Sphingosine 1-phosphate and lysophosphatidic acid receptors: agonist and antagonist binding and progress toward development of receptor-specific ligands

Mills, 2003, The emerging role of lysophosphatidic acid in cancer, Nat. Rev. Cancer, 3, 582, 10.1038/nrc1143 Spiegel, 2003, Exogenous and intracellularly generated sphingosine 1-phosphate can regulate cellular processes by divergent pathways, Biochem. Soc. Trans., 31, 1216, 10.1042/bst0311216 Hla, 2003, Signaling and biological actions of sphingosine 1-phosphate, Pharmacol. Res., 47, 401, 10.1016/S1043-6618(03)00046-X Spiegel, 2002, Sphingosine 1-phosphate as a therapeutic agent, Leukemia, 16, 1596, 10.1038/sj.leu.2402611 Osborne, 2003, Lipid receptors in cardiovascular development, Annu. Rev. Physiol., 65, 23, 10.1146/annurev.physiol.65.092101.142235 Brinkmann, 2002, The immune modulator, FTY720, targets sphingosine 1-phosphate receptors, J. Biol. Chem., 277, 21453, 10.1074/jbc.C200176200 Mandala, 2002, Alteration of lymphocyte trafficking by sphingosine 1-phosphate receptor agonists, Science, 296, 346, 10.1126/science.1070238 Yanagawa, 1998, FTY720, a novel immunosuppressant, induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats. II. FTY720 prolongs skin allograft survival by decreasing T cell infiltration into grafts but not cytokine production in vivo, J. Immunol., 160, 5493, 10.4049/jimmunol.160.11.5493 Chiba, 1998, FTY720, a novel immunosuppressent, induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats. I. FTY720 selectively decreases the number of circulating mature lymphocytes by acceleration of lymphocyte homing, J. Immunol., 160, 5037, 10.4049/jimmunol.160.10.5037 Suzuki, 1996, A novel immunosuppressant, FTY720, with a unique mechanism of action, induces long-term graft acceptance in rat and dog allotransplantation, Transplantation, 61, 200, 10.1097/00007890-199601270-00006 Brinkmann, 2001, FTY720: altered lymphocyte traffic results in allograft protection, Transplantation, 72, 764, 10.1097/00007890-200109150-00002 Suzuki, 1999, FTY720: mechanisms of action and its effect on organ transplantation (review), Transplant Proc., 31, 2779, 10.1016/S0041-1345(99)00564-3 Deng, 2002, Lysophosphatidic acid protects and rescues intestinal epithelial cells from radiation- and chemotherapy-induced apoptosis, Gastroenterology, 123, 206, 10.1053/gast.2002.34209 Deng, 2003, LPA protects intestinal epithelial cells from apoptosis by inhibiting the mitochondrial pathway, Am. J. Physiol. Gastrointest. Liver Physiol., 284, G821, 10.1152/ajpgi.00406.2002 Tilly, 2002, Sphingolipids, apoptosis, cancer treatments and the ovary: investigating a crime against female fertility, Biochim. Biophys. Acta, 1585, 135, 10.1016/S1388-1981(02)00333-5 Uhlenbrock, 2002, Sphingosine 1-phosphate is a ligand of the human GPR3, GPR6 and GPR12 family of constitutively active G protein-coupled receptors, Cell. Signall., 14, 941, 10.1016/S0898-6568(02)00041-4 Ignatov, 2003, Sphingosine-1-phosphate is a high-affinity ligand for the G protein-coupled receptor GPR6 from mouse and induces intracellular Ca2+ release by activating the sphingosine-kinase pathway, Biochem. Biophys. Res. Commun., 311, 329, 10.1016/j.bbrc.2003.10.006 Ignatov, 2003, Role of the G-protein-coupled receptor GPR12 as high-affinity receptor for sphingosylphosphorylcholine and its expression and function in brain development, J. Neurosci., 23, 907, 10.1523/JNEUROSCI.23-03-00907.2003 Lee, 1998, Sphingosine-1-phosphate as a ligand for the G protein-coupled receptor EDG-1, Science, 279, 1552, 10.1126/science.279.5356.1552 Hla, 1990, An abundant transcript induced in differentiating human endothelial cells encodes a polypeptide with structural similarities to G-protein-coupled receptors, J. Biol. Chem., 265, 9306, 10.1016/S0021-9258(19)38849-0 MacLennan, 1994, Cloning and characterization of a putative G-protein coupled receptor potentially involved in development, Mol. Cell Neurosci., 5, 201, 10.1006/mcne.1994.1024 An, 1997, Identification of cDNAs encoding two G protein-coupled receptors for lysosphingolipids, FEBS