Drug discovery approaches targeting 5-lipoxygenase-activating protein (FLAP) for inhibition of cellular leukotriene biosynthesis
Tài liệu tham khảo
Back, 2008, Inflammatory signaling through leukotriene receptors in atherosclerosis, Curr. Atheroscler. Rep., 10, 244, 10.1007/s11883-008-0038-7
Back, 2009, Inhibitors of the 5-lipoxygenase pathway in atherosclerosis, Curr. Pharm. Des., 15, 3116, 10.2174/138161209789058020
De Caterina, 2004, From asthma to atherosclerosis-5-lipoxygenase, leukotrienes, and inflammation, N. Engl. J. Med., 350, 4, 10.1056/NEJMp038190
Sampson, 2009, FLAP inhibitors for the treatment of inflammatory diseases, Expert Opin. Invest. Drugs, 10, 1163
Wang, 2010, Eicosanoids and cancer, Nat. Rev. Cancer, 10, 181, 10.1038/nrc2809
Panossian, 1982, On the mechanism of biosynthesis of leukotrienes and related compounds, FEBS Lett., 150, 511, 10.1016/0014-5793(82)80801-6
Gerstmeier, 2016, 5-Lipoxygenase-activating protein rescues activity of 5-lipoxygenase mutations that delay nuclear membrane association and disrupt product formation, FASEB J., 30, 1892, 10.1096/fj.201500210R
Hill, 1992, Reversible membrane association of neutrophil 5-lipoxygenase is accompanied by retention of activity and a change in substrate specificity, J. Biol. Chem., 267, 22048, 10.1016/S0021-9258(18)41633-X
Radmark, 2015, 5-Lipoxygenase, a key enzyme for leukotriene biosynthesis in health and disease, Biochim. Biophys. Acta, 1851, 331, 10.1016/j.bbalip.2014.08.012
Noguchi, 1994, Human 5-lipoxygenase associates with phosphatidylcholine liposomes and modulates LTA4 synthetase activity, Biochim. Biophys. Acta, 1215, 300, 10.1016/0005-2760(94)90057-4
Wiseman, 1987, Kinetics of leukotriene A4 synthesis by 5-lipoxygenase from rat polymorphonuclear leukocytes, Biochemistry, 26, 5684, 10.1021/bi00392a016
Gerstmeier, 2015, Time-resolved in situ assembly of the leukotriene-synthetic 5-lipoxygenase/5-lipoxygenase-activating protein complex in blood leukocytes, FASEB J., 30, 276, 10.1096/fj.15-278010
Folco, 2006, Eicosanoid transcellular biosynthesis: from cell-cell interactions to in vivo tissue responses, Pharmacol. Rev., 58, 375, 10.1124/pr.58.3.8
Afonso, 2012, LTB4 is a signal-relay molecule during neutrophil chemotaxis, Dev. Cell, 22, 1079, 10.1016/j.devcel.2012.02.003
Ciana, 2006, The orphan receptor GPR17 identified as a new dual uracil nucleotides/cysteinyl-leukotrienes receptor, EMBO J., 25, 4615, 10.1038/sj.emboj.7601341
Serhan, 2008, Resolving inflammation: dual anti-inflammatory and pro-resolution lipid mediators, Nat. Rev. Immunol., 8, 349, 10.1038/nri2294
Serhan, 1984, Lipoxins: novel series of biologically active compounds formed from arachidonic acid in human leukocytes, Proc. Natl. Acad. Sci. U. S. A., 81, 5335, 10.1073/pnas.81.17.5335
Serhan, 2011, Novel anti-inflammatory–pro-resolving mediators and their receptors, Curr. Top. Med. Chem., 11, 629, 10.2174/1568026611109060629
Fredman, 2014, Resolvin D1 limits 5-lipoxygenase nuclear localization and leukotriene B4 synthesis by inhibiting a calcium-activated kinase pathway, Proc. Natl. Acad. Sci. U. S. A., 111, 14530, 10.1073/pnas.1410851111
Lehmann, 2015, Lipoxin and resolvin biosynthesis is dependent on 5-lipoxygenase activating protein, FASEB J., 29, 5029, 10.1096/fj.15-275487
