5-Lipoxygenase inhibitors: a review of recent patents (2010 – 2012)

Bibliography

• Funk CD. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001;294:1871-5
   PubMed Web of Science ®Google Scholar
• Samuelsson B, Rouzer CA, Matsumoto T. Human leukocyte 5-lipoxygenase: an enzyme possessing dual enzymatic activities and a multicomponent regulatory system. Adv Prostaglandin Thromboxane Leukot Res 1987;17A:1-11
   PubMedGoogle Scholar
• Haeggstrom JZ. Leukotriene A4 hydrolase/aminopeptidase, the gatekeeper of chemotactic leukotriene B4 biosynthesis. J Biol Chem 2004;279:50639-42
   PubMed Web of Science ®Google Scholar
• Sjöström M, Jakobsson PJ, Heimburger M, et al. Human umbilical vein endothelial cells generate leukotriene C4 via microsomal glutathione S-transferase type 2 and express the CysLT(1) receptor. Eur J Biochem 2001;268:2578-86
   PubMedGoogle Scholar
• Montuschi P. Leukotrienes, antileukotrienes and asthma. Mini Rev Med Chem 2008;8:647-56
   PubMed Web of Science ®Google Scholar
• Werz O, Steinhilber D. Therapeutic options for 5-lipoxygenase inhibitors. Pharmacol Ther 2006;112:701-18
   PubMed Web of Science ®Google Scholar
• Chen Y, Hu Y, Zhang H, et al. Loss of the Alox5 gene impairs leukemia stem cells and prevents chronic myeloid leukemia. Nat Genet 2009;41:783-92
   PubMed Web of Science ®Google Scholar
• Serhan CN, Krishnamoorthy S, Recchiuti A, et al. Novel anti-inflammatory–pro-resolving mediators and their receptors. Curr Top Med Chem 2011;11:629-47
   PubMed Web of Science ®Google Scholar
• Serhan CN, Yang R, Martinod K, et al. Maresins: novel macrophage mediators with potent antiinflammatory and proresolving actions. J Exp Med 2009;206:15-23
   PubMed Web of Science ®Google Scholar
• Gilbert NC, Bartlett SG, Waight MT, et al. The structure of human 5-lipoxygenase. Science 2011;331:217-19
   PubMed Web of Science ®Google Scholar
• Rådmark O. Arachidonate 5-lipoxygenase. J Lipid Mediat Cell Signal 1995;12:171-84
   PubMedGoogle Scholar
• Rådmark O, Werz O, Steinhilber D, et al. 5-Lipoxygenase: regulation of expression and enzyme activity. Trends Biochem Sci 2007;32:332-41
   PubMed Web of Science ®Google Scholar
• Werz O, Szellas D, Steinhilber D, et al. Arachidonic acid promotes phosphorylation of 5-lipoxygenase at Ser-271 by MAPK-activated protein kinase 2 (MK2). J Biol Chem 2002;277:14793-800
   PubMed Web of Science ®Google Scholar
• Werz O, Burkert E, Fischer L, et al. Extracellular signal-regulated kinases phosphorylate 5-lipoxygenase and stimulate 5-lipoxygenase product formation in leukocytes. FASEB J 2002;16:1441-3
   PubMed Web of Science ®Google Scholar
• Hanaka H, Shimizu T, Izumi T. Stress-induced nuclear export of 5-lipoxygenase. Biochem Biophys Res Commun 2005;338:111-16
   PubMed Web of Science ®Google Scholar
• Luo M, Jones SM, Peters-Golden M, et al. Nuclear localization of 5-lipoxygenase as a determinant of leukotriene B4 synthetic capacity. Proc Natl Acad Sci USA 2003;100:12165-70
   PubMed Web of Science ®Google Scholar
• Flamand N, Luo M, Peters-Golden M, et al. Phosphorylation of serine 271 on 5-lipoxygenase and its role in nuclear export. J Biol Chem 2009;284:306-13
   PubMed Web of Science ®Google Scholar
• Luo M, Jones SM, Flamand N, et al. Phosphorylation by protein kinase A inhibits nuclear import of 5-lipoxygenase. J Biol Chem 2005;280:40609-16
   PubMed Web of Science ®Google Scholar
• Pergola C, Dodt G, Rossi A, et al. ERK-mediated regulation of leukotriene biosynthesis by androgens: a molecular basis for gender differences in inflammation and asthma. Proc Natl Acad Sci USA 2008;105:19881-6
   PubMed Web of Science ®Google Scholar
