Quantitative antidiabetic activity prediction for the class of guanidino- and aminoguanidinopropionic acid analogs based on electron-conformational studies

Journal of Chemical Information and Modeling

Volumn 48, Issue 3, 2008, Pages 556-568

  Marenich, Aleksandr V ^a   Yong, Pei Han ^a   Bersuker, Isaac B ^a   Boggs, James E ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MEDICAL PROBLEMS; OXYGEN;

HYPOGLYCEMIC ACTIVITIES; PHARMACOPHORE (PHA);

DRUG THERAPY;

ANTIDIABETIC AGENT; GUANIDINE; PROPIONIC ACID; PROPIONIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; ELECTRON; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ELECTRONS; GUANIDINE; HYPOGLYCEMIC AGENTS; MOLECULAR CONFORMATION; PROPIONIC ACIDS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 42149117936     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci700401p     Document Type: Article

References (39)

1. Karam, J. H. In Basic & Clinical Pharmacology; Katzung, B. G., Ed.; Appleton & Lange: Stamford, CT, 1998; pp 684-705.
2. Larsen, S. D.; Connell, M. A.; Cudahy, M. M.; Evans, B. R.; May, P. D.; Meglasson, M. D.; O'Sullivan, T. J.; Schostarez, H. J.; Sih, J. C.; Stevens, F. C.; Tanis, S. P.; Tegley, C. M.; Tucker, J. A.; Vaillancourt, V. A.; Vidmar, T. J.; Watt, W.; Yu, J. H. Synthesis and Biological Activity of Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid: Discovery of a Novel Aminoguanidinoacetic Acid Antidiabetic Agent. J. Med. Chem. 2001, 44, 1217-1230.
3. Vaillancourt, V. A.; Larsen, S. D.; Tanis, S. P.; Burr, J. E.; Connell, M. A.; Cudahy, M. M.; Evans, B. R.; Fisher, P. V.; May, P. D.; Meglasson, M. D.; Robinson, D. D.; Stevens, F. C.; Tucker, J. A.; Vidmar, T. J.; Yu, J. H. Synthesis and Biological Activity of Aminoguanidine and Diaminoguanidine Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid. J. Med. Chem. 2001, 44, 1231-1248.
4. Pharmacophore Perception, Development and Use in Drug Design; Güner, O. F., Ed.; International University Line: La Jolla, CA, 2000.
5. Venkatarangan, P.; Hopfinger, A. J. Prediction of Ligand-Receptor Binding Thermodynamics by Free Energy Force Field Three-Dimensional Quantitative Structure-Activity Relationship Analysis: Applications to a Set of Glucose Analogue Inhibitors of Glycogen Phosphorylase. J. Med. Chem. 1999, 42, 2169-2179.
6. Liao, C.; Xie, A.; Shi, L.; Zhou, J.; Lu, X. Eigenvalue Analysis of Peroxisome Proliferator-Activated Receptor y Agonists. J. Chem. Inf. Comput. Sci. 2004, 44, 230-238.
7. Calabuig, C.; Antón-Fos, G. M.; Gálvez, J.; García-Doménech, R. New Hypoglycaemic Agents Selected by Molecular Topology. Int. J. Pharm. 2004, 278, 111-118.
8. Bersuker, I. B.; Bahceci, S.; Boggs, J. E.; Pearlman, R. S. An Electron-Conformational Method of Identification of Pharmacophore and AntiPharmacophore Shielding: Application to Rice Blast Activity. J. Comput.-Aided Mol. Des. 1999, 13, 419-434.
9. Bersuker, I. B.; Bahceci, S.; Boggs, J. E. improved Electron- Conformational Method of Pharmacophore Identification and Bioactivity Prediction. Application to Angiotensin Converting Enzyme Inhibitors. J. Chem. Inf. Comput. Sci. 2000, 40, 1363-1376.
