Targeting the lysosome: Fluorescent iron(III) chelators to selectively monitor endosomal/ lysosomal labile iron pools

Journal of Medicinal Chemistry

Volumn 51, Issue 15, 2008, Pages 4539-4552

  Fakih, Sarah ^b   Podinovskaia, Maria ^c   Kong, Xiaole ^a   Collins, Helen L ^a   Schaible, Ulrich E ^c   Hider, Robert C ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

^c LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 4 PYRIDONE DERIVATIVE; DEFERASIROX; DEFERIPRONE; DEFEROXAMINE; FLUORESCENT DYE; IRON; IRON CHELATING AGENT;

ANIMAL CELL; ARTICLE; CHEMOSENSITIVITY; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DIAGNOSTIC ACCURACY; DRUG TARGETING; ENDOSOME; FLUORESCENCE SPECTROSCOPY; LYSOSOME; MACROPHAGE; MOUSE; NONHUMAN;

ANIMALS; CELLS, CULTURED; CHEMISTRY, PHYSICAL; ENDOSOMES; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; IRON; LYSOSOMES; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; SENSITIVITY AND SPECIFICITY;

EID: 49449091809     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8001247     Document Type: Article

References (45)

1. Lippard, S. J.; Berg, J. M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, CA, 1994.
2. Kaim, W.; Schwederski, B. Bioinorganic Chemistry, 2nd ed.; B. G. Teubner: Stuttgart, Germany, 1995.
3. Halliwell, B.; Gutteridge, J. M. C. Role of free radicals and catalytic metal ions in human disease: an overview. Methods Enzymol. 1990, 186, 1-85.
4. Halliwell, B.; Gutteridge, J. M. C. Biologically relevant metal ion-dependent hydroxyl radical generation. An update. FEBS Lett. 1992, 307, 108-112.
5. Gaeta, A.; Hider, R. C. The crucial role of metal ions in neurodegeneration: the basis for a promising therapeutic strategy. Br. J. Pharmacol. 2005, 146, 1041-1059.
6. Molina-Holgado, M.; Hider, R. C.; Gaeta, A.; Williams, R.; Francis, P. Metals ions and neurodegeneration. BioMetals, in press.
7. Bacon, B. R.; Britton, R. S. Hepatic injury in chronic iron overload. Role of lipid peroxidation. Chem.-Biol. Interact. 1989, 70, 183-226.
8. Bacon, B. R.; Britton, R. S. The pathology of hepatic iron overload: a free radical-mediated process. Hepatology 1990, 11, 127-137.
9. Kehrer, J. P. The Haber-Weiss reaction and mechanisms of toxicity. Toxicology 2000, 149, 43-50.
10. Kowdley, K. V. Iron, hemochromatosis, and hepatocellular carcinoma. Gastroenterology 2004, 127, S79-S86.
11. Valko, M.; Rhodes, C. J.; Moncol, J.; Izakovic, M.; Mazur, M. Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chem.-Biol. Interact. 2006, 1, 1-40.
12. Valko, M.; Leibfritz, D.; Moncol, J.; Cronin, M. T. D.; Mazur, M.; et al. Free radicals and antioxidants in normal physiological functions and human disease. Int. J. Biochem. Cell Biol. 2007, 39, 44-84.
13. Petrat, F.; De Groot, H.; Rauen, U. Subcellular distribution of chelatable iron: a laser scanning microscopic study in isolated hepatocytes and liver endothelial cells. Biochem. J. 2001, 356, 61-69.
14. Yu, Z.; Persson, H. L.; Eaton, J. W.; Brunk, U. T. Intralysosomal iron: a major determinant of oxidant-induced cell death. Free Radical Biol. Med. 2003, 34, 1243-1252.
15. Kurz, T.; Leake, A.; von Zglinicki, T.; Brunk, U. T. Lysosomal redox-active iron is important for oxidative stress-induced DNA damage. Ann. N.Y. Acad. Sci. 2004, 1019, 285-288.
16. Kurz, T.; Leake, A.; von Zglinicki, T.; Brunk, U. T. Relocalized redox-active lysosomal iron is an important mediator of oxidative-stress-induced DNA damage. Biochem. J. 2004, 378, 1039-1045.
17. Terman, A.; Gustafsson, B.; Brunk, U. T. The lysosomal-mitochondrial axis theory of postmitotic aging and cell death. Chem.-Biol. Interact. 2006, 163, 29-37.
18. Kurz, T.; Gustafsson, B.; Brunk, U. T. Intralysosomal iron chelation protects against oxidative stress-induced cellular damage. FEBS J. 2006, 273, 3106-3117.
19. Persson, H. L.; Yu, Z.; Tirosh, O.; Eaton, J. W.; Brunk, U. T. Prevention of oxidant-induced cell death by lysosomotropic iron chelators. Free Radical Biol. Med. 2003, 34, 1295-1305.
20. 2 injury in adult cardiomyocytes. Cardiovasc. Res. 2000, 47, 529-536.
21. Simunek, T.; Boer, C.; Bouwman, R. A.; Vlasblom, R.; Versteilen, A. M. G.; et al. SIH, a novel lipophilic iron chelator, protects H9c2 cardiomyoblasts from oxidative stress-induced mitochondrial injury and cell death. J. Mol. Cell. Cardiol. 2005, 39, 345-354.
