., El, H. M., Gimenez-Gallego, G., and Parody-Morreale, A. (2000) Energetics of myoinositol hexasulfate binding to human acidic fibroblast growth factor effect of ionic strength and temperature. Eur. J. Biochem. 267, 3477-3486.
23. Murphy, K. P., Xie, D., Garcia, K. C., Amzel, L. M., and Freire, E. (1993) Structural energetics of peptide recognition: Angiotensin II/antibody binding. Proteins 15, 113-120.
24. Fukada, H., and Takahashi, K. (1998) Enthalpy and heat capacity changes for the proton dissociation of various buffer components in 0.1 M potassium chloride. Proteins 33, 159-166.
25. Bates, R. G., and Hetzer, H. B. (1961) Dissociation constant of the protonated acid form of 2-amino-2-(hydroxymethyl)-1,3-propanediol [tris(hydroxymethyl)-aminomethane] and related thermodynamic quantities from 0 to 50°. J. Phys. Chem. 65, 667-671.
26. Thomson, J. A., and Ladbury, J. E. (2004) Isothermal Titration Calorimetry: A Tutorial, in Biocalorimetrv 2 (Ladbury, J. E., and Doyle, M. L., Eds.) 1st ed., pp 37-58, John Wiley & Sons Ltd., Chichester, England.
27. Sprang, S., and Fletterick, R. J. (1980) Subunit interactions and the allosteric response in phosphorylase. Biophys. J. 32, 175-192.
28. Buchbinder, J. L., Rath, V. L., and Fletterick, R. J. (2001) Structural relationships among regulated and unregulated phosphorylases. Annu. Rev. Biophys. Biomol. Struct. 30, 191-209.
29. Baron, C., Gonzalez, J. F., Mateo, P. L., and Cortijo, M. (1989) Thermodynamic analysis of the activation of glycogen phosphorylase b over a range of temperatures. J. Biol. Chem. 264, 12872-12878.
30. Leder, L., Berger, C., Bornhauser, S., Wendt, H., Ackermann, F., Jelesarov, I., and Bosshard, H. R. (1995) Spectroscopic, calorimetric, and kinetic demonstration of conformational adaptation in peptide-antibody recognition. Biochemistry 34, 16509-16518.
31. Rath, V. L., Newgard, C. B., Sprang, S. R., Goldsmith, E. J., and Fletterick, R. J. (1987) Modeling the biochemical differences between rabbit muscle and human liver phosphorylase. Proteins 2, 225-235.
32. Holdgate, G. A., and Ward, W. H. (2005) Measurements of binding thermodynamics in drug discovery. Drug Discovery Today 10, 1543-1550.
33. Velazquez, C. A., and Freire, E. (2005) ITC in the post-genomic era. .? Priceless. Biophys. Chem. 115, 115-124.
34. Ward, W. H., and Holdgate, G. A. (2001) Isothermal titration calorimetry in drug discovery. Prog. Med. Chem. 38, 309-376.
35. Holdgate, G. A. (2001) Making cool drugs hot: Isothermal titration calorimetry as a tool to study binding energetics. BioTechniques 31, 164-184.
36. Oikonomakos, N. G., Tsitsanou, K. E., Zographos, S. E., Skamnaki, V. T., Goldmann, S., and Bischoff, H. (1999) Allosteric inhibition of glycogen phosphorylase a by the potential antidiabetic drug 3-isopropyl 4-(2-chlorophenyl)-1,4-dihydro-1-ethyl-2-methyl-pyridine-3,5,6-tricarboxylate. Protein Sci. 8, 1930-1945.
37. Steuber, H., Heine, A., and Klebe, G. (2007) Structural and thermodynamic study on aldose reductase: Nitro-substituted inhibitors with strong enthalpic binding contribution. J. Mol. Biol. 368, 618-638.