Synthesis, physicochemical properties, and biological evaluation of hydroxypyranones and hydroxypyridinones: Novel bidentate ligands for cell- labeling

Journal of Medicinal Chemistry

Volumn 39, Issue 19, 1996, Pages 3659-3670

  Ellis, Beverley L ^a,c   Duhme, Anne K ^a   Hider, Robert C ^a   Hossain, M Bilayet ^b   Rizvi, Safia ^b   Van Der Helm, Dick ^b  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF OKLAHOMA   (United States)

^c MANCHESTER ROYAL INFIRMARY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 PYRONE DERIVATIVE; LIGAND; PYRIDONE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CELL LABELING; HYDROLYSIS; LEUKOCYTE FUNCTION; LIGAND BINDING;

CELLS; CHEMISTRY, PHYSICAL; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; DRUG STABILITY; ERYTHROCYTES; GALLIUM; HUMANS; HYDROGEN-ION CONCENTRATION; INDIUM RADIOISOTOPES; IRON; LEUKOCYTES; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRANS; PYRIDONES; PYRONES;

EID: 0029795421     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960220g     Document Type: Article

References (43)

1. Peters, A. M.; Saverymuttu, S. H. The value of indium-labeled leucocytes in clinical practice. Blood Rev. 1987, 1, 65-76.
2. Thakur, M. L.; Segal, A. W.; Louis, L.; Welch, M. J.; Hopkins, J.; Peters, T. J. Indium-111-labeled cellular blood components: mechanism of labeling and intracellular location in human neutrophils. J. Nucl. Med. 1977, 18, 1020-1024.
3. Thakur, M. L.; Lavender, J. P.; Arnot, R. N.; Silvester, D. J.; Segal, A. W. Indium-111-labeled autologous leukocytes in man. J. Nucl. Med. 1977, 18, 1012-1019.
4. Dewanjee, M. K.; Rao, S. A.; Didsheim, P. Indium-111 tropolone, a new high-affinity platelet label: preparation and evaluation of labeling parameters. J. Nucl. Med. 1981, 22, 981-987.
5. 111In. Br. J. Radiol. 1982, 55, 247-249.
6. 111In-tropolonate. Eur. J. Nucl. Med. 1988, 13, 537-542.
7. Thakur, M. L.; Barry, M. J. Preparation and evaluation of a new indium-111 agent for efficient labeling of human platelets in plasma. J. Labelled Compounds Radiopharm. 1982, 19, 1410-1412.
8. Thakur, M. L.; McKenney, S. L.; Park, C. H. Evaluation of indium-111-2-mercaptopyridine-N-oxide for labeling leukocytes in plasma: a kit preparation. J. Nucl. Med. 1985, 26, 518-523.
9. Segal, A. W.; Deteix, P.; Garcia, R.; Tooth, P.; Zanneli, G. D.; Allison, A. C.; Indium-111 labeling of leucocytes: a detrimental effect on neutrophil and lymphocyte function and an improved method of cell labeling. J. Nucl. Med. 1978, 19, 1238-1244.
10. Chisholm, P. M.; Danpure, H. J.; Healey, G.; Osman, S. Cell damage resulting from the labeling of rat lymphocytes and HeLa S3 cells with In-111 oxine. J. Nucl. Med. 1979, 20, 1308-1311.
11. ten Berge, R. J. M.; Natarajan, A. T.; Hardeman, M. R.; van Royen, E. A.; Schellekens, P. T. Labeling with indium-111 has detrimental effects on human lymphocytes; concise comunication. J. Nucl. Med. 1983, 24, 615-620.
12. Kassis, A. I.; Adelstein, S. J. Chemotoxicity of indium-111 oxine in mammalian cells. J. Nucl. Med. 1985, 26, 187-190.
13. Hider, R. C.; Hall, A. D. Clinically useful chelators of tripositive elements. In: Progress in Medicinal Chemistry; Ellis, G. P., West, G. B., Eds.; Elsevier: New York, 1991; Vol. 28, pp 41-173.
14. Finnegan, M. M.; Lutz, T. G.; Nelson, W. O.; Smith, A.; Orvig, C. Neutral water-soluble post-transition-metal chelate complexes of medical interest: aluminium and gallium tris3-hydroxy-4-pyronates. Inorg. Chem. 1987, 26, 2171-2176.
15. Matsuba, A.; Nelson, W. O.; Rettig, S. J.; Orvig, C. Neutral water-soluble indium complexes of 3-hydroxy-4-pyrones and 3-hydroxy-4-pyridinones. Inorg. Chem. 1988, 27, 3935-3939.
16. Clevett, D. J.; Lyster, D. M.; Nelson, W. O.; Rihela, T.; Webb, G. A.; Orvig, C. Solution chemistry of gallium and indium 3-hydroxy-4-pyridinone complexes in vitro and in vivo. Inorg. Chem. 1990, 29, 667-672.
17. Porter, J. B.; Huehns, E. R.; Hider, R. C. The development of iron chelating drugs. In Balliere's Clinical Haematology; Hershko, C., Ed.; Balliére Tindall: London, 1989; Vol. 2, pp 257-292.
