Conversion of the synthetic catalase mimic precursor TAA-1 into the active catalase mimic in isolated hepatocytes

Chemical Biology and Drug Design

Volumn 73, Issue 5, 2009, Pages 494-501

  Rauen, Ursula ^a   Kettler Thiel, Thorsten ^b   De Groot, Herbert ^a   Korth, Hans Gert ^b   Sustmann, Reiner ^b  

^a UNIVERSITY HOSPITAL ESSEN   (Germany)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

Catalase mimetic; Catalase mimic; Chelatable iron; Enzyme mimic; Hydrogen peroxide; Iron; Tetraaza macrocycles

Indexed keywords

5,4 DIDEHYDRO 5,9,14,18 TETRAAZABIS(2,2 DIMETHYL[5,6]BENZO[1,3]DIOXOLO)[A,H]CYCLOTETRADECENE FERRIC CHLORIDE; 8 QUINOLINOL; ANNULENE DERIVATIVE; CATALASE; HYDROGEN PEROXIDE; IRON; IRON COMPLEX; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CELL ISOLATION; CHELATION; CONTROLLED STUDY; ENZYME SYNTHESIS; INTRACELLULAR TRANSPORT; LIGAND BINDING; LIVER CELL; MALE; MEMBRANE PERMEABILITY; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; RAT; ULTRAFILTRATION;

ANIMALS; AZA COMPOUNDS; BENZODIOXOLES; CATALASE; CELL SURVIVAL; CELLS, CULTURED; FERRIC COMPOUNDS; HEPATOCYTES; HYDROGEN PEROXIDE; IRON; MALE; OXIDATIVE STRESS; OXYQUINOLINE; RATS; RATS, WISTAR;

RATTUS;

EID: 64249145616     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00808.x     Document Type: Article

References (40)