Lett., 417, 279, 10.1016/S0014-5793(97)01301-X Yamaguchi, 1996, Molecular cloning of the novel human G protein-coupled receptor (GPCR) gene mapped on chromosone 9, Biochem. Biophys. Res. Commun., 227, 608, 10.1006/bbrc.1996.1553 Gräler, 1998, EDG6, a novel G-protein-coupled receptor related to receptors for bioactive lysophospholipids, is specifically expressed in lymphoid tissue, Genomics, 53, 164, 10.1006/geno.1998.5491 Malek, 2001, Nrg-1 belongs to the endothelial differentiation gene family of G protein-coupled sphingosine-1-phosphate receptors, J. Biol. Chem., 276, 5692, 10.1074/jbc.M003964200 Glickman, 1999, Molecular cloning, tissue-specific expression, and chromosomal localization of a novel nerve growth factor-regulated G-protein- coupled receptor, nrg-1, Mol. Cell. Neurosci., 14, 141, 10.1006/mcne.1999.0776 Hecht, 1996, Ventricular zone gene-1 (vzg-1) encodes a lysophosphatidic acid receptor expressed in neurogenic regions of the developing cerebral cortex, J. Cell Biol., 135, 1071, 10.1083/jcb.135.4.1071 An, 1997, Molecular cloning of the human Edg2 protein and its identification as a functional cellular receptor for lysophosphatidic acid, Biochem. Biophys. Res. Commun., 231, 619, 10.1006/bbrc.1997.6150 An, 1998, Characterization of a novel subtype of human G protein-coupled receptor for lysophosphatidic acid, J. Biol. Chem., 273, 7906, 10.1074/jbc.273.14.7906 Fitzgerald, 2000, Identification of an EDG7 variant, HOFNH30, a G-protein-coupled receptor for lysophosphatidic acid, Biochem. Biophys. Res. Commun., 273, 805, 10.1006/bbrc.2000.2943 Bandoh, 1999, Molecular cloning and characterization of a novel human G-protein-coupled receptor, EDG7, for lysophosphatidic acid, J. Biol. Chem., 274, 27776, 10.1074/jbc.274.39.27776 Im, 2000, Molecular cloning and characterization of a lysophosphatidic acid receptor, Edg-7, expressed in prostate, Mol. Pharmacol., 57, 753, 10.1124/mol.57.4.753 Noguchi, 2003, Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family, J. Biol. Chem., 278, 25600, 10.1074/jbc.M302648200 Niedernberg, 2003, Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63, Cell. Signall., 15, 435, 10.1016/S0898-6568(02)00119-5 Guo, 1996, Molecular cloning of a high-affinity receptor for the growth factor-like lipid mediator lysophosphatidic acid from Xenopus oocytes, Proc. Natl. Acad. Sci. U.S.A., 93, 14367, 10.1073/pnas.93.25.14367 McIntyre, 2003, Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARgamma agonist, Proc. Natl. Acad. Sci. U.S.A., 100, 131, 10.1073/pnas.0135855100 Gobeil, 2003, Modulation of pro-inflammatory gene expression by nuclear lysophosphatidic acid receptor type-1, J. Biol. Chem., 278, 38875, 10.1074/jbc.M212481200 Niedernberg, 2002, Comparative analysis of human and rat S1P5 (edg8): differential expression profiles and sensitivities to antagonists, Biochem. Pharmacol., 64, 1243, 10.1016/S0006-2952(02)01289-3 Van Brocklyn, 1999, Sphingosine 1-phosphate-induced cell rounding and neurite retraction are mediated by the G protein-coupled receptor H218, J. Biol. Chem., 274, 4626, 10.1074/jbc.274.8.4626 Sanna MG, Liao J, Jo E, Alfonso C, Ahn M, Peterson MS, et al. Distinct S1P receptor subtypes S1P1 and S1P3 respectively regulate lymphocyte recirculation and heart rate. J. Biol. Chem 2004;279(14):13839–48. Van Brocklyn, 1998, Dual actions of sphingosine-1-phosphate: extracellular through the Gi-coupled receptor Edg-1 and intracellular to regulate proliferation and survival, J. Cell Biol., 142, 229, 10.1083/jcb.142.1.229 Van Brocklyn, 2000, Sphingosine-1-phosphate is a ligand for the G protein-coupled receptor EDG-6, Blood, 95, 2624, 10.1182/blood.V95.8.2624 Okamoto, 1998, EDG1 is a functional sphingosine-1-phosphate receptor that is linked via a Gi/o to multiple signaling pathways, including phospholipase C activation, Ca2+ mobilization, ras-mitogen-activated protein kinase activation, and adenylate cyclase inhibition, J. Biol. Chem., 273, 27104, 10.1074/jbc.273.42.27104 Lim, 2003, Syntheses of sphingosine-1-phosphate stereoisomers and analogues and their interaction