Overview of recent drug discovery approaches for new generation leukotriene A₄ hydrolase inhibitors

Bibliography

• Peters-Golden M, Henderson WR Jr. Leukotrienes. N Engl J Med 2007;357(18):1841-54
   PubMed Web of Science ®Google Scholar
• Samuelsson B. The discovery of the leukotrienes. Am J Respir Crit Care Med 2000;161(2 Pt 2):S2-6
   PubMed Web of Science ®Google Scholar
• Samuelsson B, Borgeat P, Hammarstrm S. Leukotrienes: a new group of biologically active compounds. In Samuelsson B, Ramwell P, Paoletti R. editors. Adv Prostaglandin Thromboxane Res. Raven Press; New York: 1998;1-18
   Google Scholar
• Bell RL, Young PR, Albert D, The discovery and development of zileuton: an orally active 5-lipoxygenase inhibitor. Int J Immunopharmacol 1992;14(3):505-10
   PubMed Web of Science ®Google Scholar
• Mandal AK, Jones PB, Bair AM, The nuclear membrane organization of leukotriene synthesis. Proc Natl Acad Sci USA 2008;105(51):20434-9
   PubMed Web of Science ®Google Scholar
• Werz O. 5-lipoxygenase: cellular biology and molecular pharmacology. Curr Drug Targets Inflamm Allergy 2002;1(1):23-44
   PubMedGoogle Scholar
• Radmark O, Werz O, Steinhilber D, 5-Lipoxygenase: regulation of expression and enzyme activity. Trends Biochem Sci 2007;32(7):332-41
   PubMed Web of Science ®Google Scholar
• Funk CD. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001;294(5548):1871-5
   PubMed Web of Science ®Google Scholar
• Usery JB, Self TH, Muthiah MP, Potential role of leukotriene modifiers in the treatment of chronic obstructive pulmonary disease. Pharmacotherapy 2008;28(9):1183-7
   PubMed Web of Science ®Google Scholar
• Werz O, Steinhilber D. Therapeutic options for 5-lipoxygenase inhibitors. Pharmacol Ther 2006;112(3):701-18
   PubMed Web of Science ®Google Scholar
• Wenzel SE, Kamada AK. Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother 1996;30(7-8):858-64
   PubMed Web of Science ®Google Scholar
• Ducharme Y, Blouin M, Brideau C, The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor. ACS Med Chem Lett 2010;1:170-4
   PubMed Web of Science ®Google Scholar
• Drazen J. Clinical pharmacology of leukotriene receptor antagonists and 5-lipoxygenase inhibitors. Am J Respir Crit Care Med 1998;157(6 Pt 2):S233-7; discussion S47-8
   Web of Science ®Google Scholar
• Hutchinson JH, Li Y, Arruda JM, 5-lipoxygenase-activating protein inhibitors: development of 3-[3-tert-butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-5- (pyridin-2-ylmeth oxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (AM103). J Med Chem 2009;52(19):5803-15
   PubMed Web of Science ®Google Scholar
• Stock N, Baccei C, Bain G, 5-Lipoxygenase-activating protein inhibitors. Part 2: 3-{5-((S)-1-Acetyl-2,3-dihydro-1H-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5 - methoxy-pyrimidin-2-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid (AM679)-a potent FLAP inhibitor. Bioorg Med Chem Lett 2010;20(1):213-17
   PubMed Web of Science ®Google Scholar
• Stock N, Baccei C, Bain G, 5-Lipoxygenase-activating protein inhibitors. Part 3: 3-{3-tert-Butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-5-(5-methyl-pyrid in-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (AM643)-A potent FLAP inhibitor suitable for topical administration. Bioorg Med Chem Lett 2010;20(15):4598-601
   PubMed Web of Science ®Google Scholar
• Stock NS, Bain G, Zunic J, 5-Lipoxygenase-activating protein (FLAP) inhibitors. Part 4: development of 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5- (5-methylpyridin-2-y lmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid (AM803), a potent, oral, once daily FLAP inhibitor. J Med Chem 2011;54(23):8013-29
   PubMed Web of Science ®Google Scholar
