Autotaxin inhibitors: a patent review

Bibliography

• Stracke ML, Krutzsch HC, Unsworth EJ, et al. Identification, purification, and partial sequence analysis of autotaxin, a novel motility-stimulating protein. J Biol Chem 1992;267:2524-9
   PubMed Web of Science ®Google Scholar
• Tokumura A, Majima E, Kariya Y, et al. Identification of human plasma lysophospholipase D, a lysophosphatidic acid-producing enzyme, as autotaxin, a multifunctional phosphodiesterase. J Biol Chem 2002;277:39436-42
   PubMed Web of Science ®Google Scholar
• Umezu-Goto M, Kishi Y, Taira A, et al. Autotaxin has lysophospholipase D activity leading to tumor cell growth and motility by lysophosphatidic acid production. J Cell Biol 2002;158:227-33
   PubMed Web of Science ®Google Scholar
• Pyne S. Lysolipids: Sphingosine 1-phosphate and lysophosphatidic acid. In: Nicolaou A, Kokotos G, editors. Bioactive lipids. The Oily Press; England: 2004
   Google Scholar
• Moolenaar WH, van Meeteren LA, Giepmans BN. The ins and outs of lysophosphatidic acid signaling. Bioessays 2004;26:870-81
   PubMed Web of Science ®Google Scholar
• van Meeteren LA, Moolenaar WH. Regulation and biological activities of the autotaxin-LPA axis. Prog Lipid Res 2007;46:145-60
   PubMed Web of Science ®Google Scholar
• Noguchi K, Herr D, Mutoh T, et al. Lysophosphatidic acid (LPA) and its receptors. Curr Opin Pharmacol 2009;9:15-23
   PubMed Web of Science ®Google Scholar
• Prestwich GD, Gajewiak J, Zhang H, et al. Phosphatase-resistant analogues of lysophosphatidic acid: agonists promote healing, antagonists and autotaxin inhibitors treat cancer. Biochim Biophys Acta 2008;1781:588-94
   PubMed Web of Science ®Google Scholar
• Parrill AL, Baker DL. Autotaxin inhibition: challenges and progress toward novel anti-cancer agents. Anticancer Agents Med Chem 2008;8:917-23
   PubMedGoogle Scholar
• Federico L, Pamuklar Z, Smyth SS, et al. Therapeutic potential of autotaxin/lysophospholipase d inhibitors. Curr Drug Targets 2008;9:698-708
   PubMed Web of Science ®Google Scholar
• Albers HMHG, Ovaa H. Chemical evolution of autotaxin inhibitors. Chem Rev 2012;112:2593-603
   PubMed Web of Science ®Google Scholar
• Parrill AL, Baker DL. Autotaxin inhibitors: a perspective on initial medicinal chemistry efforts. Expert Opin Ther Pat 2010;20:1619-25
   PubMed Web of Science ®Google Scholar
• Murata J, Lee HY, Clair T, et al. cDNA cloning of the human tumor motility-stimulating protein, autotaxin, reveals a homology with phosphodiesterases. J Biol Chem 1994;269:30479-84
   PubMed Web of Science ®Google Scholar
• Giganti A, Rodriguez M, Fould B, et al. Murine and human autotaxin alpha, beta, and gamma isoforms: gene organization, tissue distribution, and biochemical characterization. J Biol Chem 2008;283:7776-89
   PubMed Web of Science ®Google Scholar
• Hashimoto T, Okudaira S, Igarashi K, et al. Identification and biochemical characterization of a novel autotaxin isoform, ATXdelta, with a four-amino acid deletion. J Biochem 2012;151:89-97
   PubMed Web of Science ®Google Scholar
• Houben AJS, van Wijk XMR, van Meeteren LA, et al. The polybasic insertion in autotaxin alpha confers specific binding to heparin and cell surface heparan sulfate proteoglycans. J Biol Chem 2013;288:510-19
   PubMed Web of Science ®Google Scholar
• Gijsbers R, Aoki J, Arai H, et al. The hydrolysis of lysophospholipids and nucleotides by autotaxin (NPP2) involves a single catalytic site. FEBS Lett 2003;538:60-4
