A novel approach for the virtual screening and rational design of anticancer compounds

Journal of Medicinal Chemistry

Volumn 43, Issue 10, 2000, Pages 1975-1985

  Estrada, Ernesto ^a   Uriarte, Eugenio ^a   Montero, Alina ^b   Teijeira, Marta ^a   Santana, Lourdes ^a   De Clercq, Erik ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b CENTRAL UNIVERSITY OF LAS VILLAS   (Cuba)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ENZYME INHIBITOR;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXIC T LYMPHOCYTE; DRUG DESIGN; DRUG SYNTHESIS; LEUKEMIA CELL; MOLECULAR MODEL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SCREENING;

ALKYL AND ARYL TRANSFERASES; ANIMALS; ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL SURVIVAL; DATABASES, FACTUAL; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; LEUKEMIA L1210; MICE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PURINES; SOFTWARE; T-LYMPHOCYTES; TUMOR CELLS, CULTURED;

EID: 0034038110     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991172d     Document Type: Article

References (43)

1. Kubinyi, H. Chance favors the prepared mind - from serendipity to rational drug design. J. Recept. Signal Transduct. Res. 1999, 19, 15-39.
2. Lien, E. J.; Lien, L. L. L. New drug design, discovery and development: retrospective and perspective views. Chin. Pharm. J. (Taipei) 1998, 50, 249-256.
3. Lunney, E. A. Structure-based drug design begins a new era. Med. Chem. Res. 1998, 8, 352-361.
4. Walters, W. P.; Stahl, M. T.; Murcko, M. A. Virtual Screening-An Overview. Drug Discovery Today 1998, 3, 160-178.
5. Drie, J. H. V.; Lajiness, M. S. Approaches to virtual library design. Drug Discovery Today 1998, 3, 274-283.
6. Julián-Ortiz, J. V.; Gálvez, J.; Munoz-Collado, C.; García-Domenech, R.; Gimeno-Cardona, C. Virtual Combinatorial Synthesis and Computational Screening of NewPotential Anti-Herpes Compounds. J. Med. Chem. 1999, 42, 3308-3314.
7. Denny, W. A. The role of medicinal chemistry in the discovery of DNA-active anticancer drugs: from random searching, through lead development, to de novo design. In The Search for Anticancer Drugs; Waring, M. J., Ponder, B. A. J., Eds.; Kluwer Academic Publishers: Dordrecht, 1992; Chapter 2.
8. Menta, E.; Palumbo, M. Antmeoplastic agents 1998. Expert Opin. Ther. Pat. 1998, 8, 1627-1672.
9. Balasubramanian, B. N.; Kadow, J. F.; Kramer, R. A.; Vyas, D. M. Recent developments in cancer cytotoxics. Annu. Rep. Med. Chem. 1998, 33, 151-162.
10. Ferrante, K.; Winograd, B.; Canetta, R. Promising new developments in cancer chemotherapy. Cancer Chemother. Pharmacol. 1999, 43 (Suppl.), S61-S83.
11. Ishioka, C.; Kato, S.; Kanamura, R. Current strategies on discovery of anticancer drugs in the United States of America. Saishin Igaku 1998, 53, 1940-1945.
12. Buolamwini, J. K. Novel anticancer drug discovery. Curr. Opin. Chem. Biol. 1999, 3, 500-509.
13. Estrada, E.; Peña, A.; García-Domenech, R. Designing sedative/ hypnotic compounds from a novel substructural graph-theoretical approach. J. Comput.-Aided Mol. Des. 1998, 2, 583-595.
14. Estrada, E. Spectral moments of the edge adjacency matrix in molecular graphs. 1. Definition and applications to the prediction of physical properties of alkanes. J. Chem. Inf. Comput. Sci. 1996, 36, 844-849.
15. Estrada, E. Spectral moments of the edge adjacency matrix in molecular graphs. 2. Molecules containing heteroatoms and QSAR applications. J. Chem. Inf. Comput. Sci. 1997, 37, 320-328.
16. Estrada, E. Spectral moments of the edge adjacency matrix in molecular graphs. 3. Molecules containing cycles. J. Chem. Inf. Comput. Sci. 1998, 38, 23-27.
17. Estrada, E. Modelling the diamagnetic susceptibilities of organic compounds by a substructural graph theoretical approach. J. Chem. Soc., Faraday Trans. 1998, 94, 1407-1411.
18. Estrada, E.; Gutierrez, Y. Modeling chromatographic parameters by a novel graph theoretical sub-structural approach. J. Chromatogr. A 1999, 858, 187-199.
19. Estrada, E. Edge adjacency relationships and a novel topological index related to molecular volume. J. Chem. Inf. Comput. Sci. 1995, 35, 31-33.