• Grice CA, Gomez L. Current status of leukotriene A4 hydrolase inhibitors. Expert Opin Ther Patents 2008;18(12):1333-50
   Web of Science ®Google Scholar
• Haeggstrom JZ. Leukotriene A4 hydrolase/aminopeptidase, the gatekeeper of chemotactic leukotriene B4 biosynthesis. J Biol Chem 2004;279(49):50639-42
   PubMed Web of Science ®Google Scholar
• Penning TD. Inhibitors of leukotriene A4 (LTA4) hydrolase as potential anti- inflammatory agents. Curr Pharm Des 2001;7(3):163-79
   PubMed Web of Science ®Google Scholar
• Haeggstrom JZ, Tholander F, Wetterholm A. Structure and catalytic mechanisms of leukotriene A4 hydrolase. Prostaglandins Other Lipid Mediat 2007;83(3):198-202
   PubMed Web of Science ®Google Scholar
• Malfroy B, Kado-Fong H, Gros C, Molecular cloning and amino acid sequence of rat kidney aminopeptidase M: a member of a super family of zinc- metallohydrolases. Biochem Biophys Res Commun 1989;161(1):236-41
   PubMed Web of Science ®Google Scholar
• Vallee BL, Auld DS. Zinc coordination, function, and structure of zinc enzymes and other proteins. Biochemistry 1990;29(24):5647-59
   PubMed Web of Science ®Google Scholar
• Haeggstrom JZ, Wetterholm A, Vallee BL, Leukotriene A4 hydrolase: an epoxide hydrolase with peptidase activity. Biochem Biophys Res Commun 1990;173(1):431-7
   PubMed Web of Science ®Google Scholar
• Orning L, Fitzpatrick FA. Albumins activate peptide hydrolysis by the bifunctional enzyme LTA4 hydrolase/aminopeptidase. Biochemistry 1992;31(17):4218-23
   PubMed Web of Science ®Google Scholar
• Orning L, Gierse JK, Fitzpatrick FA. The bifunctional enzyme leukotriene-A4 hydrolase is an arginine aminopeptidase of high efficiency and specificity. J Biol Chem 1994;269(15):11269-73
   PubMed Web of Science ®Google Scholar
• Barret AJ, Rawlings ND, Woessner JF. editors. Handbook of proteolytic enzymes. Academic Press; London: 1998
   Google Scholar
• Tholander F, Muroya A, Roques BP, Structure-based dissection of the active site chemistry of leukotriene A4 hydrolase: implications for M1 aminopeptidases and inhibitor design. Chem Biol 2008;15(9):920-9
   PubMed Web of Science ®Google Scholar
• Thunnissen MM, Nordlund P, Haeggstrom JZ. Crystal structure of human leukotriene A(4) hydrolase, a bifunctional enzyme in inflammation. Nat Struct Biol 2001;8(2):131-5
   PubMedGoogle Scholar
• Haeggstrom JZ, Funk CD. Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease. Chem Rev 2011;111(10):5866-98
   PubMed Web of Science ®Google Scholar
• Rinaldo-Matthis A, Haeggstrom JZ. Structures and mechanisms of enzymes in the leukotriene cascade. Biochimie 2010;92(6):676-81
   PubMed Web of Science ®Google Scholar
• Tholander F, Roques BP, Fournie-Zaluski MC, Crystal structure of leukotriene A4 hydrolase in complex with kelatorphan, implications for design of zinc metallopeptidase inhibitors. FEBS Lett 2010;584(15):3446-51
   PubMed Web of Science ®Google Scholar
• GD Searle&Co. Novel Leukotriene A4 hydrolase inhibitors. Expert Opin Ther Patents 1999;9(1):91-5
   Google Scholar
• Penning TD, Chandrakumar NS, Chen BB, Structure-activity relationship studies on 1-[2-(4-Phenylphenoxy)ethyl]pyrrolidine (SC-22716), a potent inhibitor of leukotriene A(4) (LTA(4)) hydrolase. J Med Chem 2000;43(4):721-35
   PubMed Web of Science ®Google Scholar
• Penning TD, Chandrakumar NS, Desai BN, Pyrrolidine and piperidine analogues of SC-57461A as potent, orally active inhibitors of leukotriene A(4) hydrolase. Bioorg Med Chem Lett 2002;12(23):3383-6
   PubMed Web of Science ®Google Scholar
• Penning TD, Chandrakumar NS, Desai BN, Synthesis of imidazopyridines and purines as potent inhibitors of leukotriene A4 hydrolase. Bioorg Med Chem Lett 2003;13(6):1137-9
   PubMed Web of Science ®Google Scholar