   PubMed Web of Science ®Google Scholar
• Nishimasu H, Okudaira S, Hama K, et al. Crystal structure of autotaxin and insight into GPCR activation by lipid mediators. Nat Struct Mol Biol 2011;18:205-12
   PubMed Web of Science ®Google Scholar
• Hausmann J, Kamtekar S, Christodoulou E, et al. Structural basis of substrate discrimination and integrin binding by autotaxin. Nat Struct Mol Biol 2011;18:198-204
   PubMed Web of Science ®Google Scholar
• Day JE, Hall T, Pegg LE, et al. Crystallization and preliminary X-ray diffraction analysis of rat autotaxin. Acta Crystallogr Sect F Struct Biol Cryst Commun 2010;66:1127-9
   PubMedGoogle Scholar
• Inoue K, Tanaka N, Haga A, et al. Crystallization and preliminary X-ray crystallographic analysis of human autotaxin. Acta Crystallogr Sect F Struct Biol Cryst Commun 2011;67:450-3
   PubMedGoogle Scholar
• Clair T, Aoki J, Koh E, et al. Autotaxin hydrolyzes sphingosylphosphorylcholine to produce the regulator of migration, sphingosine-1-phosphate. Cancer Res 2003;63:5446-53
   PubMed Web of Science ®Google Scholar
• Nam SW, Clair T, Campo CK, et al. Autotaxin (ATX), a potent tumor motogen, augments invasive and metastatic potential of ras-transformed cells. Oncogene 2000;19:241-7
   PubMed Web of Science ®Google Scholar
• Mills GB, Moolenaar WH. The emerging role of lysophosphatidic acid in cancer. Nat Rev Cancer 2003;3:582-91
   PubMed Web of Science ®Google Scholar
• David M, Wannecq E, Descotes F, et al. Cancer cell expression of autotaxin controls bone metastasis formation in mouse through lysophosphatidic acid-dependent activation of osteoclasts. PLoS ONE 2010;5:e9741
   PubMed Web of Science ®Google Scholar
• Kanda H, Newton R, Klein R, et al. Autotaxin, an ectoenzyme that produces lysophosphatidic acid, promotes the entry of lymphocytes into secondary lymphoid organs. Nat Immunol 2008;9:415-23
   PubMed Web of Science ®Google Scholar
• Inoue M, Ma L, Aoki J, et al. Autotaxin, a synthetic enzyme of lysophosphatidic acid (LPA), mediates the induction of nerve-injured neuropathic pain. Mol Pain 2008;4:6
   PubMed Web of Science ®Google Scholar
• Inoue M, Xie W, Matsushita Y, et al. Lysophosphatidylcholine induces neuropathic pain through an action of autotaxin to generate lysophosphatidic acid. Neuroscience 2008;152:296-8
   PubMedGoogle Scholar
• Ma L, Uchida H, Nagai J, et al. Evidence for de novo synthesis of lysophosphatidic acid in the spinal cord through phospholipase A2 and autotaxin in nerve injury-induced neuropathic pain. J Pharmacol Exp Ther 2010;333:540-6
   PubMed Web of Science ®Google Scholar
• Ueda H, Matsunaga H, Olaposi OI, et al. Lysophosphatidic acid: chemical signature of neuropathic pain. Biochim Biophys Acta 2013;1831:61-73
   PubMed Web of Science ®Google Scholar
• Zhou Z, Subramanian P, Sevilmis G, et al. Lipoprotein-derived lysophosphatidic acid promotes atherosclerosis by releasing CXCL1 from the endothelium. Cell Metab 2011;13:592-600
   PubMed Web of Science ®Google Scholar
• Nikitopoulou I, Oikonomou N, Karouzakis E, et al. Autotaxin expression from synovial fibroblasts is essential for the pathogenesis of modeled arthritis. J Exp Med 2012;209:925-33
   PubMed Web of Science ®Google Scholar
• Oikonomou N, Mouratis MA, Tzouvelekis A, et al. Pulmonary autotaxin expression contributes to the pathogenesis of pulmonary fibrosis. Am J Respir Cell Mol Biol 2012;47:566-74
   PubMed Web of Science ®Google Scholar
