Molecular quantum similarity-based QSARs for binding affinities of several steroid sets

Journal of Chemical Information and Computer Sciences

Volumn 42, Issue 5, 2002, Pages 1185-1193

  Gironés, Xavier ^a   Carbó Dorca, Ramon ^a  

^a UNIVERSITY OF GIRONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING AFFINITY;

BIOLOGICAL MATERIALS; COMPUTATION THEORY; INTEGRAL EQUATIONS; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY;

MOLECULAR STRUCTURE;

AROMATASE; CHOLESTENONE 5ALPHA REDUCTASE; OXIDOREDUCTASE; STEROID; TRANSCORTIN;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; DRUG DESIGN; HUMAN; IN VITRO STUDY; METABOLISM; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM THEORY;

AROMATASE; CHOLESTENONE 5 ALPHA-REDUCTASE; COMPUTER SIMULATION; DRUG DESIGN; HUMANS; MODELS, CHEMICAL; OXIDOREDUCTASES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY; STEROIDS; TRANSCORTIN;

EID: 0036708525     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci0202842     Document Type: Article

References (68)

1. Juts, P.C. Quantitative Structure-Property Relationships (QSPR). In Encyclopedia of Computational Chemistry; Schleyer, P.v.R., Allinger, N.L., Clark, T., Gasteiger, J., Kollman, P.A., Schaefer, H.F., III, Schreiner, P.R., Eds.; John Wiley and Sons Ltd.: Chichester, UK, 1998; Vol. 4, pp 2320-2330.
2. Kubinyi, H. Quantitative Structure-Activity Relationships in Drug Design. In Encyclopedia of Computational Chemistry; Schleyer, P.v.R., Allinger, N.L., Clark, T., Gasteiger, J., Kollman, P.A., Schaefer, H.F., III, Schreiner, P.R., Eds.; John Wiley and Sons Ltd.: Chichester, UK, 1998; Vol. 4, pp 2309-2319.
3. Quoted in the following: Borman, S. New QSAR Techniques Eyed for Environmental Assessments. Chem. Eng. News 1990, 68, 20-23.
4. Hammett, L.P. The Effect of Structures upon the Reactions of Organic Compounds. Benzene Derivatives. J. Am. Chem. Soc. 1937, 59, 96-103.
5. Hansch, C.; Fujita, T. σ-ρ-π analysis. A method for the correlation of biological activity and chemical structure. J. Am. Chem. Soc. 1964, 86, 5175-5180.
6. Structure-Property Correlations in Drug Research; Waterbeemd, van de H., Ed.; Academic, R.G. Landes Company: Austin, 1996.
7. Carbó, R.; Arnau, J.; Leyda, L. How similar is a molecule to another? An electron density measure of similarity between two molecular structures. Int. J. Quantum Chem. 1980, 17, 1185-1189.
8. Carbó-Dorca, R.; Besalú, E. A general survey of molecular quantum similarity. TEOCHEM 1998, 451, 11-23.
9. Carbó-Dorea, R.; Amat, L.; Besalú, E.; Lobato, M. Quantum Similarity. In Advances in Molecular Similarity; Carbó-Dorea, R., Mezey, P.G., Eds.; JAI Press: Greenwich, CT, 1998; Vol. 2, pp 1-42.
10. Carbó-Dorca, R. Fuzzy sets and Boolean tagged sets; vector semispaces and convex sets; quantum similarity measures and ASA density functions; diagonal vector spaces and quantum chemistry. In Advances in molecular similarity; Carbó-Dorca, R., Mezey, P.G., Eds.; JAI Press: Greenwich, CT, 1998; Vol. 2, pp 43-72.
11. Besalú, E.; Carbó, R.; Mestres, J.; Solà, M. Foundations and recent developments on molecular quantum similarity. Top. Curr. Chem. 1995, 173, 31-62.