10. Bersuker, I. B. Pharmacophore Identification and Quantitative Bioactivity Prediction Using the Electron-Conformational Method. Curr. Pharm. Des. 2003, 9, 1575-1606.
11. Bersuker, I. B.; Dimoglo, A. S. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York, 1991; Vol. 2, pp 423-460.
12. Rosines, E.; Bersuker, I. B.; Boggs, J. E. Pharmacophore Identification and Bioactivity Prediction for Group I Metabotropic Glutamate Receptor Agonists by the Electron-Conformational QSAR Method. Quant. Struct.-Act. Relat. 2001, 20, 327-334.
13. Makkouk, A. H.; Bersuker, I. B.; Boggs, J. E. Quantitative Drug Activity Prediction for Inhibitors of Human Breast Carcinoma. Int. J. Pharm. Med 2004, 18, 81-89.
14. Liu, S.-S.; Yin, C.-S.; Li, Z.-L.; Cai, S.-X. QSAR Study of Steroid Benchmark and Dipeptides Based on MEDV-13. J. Chem. Inf. Comput. Sci. 2001, 41, 321-329.
15. Guzel, Y.; Ozturk, E. Study of the Binding Affinity for Corticosteroid-Binding Globulin (CBG) Using the Electron Topological Method (ETM) as Three-Dimensional Quantitative Structure-Activity Relationship (3D QSAR). Bioorg. Med Chem. 2003, 11, 4383-4388.
16. Alton, A.; Golcuk, K.; Kumru, M.; Jalbout, A. F. Electron-Conformational Study for the Structure-Hallucinogenic Activity Relationships of Phenylalkylamines. Bioorg. Med. Chem. 2003, 11, 3861-3868.
17. Oruc, E. E.; Rollas, S.; Kandemirli, F.; Shvets, N.; Dimoglo, A. S. 1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure-Antituberculosis Activity Relationship Investigation. J. Med. Chem. 2004, 47, 6760-6767.
18. Halgren, T. A. Merck Molecular Force Field. I. Basis, Form, Scope, Parameterization, and Performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519.
19. Stewart, J. J. P. Optimization of Parameters for Semiempirical Methods. I. Method. J. Comput. Chem. 1989, 10, 209-220.
20. Møller, C.; Plesset, M. S. Note on an Approximation Treatment for Many-Electron Systems. Phys. Rev. 1934, 46, 618-622.
21. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
22. Spartan'02 is available from Wavefunction, Inc., Irvine, CA, U.S.A. Except for molecular mechanics and semiempirical models, the calculation methods used in Spartan'02 have been documented in the following: Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, D.; Adamson, R. D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C.; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.; Maurice, D. R.; Nair, N.; Shao, Y.; Besley, N. A.; Maslen, P. E.; Dombroski, J. P.; Daschel, H.; Zhang, W.; Korambath, P. P.; Baker, J.; Byrd, E. F. C.; Voorhis, T. V.; Oumi, M.; Hirata, S.; Hsu, C.-P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-Gordon, M.; Pople, J. A. Q-Chem 2.0: a High-Performance Ab Initio Electronic Structure Program Package. J. Comput. Chem. 2000, 21, 1532-1548.
23. Hehre, W. J. A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction, Inc.: Irvine, CA, 2003.
24. Mulliken, R. S. Electronic Population Analysis on LCAO-MO Molecular Wave Functions. J. Chem. Phys. 1955, 23, 1833-1840.
25. Pauling, L. The Nature of The Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, New York, 1960.
