Drug evolution concept in drug design: 1. Hybridization method

Journal of Medicinal Chemistry

Volumn 47, Issue 27, 2004, Pages 6973-6982

  Lazar, Carmen ^a   Kluczyk, Alicja ^a,b   Kiyota, Taira ^a   Konishi, Yasuo ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF WROC AW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 5 CHLORO 2 METHOXYBENZOIC ACID 2 (DIETHYLAMINO)ETHYL ESTER; 4 AMINOBENZOIC ACID; ACETYLSALICYLIC ACID; ANALGESIC AGENT; ANTIARRHYTHMIC AGENT; ANTIASTHMATIC AGENT; ANTICONVULSIVE AGENT; ANTIEMETIC AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ANTIPYRETIC AGENT; ANTIRHEUMATIC AGENT; ANTITUSSIVE AGENT; BENZOCAINE; CENTRAL STIMULANT AGENT; CRESOTAMIDE; DECLOPRAMIDE; DOPAMINE RECEPTOR BLOCKING AGENT; IMMUNOSTIMULATING AGENT; KERATOLYTIC AGENT; LOCAL ANESTHETIC AGENT; METOCLOPRAMIDE; PROCAINAMIDE; PROCAINE; RADIOSENSITIZING AGENT; SEDATIVE AGENT; SEROTONIN ANTAGONIST; SODIUM CHANNEL BLOCKING AGENT; SPASMOLYTIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BIOTECHNOLOGY; DRUG DESIGN; DRUG INDUSTRY; DRUG STRUCTURE; GENETIC ALGORITHM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN GENOME; HYBRIDIZATION;

4-AMINOBENZOIC ACID; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; EVOLUTION;

EID: 11144239571     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049637+     Document Type: Article

References (64)