12. Carbó, R.; Besalú, E.; Theoretical foundations of quantum molecular similarity. In Molecular similarity and reactivity: from quantum chemical to phenomenological approaches; Carbo, R., Ed.; Kluwer: Amsterdam, 1995; pp 3-30.
13. Carbó-Dorea R.; Besalú, E.; Amat, L.; Fradera, X. Quantum molecular similarity measures: concepts, definitions and applications to quantitative structure-properties relationships. In Advances in molecular similarity; Carbó-Dorca, R., Mezey, P.G., Eds.; JAI Press: Greenwich, CT, 1996; Vol. 1, pp 1-42.
14. Carbó, R.; Besalú, E.; Amat, L.; Fradera, X. Quantum molecular similarity measures (QMSM) as a natural way leading towards a theoretical foundation of quantitative structure-properties relationships. J. Math. Chem. 1995, 18, 237-246.
15. Fradera, X.; Amat, L.; Besalú, E.; Carbó-Dorca, R. Application of molecular quantum similarity to QSAR. Quant. Struct.-Act. Relat. 1997, 16, 25-32.
16. Lobato, M.; Amat, L.; Carbó-Dorca, R. Structure-activity relationships of a steroid family using quantum similarity measures and topological quantum similarity indices. Quant. Struct.-Act. Relat. 1997, 16, 465-472.
17. Amat, L.; Robert, D.; Besalú, E.; Carbó-Dorca, R. Molecular quantum similarity measures tuned 3D QSAR: an antitumoral family validation study. J. Chem. Inf. Comput. Sci. 1998, 38, 624-631.
18. Robert, D.; Amat, L.; Carbó-Dorca, R. Three-dimensional quantitative structure-activity relationships from tuned molecular quantum similarity measures. Prediction of the corticosteroid-binding globulin binding affinity for a steroid family. J. Chem. Inf. Comput. Sci. 1999, 39, 333-344.
19. Robert, D.; Gironés, X.; Carbó-Dorca, R. Facet diagrams for quantum similarity data. J. Comput.-Aided Mol. Des. 1999, 13, 597-610.
20. Gironés, X.; Amat, L.; Robert, D.; Carbó-Dorca, R. Use of electron-electron repulsion energy as a molecular descriptor in QSAR and QSPR studies. J. Comput.-Aided Mol. Des. 2000, 14, 477-485.
21. Robert, D.; Carbó-Dorca, R., Aromatic compounds aquatic toxicity QSAR using quantum similarity measures. SAR QSAR Environ. Res. 1999, 10, 401-422.
22. Gironés, X.; Amat, L.; Carbó-Dorca, R. Using molecular quantum similarity measures as descriptors in quantitative structure-toxicity relationships. SAR QSAR Environ. Res. 1999, 10, 545-556.
23. Dean, P.M. Molecular Similarity. In 3D QSAR in Drug Design: Theory, Methods and Applications; Kubinyi, H., Ed.; ESCOM Science Publishers B.V.: Leiden, The Netherlands, 1993; pp 150-172.
24. Richards, W.G. Molecular Similarity and Dissimilarity. In Modeling of Biomolecular Structures and Mechanisms; Pullman, A., Jortner, J., Pullman, B., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995; pp 365-369.
25. Gironés, X.; Robert, D.; Carbó-Dorca, R. TGSA: a molecular superposition program based on Topo-Geometrical Considerations. J. Comput. Chem. 2001, 22, 255-263.
26. Carbó-Dorca, R. Stochastic Transformation of Quantum Similarity Matrices and Their Use in Quantum QSAR (QQSAR) Models. Int. J. Quantum. Chem. 2000, 79, 163-177.
27. Constants, P.; Carbó, R. Atomic shell approximation: electron density fitting algorithm restricting coefficients to positive values. J. Chem. Inf. Comput. Sci. 1995, 35, 1046-1053.