• Dixon RA, Diehl RE, Opas E, et al. Requirement of a 5-lipoxygenase-activating protein for leukotriene synthesis. Nature 1990;343:282-4
   PubMed Web of Science ®Google Scholar
• Lam BK, Penrose JF, Freeman GJ, et al. Expression cloning of a cDNA for human leukotriene C4 synthase, an integral membrane protein conjugating reduced glutathione to leukotriene A4. Proc Natl Acad Sci USA 1994;91:7663-7
   PubMed Web of Science ®Google Scholar
• Jakobsson PJ, Morgenstern R, Mancini J, et al. Membrane-associated proteins in eicosanoid and glutathione metabolism (MAPEG). A widespread protein superfamily. Am J Respir Crit Care Med 2000;161:S20-4
   PubMed Web of Science ®Google Scholar
• Rouzer CA, Ford-Hutchinson AW, Morton HE, et al. MK886, a potent and specific leukotriene biosynthesis inhibitor blocks and reverses the membrane association of 5-lipoxygenase in ionophore-challenged leukocytes. J Biol Chem 1990;265:1436-42
   PubMed Web of Science ®Google Scholar
• Abramovitz M, Wong E, Cox ME, et al. 5-lipoxygenase-activating protein stimulates the utilization of arachidonic acid by 5-lipoxygenase. Eur J Biochem 1993;215:105-11
   PubMedGoogle Scholar
• Jakobsson PJ, Shaskin P, Larsson P, et al. Studies on the regulation and localization of 5-lipoxygenase in human B-lymphocytes. Eur J Biochem 1995;232:37-46
   PubMedGoogle Scholar
• Steinhilber D, Hoshiko S, Grunewald J, et al. Serum factors regulate 5-lipoxygenase activity in maturating HL60 cells. Biochim Biophys Acta 1993;1178:1-8
   PubMedGoogle Scholar
• Chen XS, Sheller JR, Johnson EN, et al. Role of leukotrienes revealed by targeted disruption of the 5-lipoxygenase gene. Nature 1994;372:179-82
   PubMed Web of Science ®Google Scholar
• Byrum RS, Goulet JL, Snouwaert JN, et al. 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 1999;163:6810-19
   PubMed Web of Science ®Google Scholar
• Irvin CG, Tu YP, Sheller JR, et al. 5-Lipoxygenase products are necessary for ovalbumin-induced airway responsiveness in mice. Am J Physiol 1997;272:L1053-8
   Web of Science ®Google Scholar
• Byrum RS, Goulet JL, Griffiths RJ, et al. Role of the 5-lipoxygenase-activating protein (FLAP) in murine acute inflammatory responses. J Exp Med 1997;185:1065-75
   PubMed Web of Science ®Google Scholar
• Montuschi P. LC/MS/MS analysis of leukotriene B4 and other eicosanoids in exhaled breath condensate for assessing lung inflammation. J Chromatogr B Analyt Technol Biomed Life Sci 2009;877:1272-80
   PubMed Web of Science ®Google Scholar
• Montuschi P, Martello S, Felli M, et al. Liquid chromatography/mass spectrometry analysis of exhaled leukotriene B4 in asthmatic children. Respir Res 2005;6:119
   PubMed Web of Science ®Google Scholar
• Montuschi P, Barnes PJ. New perspectives in pharmacological treatment of mild persistent asthma. Drug Discov Today 2011;16:1084-91
   PubMed Web of Science ®Google Scholar
• Montuschi P, Mondino C, Koch P, et al. Effects of montelukast treatment and withdrawal on fractional exhaled nitric oxide and lung function in children with asthma. Chest 2007;132:1876-81
   PubMed Web of Science ®Google Scholar
• Montuschi P. Pharmacotherapy of patients with mild persistent asthma: strategies and unresolved issues. Front Pharmacol 2011;2:35
   PubMed Web of Science ®Google Scholar
• Steinhilber D, Fischer AS, Metzner J, et al. 5-Lipoxygenase: underappreciated role of a pro-inflammatory enzyme in tumorigenesis. Front Pharmacol 2010;1:143
   PubMed Web of Science ®Google Scholar
• Fischer AS, Metzner J, Steinbrink SD, et al. 5-Lipoxygenase inhibitors induce potent anti-proliferative and cytotoxic effects in human tumour cells independently of suppression of 5-lipoxygenase activity. Br J Pharmacol 2010;161:936-49
   PubMed Web of Science ®Google Scholar