• Tager AM. Autotaxin emerges as a therapeutic target for idiopathic pulmonary fibrosis: limiting fibrosis by limiting lysophosphatidic acid synthesis. Am J Respir Cell Mol Biol 2012;47:563-5
   PubMed Web of Science ®Google Scholar
• Nakagawa H, Ikeda H, Nakamura K, et al. Autotaxin as a novel serum marker of liver fibrosis. Clin Chim Acta 2011;412:1201-6
   PubMedGoogle Scholar
• Ikeda H, Yatomi Y. Autotaxin in liver fibrosis. Clin Chim Acta 2012;413:1817-21
   PubMedGoogle Scholar
• Savaskan NE, Rocha L, Kotter MR, et al. Autotaxin (NPP-2) in the brain: cell type-specific expression and regulation during development and after neurotrauma. Cell Mol Life Sci 2007;64:230-43
   PubMedGoogle Scholar
• Frugier T, Crombie D, Conquest A, et al. Modulation of LPA receptor expression in the human brain following neurotrauma. Cell Mol Neurobiol 2011;31:569-77
   PubMedGoogle Scholar
• Fotopoulou S, Oikonomou N, Grigorieva E, et al. ATX expression and LPA signalling are vital for the development of the nervous system. Dev Biol 2010;339:451-64
   PubMed Web of Science ®Google Scholar
• Moolenaar WH, Houben AJ, Lee SJ, et al. Autotaxin in embryonic development. Biochim Biophys Acta 2013;1831:13-19
   PubMedGoogle Scholar
• Sevastou I, Kaffe E, Mouratis MA, et al. Lysoglycerophospholipids in chronic inflammatory disorders: The PLA(2)/LPC and ATX/LPA axes. Biochim Biophys Acta 2013;1831:42-60
   PubMed Web of Science ®Google Scholar
• Tokumura A, Miyake M, Yoshimoto O, et al. Metal-ion stimulation and inhibition of lysophospholipase D which generates bioactive lysophosphatidic acid in rat plasma. Lipids 1998;33:1009-15
   PubMed Web of Science ®Google Scholar
• van Meeteren LA, Ruurs P, Christodoulou E, et al. Inhibition of autotaxin by lysophosphatidic acid and sphingosine 1-phosphate. J Biol Chem 2005;280:21155-61
   PubMed Web of Science ®Google Scholar
• Scherer M, Schmitz G, Liebisch G. High-throughput analysis of sphingosine 1-phosphate, sphinganine 1-phosphate, and lysophosphatidic acid in plasma samples by liquid chromatography–tandem mass spectrometry. Clin Chem 2009;55:1218-22
   PubMed Web of Science ®Google Scholar
• Murph M, Tanaka T, Pang J, et al. Liquid chromatography mass spectrometry for quantifying plasma lysophospholipids: potential biomarkers for cancer diagnosis. Methods Enzymol 2007;433:1-25
   PubMed Web of Science ®Google Scholar
• Imamura S, Horiuti Y. Enzymatic determination of phospholipase D activity with choline oxidase. J Biochem 1978;83:677-80
   PubMed Web of Science ®Google Scholar
• Albers HMHG, van Meeteren LA, Egan DA, et al. Discovery and optimization of boronic acid based inhibitors of autotaxin. J Med Chem 2010;53:4958-67
   PubMed Web of Science ®Google Scholar
• Albers HMHG, Dong A, van Meeteren LA, et al. Boronic acid-based inhibitor of autotaxin reveals rapid turnover of LPA in the circulation. Proc Natl Acad Sci USA 2010;107:7257-62
   PubMed Web of Science ®Google Scholar
• Ferry G, Moulharat N, Pradère J-P, et al. S32826, A nanomolar inhibitor of autotaxin: discovery, synthesis and applications as a pharmacological tool. J Pharmacol Exp Ther 2008;327:809-19
   PubMed Web of Science ®Google Scholar
• Ferguson CG, Bigman CS, Richardson RD, et al. Fluorogenic phospholipid substrate to detect lysophospholipase D/autotaxin activity. Org Lett 2006;8:2023-6
   PubMed Web of Science ®Google Scholar
• Miller DD, Tigyi GJ, Gududuru V, et al. Acetal phosphate-derived LPA mimics, PPARgamma activators, and autotaxin inhibitors. US2006270634A1; 2006