18. Gralla, E. J.; Stebbins, R. B.; Coleman, G. L.; Delahunt, C. S. Toxicity studies with ethyl maltol. Toxicol. Appl. Pharmacol. 1969, 15, 604-613.
19. Rennhard, H. H. The metabolism of ethyl maltol in the dog. J. Agric. Food Chem. 1971, 19, 152-154.
20. Singh, S.; Epemolu, R. O. Dobbin, P. S.; Tilbrook, G. S.; Ellis, B. L.; Damani, L. A.; Hider, R. C. Urinary metabolic profiles in human and rat of 1,2-dimethyl- and 1,2-diethyl-substituted 3-hydroxypyridin-4-ones. Drug Metab. Dispos. 1992, 20, 256-261.
21. Tate, B. E.; Miller, R. L. Preparation of gamma-pyrones US Patent 3130204, 1964.
22. Bowden, K.; Heibron, I. M.; Jones, E. R. H.; Weedon, B. C. L. Researches on Acetylenic compounds. Part 1. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols. J. Chem. Soc. 1946, 39-45.
23. Hare, L. E.; Lu, M. C.; Sullivan, C. B.; Sullivan, P. T.; Counsell, R. E. Aromatic amino acid hydroxylase inhibitors. 3. In vitro inhibition by azadopamine analogs. J. Med. Chem. 1974, 17, 1-5.
24. Campbell, K. N.; Ackermann, J. F.; Campbell, B. K. Studies on γ-pyrones. I. Derivatives of kojic acid. J. Org. Chem. 1950, 15, 221-226.
25. Rogers, E. F.; Dybas, R. A.; Hannah, J. Anticoccidal complexes. US Patent 3926935, 1975.
26. McOrmie, J. F. W.; Watts, M. L.; West, D. E. Demethylation of aryl methyl ethers by boron tribromide. Tetrahedron 1968, 24, 2289-2292.
27. Harris, W. R.; Carrano, C. J.; Cooper, S. R.; Sofen, S. R.; Avdeef, A. E.; McArdle, J. V.; Raymond, K. N. Co-ordination chemistry of microbial iron transport compounds. 19. Stability constants and electrochemical behavior of ferric enterobactin and model complexes. J. Am. Chem. Soc. 1979, 101, 6097-6104.
28. Dobbin, P. S.; Hider, R. C.; Hall, A. D.; Taylor, P. D.; Sarpong, P.; Porter, J. B.; Xiao, G.; van der Helm, D. Synthesis, physiochemical properties and biological evaluation of N-substituted 2-alkyl-3-hydroxy-4(1H)-pyridinones: Orally active iron chelators with clinical potential. J. Med. Chem. 1993, 36, 2448-2458.
29. Tomlinson, E. Filter-probe extractor: a tool for the rapid determination of oil-water partition coefficients. J. Pharm. Sci. 1982, 71, 602-604.
30. Cantwell, F. F.; Mohammed, H. Y. Photometric acid-base titrations in the presence of an immiscible solvent. Anal. Chem. 1979, 51, 218-223.
31. Fujita, T.; Iwasa, J.; Hansch, C. A substituent constant, π, derived from partition coefficients. J. Am. Chem. Soc. 1964, 86, 5175-5180.
32. Matsuba, C. A.; Nelson, W. O.; Rettig, J.; Orvig, C. Neutral Water-Soluble Indium complexes of 3-Hydroxy-4-pyrones and 3-Hydroxy-4-pyridinones. Inorg. Chem. 1988, 27, 3935-3939.
33. Matsuba, C. A.; Rettig, S. J.; Orvig, C. Main group (IIIA) complexes of benzohydroxamic acid and the crystal structure of tris(benzohydroxamato)mdium(III). Can. J. Chem. 1988, 66, 1809-181.
34. Finnegan, M. M.; Rettig, S. J.; Orvig, C. A Neutral Water-Soluble Aluminium Complex of Neurological Interest. J. Am. Chem. Soc. 1986, 5033-5035.
35. Brown, S. D.; Burgess, J.; Fawcett, J.; Parsons, S. A.; Russell, Waltham. E. Three Polymorphic Forms of 2-Ethyl-3-hydroxy-4-pyranone- (Ethyl Maltol). Acta Crystallogr. 1995, C51, 1335-1338.
36. Hider et al. (1995), unpublished results.
37. Tute, M. S. Principles and practice of Hansch Analysis: A guide to structure-activity correlation for the medicinal chemist. In Advances in Drug Research; Harper, N. J., Simmonds, A. B., Eds.; Academic Press: London, 1971; Vol. 6, pp 1-77.
38. Albert, A.; Hampton, A.; Selbie, F. R. The influence of chemical constitution on anti-bacterial activity. Part VII: The site of action of 8-hydroxyquinoline (oxine). Br. J. Exp. Pathol. 1954, 35, 75-84.
39. Albert, A.; Rees, C. W.; Tomlinson, A. J. H.; Why are some metal-binding substances anti-bacterial? Recueil 1956, 75, 819-824.
40. Hall, A. D. TOPCAT Program for Determination of Distribution Coefficients, King's College, University of London, 1990.
41. Sheldrick, G. M. SHELX76, Program for the Solution of Crystal Structure, University of Cambridge, England, 1984.
42. Sheldrick, G. M. SHELX-86. Program for the solution of Crystal Structures, University of Gottingen, Germany, 1986.
43. Sheldrick, G. M. SHELXTL-plus. Siemens Analytical X-ray Instruments Inc., Madison, WI, 1993.