Gillard, 1989, L-663,536 (MK-886) (3-[1-(4-chlorobenzyl)-3-t-butyl-thio-5-isopropylindol-2-yl]-2,2-dimethylpropanoic acid), a novel, orally active leukotriene biosynthesis inhibitor, Can. J. Physiol. Pharmacol., 67, 456, 10.1139/y89-073
Evans, 1991, 5-Lipoxygenase-activating protein is the target of a quinoline class of leukotriene synthesis inhibitors, Mol. Pharmacol., 40, 22
Dixon, 1990, Requirement of a 5-lipoxygenase-activating protein for leukotriene synthesis, Nature, 343, 282, 10.1038/343282a0
Miller, 1990, Identification and isolation of a membrane protein necessary for leukotriene production, Nature, 343, 278, 10.1038/343278a0
Bresell, 2005, Bioinformatic and enzymatic characterization of the MAPEG superfamily, FEBS J., 272, 1688, 10.1111/j.1742-4658.2005.04596.x
Basavarajappa, 2014, Roles of coactosin-like protein (CLP) and 5-lipoxygenase-activating protein (FLAP) in cellular leukotriene biosynthesis, Proc. Natl. Acad. Sci. U. S. A., 111, 11371, 10.1073/pnas.1410983111
Rouzer, 1990, MK886, a potent and specific leukotriene biosynthesis inhibitor blocks and reverses the membrane association of 5-lipoxygenase in ionophore-challenged leukocytes, J. Biol. Chem., 265, 1436, 10.1016/S0021-9258(19)40034-3
Ferguson, 2007, Crystal structure of inhibitor-bound human 5-lipoxygenase-activating protein, Science, 317, 510, 10.1126/science.1144346
Mancini, 1993, 5-lipoxygenase-activating protein is an arachidonate binding protein, FEBS Lett., 318, 277, 10.1016/0014-5793(93)80528-3
Mandal, 2008, The nuclear membrane organization of leukotriene synthesis, Proc. Natl. Acad. Sci. U. S. A., 105, 20434, 10.1073/pnas.0808211106
Vickers, 1993, Amino acid residues of 5-lipoxygenase-activating protein critical for the binding of leukotriene biosynthesis inhibitors, J. Lipid Mediat., 6, 31
Plante, 2006, 5-Lipoxygenase-activating protein homodimer in human neutrophils: evidence for a role in leukotriene biosynthesis, Biochem. J., 393, 211, 10.1042/BJ20060669
Woods, 1993, Singer, II, 5-lipoxygenase and 5-lipoxygenase-activating protein are localized in the nuclear envelope of activated human leukocytes, J. Exp. Med., 178, 1935, 10.1084/jem.178.6.1935
Hafner, 2015, Characterization of the interaction of human 5-lipoxygenase with its activating protein FLAP, Biochim. Biophys. Acta, 1851, 1465, 10.1016/j.bbalip.2015.08.010
Mandal, 2004, The membrane organization of leukotriene synthesis, Proc. Natl. Acad. Sci. U. S. A., 101, 6587, 10.1073/pnas.0308523101
Ferguson, 2012, Structure-based drug design on membrane protein targets: human integral membrane protein 5-lipoxygenase-activating protein, 267
Pettersen, 2015, Recent advances for FLAP inhibitors, Bioorg. Med. Chem. Lett., 25, 2607, 10.1016/j.bmcl.2015.04.090
Antoniu, 2014, Targeting 5-lipoxygenase-activating protein in asthma and chronic obstructive pulmonary disease, Expert Opin. Ther. Targets, 18, 1285, 10.1517/14728222.2014.945425
Coutts, 1985, Arymethyl phenyl ethers. A new class of specific inhibitors of 5-lipoxygenase, 627
Young, 1991, Development of novel leukotriene–based anti-asthma drugs: MK-886 and MK-571, Agents Actions Suppl., 34, 179