20. Ferguson, L. N. The Modern Structural Theory of Organic Chemstry; Prentice Hall: Englewood Cliffs, NJ, 1963; pp 200-203.
21. Estrada, E. On the topological sub-structural molecular design (TOSS-MODE) in QSPR/QSAR and drug design research. SAR QSAR Environ. Res. 2000, 11, 55-73.
22. Albert, A. Selective Toxicity. The Physico-Chemical Basis of Therapy; Chapman and Hall: London, 1984.
23. Willet, P.; Barnard, J. M.; Downs, G. M. Chemical similarity searching. J. Chem. Inf. Comput. Sci. 1998, 38, 983-996 and references therein.
24. Estrada, E. Characterization of 3D molecular structure. Chem. Phys. Lett. 2000, 319, 713-718.
25. Estrada, E. Generalized spectral moments of the iterated line graph sequence. A novel approach to QSPR studies. J. Chem. Inf. Comput. Sci. 1999, 39, 90-95.
26. Randic, M. On characterization of chemical structure. J. Chem. Inf. Comput. Sci. 1997, 37, 672-687.
27. Negwer, M. Organic-Chemical Drugs and their Synonyms; Akademie-Verlag: Berlin, 1987.
28. STATISTICA, version 4.13; Statsoft Inc., 1993.
29. Craig, P. N. Substructural Analysis and Compound Selection. In Comprehensive Medicinal Chemistry. The Rational Design, Mechanistic Study & Therapeutic Application of Chemical Compounds. Vol. 4. Quantitative Drug Design; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; pp 645-666.
30. Chu, K. C.; Feldman, R. J.; Shapiro, M. B.; Haza, G. F. pattern recognition and structure-activity relationship studies. Computer-assisted prediction of antitumor activity in structurally diverse drugs in an experimental mouse brain tumor system. J. Med. Chem. 1975, 18, 539-545.
31. Leonard, D. M. Ras Farnesyltransferase: A New Therapeutic Target. J. Med. Chem. 1997, 40, 2971-2990.
32. Gibbs, J. B.; Graham, S. L.; Hartmen, G. D.; Koblan, K. S.; Kohl, N. E.; Omer, C. A.; Oliff, A. Franesyltransferase inhibitors verus Ras inhibitors. Curr. Opin. Biol. Chem. 1997, 1, 197-203.
33. Singh, S. B.; Zink, D. L.; Willians, M.; Polishook, J. D.; Sanchez, M.; Silverman, K. C.; Lingham, R. B. Kampanols: novel Ras farnesyl-protein transferase from Stachybotrys kampalensis. Bioog. Med. Chem. Lett. 1998, 8, 2071-2076.
34. Kaminski, J. J.; Rane, D. F.; Snow, M. E.; Weber, L.; Rothofsky, M. L.; Anderson, S. D.; Lin, S. L. Identification of Novel Farnesyl Protein Transferase Inhibitors Using Three-Dimensional Database Searching Methods. J. Med. Chem. 1997, 40, 4103-4112.
35. Teijeira, M. Nucleosidos carbocíclicos 1,2-disubstituidos. Ph.D. Thesis, Universidad de Santiago de Compostela, Spain, 1996.
36. Shealy, Y. F.; O'Dell, C. A. Synthesis of the Carbocyclic Analogues of Uracil Nucleosides. J. Heterocycl. Chem. 1976, 13, 1015-1020.
37. Hronowski, L. J. J.; Szarek, W. A. Regioespecific Synthesis of Cyclopentane Analogues of (2′-and 3′-deoxy-treo-pentofuranosyl)-uracil and -2-thiouracil Nucleosides. Can. J. Chem. 1985, 63, 2787-2797.
38. Herdewijn, P.; De Clercq, E.; Balzarini, J.; Vanderhaeghe, H. Synthesis and Antiviral Activity of the Carbocyclic Analogues of (E)-5-(2-halovinyl)-2′-deoxyuridines and (E)-5-(2-halovinyl)-2′-deoxycytidines. J. Med. Chem. 1985, 28, 550-555.
39. Katagiri, N.; Nomura, M.; Sano, H.; Kaneko, C.; Yusa, K.; Tsuruo, T. Synthesis and Anti-HIV Activity of 9-[c-4,t-5-Bis-(hydroxymethyl)cyclopent-2-en-r-l-yl]-9H-adenine. J. Med. Chem. 1992, 35, 1882-1886.
40. Vince, R.; Hua, M. Synthesis and Anti-HIV Activity of Carbocyclic 2′,3′-Didehydro-2′,3′-dideoxy 2,6-Disubstituted Purine Nucleosides. J. Med. Chem. 1990, 33, 17-21.
41. Santana, L.; Teijeira, M.; Uriarte, E. A Sligtly Shorter Route to Carbocyclic Nucleosides. Synthesis of (±)-trans-1-[2-(Hydroxymethyl)cyclopentylmethyl]uracil. J. Heterocycl. Chem. 1999, 36, 293-295.
42. Santana, L.; Teijeira, M.; Uriarte, E.; Terán, C.; Castellato, U.; Grazini, R. Synthesis of cis-1-[(2-hydroxymethyl)cyclopentyl]-uridine and determination of its conformation by X-ray crystallography and AMI theoretical calculations. Nucleosides Nucleotides 1996, 15, 1179-1187.
43. De Clercq, E. In In vivo and ex vivo test systems to rationalize drug design and delivery; Crommelin, D., Couvreur, P., Duchene, D., Eds.; Editions de Santé: Paris, France, 1994; pp 108-125.