   Google Scholar
• Gududuru V, Zeng K, Tsukahara R, et al. Identification of Darmstoff analogs as selective agonists and antagonists of lysophosphatidic acid receptors. Bioorg Med Chem Lett 2006;16:451-6
   PubMedGoogle Scholar
• van Meeteren LA, Brinkmann V, Saulnier-Blache JS, et al. Anticancer activity of FTY720: Phosphorylated FTY720 inhibits autotaxin, a metastasis-enhancing and angiogenic lysophospholipase D. Cancer Lett 2008;266:203-8
   PubMedGoogle Scholar
• Parrill-Baker AL, Baker DL, Montedonico LE. Mechanism-based inactivators of autotaxin. WO2010040080A1; 2010
   Google Scholar
• University of Utah Research Foundation, University of Tennessee Research Foundation. a-Chloro and a-bromo phosphonate analogs of lysophosphatidic acid and methods of making and using thereof. WO2008157361A1; 2008
   Google Scholar
• Zhang H, Xu X, Gajewiak J, et al. Dual activity lysophosphatidic acid receptor pan-antagonist/autotaxin inhibitor reduces breast cancer cell migration in vitro and causes tumor regression in vivo. Cancer Res 2009;69:5441-9
   PubMed Web of Science ®Google Scholar
• University of Virginia Patent Foundation. Phosphonate derivatives as autotaxin inhibitors. US2010016258A1; 2010
   Google Scholar
• Cui P, Tomsig JL, McCalmont WF, et al. Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors. Bioorg Med Chem Lett 2007;17:1634-40
   PubMed Web of Science ®Google Scholar
• Jiang G, Madan D, Prestwich GD. Aromatic phosphonates inhibit the lysophospholipase D activity of autotaxin. Bioorg Med Chem Lett 2011;21:5098-101
   PubMed Web of Science ®Google Scholar
• Gupte R, Patil R, Liu J, et al. Benzyl and naphthalene methylphosphonic acid inhibitors of autotaxin with anti-invasive and anti-metastatic activity. ChemMedChem 2011;6:922-35
   PubMedGoogle Scholar
• University of Tennessee Research Foundation. Inhibitors of autotaxin. WO2012100018A1; 2012
   Google Scholar
• Merck Patent GMBH. Piperidine and piperazine derivatives. WO2009046841A2; 2009
   Google Scholar
• Merck Patent GMBH. Heterocyclic compounds as autotaxin inhibitors. WO2010112116A1; 2010
   Google Scholar
• Merck Patent GMBH. Piperidine and piperazine derivatives as autotaxin inhibitors. WO2010115491A2; 2010
   Google Scholar
• Gierse J, Thorarensen A, Beltey K, et al. A novel autotaxin inhibitor reduces lysophosphatidic acid levels in plasma and the site of inflammation. J Pharmacol Exp Ther 2010;334:310-17
   PubMed Web of Science ®Google Scholar
• Merck Patent GMBH. Autotaxin inhibitors. WO2010112124A1; 2010
   Google Scholar
• Merck Patent GMBH. Imidazole derivatives. WO2009046804A1; 2009
   Google Scholar
• Merck Patent GMBH. Benzonaphthyridine compounds used as inhibitors of autotaxin. WO2010060532A1; 2010
   Google Scholar
• Merck Patent GMBH. Benzonaphthyridinamines as autotaxin inhibitors. WO2011116867A1; 2011
   Google Scholar
• Merck Patent GMBH. 2,5-Diamino-substituted pyrido[4,3-d]pyrimidines as autotaxin inhibitors against cancer. WO2010063352A1; 2010
   Google Scholar
• The University of Memphis Research Foundation. Pipemidic acid derivative autotaxin inhibitors. WO2011053597A1; 2011
   Google Scholar
• The University of Memphis Research Foundation. Autotaxin inhibitors. US8268891B1; 2012
   Google Scholar
• Parrill AL, Echols U, Nguyen T, et al. Virtual screening approaches for the identification of non-lipid autotaxin inhibitors. Bioorg Med Chem 2008;16:1784-95
   PubMedGoogle Scholar