Prasit, 1995, Development of MK 0591 : an orally active leukotriene biosynthesis inhibitor with a novel mechanism of action, 233
Prasit, 1993, A new class of leukotriene biosynthesis inhibitor: the development of MK-0591, J. Lipid Mediat., 6, 239
Mancini, 1992, 5-Lipoxygenase-activating protein is the target of a novel hybrid of two classes of leukotriene biosynthesis inhibitors, Mol. Pharmacol., 41, 267
Young, 2012, Discovery and development of montelukast (Singulair®), 154
Brideau, 1992, Pharmacology of MK-0591 (3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(quinolin-2-yl-methoxy)- indol-2-yl]-2,2-dimethyl propanoic acid), a potent, orally active leukotriene biosynthesis inhibitor, Can. J. Physiol. Pharmacol., 70, 799, 10.1139/y92-107
Diamant, 1995, The effect of MK-0591, a novel 5-lipoxygenase activating protein inhibitor, on leukotriene biosynthesis and allergen-induced airway responses in asthmatic subjects in vivo, J. Allergy Clin. Immunol., 95, 42, 10.1016/S0091-6749(95)70151-6
Hatzelmann, 1993, Mode of action of the new selective leukotriene synthesis inhibitor BAY X 1005 ((R)-2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cyclopentyl acetic acid) and structurally related compounds, Biochem. Pharmacol., 45, 101, 10.1016/0006-2952(93)90382-7
Muller-Peddinghaus, 1993, BAY X1005, a new selective inhibitor of leukotriene synthesis: pharmacology and pharmacokinetics, J. Lipid Mediat., 6, 245
Fruchtmann, 1993, In vitro pharmacology of BAY X1005, a new inhibitor of leukotriene synthesis, Agents Actions, 38, 188, 10.1007/BF01976210
Muller-Peddinghaus, 1999, The development of BAY X 1005 and the Bayer series of leukotriene biosynthesis inhibitors, 251
Brooks, 1998, Design of inhibitors of leukotriene biosynthesis and their therapeutic potential, Pure Appl. Chem., 70, 10.1351/pac199870020271
Kolasa, 1997, Synthesis of indolylalkoxyiminoalkylcarboxylates as leukotriene biosynthesis inhibitors, Bioorg. Med. Chem., 5, 507, 10.1016/S0968-0896(96)00265-9
Kolasa, 2000, Symmetrical bis(heteroarylmethoxyphenyl)alkylcarboxylic acids as inhibitors of leukotriene biosynthesis, J. Med. Chem., 43, 3322, 10.1021/jm000180n
Woods, 1996, O-alkylcarboxylate oxime and N-hydroxyurea analogs of substituted indole leukotriene biosynthesis inhibitors, Bioorg. Med. Chem. Lett., 6, 1547, 10.1016/S0960-894X(96)00271-5
Hutchinson, 2009, 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., 52, 5803, 10.1021/jm900945d
Stock, 2010, 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., 20, 213, 10.1016/j.bmcl.2009.10.131
Stock, 2010, Bioorg. Med. Chem. Lett., 20, 4598, 10.1016/j.bmcl.2010.06.011
Stock, 2011, J. Med. Chem., 54, 8013, 10.1021/jm2008369
Chaudhuri, 2014, Effects of a FLAP inhibitor, GSK2190915, in asthmatics with high sputum neutrophils, Pulm. Pharmacol. Ther., 27, 62, 10.1016/j.pupt.2013.11.007
Kent, 2014, The effect of GSK2190915, a 5-lipoxygenase-activating protein inhibitor, on exercise-induced bronchoconstriction, Allergy Asthma Proc., 35, 126, 10.2500/aap.2014.35.3723
Musiyenko, 2009, A novel 5-lipoxygenase-activating protein inhibitor, AM679, reduces inflammation in the respiratory syncytial virus-infected mouse eye, Clin. Vaccine Immunol., 16, 1654, 10.1128/CVI.00220-09