1. de Groot H. (1994) Reactive oxygen species in tissue injury. Hepatogastroenterol 41 : 328 332.
2. Halliwell B., Gutteridge J.M.C. (1990) Role of free radicals and catalytic metal ions in human disease: an overview. Methods Enzymol 186 : 1 85.
3. Halliwell B., Gutteridge J.M.C. (1999) Free Radicals in Biology and Medicine, 3rd edn. Oxford : Oxford University Press.
4. Rosser B.G., Gores G.J. (1995) Liver cell necrosis: cellular mechanisms and clinical implications. Gastroenterology 108 : 252 275.
5. Stohs S.J., Bagchi D. (1995) Oxidative mechanisms in the toxicity of metal ions. Free Radic Biol Med 18 : 321 336.
6. Young S.P., Aisen P. (1994) The liver and iron. In : Arias I.M., Boyer J.L., Fausto N., Jakoby W.B., Schachter D., Shafritz D.A., editors. The Liver and Iron. New York : Raven Press p. 597 617.
7. Epsztejn S., Kakhlon O., Glickstein H., Breuer W., Cabantchik Z.I. (1997) Fluorescence analysis of the labile iron pool of mammalian cells. Anal Biochem 248 : 31 40.
8. Petrat F., de Groot H., Sustmann R., Rauen U. (2002) The chelatable iron pool in living cells: a methodically defined quantity. Biol Chem 383 : 489 502.
9. Petrat F., de Groot H., Rauen U. (2000) Determination of the chelatable iron pool of single intact cells by laser scanning microscopy. Arch Biochem Biophys 376 : 74 81.
10. Baliga R., Ueda N., Shah S.V. (1993) Increase in bleomycin-detectable iron in ischaemia/reperfusion injury to rat kidneys. Biochem J 291 : 901 905.
11. 2 formation. FASEB J 14 : 1953 1964.
12. Sergent O., Morel I., Cogrel P., Chevanne M., Pasdeloup N., Brissot P., Lescoat G., Cillard P., Cillard J. (1995) Increase in cellular pool of low-molecular-weight iron during ethanol metabolism in rat hepatocyte cultures. Relationship with lipid peroxidation. Biol Trace Elem Res 47 : 185 192.
13. Stäubli A., Boelsterli U.A. (1998) The labile iron pool in hepatocytes: prooxidant-induced increase in free iron precedes oxidative cell injury. Am J Physiol 274 : G1031 G1037.
14. Salvemini D., Wang Z.-Q., Zweier J.L., Samouilov A., Macarthur H., Misko T.P., Currie M.G., Cuzzocrea S., Sikorski J.A., Riley D.P. (1999) A nonpeptidyl mimic of superoxide dismutase with therapeutic activity in rats. Science 286 : 304 306.
15. Gianello P., Saliez A., Bufkens X., Pettinger R., Misseleyn D., Hori S., Malfroy B. (1996) EUK-134, a synthetic superoxide dismutase and catalase mimetic, protects rat kidneys from ischemia-reperfusion-induced damage. Transplantation 62 : 1664 1666.
16. Malassagne B., Ferret P.-J., Hammoud R., Tulliez M., Bedda S., Trébéden H., Jaffray P., Calmus Y., Weill B., Batteux F. (2001) The superoxide dismutase mimetic MnTBAP prevents Fas-induced acute liver failure in the mouse. Gastroenterology 121 : 1451 1459.
17. Rong Y., Doctrow S.R., Tocco G., Baudry M. (1999) EUK-134, a synthetic superoxide dismutase and catalase mimetic, prevents oxidative stress and attenuates kainate-induced neuropathy. Proc Natl Acad Sci USA 96 : 9897 9902.
18. Sies H. (1994) Ebselen: a glutathione peroxidase mimic. Methods Enzymol 234 : 476 482.
19. Doctrow S.R., Huffman K., Marcus C.B., Musleh W., Bruce A., Baudry M., Malfroy B. (1997) Salen-manganese complexes: combined superoxide dismutase/catalase mimics with broad pharmacological efficacy. Adv Pharmacol 38 : 247 269.
20. Doctrow S.R., Huffman K., Marcus C.B., Tocco G., Malfroy E., Adinolfi C.A., Kruk H., Baker K., Lazarowych N., Mascarenhas J., Malfroy B. (2002) Salen-manganese complexes as catalytic scavengers of hydrogen peroxide and cytoprotective agents: structure-activity relationship studies. J Med Chem 45 : 4549 4558.
21. Melnyk A.C., Kildahl N.K., Rendina A.R., Busch D.H. (1979) Catalysis of the decomposition of hydrogen peroxide by a complex of iron(III) with a synthetic macrocyclic ligand. J Am Chem Soc 101 : 3232 3240.
22. Triller M.U., Hsieh W.-Y., Pecoraro V.L., Rompel A., Krebs B. (2002) Preparation of highly efficient manganese catalase mimics. Inorg Chem 41 : 5544 5554.
23. Paschke J., Kirsch M., Korth H.-G., de Groot H., Sustmann R. (2001) Catalase-like activity of a non-heme dibenzotetraaza[14]annulene-Fe(III) complex under physiological conditions. J Am Chem Soc 123 : 11099 11100.
24. Rauen U., Li T., Sustmann R., de Groot H. (2004) Protection against iron- and hydrogen peroxide-dependent cell injuries by a novel synthetic iron catalase mimic and its precursor, the iron-free ligand. Free Radic Biol Med 37 : 1369 1383.
25. III complexes of 1,4,8,11-tetraaza[14]annulenes as catalase mimics. Inorg Chem 46 : 11416 11430.
26. III complexes with hydrogen peroxide - putative catalase mimics? Eur J Org Chem 3119 3125.
27. 2 liberated by sources other than xanthine oxidase. Biol Chem Hoppe Seyler 372 : 35 41.
28. Rauen U., Petrat F., Sustmann R., de Groot H. (2004) Iron-induced mitochondrial permeability transition in cultured hepatocytes. J Hepatol 40 : 607 615.
29. Martin A., Wu D., Baur W., Meydani S.N., Blumberg J.B., Meydani M. (1996) Effect of vitamin E on human aortic endothelial cell responses to oxidative injury. Free Radic Biol Med 21 : 505 511.
30. Rauen U., Polzar B., Stephan H., Mannherz H.G., de Groot H. (1999) Cold-induced apoptosis in cultured hepatocytes and liver endothelial cells: mediation by reactive oxygen species. FASEB J 13 : 155 168.
31. Drummen G.P.C., Op den Kamp J.A.F., Post J.A. (1999) Validation of the peroxidative indicators, cis-parinaric acid and parinaroyl-phospholipids, in a model system and cultured cardiac myocytes. Biochim Biophys Acta 1436 : 370 382.
32. Pap E.H.W., Drummen G.P.C., Winter V.J., Kooij T.W.A., Rijken P., Wirtz K.W.A., Op den Kamp J.A.F., Hage W.J., Post J.A. (1999) Ratio-fluorescence microscopy of lipid oxidation in living cells using C11-BODIPY581/591. FEBS Lett 453 : 278 282.
33. Aebi H.E. (1983) Catalase. In : Bergmeyer H.U., editor. Methods of Enzymatic Analysis, 3rd edn. Weinheim : Verlag Chemie pp. 273 286.
34. Corasanti J.G., Gleeson D., Boyer J.L. (1990) Effects of osmotic stresses on isolated rat hepatocytes. I. Ionic mechanisms of cell volume regulation. Am J Physiol 258 : G290 G298.
35. Sicking W., Korth H.-G., Jansen G., de Groot H., Sustmann R. (2007) Hydrogen peroxide decomposition by a non-heme iron(III) catalase mimic: a DFT study. Chem Eur J 13 : 4230 4245.
36. Greene B.T., Thorburn J., Willingham M.C., Thorburn A., Planalp R.P., Brechbiel M.W., Jennings-Gee J., Wilkinson J., IV., Torti F.M., Torti S.V. (2002) Activation of caspase pathways during iron chelator-mediated apoptosis. J Biol Chem 277 : 25568 25575.
37. Simonart T., Degraef C., Andrei G., Mosselmans R., Hermans P., Van Vooren J.P., Noel J.C., Boelaert J.R., Snoeck R., Heenen M. (2000) Iron chelators inhibit the growth and induce the apoptosis of Kaposi's sarcoma cells and of their putative endothelial precursors. J Invest Dermatol 115 : 893 900.
38. Petrat F., de Groot H., Rauen U. (2001) Subcellular distribution of chelatable iron: a laser scanning microscopic study in isolated hepatocytes and liver endothelial cells. Biochem J 356 : 61 69.
39. Petrat F., Weisheit D., Lensen M., de Groot H., Sustmann R., Rauen U. (2002) Selective determination of mitochondrial chelatable iron in viable cells with a new fluorescent sensor. Biochem J 362 : 137 147.
40. Rauen U., Springer A., Weisheit D., Petrat F., Korth H.-G., de Groot H., Sustmann R. (2007) Assessment of chelatable mitochondrial iron by using mitochondrion-selective fluorescent iron indicators with different iron-binding affinities. ChemBioChem 8 : 341 352.