28. Amat, L.; Carbó-Dorca, R. Quantum similarity measures under atomic shell approximation: first-order density fitting using elementary Jacobi rotations. J. Comput. Chem. 1997, 18, 2023-2039.
29. Amat, L.; Carbó-Dorca, R. Fitted electronic density functions from H to Rn for use in quantum similarity measures: cis-diamminedichloro-platinum(II) complex as an application example. J. Comput. Chem. 1999, 20, 911-920.
30. WebLab Viewer Pro 4.0; Molecular Simulations Inc., 2000. A free trial version is available from its website: http://www.msi.com.
31. Lovanov, V. Mopac 6.0; University of Florida, 1996.
32. Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. AM1: A New General Purpose Quantum Chemical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
33. Höskuldsson A. Prediction Methods in Science and Technology; Thor, Copenhagen, 1996.
34. Tenenhaus, M. Regression de PLS; Editions Technip: Paris, 1997.
35. Wold, S.; Johansson, E.; Cocchi, M. PLS - Partial Least-Squares Projections to Latent Structures. In 3D QSAR in Drug Desing, Theory, Methods and Applications; Kubinyi, H., Ed.; ESCOM Science: Leiden, 1993; pp 523-550.
36. Wold, S. PLS for multivariate linear modelling. In Methods and Principles in Medicinal Chemistry. Vol. 2: Chemometric Methods in Molecular Design; van de Waterbeemd, H., Ed.; VCH: Weinheim, 1995; pp 195-218.
37. Cramer, R.D., III; Patterson, D.E.; Bunce, J.D. Comparative Molecular Field Analysis (CoMFA). 1. Effect on Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
38. Wold, S.; Sjöström, M.; Eriksson, L. Partial Least Squares Projections to Latent Structures (PLS) in Chemistry. In Encyclopedia of Computational Chemistry; Schleyer, P.v.R., Allinger, N.L., Clark, T., Gasteiger, J., Kollman, P.A., Schaefer, H.F., III, Screiner, P.R., Ed.; John Wiley and Sons Ltd.: Chichester, UK, 1994; Vol. 4, pp 2006-2021.
39. Geladi, P.; Kowalski, B.R. Partial Least-Squares Regression: A Turorial. Anal. Chim. Acta 1986, 185, 1-17.
40. Montgomery, D.C.; Peck, E.A. Introduction to linear regression analysis; Wiley: New York, 1992.
41. Wold, S. Cross-validatory estimation of a number of components in factor and principal component models. Technometrics 1978, 20, 397-405.
42. 13C NMR Quantitative Spectrometric Data-Activity Relationship (QSDAR) Models of Steroids Binding the Aromatase Enzyme. J. Chem. Inf. Comput. Sci. 2001, 41, 1360-1366.
43. Bakken, G.A.; Jurs, P.C. QSARs for 6-Azasteroids as Inhibitors of Human Type 1 5alpha-Reductase: Prediction of Binding Affinity and Selectivity Relative to 3-BHSD. J. Chem. Inf. Comput. Sci. 2001, 41, 1255-1265.
44. Cramer, R.D.; Patterson, D.E.; Bunce, J.D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to cartier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
45. Maw, H.H.; Hall, L.H. E-State modeling of corticosteroid binding affinity validation of model for small data set. J. Chem. Inf. Comput. Sci. 2001, 41, 1248-1254.
46. Brodie, A.M.; Santen, R.J. Aromatase and its inhibitors in breast cancer treatment - overview and prespective. Breast Cancer Res. Treat. 1994, 30, 1-6.