Funk, 2005, Leukotriene modifiers as potential therapeutics for cardiovascular disease, Nat. Rev. Drug Discov., 4, 664, 10.1038/nrd1796
Macdonald, 2008, Substituted 2,2-bisaryl-bicycloheptanes as novel and potent inhibitors of 5-lipoxygenase activating protein, Bioorg. Med. Chem. Lett., 18, 2023, 10.1016/j.bmcl.2008.01.105
Chu, 2012, Evaluation of endo- and exo-aryl-substitutions and central scaffold modifications on diphenyl substituted alkanes as 5-lipoxygenase activating protein inhibitors, Bioorg. Med. Chem. Lett., 22, 4133, 10.1016/j.bmcl.2012.04.064
Armstrong, 2006
Chu, 2006
Chu, 2007
Ogawa, 2008
Ogawa, 2008
Lemurell, 2015, Discovery of AZD6642, an inhibitor of 5-lipoxygenase activating protein (FLAP) for the treatment of inflammatory diseases, J. Med. Chem., 58, 897, 10.1021/jm501531v
Takahashi, 2015, J. Med. Chem., 58, 1669, 10.1021/jm501185j
Berry, 2012
Bacani, 2014
Song, 2016, Polypharmacology of small-molecule modulators of the 5-lipoxygenase activating protein (FLAP) observed via a high-throughput lipidomics platform, J. Biomol. Screen., 21, 127, 10.1177/1087057115607815
Blevitt, 2016, A single amino acid difference between mouse and human 5-lipoxygenase activating protein (FLAP) explains the speciation and differential pharmacology of novel FLAP inhibitors, J. Biol. Chem., 291, 12724, 10.1074/jbc.M116.725325
Banoglu, 2012, Identification of novel benzimidazole derivatives as inhibitors of leukotriene biosynthesis by virtual screening targeting 5-lipoxygenase-activating protein (FLAP), Bioorg. Med. Chem., 20, 3728, 10.1016/j.bmc.2012.04.048
Levent, 2016, Synthesis and biological evaluation of C(5)-substituted derivatives of leukotriene biosynthesis inhibitor BRP-7, Eur. J. Med. Chem., 122, 510, 10.1016/j.ejmech.2016.07.004
Sardella, 2014, Chromatographic separation and biological evaluation of benzimidazole derivative enantiomers as inhibitors of leukotriene biosynthesis, J. Pharm. Biomed. Anal., 89, 88, 10.1016/j.jpba.2013.10.039
Pergola, 2014, The novel benzimidazole derivative BRP-7 inhibits leukotriene biosynthesis in vitro and in vivo by targeting 5-lipoxygenase-activating protein (FLAP), Br. J. Pharmacol., 171, 3051, 10.1111/bph.12625
Chen, 2012
Chen, 2013
Chai, 2014
Chai, 2014
Alvaro-Gracia, 2004, Licofelone–clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis, Rheumatol. (Oxford, U. K.), 43, i21, 10.1093/rheumatology/keh105
Ding, 2003, Licofelone (Merckle), IDrugs, 6, 802
Fischer, 2007, The molecular mechanism of the inhibition by licofelone of the biosynthesis of 5-lipoxygenase products, Br. J. Pharmacol., 152, 471, 10.1038/sj.bjp.0707416
Banoglu, 2016, 4,5-Diarylisoxazol-3-carboxylic acids: a new class of leukotriene biosynthesis inhibitors potentially targeting 5-lipoxygenase-activating protein (FLAP), Eur. J. Med. Chem., 113, 1, 10.1016/j.ejmech.2016.02.027
Garscha, 2016, BRP-187: a potent inhibitor of leukotriene biosynthesis that acts through impeding the dynamic 5-lipoxygenase/5-lipoxygenase-activating protein (FLAP) complex assembly, Biochem. Pharmacol., 119, 17, 10.1016/j.bcp.2016.08.023
Peters-Golden, 2007, Leukotrienes, N. Engl. J. Med., 357, 1841, 10.1056/NEJMra071371