• Stock NS, Bain G, Zunic J, et al. 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-ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid (AM803), a potent, oral, once daily FLAP inhibitor. J Med Chem 2011;54:8013-29
   PubMed Web of Science ®Google Scholar
• Evans JF, Ferguson AD, Mosley RT, et al. What's all the FLAP about?: 5-lipoxygenase-activating protein inhibitors for inflammatory diseases. Trends Pharmacol Sci 2008;29:72-8
   PubMed Web of Science ®Google Scholar
• Haeggstrom JZ, Funk CD. Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease. Chem Rev 2011;111:5866-98
   PubMed Web of Science ®Google Scholar
• Montuschi P, Peters-Golden ML. Leukotriene modifiers for asthma treatment. Clin Exp Allergy 2010;40:1732-41
   PubMed Web of Science ®Google Scholar
• Peters-Golden M, Henderson WR Jr. Leukotrienes. N Engl J Med 2007;357:1841-54
   PubMed Web of Science ®Google Scholar
• Ingelsson E, Yin L, Back M. Nationwide cohort study of the leukotriene receptor antagonist montelukast and incident or recurrent cardiovascular disease. J Allergy Clin Immunol 2012;129:702-7 e2
   PubMed Web of Science ®Google Scholar
• Poeckel D, Zemski Berry KA, Murphy RC, et al. Dual 12/15- and 5-lipoxygenase deficiency in macrophages alters arachidonic acid metabolism and attenuates peritonitis and atherosclerosis in ApoE knock-out mice. J Biol Chem 2009;284:21077-89
   PubMed Web of Science ®Google Scholar
• Werz O, Szellas D, Henseler M, et al. Nonredox 5-lipoxygenase inhibitors require glutathione peroxidase for efficient inhibition of 5-lipoxygenase activity. Mol Pharmacol 1998;54:445-51
   PubMed Web of Science ®Google Scholar
• Fischer L, Steinhilber D, Werz O. Molecular pharmacological profile of the nonredox-type 5-lipoxygenase inhibitor CJ-13,610. Br J Pharmacol 2004;142:861-8
   PubMed Web of Science ®Google Scholar
• Werz O, Steinhilber D. Development of 5-lipoxygenase inhibitors–lessons from cellular enzyme regulation. Biochem Pharmacol 2005;70:327-33
   PubMed Web of Science ®Google Scholar
• Wisniewska JM, Rödl CB, Kahnt AS, et al. Molecular characterization of EP6-A novel imidazo[1,2-a]pyridine based direct 5-lipoxygenase inhibitor. Biochem Pharmacol 2012;83:228-40
   PubMed Web of Science ®Google Scholar
• Pergola C, Werz O. 5-Lipoxygenase inhibitors: a review of recent developments and patents. Expert Opin Ther Pat 2010;20:355-75
   PubMed Web of Science ®Google Scholar
• Ranbaxy Laboratories Ltd., India. Preparation of sulfonamide derivatives as 5-lipoxygenase inhibitors. WO2012014127A1; 2012
   Google Scholar
• Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Peop. Rep. China. Preparation of pyrimidine derivatives as 5-lipoxygenase inhibitors. CN101684098A; 2010
   Google Scholar
• Laila Nutraceuticals, India. Analogs of 3-O-acetyl-11-keto-beta-boswellic acid as anti-inflammatory and anti-cancer agents. US20120035176A1; 2012
   Google Scholar
• India. Preparation of novel analogs of 3-O-acetyl-11-keto-beta-boswellic acid as 5-lipoxigenase inhibitors for use in pharmaceutical compositions. WO2005123649A1; 2005
   Google Scholar
• Sailer ER, Schweizer S, Boden SE, et al. Characterization of an acetyl-11-keto-beta-boswellic acid and arachidonate-binding regulatory site of 5-lipoxygenase using photoaffinity labeling. Eur J Biochem 1998;256:364-8
   PubMedGoogle Scholar
• Amira Pharmaceuticals, Inc., USA. Indolizine derivatives as 5-lipoxygenase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases. WO2011038097A2; 2011
   Google Scholar
• Amira Pharmaceuticals, Inc., USA. Preparation of indolizine inhibitors of 5-lipoxygenase for treating respiratory, cardiovascular, and other leukotriene-mediated conditions. WO2011038086A2; 2011