26. Basch, H.; Viste, A.; Gray, H. B. Valence Orbital Ionization Potentials from Atomic Spectral Data. Theor. Chim. Acta 1965, 3, 458-464.
27. Bondi, A. Van der Waals Volumes and Radii. J. Phys. Chem. 1964, 68, 441-451.
28. Livingstone, D. Data Analysis for Chemists: Applications to QSAR and Chemical Product Design; Oxford University Press: New York, 1995.
29. Chambers, C. C.; Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. Model for Aqueous Solvation Based on Class IV Atomic Charges and First Solvation Shell Effects. J. Phys. Chem. 1996, 100, 16385-16398.
30. Ghose, A. K.; Pritchett, A.; Crippen, G. M. Atomic Physicochemical Parameters for Three Dimensional Structure Directed Quantitative Structure-Activity Relationships III: Modeling Hydrophobic Interactions. J. Comput. Chem. 1988, 9, 80-90.
31. Livingstone, D. J. In Predicting Chemical Toxicity and Fate; Cronin, M. T. D., Livingstone, D. J., Eds.; CRC Press: Boca Raton, FL, 2004; Chapter 7, pp 151-170.
32. Lohray, B. B.; Bhushan, V. Advances in Insulin Sensitizers. Curr. Med. Chem. 2004, 11, 2467-2503.
33. Imoto, H.; Sugiyama, Y.; Kimura, H.; Momose, Y. Studies on Non-Thiazolidinedione Antidiabetic Agents. 2. Novel Oxyiminoalkanoic Acid Derivatives as Potent Glucose and Lipid Lowering Agents. Chem. Pharm. Bull. 2003, 51, 138-151.
34. Desai, R. C.; Han, W.; Metzger, E. J.; Bergman, J. P.; Gratale, D. F.; MacNaul, K. L.; Berger, J. P.; Doebber, T. W.; Leung, K.; Moller, D. E.; Heck, J. V.; Sahoo, S. P. 5-Aryl Thiazolidine-2,4-diones: Discovery of PPAR Dual α/γ Agonists as Antidiabetic Agents. Bioorg. Med. Chem. Lett. 2003, 13, 2795-2798.
35. Kees, K. L.; Fitzgerald, J. J., Jr.; Steiner, K. E.; Mattes, J. F.; Mihan, B.; Tosi, T.; Mondoro, D.; McCaleb, M. L. New Potent Antihyperglycemic Agents in db/db Mice: Synthesis and Structure-Activity Relationship Studies of (4-Substituted benzyl)(trifluoromethyl)pyrazoles and -pyrazolones. J. Med. Chem. 1996, 39, 3920-3928.
36. Bihan, G. L.; Rondu, F.; Pelé-Tounian, A.; Wang, X.; Lidy, S.; Touboul, E.; Lamouri, A.; Dive, G.; Huet, J.; Pfeiffer, B.; Renard, P.; Guardiola-Lemaître, B.; Manéchez, D.; Pénicaud, L.; Ktorza, A.; Godfroid, J.-J. Design and Synthesis of Imidazoline Derivatives Active on Glucose Homeostasis in a Rat Model of Type II Diabetes. 2. Syntheses and Biological Activities of 1,4-Dialkyl-, 1,4-Dibenzyl, and 1-Benzyl-4-alkyl-2- (4′,5′-dihydro-1′H-imidazole-2′-yl)piperazinesand Isosteric Analogues of Imidazoline. J. Med. Chem. 1999, 42, 1587-1603.
37. Marenich, A. V.; Olson, R. M.; Kelly, C. P.; Cramer, C. J.; Truhlar, D. G. Self-Consistent Reaction Field Model for Aqueous and Nonaqueous Solutions Based on Accurate Polarized Partial Charges. J. Chem. Theory Comput. 2007, 3, 2011 -2033.
38. Thompson, J. D.; Xidos, J. D.; Sonbuchner, T. M.; Cramer, C. J.; Truhlar, D. G. More Reliable Partial Atomic Charges When Using Diffuse Basis Sets. PhysChemComm 2002, 5, 117-134.
39. Bersuker, I. B.; Dimoglo, A. S.; Gorbachov, M. Yu.; Vlad, P. F.; Pesaro, M. Origin of Musk Fragrance Activity: the Electron-Topologic Approach. New J. Chem. 1991, 15, 307-320.