Samuelsson, 1983, Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation, Science, 220, 568, 10.1126/science.6301011
Chwiesko-Minarowska, 2012, The role of leukotrienes in the pathogenesis of systemic sclerosis, Folia Histochem. Cytobiol., 50, 180, 10.5603/FHC.2012.0027
Di Gennaro, 2012, The leukotrienes: immune-modulating lipid mediators of disease, Adv. Immunol., 116, 51, 10.1016/B978-0-12-394300-2.00002-8
Korotkova, 2014, The skeletal muscle arachidonic acid cascade in health and inflammatory disease, Nat. Rev. Rheumatol., 10, 295, 10.1038/nrrheum.2014.2
Haeggstrom, 2011, Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease, Chem. Rev., 111, 5866, 10.1021/cr200246d
Liu, 2015, The role of leukotrienes in allergic diseases, Allergol. Int., 64, 17, 10.1016/j.alit.2014.09.001
Caliskan, 2013, Overview of recent drug discovery approaches for new generation leukotriene A4 hydrolase inhibitors, Expert Opin. Drug Discov., 8, 49, 10.1517/17460441.2013.735228
Friesen, 2005, Leukotriene biosynthesis inhibitors, Annu. Rep. Med. Chem., 40, 199
Werz, 2006, Therapeutic options for 5-lipoxygenase inhibitors, Pharmacol. Ther., 112, 701, 10.1016/j.pharmthera.2006.05.009
Young, 2001, Discovery of montelukast: a once-a-day oral antagonist of leukotriene D4 for the treatment of chronic asthma, Prog. Med. Chem., 38, 249, 10.1016/S0079-6468(08)70095-X
Wenzel, 1996, Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma, Ann. Pharmacother., 30, 858, 10.1177/106002809603000725
Joshi, 2004, In vitro metabolism of 2-acetylbenzothiophene: relevance to zileuton hepatotoxicity, Chem. Res. Toxicol., 17, 137, 10.1021/tx0341409
Joshi, 2009, 2-ABT-S-oxide detoxification by glutathione S-transferases A1-1, M1-1 and P1-1: implications for toxicity associated with zileuton, Xenobiotica, 39, 197, 10.1080/00498250802651976
Capra, 2006, Cysteinyl-leukotriene receptor antagonists: present situation and future opportunities, Curr. Med. Chem., 13, 3213, 10.2174/092986706778742963
Devillier, 1999, Leukotrienes, leukotriene receptor antagonists and leukotriene synthesis inhibitors in asthma: an update. Part II: clinical studies with leukotriene receptor antagonists and leukotriene synthesis inhibitors in asthma, Pharmacol. Res., 40, 15, 10.1006/phrs.1998.0461
Dahlen, 1997, Inhibition of allergen-induced airway obstruction and leukotriene generation in atopic asthmatic subjects by the leukotriene biosynthesis inhibitor BAYx 1005, Thorax, 52, 342, 10.1136/thx.52.4.342
Friedman, 1993, Oral leukotriene inhibitor (MK-886) blocks allergen-induced airway responses, Am. Rev. Respir. Dis., 147, 839, 10.1164/ajrccm/147.4.839
Follows, 2013, Efficacy, safety and tolerability of GSK2190915, a 5-lipoxygenase activating protein inhibitor, in adults and adolescents with persistent asthma: a randomised dose-ranging study, Respir. Res., 14, 54, 10.1186/1465-9921-14-54
Poeckel, 2010, The 5-lipoxygenase/leukotriene pathway in preclinical models of cardiovascular disease, Cardiovasc. Res., 86, 243, 10.1093/cvr/cvq016
Riccioni, 2008, Leukotriene modifiers in the treatment of cardiovascular diseases, J. Leukoc. Biol., 84, 1374, 10.1189/jlb.0808476
Spanbroek, 2003, Expanding expression of the 5-lipoxygenase pathway within the arterial wall during human atherogenesis, Proc. Natl. Acad. Sci. U. S. A., 100, 1238, 10.1073/pnas.242716099