   Google Scholar
• Amira Pharmaceuticals, Inc., USA; Panmira Pharmaceuticals, LLC. Preparation of triazole derivatives as inhibitors of 5-lipoxygenase. WO2011109679A2; 2011
   Google Scholar
• Austria. Naphthalenylazo compounds as medicaments for inhibiting the synthesis of leukotrienes. WO2010055371A1; 2010
   Google Scholar
• UK. 5-lipoxygenase inhibitors. WO2009146871A1; 2009
   Google Scholar
• Tateson JE, Randall RW, Reynolds CH, et al. Selective inhibition of arachidonate 5-lipoxygenase by novel acetohydroxamic acids: biochemical assessment in vitro and ex vivo. Br J Pharmacol 1988;94:528-39
   PubMed Web of Science ®Google Scholar
• Ford-Hutchinson AW, Gresser M, Young RN. 5-Lipoxygenase. Annu Rev Biochem 1994;63:383-417
   PubMed Web of Science ®Google Scholar
• Purapharm International (Hk) Ltd., Peop. Rep. China; Versitech Ltd. Uses of cimiracemate and related compounds for treating inflammation and modulating immune responses. WO2012014085A2; 2012
   Google Scholar
• Burdette JE, Chen SN, Lu ZZ, et al. Black cohosh (Cimicifuga racemosa L.) protects against menadione-induced DNA damage through scavenging of reactive oxygen species: bioassay-directed isolation and characterization of active principles. J Agric Food Chem 2002;50:7022-8
   PubMed Web of Science ®Google Scholar
• Ammon HP, Safayhi H, Mack T, et al. Mechanism of antiinflammatory actions of curcumine and boswellic acids. J Ethnopharmacol 1993;38:113-19
   PubMed Web of Science ®Google Scholar
• He C, Wu Y, Lai Y, et al. Dynamic eicosanoid responses upon different inhibitor and combination treatments on the arachidonic acid metabolic network. Mol Biosyst 2012;8:1585-94
   PubMedGoogle Scholar
• Ranbaxy Laboratories Ltd., India. Preparation of pyrazolylalkylamide derivatives for use as 5-lipoxygenase inhibitors. WO2011161615A1; 2011
   Google Scholar
• Ranbaxy Laboratories Ltd, India. Preparation of pyrazolylalkylamide derivatives for use as 5-lipoxygenase inhibitors. WO2011161645A1; 2011
   Google Scholar
• Argentieri DC, Ritchie DM, Ferro MP, et al. Tepoxalin: a dual cyclooxygenase/5-lipoxygenase inhibitor of arachidonic acid metabolism with potent anti-inflammatory activity and a favorable gastrointestinal profile. J Pharmacol Exp Ther 1994;271:1399-408
   PubMed Web of Science ®Google Scholar
• Maier TJ, Tausch L, Hoernig M, et al. Celecoxib inhibits 5-lipoxygenase. Biochem Pharmacol 2008;76:862-72
   PubMed Web of Science ®Google Scholar
• Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Peop. Rep. China. Preparation of pyrazole derivatives as 5-lipoxygenase and/or leukotriene inhibitors. CN101544631A; 2009
   Google Scholar
• China Pharmaceutical University, Peop. Rep. China. Preparation of hydroxyamines as COX-2 and 5-LOX inhibitors. CN101805303A; 2010
   Google Scholar
• MetaProteomics, LLC, USA. Inhibition of COX-2 and/or 5-LOX activity by fractions isolated or derived from hops. US20090118373A1; 2009
   Google Scholar
• Yeungnam University, Industry-Academy Cooperation Foundation, S. Korea. Anthraquinone derivatives for preventing and treating allergic diseases. KR2011085517A; 2011
   Google Scholar
• Jin JH, Ngoc TM, Bae K, et al. Inhibition of experimental atopic dermatitis by rhubarb (rhizomes of Rheum tanguticum) and 5-lipoxygenase inhibition of its major constituent, emodin. Phytother Res 2011;25:755-9
   PubMed Web of Science ®Google Scholar
• Lu Y, Li Y, Jahng Y, et al. Citreorosein inhibits degranulation and leukotriene C(4) generation through suppression of Syk pathway in mast cells. Mol Cell Biochem 2012;365:333-41
   PubMed Web of Science ®Google Scholar