• Hoeglund AB, Howard AL, Wanjala IW, et al. Characterization of non-lipid autotaxin inhibitors. Bioorg Med Chem 2010;18:769-76
   PubMed Web of Science ®Google Scholar
• Hoeglund AB, Bostic HE, Howard AL, et al. Optimization of a pipemidic acid autotaxin inhibitor. J Med Chem 2010;53:1056-66
   PubMed Web of Science ®Google Scholar
• Merck Patent GMBH. Heterocyclic compounds as autotaxin inhibitors. WO2011006569A1; 2011
   Google Scholar
• Amira Pharmaceuticals, Inc. Autotaxin inhibitors and uses thereof. WO2012024620A2; 2012
   Google Scholar
• Amira Pharmaceuticals, Inc. Heterocyclic autotaxin inhibitors and uses thereof. WO2012166415A1; 2012
   Google Scholar
• Yale University. Small molecule inhibitors of autotaxin methods of use. WO2009151644A2; 2009
   Google Scholar
• Saunders LP, Ouellette A, Bandle R, et al. Identification of small-molecule inhibitors of autotaxin that inhibit melanoma cell migration and invasion. Mol Cancer Ther 2008;7:3352-62
   PubMedGoogle Scholar
• The University of Memphis Research Foundation. Novel diverse lead compound autotaxin inhibitors. WO2011002918A1; 2011
   Google Scholar
• North EJ, Howard AL, Wanjala IW, et al. Pharmacophore development and application toward the identification of novel, small-molecule autotaxin inhibitors. J Med Chem 2010;53:3095-105
   Google Scholar
• Albers HMHG, Hendrickx LJD, van Tol RJP, et al. Structure-based design of novel boronic acid-based inhibitors of autotaxin. J Med Chem 2011;54:4619-26
   PubMed Web of Science ®Google Scholar
• Bekele RT, Brindley DN. Role of autotaxin and lysophosphatidate in cancer progression and resistance to chemotherapy and radiotherapy. Clin Lipidol 2012;7:313-28
   Web of Science ®Google Scholar
• Panupinthu N, Lee HY, Mills GB. Lysophosphatidic acid production and action: critical new players in breast cancer initiation and progression. Br J Cancer 2010;102:941-6
   PubMed Web of Science ®Google Scholar
• Popnikolov NK, Dalwadi BH, Thomas JD, et al. Association of autotaxin and lysophosphatidic acid receptor 3 with aggressiveness of human breast carcinoma. Tumour Biol 2012;33:2237-43
   PubMedGoogle Scholar
• Chen Z, Huang Y, Shen X, et al. Short hairpin RNA targeting autotaxin reduces human gastric carcinoma AGS cell proliferative, migratory and invasive capabilities in vitro and causes tumor regression in vivo. Oncol Rep 2013;29:1087-93
   PubMedGoogle Scholar
• Kadekar S, Silins I, Korhonen A, et al. Exocrine pancreatic carcinogenesis and autotaxin expression. PLoS ONE 2012;7:e43209
   PubMed Web of Science ®Google Scholar
• Iyer P, Lalane R III, Morris C, et al. Autotaxin-lysophosphatidic acid axis is a novel molecular target for lowering intraocular pressure. PLoS ONE 2012;7:e42627
   PubMedGoogle Scholar
• Federico L, Ren H, Mueller PA, et al. Autotaxin and its product lysophosphatidic acid suppress brown adipose differentiation and promote diet-induced obesity in mice. Mol Endocrinol 2012;26:786-97
   PubMedGoogle Scholar
• Nishimasu H, Ishitani R, Aoki J, et al. A 3D view of autotaxin. Trends Pharmacol Sci 2012;33:138-45
   PubMed Web of Science ®Google Scholar
• Moolenaar WH, Perrakis A. Insights into autotaxin: how to produce and present a lipid mediator. Nat Rev Mol Cell Biol 2011;12:674-9
   PubMed Web of Science ®Google Scholar
• Mize CD, Abbott AM, Gacasan SB, et al. Ligand-based autotaxin pharmacophore models reflect structure-based docking results. J Mol Graphics Modell 2011;31:76-86
   Google Scholar