Leukotriene A4 hydrolase

Prostaglandins & Other Lipid Mediators - Tập 68-69 - Trang 495-510 - 2002
Jesper Z. Haeggström1, Filippa Kull2, Peter Rudberg2, Fredrik Tholander2, M.M.G.M. Thunnissen3
1Dept. of Medical Biochemistry and Biophysics, Karolinska Institutet, Stockholm, Sweden
2Department of Medical Biochemistry and Biophysics, Division of Chemistry II, Karolinska Institutet, S‐171 77 Stockholm, Sweden
3Department of Biochemistry, Arrhenius Laboratories A4, University of Stockholm, S-106 91 Stockholm, Sweden

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Samuelsson, 1983, Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation, Science, 220, 568, 10.1126/science.6301011

Samuelsson, 1987, Leukotrienes and lipoxins: structures, biosynthesis, and biological effects, Science, 237, 1171, 10.1126/science.2820055

Ford-Hutchinson, 1980, Leukotriene B, a potent chemokinetic and aggregating substance released from polymorphonuclear leukocytes, Nature, 286, 264, 10.1038/286264a0

Griffiths, 1997, Collagen-induced arthritis is reduced in 5-lipoxygenase-activating protein-deficient mice, J. Exp. Med., 185, 1123, 10.1084/jem.185.6.1123

Bailie, 1996, Leukotriene-deficient mice manifest enhanced lethality from Klebsiella pneumonia in association with decreased alveolar macrophage phagocytic and bactericidal activities, J. Immunol., 157, 5221, 10.4049/jimmunol.157.12.5221

Mancuso, 2001, Leukotriene B4 augments neutrophil phagocytosis of Klebsiella pneumoniae, Infect. Immun., 69, 2011, 10.1128/IAI.69.4.2011-2016.2001

Chen, 1994, Role of leukotrienes revealed by targeted disruption of the 5-lipoxygenase gene, Nature, 372, 179, 10.1038/372179a0

Byrum, 1999, Determination of the contribution of cysteinyl leukotrienes and leukotriene B4 in acute inflammatory responses using 5-lipoxygenase- and leukotriene A4 hydrolase-deficient mice, J. Immunol., 163, 6810, 10.4049/jimmunol.163.12.6810

Yokomizo, 1997, A G-protein-coupled receptor for leukotriene B4 that mediates chemotaxis, Nature, 387, 620, 10.1038/42506

Yokomizo, 2000, A second leukotriene B4 receptor, BLT2. A new therapeutic target in inflammation and immunological disorders, J. Exp. Med., 192, 421, 10.1084/jem.192.3.421

Devchand, 1996, The PPARα-leukotriene B4 pathway to inflammation control, Nature, 384, 39, 10.1038/384039a0

Haeggström, 2000, Structure, function, and regulation of LTA4 hydrolase, Am. J. Respir. Crit. Care Med., 161, S25, 10.1164/ajrccm.161.supplement_1.ltta-6

Malfroy, 1989, Molecular cloning and amino acid sequence of rat kidney aminopeptidase M: a member of a super family of zinc-metallohydrolases, Biochem. Biophys. Res. Commun., 161, 236, 10.1016/0006-291X(89)91586-6

Vallee, 1990, Zinc coordination, function, and structure of zinc enzymes and other proteins, Biochemistry, 29, 5647, 10.1021/bi00476a001

Haeggström, 1990, Leukotriene A4 hydrolase: a zinc metalloenzyme, Biochem. Biophys. Res. Commun., 172, 965, 10.1016/0006-291X(90)91540-9

Minami, 1990, Leukotriene A4 hydrolase is a zinc-containing aminopeptidase, Biochem. Biophys. Res. Commun., 173, 620, 10.1016/S0006-291X(05)80080-4

Haeggström, 1990, Leukotriene A4 hydrolase: an epoxide hydrolase with peptidase activity, Biochem. Biophys. Res. Commun., 173, 431, 10.1016/S0006-291X(05)81076-9

Barret AJ, Rawlings ND, Woessner JF. Family M1 of membrane alanyl aminopeptidase. In: Barret AJ, Rawlings ND, Woessner JF, Barret AJ, Rawlings ND, Woessner JF, et al., editors. Handbook of proteolytic enzymes. London, San Diego: Academic Press, 1998. p. 994.