• Purdue Research Foundation, USA. Long-chain carboxychromanols and analogs for use as anti-inflammatory agents. WO2010033687A1; 2010
   Google Scholar
• Medwell Laboratories Ltd., Israel. Conjugates of polyunsaturated fatty acids and amine-containing compounds and uses thereof. WO2012032509A2; 2012
   Google Scholar
• Brideau C, Chan C, Charleson S, et al. 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 1992;70:799-807
   PubMed Web of Science ®Google Scholar
• Amira Pharmaceuticals, Inc., USA. Preparation of indole and derivatives as 5-lipoxygenase-activating protein (FLAP) inhibitors. WO2009045700A2; 2009
   Google Scholar
• Bain G, King CD, Schaab K, et al. Pharmacodynamics, pharmacokinetics and safety of GSK2190915, a novel oral anti-inflammatory 5-lipoxygenase-activating protein inhibitor. Br J Clin Pharmacol 2013;43:177-86
   Google Scholar
• Kent SE, Boyce M, Diamant Z, et al. The 5-lipoxygenase-activating protein inhibitor, GSK2190915, attenuates the early and late responses to inhaled allergen in mild asthma. Clin Exp Allergy 2013;43:177-86
   PubMed Web of Science ®Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Preparation of indolizine inhibitors of leukotriene production. WO2010027762A1; 2010
   Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Benzimidazoles as inhibitors of leukotriene production and their preparation. WO2012061169A1; 2012
   Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Benzimidazole derivatives as inhibitors of leukotriene production and their preparation and use for the treatment of leukotriene-mediated diseases. WO2011068821A1; 2011
   Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Preparation of benzimidazole derivatives for use as leukotriene production inhibitors. WO2012058254A1; 2012
   Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Preparation of oxadiazole inhibitors of leukotriene production. WO2012040139A1; 2012
   Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Preparation of oxadiazole inhibitors of leukotriene production. WO2012040137A1; 2012
   Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Preparation of oxadiazole derivatives for use as leukotriene production inhibitors. WO2012024150A1; 2012
   Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Preparation of oxadiazole inhibitors of leukotriene production. WO2012027322A1; 2012
   Google Scholar
• Boehringer Ingelheim International GmbH, Germany. Biarylamide as inhibitors of leukotriene production and their preparation. WO2012082817A1; 2012
   Google Scholar
• Nasser SM, Bell GS, Hawksworth RJ, et al. Effect of the 5-lipoxygenase inhibitor ZD2138 on allergen-induced early and late asthmatic responses. Thorax 1994;49:743-8
   PubMed Web of Science ®Google Scholar
• Turner CR, Smith WB, Andresen CJ, et al. The effect of 5-lipoxygenase inhibition on Ascaris antigen (Ag)-induced responses in atopic monkeys. Inflamm Res 1996;45:42-9
   PubMed Web of Science ®Google Scholar
• Rödl CB, Tanrikulu Y, Wisniewska JM, et al. Potent inhibitors of 5-lipoxygenase identified using pseudoreceptors. ChemMedChem 2011;6:1001-5
   PubMed Web of Science ®Google Scholar
• Hofheinz K, Kakularam KR, Adel S, et al. Conversion of pro-inflammatory murine Alox5 into an anti-inflammatory 15S-lipoxygenating enzyme by multiple mutations of sequence determinants. Arch Biochem Biophys 2012;530:40-7
   PubMed Web of Science ®Google Scholar
• Feisst C, Pergola C, Rakonjac M, et al. Hyperforin is a novel type of 5-lipoxygenase inhibitor with high efficacy in vivo. Cell Mol Life Sci 2009;66:2759-71
   PubMed Web of Science ®Google Scholar
• Häfner AK, Cernescu M, Hofmann B, et al. Dimerization of human 5-lipoxygenase. Biol Chem 2011;392:1097-11
   PubMed Web of Science ®Google Scholar