Autocorrelation of molecular electrostatic potential surface properties combined with partial least squares analysis as new strategy for the prediction of the activity of human A3 adenosine receptor antagonists

Journal of Medicinal Chemistry

Volumn 48, Issue 18, 2005, Pages 5698-5704

  Moro, Stefano ^a   Bacilieri, Magdalena ^a   Cacciari, Barbara ^c   Spalluto, Giampiero ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

^c UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE A3 RECEPTOR ANTAGONIST;

ARTICLE; CORRELATION ANALYSIS; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; HUMAN; MATHEMATICAL MODEL; PREDICTION; QUANTITATIVE ANALYSIS; STRUCTURE ANALYSIS; SURFACE PROPERTY; THREE DIMENSIONAL IMAGING; VALIDATION PROCESS;

BINDING SITES; DATABASES, FACTUAL; ELECTROSTATICS; HUMANS; LEAST-SQUARES ANALYSIS; LIGANDS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, ADENOSINE A3; SURFACE PROPERTIES;

EID: 24744444738     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0502440     Document Type: Article

References (45)

1. Moro, S.; Deflorian, F.; Spalluto, G.; Pastorin, G.; Cacciari, B.; et al. Demystifying the three dimensional structure of G protein-coupled receptors (GPCRs) with the aid of molecular modeling. Chem. Commun. 2003, 24, 2949-2956.
2. 3 adenosine receptor as an example. Trends Pharmacol. Sci. 2005, 26, 44-51.
3. 3 receptor ligands. Curr. Top. Med. Chem. 2003, 3, 445-462.
4. 3 adenosine receptors. In Annual Reports in Medicinal Chemistry; Doherty, A. M., Ed.; Elsevier: San Diego, CA, 2003; Vol. 38, pp 121-130.
5. 3 adenosine receptor antagonists. J. Med. Chem. 1999, 42, 706-721.
6. 6-(2-phenylethyl)adenosine derivatives as potent ligands. Bioorg. Med. Chem. 2004, 12, 2021-2034.
7. 3 adenosine receptor antagonists: Pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine derivatives as a key study. J. Med. Chem. 2005, 48, 152-162.
8. Kubinyi, H., Folkers, G., Martin, Y. C., Eds. 3D QSAR in Drug Design; Kluwer: Dordrecht, The Netherlands, 1998; Vols. 2 and 3.
9. Moro, S.; Bacilieri, M.; Ferrari, C.; Spalluto, G. Autocorrelation of molecular electrostatic potential surface properties combined with partial least squares analysis as alternative attractive tool to generate ligand-based 3D-QSARs. Curr. Drug Discovery Technol. 2005, 2, 13-21.
10. 3 adenosine receptor antagonists. J. Med. Chem. 1996, 39, 2293-2301.
11. Ji, X.; Melman, N.; Jacobson, K. A. Interaction of flavonoids and other phytochemicals with adenosine receptors. J. Med. Chem. 1996, 39, 781-788.
12. 3 receptors. J. Med. Chem. 1996, 39, 2980-2989.
13. 3 adenosine receptor antagonists. J. Med. Chem. 1996, 39, 4667-4675.
14. 3 adenosine receptor antagonists. J. Med. Chem. 1998, 41, 3186-3201.
15. 3 receptor subtype. J. Med. Chem. 1996, 39, 4142-4148.
16. 3 receptor subtype. J. Med. Chem. 1998, 41, 2835-2845.
17. 3-adenosine receptor antagonists. J. Med. Chem. 2002, 45, 3440-3450.
18. Colotta, V.; Catarzi, D.; Varano, F.; Cecchi, L.; Filacchioni, G.; Martini, C.; Trincavelli, L.; Lucacchini, A. 1,2,4-Triazolo[4,3-a]-quinoxalin-1- one: a versatile tool for the synthesis of potent and selective adenosine receptor antagonists. J. Med. Chem. 2000, 43, 1158-1164.
19. 3 receptor ligands. 2. Structure affinity profile of a series of isoquinoline and quinazoline compounds. J. Med. Chem. 1998, 41, 3994-4000.
20. 3 receptor. J. Med. Chem. 2000, 43, 2227-2238.
21. Van Muijlwijk-Koezen, J. E.; Timmerman, H.; Vollinga, R. C.; von Drabbe Künzel, J. F.; de Groote, M.; Visser, S.; Ijzerman, A. P. Thiazole and thiazole analogues as novel class of adenosine receptor antagonists. J. Med. Chem. 2001, 44, 749-762.