22. Petrat, F.; Rauen, U.; De Groot, H. Determination of the chelatable iron pool of isolated rat hepatocytes by digital fluorescence microscopy using the fluorescent probe phen green SK. Hepatology 1999, 29, 1171-1179.
23. Petrat, F.; De Groot, H.; Rauen, U. Determination of the chelatable iron pool of single intact cells by laser scanning microscopy. Arch. Biochem. Biophys. 2000, 376, 74-81.
24. Glickstein, H.; El, R. B.; Link, G.; Breuer, W.; Konijn, A. M.; et al. Action of chelators in iron-loaded cardiac cells: accessibility to intracellular labile iron and functional consequences. Blood 2006, 108, 3195-3203.
25. Glickstein, H.; El, R. B.; Shvartsman, M.; Cabantchik, Z. I. Intracellular labile iron pools as direct targets of iron chelators: a fluorescence study of chelator action in living cells. Blood 2005, 106, 3242-3250.
26. Petrat, F.; Weisheit, D.; Lensen, M.; De Groot, H.; Sustmann, R.; et al. Selective determination of mitochondrial chelatable iron in viable cells with a new fluorescent sensor. Biochem. J. 2002, 362, 137-147.
27. Rauen, U; Springer, A; Weisheit, D; Petrat, F; H.G, K. Assessment of chelatable mitochondrial iron by using mitochondrion-selective fluorescent iron indicators with different iron-binding affinities. ChemBioChem 2007, 8, 341-352.
28. Ma, Y.; Luo, W.; Quinn, P. J.; Liu, Z. D.; Hider, R. C. Design, synthesis, physicochemical properties, and evaluation of novel iron chelators with fluorescent sensors. J. Med. Chem. 2004, 47, 6349-6362.
29. Luo, W.; Ma, Y.; Quinn, P. J.; Hider, R. C.; Liu, Z. Design, synthesis and properties of novel iron(III)-specific fluorescent probes. J. Pharm. Pharmacol. 2004, 56, 529-536.
30. Ma, Y.; De Groot, H.; Liu, Z.; Hider, R. C.; Petrat, F. Chelation and determination of labile iron in primary hepatocytes by pyridinone fluorescent probes. Biochem. J. 2006, 395, 49-55.
31. Kaufmann, A. M.; Krise, J. P. Lysosomal sequestration of amine-containing drugs: analysis and therapeutic implications. J. Pharm. Sci. 2007, 96, 729.
32. Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981, 1, 28.
33. Zhou, T.; Neubert, H.; Liu, D. Y.; Liu, Z. D.; Ma, Y.; et al. Iron binding dendrimers: a novel approach for the treatment of haemochromatosis. J. Med. Chem. 2006, 49, 4171-4182.
34. Rae, T. D. Undetectable intracellular free copper: the requirement of a copper chaperone for superoxide dismutase. Science 1999, 284, 805-808.
35. 3+ values. J. Med. Chem. 1999, 42, 4814-4823.
36. Wis Vitolo, L. M.; Hefter, G. T.; Clare, B. W.; Webb, J. Iron chelators of the pyridoxal isonicotinoyl hydrazone class part II. Formation constants with iron(III) and iron(II). Inorg. Chim. Acta 1990, 170, 171-176.
37. Zanker, V.; Peter, W. Die prototropen formen des fluoresceins. Chem. Ber. 1958, 91, 572-580.
38. Sjöback, R.; Nygren, J.; Kubista, M. Absorption and fluorescence of fluorescein. Spectrochim. Acta A 1995, 51, L7-L21.
39. Alvarez-Pez, J. M.; Ballesteros, L.; Talavera, E.; Yguerabide, J. Fluorescein excited-state proton exchange reactions: nanosecond emission kinetics and correlation with steady-state flurescence intensity. J. Phys. Chem. A 2001, 105, 6320-6332.
40. Klonis, N.; Sawyer, W. H. Spectral properties of the prototropic forms of fluorescein in aqueous solution. J. Fluoresc. 1996, 6, 147-157.
41. Liu, Z. D.; Liu, D. Y.; Hider, R. C. Iron Chelator Chemistry. Iron Chelation Therapy; Kluwer Academic/Plenum Publishers: New York, 2002; pp 141-166.
42. Fakih, S.; Podinovskaia, M.; Kong, X. L.; Schaible, U. E.; Collins, H. L.; Monitoring intracellular labile iron pools: a novel fluorescent iron(III) sensor as a potentially advanced and non-invasive diagnosis tool. J. Pharm. Sci., in press.
43. Tenopoulou, M.; Kurz, T.; Doulias, P. T.; Galaris, D.; Brunk, U. T. Does the calcein-AM method assay the total cellular "labile iron pool" or only a fraction of it? Biochem. J. 2007, 403, 261.
44. Gans, P.; Sabatini, A.; Vacca, A. Determination of equilibrium constants from spectrophotometric data obtained from solutions of known pH: the program pHab. Ann. Chim. 1999, 89, 45-49.
45. Gans, P.; O'Sullivan, B. GLEE, a new computer program for glass electrode calibration. Talanta 2000, 51, 33-37.