• Penning TD, Russell MA, Chen BB, Synthesis of potent leukotriene A(4) hydrolase inhibitors. Identification of 3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl] amino]propanoic acid. J Med Chem 2002;45(16):3482-90
   PubMed Web of Science ®Google Scholar
• Kachur JF, Askonas LJ, Villani-Price D, Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase II: in vivo studies. J Pharmacol Exp Ther 2002;300(2):583-7
   PubMed Web of Science ®Google Scholar
• Askonas LJ, Kachur JF, Villani-Price D, Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase I: in vitro studies. J Pharmacol Exp Ther 2002;300(2):577-82
   PubMed Web of Science ®Google Scholar
• Sandanayaka V, Mamat B, Mishra RK, Discovery of 4-[(2S)-2-{[4-(4- chlorophenoxy)phenoxy]methyl}-1-pyrrolidinyl]butanoic acid (DG-051) as a novel leukotriene A4 hydrolase inhibitor of leukotriene B4 biosynthesis. J Med Chem 2010;53(2):573-85
   PubMed Web of Science ®Google Scholar
• Orning L, Krivi G, Bild G, Inhibition of leukotriene A4 hydrolase/aminopeptidase by captopril. J Biol Chem 1991;266(25):16507-11
   PubMed Web of Science ®Google Scholar
• Thunnissen MM, Andersson B, Samuelsson B, Crystal structures of leukotriene A4 hydrolase in complex with captopril and two competitive tight-binding inhibitors. FASEB J 2002;16(12):1648-50
   PubMedGoogle Scholar
• Enomoto H, Morikawa Y, Miyake Y, Synthesis and biological evaluation of N- mercaptoacylproline and N-mercaptoacylthiazolidine-4-carboxylic acid derivatives as leukotriene A4 hydrolase inhibitors. Bioorg Med Chem Lett 2008;18(16):4529-32
   PubMed Web of Science ®Google Scholar
• Tsuji F, Miyake Y, Horiuchi M, Involvement of leukotriene B4 in murine dermatitis models. Biochem Pharmacol 1998;55(3):297-304
   PubMed Web of Science ®Google Scholar
• Tsuji F, Miyake Y, Enomoto H, Effects of SA6541, a leukotriene A4 hydrolase inhibitor, and indomethacin on carrageenan-induced murine dermatitis. Eur J Pharmacol 1998;346(1):81-5
   PubMed Web of Science ®Google Scholar
• Orning L, Krivi G, Fitzpatrick FA. Leukotriene A4 hydrolase. Inhibition by bestatin and intrinsic aminopeptidase activity establish its functional resemblance to metallohydrolase enzymes. J Biol Chem 1991;266(3):1375-8
   PubMed Web of Science ®Google Scholar
• Tsuji F, Oki K, Fujisawa K, Involvement of leukotriene B4 in arthritis models. Life Sci 1999;64(3):PL51-6
   PubMed Web of Science ®Google Scholar
• Enomoto H, Morikawa Y, Miyake Y, Synthesis and biological evaluation of N- mercaptoacylcysteine derivatives as leukotriene A4 hydrolase inhibitors. Bioorg Med Chem Lett 2009;19(2):442-6
   PubMed Web of Science ®Google Scholar
• Kirkland TA, Adler M, Bauman JG, Synthesis of glutamic acid analogs as potent inhibitors of leukotriene A4 hydrolase. Bioorg Med Chem 2008;16(9):4963-83
   PubMed Web of Science ®Google Scholar
• Ye B, Bauman J, Chen M, Synthesis of N-alkyl glycine amides as potent inhibitors of leukotriene A4 hydrolase. Bioorg Med Chem Lett 2008;18(14):3891-4
   PubMed Web of Science ®Google Scholar
• Khim SK, Bauman J, Evans J, Discovery of novel and potent aryl diamines as leukotriene A4 hydrolase inhibitors. Bioorg Med Chem Lett 2008;18(14):3895-8
   PubMed Web of Science ®Google Scholar
• Davies DR, Mamat B, Magnusson OT, Discovery of leukotriene A4 hydrolase inhibitors using metabolomics biased fragment crystallography. J Med Chem 2009;52(15):4694-715
   PubMed Web of Science ®Google Scholar
• Enache LA, Zhang J, Sullins DW, Synthesis and structural assignment of two major metabolites of the LTA4H inhibitor DG-051. Bioorg Med Chem Lett 2009;19(22):6275-9
   PubMed Web of Science ®Google Scholar
• Sandanayaka V, Mamat B, Bhagat N, Discovery of novel leukotriene A4 hydrolase inhibitors based on piperidine and piperazine scaffolds. Bioorg Med Chem Lett 2010;20(9):2851-4