Orning, 1994, The bifunctional enzyme leukotriene A4 hydrolase is an arginine aminopeptidase of high efficiency and specificity, J. Biol. Chem., 269, 11269, 10.1016/S0021-9258(19)78120-4

Wetterholm, 1992, Leukotriene A4 hydrolase: an anion activated peptidase, Biochim. Biophys. Acta, 1123, 275, 10.1016/0005-2760(92)90007-I

Örning, 1992, Albumins activate peptide hydrolysis by the bifunctional enzyme LTA4 hydrolase/aminopeptidase, Biochemistry, 31, 4218, 10.1021/bi00132a010

Evans, 1985, Leukotriene A3: a poor substrate but a potent inhibitor of rat and human neutrophil leukotriene A4 hydrolase, J. Biol. Chem., 260, 10966, 10.1016/S0021-9258(17)39131-7

Ohishi, 1987, Leukotriene A4 hydrolase in the human lung. Inactivation of the enzyme with leukotriene A4 isomers, J. Biol. Chem., 262, 10200, 10.1016/S0021-9258(18)61098-1

Orning, 1992, Mechanism-based inactivation of leukotriene A4 hydrolase/aminopeptidase by leukotriene A4. Mass spectrometric and kinetic characterization, J. Biol. Chem., 267, 22733, 10.1016/S0021-9258(18)50009-0

Evans, 1992, Bestatin inhibits covalent coupling of [3H]LTA4 to human leukocyte LTA4 hydrolase, FEBS Lett., 297, 139, 10.1016/0014-5793(92)80345-H

Mueller, 1995, Leukotriene A4 hydrolase: mapping of a heneicosapeptide involved in mechanism-based inactivation, Proc. Natl. Acad. Sci. U.S.A., 92, 8383, 10.1073/pnas.92.18.8383

Mueller, 1996, Leukotriene A4 hydrolase: protection from mechanism-based inactivation by mutation of tyrosine-378, Proc. Natl. Acad. Sci. U.S.A., 93, 5931, 10.1073/pnas.93.12.5931

Mueller, 1996, Leukotriene A4 hydrolase: mutation of tyrosine-383 allows conversion of leukotriene A4 into an isomer of leukotriene B4, J. Biol. Chem., 271, 24345, 10.1074/jbc.271.40.24345

Medina, 1991, Leukotriene A4 hydrolase: determination of the three zinc-binding ligands by site directed mutagenesis and zinc analysis, Proc. Natl. Acad. Sci. U.S.A., 88, 7620, 10.1073/pnas.88.17.7620

Pangburn, 1975, Thermolysin and neutral protease: mechanistic considerations, Biochemistry, 14, 4050, 10.1021/bi00689a019

Kester, 1977, Crystallographic study of the binding of dipeptide inhibitors to thermolysin: implications for the mechanism of catalysis, Biochemistry, 16, 2506, 10.1021/bi00630a030

Wetterholm, 1992, Leukotriene A4 hydrolase: abrogation of the peptidase activity by mutation of glutamic acid-296, Proc. Natl. Acad. Sci. U.S.A., 89, 9141, 10.1073/pnas.89.19.9141

Andberg, 2000, Leukotriene A4 hydrolase: a critical role of glutamic acid-296 for the binding of bestatin, Biochem. J., 345, 621, 10.1042/bj3450621

Watt, 1989, Amino acid sequence deduced from rat kidney cDNA suggests it encodes the Zn-peptidase aminopeptidase N, J. Biol. Chem., 264, 5480, 10.1016/S0021-9258(18)83570-0

Minami, 1992, Leukotriene A4 hydrolase, a bifunctional enzyme. Distinction of leukotriene A4 hydrolase and aminopeptidase activities by site-directed mutagenesis at Glu-297, FEBS. Lett., 309, 353, 10.1016/0014-5793(92)80806-R

Blomster, 1995, Evidence for a catalytic role of tyrosine 383 in the peptidase reaction of leukotriene A4 hydrolase, Eur. J. Biochem., 231, 528, 10.1111/j.1432-1033.1995.0528d.x

Blomster Andberg, 1997, Mutation of tyrosine 383 in leukotriene A4 hydrolase allows formation of 5S,6S-dihydroxy-7,9-trans-11,14-cis-eicosatetraenoic acid: implications for the epoxide hydrolase mechanism, J. Biol. Chem., 272, 23057, 10.1074/jbc.272.37.23057

Thunnissen, 2001, Crystal structure of human leukotriene A4 hydrolase, a bifunctional enzyme in inflammation, Nat. Struct. Biol., 8, 131, 10.1038/84117

Rudberg PC, Tholander F, Thunnisen MGM, Haeggström JZ. Leukotriene A4 hydrolase/aminopeptidase: glutamate 271 is a catalytic residue with specific roles in two distinct enzyme mechanisms. J Biol Chem 2002;277:1398–1404.

Vazeux, 1998, A glutamate residue contributes to the exo-peptidase specificity in aminopeptidase A, Biochem. J., 334, 407, 10.1042/bj3340407

Luciani, 1998, Characterization of Glu350 as a critical residue involved in the N-terminal amine binding site of aminopeptidase N (EC 3.4.11.2): insights into its mechanism of action, Biochemistry, 37, 686, 10.1021/bi971705p

Mueller, 1995, Chemical modification of leukotriene A4 hydrolase-indications for essential tyrosyl and arginyl residues at the active site, Biochemistry, 34, 3536, 10.1021/bi00011a007

Cadel, 1997, Aminopeptidase B from the rat testis is a bifunctional enzyme structurally related to leukotriene A4 hydrolase, Proc. Natl. Acad. Sci. U.S.A., 94, 2963, 10.1073/pnas.94.7.2963

