The inhibition of mammalian 15-lipoxygenases by the anti-inflammatory drug ebselen: Dual-type mechanism involving covalent linkage and alteration of the iron ligand sphere

Molecular Pharmacology

Volumn 56, Issue 1, 1999, Pages 196-203

  Walther, Matthias ^a   Holzhütter, Hermann Georg ^a   Kuban, Ralf Jürgen ^a   Wiesner, Rainer ^a   Rathmann, Jörg ^a   Kühn, Hartmut ^a  

^a CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONATE 15 LIPOXYGENASE; EBSELEN; IRON; LIGAND;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; ATHEROSCLEROSIS; COMPETITIVE INHIBITION; COVALENT BOND; DRUG ACTIVITY; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME INHIBITION; INFLAMMATION; MAMMAL CELL; PRIORITY JOURNAL;

EID: 0344142491     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.56.1.196     Document Type: Article

References (39)

1. Belkner J, Wiesner R, Rathman J, Barnett J, Sigal E and Kühn H (1993) Oxygenation of lipoproteins by mammalian lipoxygenases. Eur J Biochem 213:251-261.
2. Boyington JC, Gaffney BJ and Amzel LM (1993) The three-dimensional structure of an arachidonic acid 15-lipoxygenase. Science (Wash DC) 260:1482-1486.
3. Conradson SD, Burgess BK, Newton WE, Di Cicco WE, Filliponi A, Wu ZY, Natoli CR, Hedman B and Hodgson KO (1994) Selenol binds to iron in nitrogenase iron-molybdenum cofactor: An extended x-ray absorption fine structure study. Proc Natl Acad Sci USA 91:1290-1293.
4. Cotgreave LA, Duddy SK, Kass GE, Thompson D and Moldeus P (1989) Studies on the anti-inflammatory activity of ebselen. Ebselen interferes with granulocyte oxidative burst by dual inhibition of NADPH oxidase and protein kinase C? Biochem Pharmacol 38:649-656.
5. Cotgreave IA, Johannson V, Westergren G, Moldeus PW and Brattsand R (1988) The anti-inflammatory activity of ebselen but not of thiols in experimental alveolitis and bronchiolitis. Agents Actions 24:313-319.
6. Funk CD (1996) The molecular biology of mammalian lipoxygenases and the quest for eicosanoid functions using lipoxygenase-deficient mice. Biochim Biophys Acta 1304:65-84.
7. Gao JX and Issekutz AC (1993) The effect of ebselen on polymorphonuclear leukocyte and lymphocyte migration to inflammatory reactions in rats. J Immunopharmacol 25:239-251.
8. Gillmor SA, Villasenor A, Fletterick R, Sigal E and Browner MF (1997) The structure of mammalian 15-lipoxygenase reveals similarities to the lipases and the determinants of substrate specificity. Nature Struct Biol 4:1003-1009.
9. Hattori R, Inoue R, Sase K, Eizawa H, Kosuga K, Aoyama T, Masayasu H, Kawai C, Sasayama S and Yui Y (1994) Preferential inhibition of inducible nitric oxide synthase by ebselen. Eur J Pharmacol 267: R1-R2.
10. Hermes C, Gilberg E and Koch MHJ (1984) A double-focusing EXAFS beam line, data acquisition and evaluation system for biological applications. Nucl Instrum Meth 222:207-214.
11. Holman RT, Zhou J and Solomon EI (1998) Spectroscopic and functional characterization of a ligand coordination mutant of soybean lipoxygenase-1: First coordination sphere analogue of human 15-lipoxygenase. J Am Chem Soc 120:12564-12572.
12. Kuban RJ, Wiesner R, Rathman J, Veldink G, Nolting H, Solé VA and Kühn H (1998) The iron ligand sphere geometry of mammalian 15-lipoxygenases. Biochem J 332:237-242.
13. Kühn H and Chan L (1997) The role of 15-lipoxygenase in atherogenesis. Pro- and/or anti-atherogenic action. Curr Opinion Lipidol 8:111-117.
14. Lewis RA, Austen AFN and Sobennan RJ (1990) Leukotrienes and other products of the 5-lipoxygenase pathway. Biochemistry and relation to pathobiology in human diseases. N Engl J Med 323:645-655.
15. Li QJ, Bessems JGM, Commandeur JMN, Adams B and Vermeulen NPE (1994) Mechanism of protection of ebselen against paracetamol-induced toxicity in rat hepatocytea. Biochem Pharmacol 48:1631-1640.
16. Lin F and Girotti AW (1994) Cytoprotection against merocyanine 540-sensitized photoinactivation of the Na, K-adenosintriphosphatase in leukemia cells: Glutathione and selenoperoxidaae involvement. Photochem Photobiol 59:320-327
17. Ludwig P, Holzhütter HG, Colosimo A, Silvestrini MC, Schewe T and Rapoport SM (1987) A kinetic model for lipoxygenases based on experimental data with the lipoxygenase of reticulocytes. Eur J Biochem 168:325-337.