Spanbroek, 2003, The potential role of antileukotriene drugs in atherosclerosis, Drug News Perspect., 16, 485, 10.1358/dnp.2003.16.8.829345
Jawien, 2006, Inhibition of five lipoxygenase activating protein (FLAP) by MK-886 decreases atherosclerosis in apoE/LDLR-double knockout mice, Eur. J. Clin. Invest., 36, 141, 10.1111/j.1365-2362.2006.01606.x
Back, 2007, 5-Lipoxygenase-activating protein: a potential link between innate and adaptive immunity in atherosclerosis and adipose tissue inflammation, Circ. Res., 100, 946, 10.1161/01.RES.0000264498.60702.0d
Jawien, 2007, BAY x 1005 attenuates atherosclerosis in apoE/LDLR - double knockout mice, J. Physiol. Pharmacol., 58, 583
Qiu, 2006, Expression of 5-lipoxygenase and leukotriene A4 hydrolase in human atherosclerotic lesions correlates with symptoms of plaque instability, Proc. Natl. Acad. Sci. U. S. A., 103, 8161, 10.1073/pnas.0602414103
Girelli, 2007, ALOX5AP gene variants and risk of coronary artery disease: an angiography-based study, Eur. J. Hum. Genet., 15, 959, 10.1038/sj.ejhg.5201854
Helgadottir, 2004, The gene encoding 5-lipoxygenase activating protein confers risk of myocardial infarction and stroke, Nat. Genet., 36, 233, 10.1038/ng1311
Holloway, 2008, The role of LTA4H and ALOX5AP polymorphism in asthma and allergy susceptibility, Allergy, 63, 1046, 10.1111/j.1398-9995.2008.01667.x
Ji, 2011, Genetic variants in the promoter region of the ALOX5AP gene and susceptibility of ischemic stroke, Cerebrovasc. Dis., 32, 261, 10.1159/000330341
Kajimoto, 2005, Validation of the association between the gene encoding 5-lipoxygenase-activating protein and myocardial infarction in a Japanese population, Circ. J., 69, 1029, 10.1253/circj.69.1029
Kaushal, 2007, Association of ALOX5AP with ischemic stroke: a population-based case-control study, Hum. Genet., 121, 601, 10.1007/s00439-007-0338-y
Lohmussaar, 2005, ALOX5AP gene and the PDE4D gene in a central European population of stroke patients, Stroke, 36, 731, 10.1161/01.STR.0000157587.59821.87
Nair, 2014, Expression analysis of leukotriene-inflammatory gene interaction network in patients with coronary artery disease, J. Atheroscler. Thromb., 21, 329, 10.5551/jat.20123
Hakonarson, 2005, Effects of a 5-lipoxygenase-activating protein inhibitor on biomarkers associated with risk of myocardial infarction: a randomized trial, JAMA, J. Am. Med. Assoc., 293, 2245, 10.1001/jama.293.18.2245
Gaztanaga, 2015, A phase 2 randomized, double-blind, placebo-controlled study of the effect of VIA-2291, a 5-lipoxygenase inhibitor, on vascular inflammation in patients after an acute coronary syndrome, Atherosclerosis, 240, 53, 10.1016/j.atherosclerosis.2015.02.027
Tardif, 2010, Treatment with 5-lipoxygenase inhibitor VIA-2291 (Atreleuton) in patients with recent acute coronary syndrome, Circ. Cardiovasc. Imaging, 3, 298, 10.1161/CIRCIMAGING.110.937169
De Caterina, 1988, Leukotriene B4 production in human atherosclerotic plaques, Biomed. Biochim. Acta, 47, S182
Evans, 2008, What's all the FLAP about?: 5-lipoxygenase-activating protein inhibitors for inflammatory diseases, Trends Pharmacol. Sci., 29, 72, 10.1016/j.tips.2007.11.006