22. 3 receptor antagonists. Bioorg. Med. Chem. 2004, 12, 613-623.
23. Camaioni, E.; Costanzi, S.; Vittori, S.; Volpini, R.; Klotz, K.; Cristalli, G. New substituted 9-alkylpurines as adenosine receptor ligands. Bioorg. Med. Chem. 1998, 6, 523-533.
24. Colotta, V.; Catarzi, D.; Varano, F.; Cecchi, L.; Filacchioni, G.; Martini, C.; Trincavelli, L.; Lucacchini, A. Synthesis and structure-activity relationships of new set of 2-arylpyrazolo[3,4-c]-quinoline derivatives as adenosine receptor antagonists. J. Med. Chem. 2000, 43, 3118-3124.
25. 3 adenosine receptor antagonists. J. Med. Chem. 2002, 45, 3337-3344.
26. 2B-selective adenosine receptor antagonists. J. Med. Chem. 2002, 45, 1500-1510.
27. q in human embryonic kidney 293 cells and HMC-1 mast cells. Mol. Pharmacol. 1999, 56, 705-713.
28. 3 adenosine receptors antagonists. J. Med. Chem. 2003, 46, 1229-1241.
29. 3 adenosine receptor antagonists. J. Med. Chem. 2000, 43, 4636-4646.
30. Gasteiger, J.; Li, X.; Rudolph, C.; Sadowsky, J.; Zupan, J. Representation of molecular electrostatic potentials by topological feature maps. J. Am. Chem. Soc. 1994, 116, 4608-4620.
31. Wagener, M.; Sadowsky, J.; Gasteiger. J. Autocorrelation of molecular surface properties for modeling corticosteroid binding globulin and cytosolic Ah receptor activity by neural networks, J. J. Am. Chem. Soc. 1995, 117, 7769-7775.
32. Clementi, S.; Cruciani, G.; Riganelli, D.; Valigi, R.; Costantino, G.; Baroni, M.; Wold, S. Autocorrelation as a Tool for a congruent description of molecules in 3D QSAR studies. Pharm. Pharmacol. Lett. 1993, 3, 5-8.
33. Blin, N.; Federici, C.; Koscielniak, T.; Strosberg, A. D. Predictive quantitative structure-activity relationships (QSAR) analysis of beta 3-adrenergic ligands. Drug Des. Discovery 1995, 12, 297-311.
34. Gancia, E.; Bravi, G.; Mascagni, P.; Zaliani, A. Global 3D-QSAR methods: MS-WHIM and autocorrelation. J. Comput.-Aided Mol. Des. 2000, 14, 293-306.
35. Pastor, M.; Cruciani, G.; McLay, I.; Pickett, S.; Clementi, S. Grid independent descriptors (GRIND). A novel class of alignment-independent three-dimensional molecular descriptors. J. Med. Chem. 2000, 43, 3233-3243.
36. Klein, C. T.; Kaiser, D.; Ecker, G. Topological distance based 3D descriptors for use in QSAR and diversity analysis. J. Chem. Inf. Comput. Sci. 2004, 44, 200-209.
37. Gupta, M. K.; Sagar, R.; Shaw, A. K.; Prabhakar, Y. S. CP-MLR directed QSAR studies on the antimycobacterial activity of functionalized alkenols-topological descriptors in modeling the activity. Bioorg. Med. Chem. 2005, 13, 343-351.
38. OpenMosix; http://www.openMosix.org, 2004.
39. ADRIANA.; Molecular Networks GmbH: Erlangen, Germany, 2003.
40. Gasteiger, J.; Marsili, M. Iterative Partial equalization of orbital electronegativity. A rapid access to atomic charges. Tetrahedron 1980, 36, 3219-3228.
41. Gasteiger, J.; Saller, H. Berechnung der ladungsverteilung in konjugierten systemen durch eine quantifizierung des mesomeriekonzeptes. Angew. Chem. 1985, 97, 699-701.
42. Moreau, G.; Broto, P. The autocorrelation of a topological structure: a new molecular descriptor. Nouv. J. Chim. 1980, 4, 359-360.
43. Moreau, G.; Broto, P. Autocorrelation of molecular structures. Application to SAR Studies. Nouv. J. Chim. 1980, 4, 757-764.
44. The Unscrambler, version 9.0; CAMO Process AS: Oslo, Norway 2003.
45. Handbook of Computational Statistics: Concepts and Methods; Gentle, James, E., Härdle, W., Mori, Y., Eds.; Springer-Verlag: New York, 2004.