   PubMed Web of Science ®Google Scholar
• Axe FU, Bembenek SD, Butler CR, Benzimidazole, benzthiazole and benzoxazole derivatives and their use as LTA4H modulators. WO2005012297A1; 2005
   Google Scholar
• Rao NL, Dunford PJ, Xue X, Anti-inflammatory activity of a potent, selective leukotriene A4 hydrolase inhibitor in comparison with the 5-lipoxygenase inhibitor zileuton. J Pharmacol Exp Ther 2007;321(3):1154-60
   PubMed Web of Science ®Google Scholar
• Grice CA, Tays KL, Savall BM, Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity. J Med Chem 2008;51(14):4150-69
   PubMed Web of Science ®Google Scholar
• Morphy R, Kay C, Rankovic Z. From magic bullets to designed multiple ligands. Drug Discov Today 2004;9(15):641-51
   PubMed Web of Science ®Google Scholar
• Wei D, Jiang X, Zhou L, Discovery of multitarget inhibitors by combining molecular docking with common pharmacophore matching. J Med Chem 2008;51(24):7882-8
   PubMed Web of Science ®Google Scholar
• Jiang X, Zhou L, Wei D, Activation and inhibition of leukotriene A4 hydrolase aminopeptidase activity by diphenyl ether and derivatives. Bioorg Med Chem Lett 2008;18(24):6549-52
   PubMed Web of Science ®Google Scholar
• Chen Z, Wu Y, Liu Y, Discovery of dual target inhibitors against cyclooxygenases and leukotriene A4 hydrolyase. J Med Chem 2011;54(10):3650-60
   PubMed Web of Science ®Google Scholar
• Jeong CH, Bode AM. Pugliese A, et al. [6]-Gingerol suppresses colon cancer growth by targeting leukotriene A4 hydrolase. Cancer Res 2009;69(13):5584-91
   PubMed Web of Science ®Google Scholar
• Thangapandian S, John S, Sakkiah S, Molecular docking and pharmacophore filtering in the discovery of dual-inhibitors for human leukotriene A4 hydrolase and leukotriene C4 synthase. J Chem Inf Model 2011;51(1):33-44
   PubMed Web of Science ®Google Scholar
• Thangapandian S, John S, Sakkiah S, Pharmacophore-based virtual screening and Bayesian model for the identification of potential human leukotriene A4 hydrolase inhibitors. Eur J Med Chem 2011;46(5):1593-603
   PubMed Web of Science ®Google Scholar
• Thangapandian S, John S, Arooj M, Molecular dynamics simulation study and hybrid pharmacophore model development in human LTA4H inhibitor design. PLoS ONE 2012;7(4):e34593
   PubMedGoogle Scholar
• Gaggar A, Jackson PL, Noerager BD, A novel proteolytic cascade generates an extracellular matrix-derived chemoattractant in chronic neutrophilic inflammation. J Immunol 2008;180(8):5662-9
   PubMed Web of Science ®Google Scholar
• Weathington NM, van Houwelingen AH, Noerager BD, A novel peptide CXCR ligand derived from extracellular matrix degradation during airway inflammation. Nat Med 2006;12(3):317-23
   PubMed Web of Science ®Google Scholar
• Hardison MT, Galin FS, Calderon CE, The presence of a matrix-derived neutrophil chemoattractant in bronchiolitis obliterans syndrome after lung transplantation. J Immunol 2009;182(7):4423-31
   PubMed Web of Science ®Google Scholar
• O'Reilly P, Jackson PL, Noerager B, N-alpha-PGP and PGP, potential biomarkers and therapeutic targets for COPD. Respir Res 2009;10:38
   PubMedGoogle Scholar
• Snelgrove RJ. Leukotriene A4 hydrolase: an anti-inflammatory role for a proinflammatory enzyme. Thorax 2011;66(6):550-1
   PubMed Web of Science ®Google Scholar
• Snelgrove RJ, Jackson PL, Hardison MT, A critical role for LTA4H in limiting chronic pulmonary neutrophilic inflammation. Science 2010;330(6000):90-4
   PubMed Web of Science ®Google Scholar
• De Oliveira EO, Wang K, Kong HS, Effect of the leukotriene A4 hydrolase aminopeptidase augmentor 4-methoxydiphenylmethane in a pre-clinical model of pulmonary emphysema. Bioorg Med Chem Lett 2011;21(22):6746-50