47. Brodie, A.M. Aromatase inhibitors in the treatment of breast cancer. J. Steroid Biochem. Mol. Biol. 1994, 49, 281-287.
48. Singh, S.M.; Gauthier, S.; Labrie, F. Androgen receptor antagonists (antiandrogens): structure-activity relationships. Curt. Med. Chem. 2000, 7, 211-247.
49. Clifford, G.M.; Farmer, R.D.T.; Medical therapy for benign prostatic hyperplasia: a review of the literature. Eur. Urol. 2000, 38, 2-19.
50. Bartsch, G.; Rittmaster, R.S.; Klocker, H. Dihydrotestosterone and the concept of 5α-reductase inhibition in human benign prostatic hyperplasia. Ear. Urol. 2000, 37, 367-380.
51. Weisser, H.; Tunn, S.; Debus, M.; Krieg, M. 5α-reductase inhibition by finasterine (Proscar) in epithelium and stroma of human benign prostatic hyperplasia. Steroids 1994, 59, 616-620.
52. Tolman, R.L.; Sahoo, S.P., Bakshi, R.K.; Gratale, D.; Patel, G.; Patel, S.; Toney, J.; Chang, B.; Harris, G.S. 4-methyl-3-oxo-4-aza-5α-androst-1-ene-17β-aryl-carboxamides: an approach to combined androgen blockade. J. Steroid Biochem. Mol. Biol. 1997, 60, 303-309.
53. 17α): potential agents for the treatment of prostate cancer. J. Med. Chem. 1998, 41, 902-912.
54. 17α). J. Med. Chem. 1997, 40, 297-3304.
55. Thiboutot, D.; Bayne, E.; Thorne, J. Gilligard, K.; Flanagan, J.; Shao, Q.; Light, J.; Helm, K. Immunolocalization of 5α-reductase isozyme in acne lesions and normal skin. Arch. Dermantol. 2000, 136, 11251129.
56. Guarna, A.; Occihiato, E.G.; Banzo, G.; Conti, A.; Serio, M. 5α-reductase inhibitors, chemical and clinical models. Steroids 1998, 63, 355-361.
57. Guarna, A.; Mechetti, F.; Occhiato, E.G.; Scarpi, D. Benzo[c]-quinolin-3-ones: a novel class of potent and selective nonsteroidat inhibitors of human 5α-reductase 1. J. Med. Chem. 2000, 43, 3718-3735.
58. Hogan, D.J.; Chamberlain, M. Male pattern baldness. South. Med. J. 2000, 93, 657-662.
59. Rusell, D.W.; Wilson, J.D. Steroid 5α-reductase: two genes/two enzymes. Annu. Rev. Biochem. 1994, 63, 25-61.
60. 5-steroid isomerase by 6-azaandrost-4-en-3-ones: optimization of C17 substituent. J. Med. Chem. 1995, 38, 2621-2627.
61. 5-steroid isomerase. J. Med. Chem. 1994, 37, 2352-2360.
62. Kurup, A.; Garg, R.; Hansch, C. Comparative QSAR analysis of 5α-reductase inhibitors. Chem. Rev. 2000, 100, 909-924.
63. Foye, W.O. Principles of medicinal chemistry, 3rd ed.; Lea & Febiger: Philadelphia, 1989.
64. McCluskey, P.J.; Towler, H.M.; Lightman, S. Management of chronic uveitis. S. Br. Med. J. 2000, 320, 555-558.
65. Slavkin, H.C. The body's skin frontier and the challenges of wound healing: keloids. J. Am. Dental Assoc. 2000, 131, 362-365.
66. Rampton, D.S. Management of Crohn's disease. Br. Med. J. 1999, 319, 1480-1485.
67. Baud, O.; Foix-L'Helias, L.; Kamiski, M.; Audibert, F.; Jarreau, P.; Papiernick, E.; Huon, C.; Lepercq, J.; Dehan, M.; Lacaze-Masmonteil, T. Antenatal glucocorticoid treatment and cystic periventricular leukornalacia in very premature infants. New Engl. J. Med. 1999, 341, 1190-1196.
68. Gregorio, C.; Kier, L.B.; Hall, L.H. QSAR modeling with the electrotopological state indices: corticosteroids. J. Comput.-Aided Mol. Des. 1998, 12, 557-561.