1. Hoegl, L.; Korting, H. C.; Klebe, G. Inhibitors of aspartic proteases in human diseases: molecular modeling comes of age. Pharmazie 1999, 54, 319-329.
2. Armstrong, J. W. A review of high-throughput screening approaches for drug discovery American Biotechnology Laboratory; International Scientific Communications Inc.: Fairfield, CT, 1999, April.
3. Yu, H.; Adedoyin, A. ADME-Tox in drug discovery: Integration of experimental and computational technologies. Drug Discovery Today 2003, 8, 852-861.
4. Holland, J. H. Computer programs that "evolve" in ways that resemble natural selection can solve complex problems even their creators do not fully understand Adaptation in Natural and Artificial Systems; MIT Press: Cambridge, 1992.
5. Venkatasubramanian, V.; Chan, K.; Caruthers, J. M. Evolutionary design of molecules with desired properties using the genetic algorithm. J. Chem. Inf. Comput. Sci. 1995, 35, 188-195.
6. Weber, L. Applications of genetic algorithms in molecular diversity. Curr. Opin. Chem. Biol. 1998, 2, 381-385.
7. Negwer, M. Organic-chemical drugs and their synonyms database; Akademie Verlag GmbH: Berlin, Germany, 1994.
8. Kluczyk, A.; Kiyota, T.; Lazar, C.; Cho, S.-J.; de Macedo, P.; Konishi, Y. Drug evolution - Drug design at hot spots. PCT Int. Appl., WO 02095393, 2002.
9. a values of clinically used drugs. Anesth. Analg. 1980, 71, 158-170.
10. Li, R. A.; Tsushima, R. G.; Himmeldirk, K.; Dime, D. S.; Backx, P. H. Local anesthetic anchoring to cardiac sodium channels. Implications into tissue-selective drug targeting. Circ Res. 1999, 85, 88-98.
11. Czinn, S. J.; Carr, H. S.; Speck, W. T. Effects of topical anesthetic agents on Campylobacter pylori. J. Pediatr. Gastroenterol. Nutr. 1989, 9, 46-48.
12. Chipley, J. R.; Uraih, N. Inhibition of Aspergillus growth and aflatoxin release by derivatives of benzoic acid. Appl. Environ. Microbiol. 1980, 40, 352-357.
13. Greenway, F.; Herber, D.; Raum, W.; Morales, S. Double-blind, randomized, placebo-controlled clinical trials with nonprescription medications for the treatment of obesity. Obes. Res. 1999, 7, 370-378.
14. Charbonneau, M. Weak bases mimic the fertilization-associated chloride conductance increase and induce morphological changes in the cortex of Xenopus laevis eggs. Cell. Differ. Dev. 1989, 26, 39-51.
15. Semin, B. K.; Tshudinovskich, M. N.; Ivanov, I. I. Local anesthetics-induced inhibition of chloroplast electron transport. Gen. Physiol. Biophys. 1989, 8, 233-244.
16. Adade, A. B.; Chignell, D.; Vanderkooi, G. Local anesthetics: a new class of partial inhibitors of mitochondrial ATPase. J. Bioenerg. Biomembr. 1984, 16, 353-363.
17. Traynor, J. R.; Kunze, H. Inhibition of rat liver cholesterol esterase by local anaesthetics. Biochim. Biophys. Acta 1975, 409, 68-74.
18. Bell, F. P.; Hubert, E. V. Effect of local anesthetics on sterol biosynthesis and sterol esterification in rat liver in vitro. Biochim. Biophys. Acta 1980, 619, 302-307.
19. Bell, F. P.; Hubert, E. V. Lecithin-cholesterol acyltransferase: inhibition by local anesthetics in plasma from man and experimental animals in vitro. Lipids 1980, 15, 811-814.
20. Clark, C. R.; Wells, M. J.; Sansom, R. T.; Norris, G. N.; Dockens, R. C.; Ravis, W. R. Anticonvulsant activity of some 4-amino-benzamides. J. Med. Chem. 1984, 27, 779-782.
21. + channels in peripheral nerve. Anesth Analg. 1998, 87, 885-889.
22. Smirnov, D. A.; Plashchevskii, A. T. Retrosternal novocaine blockade in the treatment of severe forms of bronchial asthma and status asthmaticus. Anesteziol Reanimatol. 1991, 2, 49-50 (Russian).
23. Kasai, M.; Ide, T. Regulation of calcium release channel in sarcoplasmic reticulum. Ion Channels 1996, 4, 303-331.
24. Villar-Garea, A.; Fraga, M. F.; Espada, J.; Esteller, M. Procaine is a DNA-demethylating agent with growth-inhibitory effects in human cancer cells. Cancer Res. 2003, 63, 4984-4989.