   PubMed Web of Science ®Google Scholar
• Lewis RA, Austen KF, Soberman RJ. Leukotrienes and other products of the 5- lipoxygenase pathway. Biochemistry and relation to pathobiology in human diseases. N Engl J Med 1990;323(10):645-55
   PubMed Web of Science ®Google Scholar
• Friesen RW, Riendeau D. Leukotriene biosynthesis inhibitors. Annu Rep Med Chem 2005;40:199-214
   Web of Science ®Google Scholar
• De Caterina R, Mazzone A, Giannessi D, Leukotriene B4 production in human atherosclerotic plaques. Biomed Biochim Acta 1988;47(10-11):S182-5
   PubMedGoogle Scholar
• Allen S, Dashwood M, Morrison K, Differential leukotriene constrictor responses in human atherosclerotic coronary arteries. Circulation 1998;97(24):2406-13
   PubMed Web of Science ®Google Scholar
• Funk CD. Leukotriene modifiers as potential therapeutics for cardiovascular disease. Nat Rev Drug Discov 2005;4(8):664-72
   PubMed Web of Science ®Google Scholar
• Hakonarson H, Thorvaldsson S, Helgadottir A, Effects of a 5-lipoxygenase-activating protein inhibitor on biomarkers associated with risk of myocardial infarction: a randomized trial. JAMA 2005;293(18):2245-56
   PubMed Web of Science ®Google Scholar
• Jawien J, Korbut R. The current view on the role of leukotrienes in atherogenesis. J Physiol Pharmacol 2010;61(6):647-50
   PubMed Web of Science ®Google Scholar
• Riccioni G, Back M, Capra V. Leukotrienes and atherosclerosis. Curr Drug Targets 2010;11(7):882-7
   PubMed Web of Science ®Google Scholar
• Helgadottir A, Manolescu A, Helgason A, A variant of the gene encoding leukotriene A4 hydrolase confers ethnicity-specific risk of myocardial infarction. Nat Genet 2006;38(1):68-74
   PubMed Web of Science ®Google Scholar
• Qiu H, Gabrielsen A, Agardh HE, Expression of 5-lipoxygenase and leukotriene A4 hydrolase in human atherosclerotic lesions correlates with symptoms of plaque instability. Proc Natl Acad Sci USA 2006;103(21):8161-6
   PubMed Web of Science ®Google Scholar
• Davidson EM, Rae SA, Smith MJ. Leukotriene B4, a mediator of inflammation present in synovial fluid in rheumatoid arthritis. Ann Rheum Dis 1983;42(6):677-9
   PubMed Web of Science ®Google Scholar
• Shao WH, Del Prete A, Bock CB, Targeted disruption of leukotriene B4 receptors BLT1 and BLT2: a critical role for BLT1 in collagen-induced arthritis in mice. J Immunol 2006;176(10):6254-61
   PubMed Web of Science ®Google Scholar
• Chen X, Li N, Wang S, Leukotriene A4 hydrolase in rat and human esophageal adenocarcinomas and inhibitory effects of bestatin. J Natl Cancer Inst 2003;95(14):1053-61
   PubMed Web of Science ®Google Scholar
• Tong WG, Ding XZ, Hennig R, Leukotriene B4 receptor antagonist LY293111 inhibits proliferation and induces apoptosis in human pancreatic cancer cells. Clin Cancer Res 2002;8(10):3232-42
   PubMed Web of Science ®Google Scholar
• Bain G, King CD, Schaab K, Pharmacodynamics, pharmacokinetics and safety of GSK2190915, a novel oral anti-inflammatory 5-lipoxygenase-activating protein inhibitor. Br J Clin Pharmacol 2012; published on line 18 July 2012; doi: 10.1111/j.1365-2125.2012.04386.x
   Google Scholar
• Serhan CN. Lipoxins and aspirin-triggered 15-epi-lipoxins are the first lipid mediators of endogenous anti-inflammation and resolution. Prostaglandins Leukot Essent Fatty Acids 2005;73(3-4):141-62
   PubMed Web of Science ®Google Scholar
• Serhan CN. Novel lipid mediators and resolution mechanisms in acute inflammation: to resolve or not? Am J Pathol 2010;177(4):1576-91
   PubMed Web of Science ®Google Scholar
• Serhan CN, Krishnamoorthy S, Recchiuti A, Novel anti-inflammatory–pro-resolving mediators and their receptors. Curr Top Med Chem 2011;11(6):629-47
   PubMed Web of Science ®Google Scholar