Fukasawa, 1999, Aminopeptidase B is structurally related to leukotriene A4 hydrolase but is not a bifunctional enzyme with epoxide hydrolase activity, Biochem. J., 339, 497, 10.1042/bj3390497

Green, 1987, Monohydroxyeicosatetraenoic acid and leukotriene production by the inflammatory cells of Xenopus laevis, J. Exp. Zool., 243, 211, 10.1002/jez.1402430206

Green, 1987, In vivo generation of 5-lipoxygenase products in frogs and toads, Biochem. Biophys. Res. Commun., 148, 1533, 10.1016/S0006-291X(87)80306-6

Pettitt, 1991, Synthesis of lipoxins and other lipoxygenase products by macrophages from the rainbow trout, Oncorhynchus mykiss, J. Biol. Chem., 266, 8720, 10.1016/S0021-9258(18)31505-9

Knight, 1995, Eicosanoid generating capacities of different tissues from the rainbow trout, Oncorhynchus mykiss, Lipids, 30, 451, 10.1007/BF02536304

Strömberg-Kull, 1998, Purification and characterization of leukotriene A4 hydrolase from Xenopus laevis oocytes, FEBS Lett., 433, 219, 10.1016/S0014-5793(98)00918-1

Nasr, 1996, Yeast, 12, 493, 10.1002/(SICI)1097-0061(199604)12:5<493::AID-YEA929>3.0.CO;2-W

Kull, 1999, Cloning and characterization of a bifunctional leukotriene A4 hydrolase from Saccharomyces cerevisiae, J. Biol. Chem., 274, 34683, 10.1074/jbc.274.49.34683

Kull, 2001, Leukotriene A4 hydrolase from Saccharomyces cerevisiae, formation of leukotriene B4 and identification of catalytic residues, Biochemistry, 40, 12695, 10.1021/bi011348p

Baset, 1998, Molecular cloning and functional expression of a Caenorhabditis elegans aminopeptidase structurally related to mammalian leukotriene A4 hydrolases, J. Biol. Chem., 273, 27978, 10.1074/jbc.273.43.27978

Mancini, 1995, Cloning and characterization of the human leukotriene A4 hydrolase gene, Eur. J. Biochem., 231, 65, 10.1111/j.1432-1033.1995.tb20671.x

Ishizaka, 1999, Increased leukotriene A4 hydrolase expression in the heart of angiotensin II-induced hypertensive rat, FEBS Lett., 463, 155, 10.1016/S0014-5793(99)01607-5

Örning, 1991, Inhibition of leukotriene A4 hydrolase/aminopeptidase by captopril, J. Biol. Chem., 266, 16507, 10.1016/S0021-9258(18)55329-1

Penning, 1995, Kelatorphan and related analogs-potent and selective inhibitors of leukotriene A4 hydrolase, Bioorg. Med. Chem. Lett., 5, 2517, 10.1016/0960-894X(95)00441-U

Labaudinière, 1992, ω-[(ω-Arylalkyl)aryl]alkanoic acids: a new class of specific LTA4 hydrolase inhibitors, J. Med. Chem., 35, 3156, 10.1021/jm00095a010

Yuan, 1992, Novel tight-binding inhibitors of leukotriene A4 hydrolase, J. Am. Chem. Soc., 114, 6552, 10.1021/ja00042a041

Hogg, 1995, Amino hydroxamic acids as potent inhibitors of LTA4 hydrolase, Bioorg. Med. Chem. Lett., 3, 1405, 10.1016/0968-0896(95)00128-4

Wetterholm, 1995, Potent and selective inhibitors of leukotriene A4 hydrolase: effects on purified enzyme and human polymorphonuclear leukocytes, J. Pharmacol. Exp. Ther., 275, 31

Yuan, 1996, Isolation and identification of metabolites of leukotriene A4 hydrolase inhibitor SC-57461 in rats, Drug Metab. Dispos., 24, 1124

Penning, 2000, Structure-activity relationship studies on 1-[2-(4-phenylphenoxy)ethyl]pyrrolidine (SC-22716), a potent inhibitor of leukotriene A4 (LTA4) hydrolase, J. Med. Chem., 43, 721, 10.1021/jm990496z

Smith, 1996, Pharmacological characterization of selective inhibitors of leukotriene A4 hydrolase, Prostaglandins Leukot. Essent. Fatty Acids, 55, 13

Guex, 1997, SWISS-MODEL and the Swiss-PDB viewer: an environment for comparative protein modeling, Electrophoresis, 18, 2714, 10.1002/elps.1150181505

Altschul, 1997, Gapped BLAST and PSI-BLAST: a new generation of protein database search programs, Nucleic Acids Res., 25, 3389, 10.1093/nar/25.17.3389

Thompson, 1994, CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice, Nucleic Acids Res., 22, 4673, 10.1093/nar/22.22.4673