25. Azuma, Y.; Shinohara, M.; Wang, P. L.; Suese, Y.; Yasuda, H.; Okura, K. Comparison of inhibitory effects of local anesthetics on immune functions of neutrophils. Int. J. Immunopharmacol. 2000, 22, 789-796.
26. Tan, Z.; Dohi, S.; Ohguchi, K; Nakashima, S.; Banno, Y.; Ono, Y.; Nozawa, Y. Effects of local anesthetics on phospholipase D activity in differentiated human promyelocytic leukemic HL60 cells. Biochem. Pharmacol. 1999, 58, 1881-1889.
27. Senisterra, G. A.; Lepock, J. R. Thermal destabilization of transmembrane proteins by local anaesthetics. Int. J. Hyperthermia 2000, 16, 1-17.
28. Suzuki, T.; Ezure, T.; Yamaguchi, T.; Domen, H.; Ishida, M.; Schmidt, W. Stimulatory effect of procaine on the growth of several microalgae and cyanobaeteria. J. Pharm. Pharmacol. 2000, 52, 243-251.
29. Cabellos, C.; Ariza, J.; Barreiro, B.; Tubau, F.; Linares, J.; Pallares, R.; Manresa, F.; Gudiol, F. Current usefulness of procaine penicillin in the treatment of pneumococcal pneumonia. Eur. J. Clin. Microbiol. Infect. Dis. 1998, 17, 265-268.
30. Hirota, K.; Okawa, H.; Appadu, B. L.; Grandy, D. K.; Lambert, D. G. Interaction of local anaesthetics with recombinant mu, kappa, and delta-opioid receptors expressed in Chinese hamster ovary cells. Br. J. Anaesth. 2000, 85, 740-746.
31. Fan, P.; Weight, F. F. Procaine impairs the function of 5-HT3 receptor-ion channel complex in rat sensory ganglion neurons. Neuropharmacology 1994, 33, 1573-1579.
32. Bencherif, M.; Eisenhour, C. M.; Prince, R. J.; Lippiello, P. M.; Lukas, R. J. The "calcium antagonist" TMB-8 [3,4,5-trimethoxy-benzoic acid 8-(diethylamino)octyl ester] is a potent, noncompetitive, functional antagonist at diverse nicotinic acetylcholine receptor subtypes. J. Pharmacol. Exp. Ther. 1995, 275, 1418-1426.
33. Kutchai, H.; Geddis, L. M. Inhibition of the Na,K-ATPase of canine renal medulla by several local anesthetics. Pharmacol. Res. 2001, 43, 399-403.
34. Graham, J. H. 3rd; Maher, J. R.; Robinson, S. E. The effect of cocaine and other local anesthetics on central dopaminergic neurotransmission. J. Pharmacol. Exp. Ther. 1995, 274, 707-717.
35. Wilcox, K. M.; Rowlett, J. K.; Paul, I. A.; Ordway, G. A.; Woolverton, W. L. On the relationship between the dopamine transporter and the reinforcing effects of local anesthetics in rhesus monkeys: practical and theoretical concerns. Psychopharmacology 2000, 153, 139-147.
36. Pinter, A.; Dorian, P. Intravenous antiarrhythmic agents. Curr. Opin. Cardiol. 2001, 16, 17-22.
37. Igawa, M.; Aonuma, K.; Okamado. Y.; Hiroe, M.; Hiraoka, M.; Isobe, M. Anti-arrhythmic efficacy of nifekalant hydrochloride, a pure class III anti-arrhythmic agent, in patients with healed myocardial infarction and inducible sustained ventricular tachycardia. J. Cardiovasc. Pharmacol. 2002, 40, 735-742.
38. Matyus, P.; Varro, A.; Papp, J. G.; Wamhoff, H.; Varga, I.; Virag, L. Antiarrhythmic agents: current status and perspectives. Med. Res. Rev. 1997, 17, 427-451.
39. Das, K. C.; Misra, H. P. Antiarrhythmic agents. Scavengers of hydroxyl radicals and inhibitors of NADPH-dependent lipid peroxidation in bovine lung microsomes. J. Biol. Chem. 1992, 267, 19172-19178.
40. Friedrich, A.; George, R. L.; Bridges, C. C.; Prasad, P. D.; Ganapathy, V. Transport of choline and its relationship to the expression of the organic cation transporters in a rat brain microvessel endothelial cell line (RBE4). Biochim. Biophys. Acta 2001, 1512, 299-307.
41. Yanagisawa, H.; Takamura, M.; Fujioka, T. Phenylenediamine derivative as ACAT inhibitors and their use. Jpn. Kokai Tokkyo Koho, JP 2000026293, 2000.
42. Markwell, R. E.; Stemp, G.; Wadsworth, H. J.; Watts, E. A. Aminosulphonyl-phenyl-1H-pyrrole derivatives, method of their preparation and their use. PCT Int. Appl., WO9516674, 1995.