18. Minor W, Steczko J, Stec B, Otwinowski Z, Bolin JT, Walter R and Axelrod B (1996) Crystal structure of soybean lipoxygenase L-1 at 1.4 Ȧ resolution. Biochemistry 35:10687-10701.
19. Morgenstern R, Cotgreave IA and Engman L (1992) Determination of the relative contributions of the diselenide and selenol forms of ebselen in the mechanism of its glutathione peroxidase-like activity. Chem-Biol Interact 84:77-84.
20. Murakami M., Austen KF and Arm JP (1995) The immediate phase of c-kit ligand stimulation of mouse bone marrow-derived mast cells elicits rapid leukotriene C4 generation through posttranslational activation of cytosolic phospholipase A2 and 5-lipoxygenase. J Exp Med. 182:197-206.
21. Ozaki M, Nakamura M, Teraoka S and Ota K (1997) Ebselen, a novel anti-oxidant compound, protects the rat liver from ischemia-reperfusion injury. Transpl Int 10:96-102.
22. Pavlosky MA, Zhang Y, Westre TE, Gan QF, Pavel E, Campochiaro C, Hedman B, Hodgson KO and Solomon EI (1995) Near-infrared circular dichroism, magnetic circular dichroism, and X-ray absorption spectral comparison of the non-heme ferrous active sites of plant and mammalian 15-lipoxygenases. J Am Chem Soc 117:4316-4327.
23. Pettifer RF and Hermes C (1985) Absolute energy calibration of X-ray radiation from synchrotron sources. J Appl Crystall 18:404-412.
24. Ramakrishnan N, Kalinich JF and McClain DE (1996) Ebselen inhibition of apoptosis by reduction of peroxides. Biochem Pharmacol 51:1443-1451.
25. Rapoport SM, Schewe T and Thiele BJ (1990) Maturational breakdown of mitochondria and other organelles in reticulocytes. Blood Cell Biochem 1:151-194.
26. Rapoport SM, Schewe T, Wiesner R, Halangk W, Ludwig P, Janicke-Hohne M, Tannert C, Hiebsch C and Klatt D (1979) The lipoxygenase of reticulocytes. Purification, characterization and biological dynamics of the lipoxygenase; its identity with the respiratory inhibitors of the reticulocyte. Eur J Biochem 96:545-561.
27. Schewe C, Schewe T and Wendel A (1994) Strong inhibition of mammalian lipoxygenases by the antiinflammatory seleno-organic compound ebselen in the absence of glutathione. Biochem Pharmacol 48:65-74.
28. Schewe T (1995) Molecular actions of ebselen - An antiinflammatory antioxidant. Gen Pharmacol 26:1153-1169.
29. Schewe T, Kühn H and Rapoport, SM (1986) Positional specificity of lipoxygenases and their suitability for testing potential drugs. Prostaglandins Leukotr Med 23:155-160.
30. Sendobry SM, Cornicelli JA, Welch K, Bocan T, Tait B, Trivedi BK, Colbry N, Dyer RD, Feinmark SJ and Daugherty A (1997) Attenuation of diet-induced atherosclerosis in rabbits with a highly selective 15-lipoxygenase inhibitor lacking significant antioxidant properties. Br J Pharmacol 120:1199-1206.
31. Sies H (1994) Ebselen: A glutathione peroxidase mimic. Methods Enzymol 234:476-482.
32. Sies H and Masumoto H (1997) Ebselen as a glutathione peroxidase mimic and as a scavenger of peroxynitrite. Adv Pharmacol 38:229-46.
33. Sies H, Sharov VS, Klotz LO and Briviba K (1997) Glutathione peroxidase protects against peroxynitrite-mediated oxidations. A new function for selenoproteins as peroxynitrite reductase. J Biol Chem 272:27812-27817.
34. Skrzypczak-Jankun E, Amzel M, Kroa BA and Funk MO (1997) Structure of soybean lipoxygenase L3 and comparison with its L1 isoenzyme. Proteins 29:15-31.
35. Solomon EI, Zhou J, Neese F and Pavel EG (1997) New insights from spectroscopy into the structure/function relationship of lipoxygenases. Chem Biol 4:795-808.
36. Takasago T, Peters EE, Graham DI, Masayasu H and Macrae IM (1997) Neuroprotective efficacy of ebselen, an antioxidant with anti-inflammatory actions, in rodent model of permanent middle cerebral artery occlusion. Br J Pharmacol 122:1251-1256.
37. Ullrich V, Weber P, Meisch F and von-Appen F (1996) Ebselen-binding equilibria between plasma and target proteins. Biochem Pharmacol 52:15-19.
38. Wendel A, Kuesters S and Tiegs G (1997) Ebselen - An in vivo immune response modifier. Biomed Environ Sci 10:253-259.
39. Yamaguchi T, Sano K, Kakakura K, Saito I, Shinohara Y, Asano T and Yasuhara H (1998) Ebselen in acute ischemic stroke. A placebo-controlled, double blind clinical trial. Ebselen study group. Stroke 29:12-17.