43. Lee, N. S.; Jung, G. L.; Jeong H. W.; Seo, H. Y. Studies on the synthesis and antibacterial activity of PAS-sulfonamide derivatives. J. Pharm. Soc. Korea 1979, 23, 159-166.
44. Cho, B. T.; Lee, J. B. Manufacture of N,N-substituted benzamide derivative and salts. Jpn. Kokai Tokkyo Koho, JP 54128540, 1979.
45. Albright, J. D.; Reich, M. F.; Sum, F.-W.; Santos, E. G. D. Tricyclic diazepine vasopressin antagonists and oxytocin antagonists. U.S. Patent 5733905, 1998.
46. William, R. J.; Anderson, R. C.; Bajwa, J. S. Benzoic acid derivatives as antidiabetic agents. U.S. Patent 5378728, 1995.
47. Pero, R. W.; Axelsson, B.; Siemann, D.; Chaplin, D.; Dougherty, G. Newly discovered antiinflammatory properties of the benzamides and nicotinamides. Mol. Cell. Biochem. 1999, 793, 119-125.
48. Ray, N. C.; White, C. J.; Gingell, M.; Pettit, S. N.; Raphy, G. Aryl vinyl ether derivatives and their use as herbicides. PCT Int. Appl. WO 0003975, 2000.
49. Hua, J.; Pero, R. W.; Kane, R. Pharmacokinetics and central nervous system toxicity of declopramide (3-chloroprocainamide) in rats and mice. Anticancer Drugs 1999, 10, 79-88.
50. Uetrecht, J. P.; Zahid, N. N-Chlorination and oxidation of procainamide by myeloperoxidase: toxicological implications. Chem. Res. Toxicol. 1991, 4, 218-222.
51. Lindgren, H.; Olsson, A. R.; Pero, R. W.; Leanderson, T. Differential usage of IkappaBalpha and IkappaBbeta in regulation of apoptosis versus gene expression. Biochem. Biophys. Res. Commun. 2003, 301, 204-211.
52. Podesva, C.; Kohan, G.; Scott, W. Process and intermediates for preparing benzamide compounds. Ger. Offen. 71-2102848, 1971.
53. Buchheit, K. H.; Gamse, R.; Pfannkuche, H. J. SDZ 205-557, a selective antagonist at 5-HT4 receptors in the isolated guinea pig ileum. Eur. J. Pharmacol. 1991, 200, 373-374.
54. Eglen, R. M.; Alvarez, R.; Johnson, L. G.; Leung, E.; Wong, E. H. The action of SDZ 205,557 at 5-hydroxytryptamine (5-HT3 and 5-HT4) receptors. Br. J. Pharmacol. 1993, 108, 376-382.
55. Espejo, E. F.; Gil, E. Antagonism of peripheral 5-HT4 receptors reduces visceral and cutaneous pain in mice, and induces visceral analgesia after simultaneous inactivation of 5-HT3 receptors. Brain Res. 1998, 788, 20-24
56. Meneses, A.; Hong, E. Effects of 5-HT4 receptor agonists and antagonists in learning. Pharmacol. Biochem. Behav. 1997, 56, 347-351.
57. Lopez-Rodriguez, M. L.; Benhamu. B.; Viso, A.; Morcillo, M. J.; Murcia M.; Oresanz, L.; Alfaro, M. J.; Martin, M. I. Benzimidazole derivatives. Part 1: Synthesis and structure-activity relationships of new benzimidazole-4- carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists. Bioorg. Med. Chem. 1999, 7, 2271-2281.
58. Dahlof, C. G.; Hargreaves, R. J. Pathophysiology and pharmacology of migraine. Is there a place for antiemetics in future treatment strategies? Cephalalgia 1998, 18, 593-604.
59. Poe, R. H.; Kallay, M. C. Chronic cough and gastroesophageal reflux disease: experience with specific therapy for diagnosis and treatment. Chest 2003, 123, 679-684.
60. Valls, C.; Andia, E.; Sanchez, A.; Moreno, V. Selective use of low-osmolality contrast media in computed tomography. Eur. Radiol. 2003, 13, 2000-2005.
61. Tolstoi, L. G. The role of pharmacotherapy in anorexia nervosa and bulimia. J. Am. Diet. Assoc. 1989, 89, 1640-1646.
62. Rizzi, C. A.; Mierau, J.; Ladinsky, H. Regulation of plasma aldosterone levels by metoclopramide: a reappraisal of its mechanism from dopaminergic antagonism to serotonergic agonism. Neuropharmacology 1997, 36, 763-768.
63. Shaughnessy, A. F. Potential uses for metoclopramide. Drug Intell. Clin. Pharm. 1985, 19, 723-728.
64. Lambert, H. W.; Lauder, J. M. Serotonin receptor agonists that increase cyclic AMP positively regulate IGF-I in mouse mandibular mesenchymal cells. Dev. Neurosci. 1999, 21, 105-112.