with EDG receptors, Bioorg. Med. Chem. Lett., 13, 237, 10.1016/S0960-894X(02)00893-4 Im, 2001, Characterization of the human and mouse sphingosine 1-phosphate receptor, S1P5 (Edg-8): structure–activity relationship of sphingosine 1-phosphate receptors, Biochemistry, 40, 14053, 10.1021/bi011606i Hakogi, 2003, Synthesis of fluorescence-labeled sphingosine and sphingosine 1-phosphate; effective tools for sphingosine and sphingosine 1-phosphate behavior, Bioorg. Med. Chem. Lett., 13, 661, 10.1016/S0960-894X(02)00999-X Lu, 2003, Total synthesis of two photoactivatable analogues of the growth-factor-like mediator sphingosine 1-phosphate: differential interaction with protein targets, J. Org. Chem., 68, 7046, 10.1021/jo034828q Kiuchi, 2000, Synthesis and immunosuppressive activity of 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols, J. Med. Chem., 43, 2946, 10.1021/jm000173z Clemens, 2003, Synthesis of para-alkyl aryl amide analogues of sphingosine-1-phosphate: discovery of potent S1P receptor agonists, Bioorg. Med. Chem. Lett., 13, 3401, 10.1016/S0960-894X(03)00812-6 Brinkmann, 2002, FTY720: targeting G-protein-coupled receptors for sphingosine 1-phosphate in transplantation and autoimmunity, Curr. Opin. Immunol., 14, 569, 10.1016/S0952-7915(02)00374-6 Holdsworth G, Osborne DA, Pham TT, Fells JI, Hutchinson G, Milligan G, et al. A single amino acid determines preference between phospholipids and reveals length restriction for activation of the S1P4 receptor, submitted for publication. Tigyi, 2003, Molecular mechanisms of lysophosphatidic acid action, Prog. Lipid Res., 42, 498, 10.1016/S0163-7827(03)00035-3 Xu, 2003, Synthesis of monofluorinated analogues of lysophosphatidic acid, J. Org. Chem., 68, 5320, 10.1021/jo020729l Hasegawa, 2003, Identification of a phosphothionate analogue of lysophosphatidic acid as a selective agonist of the LPA3 receptor, J. Biol. Chem., 278, 11962, 10.1074/jbc.M209168200 Qian, 2003, Enantioselective responses to a phosphorothioate analogue of lysophosphatidic acid with LPA3 receptor-selective agonist activity, J. Med. Chem., 46, 5575, 10.1021/jm034207p Yokoyama, 2002, Stereochemical properties of lysophosphatidic acid receptor activation and metabolism, Biochim. Biophys. Acta, 1582, 295, 10.1016/S1388-1981(02)00184-1 Heise, 2001, Activity of 2-substituted LPA analogs at LPA receptors: discovery of a LPA1/LPA3 receptor antagonist, Mol. Pharmacol., 60, 1173, 10.1124/mol.60.6.1173 Bandoh, 2000, Lysophosphatidic acid (LPA) receptors of the EDG family are differentially activated by LPA species: structure–activity relationship of cloned LPA receptors, FEBS Lett., 478, 159, 10.1016/S0014-5793(00)01827-5 Qian, 2003, Synthesis of migration-resistant hydroxyethoxy analogues of lysophosphatidic acid, Org. Lett., 5, 4685, 10.1021/ol0358758 Corton, 2000, Central role of peroxisome proliferator-activated receptors in the actions of peroxisome proliferators, Annu. Rev. Pharmacol. Toxicol., 40, 491, 10.1146/annurev.pharmtox.40.1.491 Davies, 2001, Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor gamma ligands and agonists, J. Biol. Chem., 276, 16015, 10.1074/jbc.M100878200 Xu, 2002, Concise synthesis of acyl migration-blocked 1,1-difluorinated analogues of lysophosphatidic acid, J. Org. Chem., 67, 7158, 10.1021/jo0203037 Xu, 2004, Synthesis of difluoromethyl-substituted lysophosphatidic acid analogues, Tetrahedron, 60, 47, 10.1016/j.tet.2003.11.001 Pierce, 2002, Seven-transmembrane receptors, Nat. Rev., 3, 639, 10.1038/nrm908 Palczewski, 2000, Crystal structure of rhodopsin: a G protein-coupled receptor, Science, 289, 739, 10.1126/science.289.5480.739 Sardar, 2002, Molecular basis for lysophosphatidic acid receptor antagonist selectivity, Biochim. Biophys. Acta, 1582, 309, 10.1016/S1388-1981(02)00185-3 Wang, 2001, A single amino acid determines ligand specificity of the S1P1 (EDG1) and LPA1 (EDG2) phospholipid growth factor receptors, J. Biol. Chem., 276, 49213, 10.1074/jbc.M107301200 Virag, 2003, Fatty alcohol phosphates are subtype-selective agonists and antagonists of LPA receptors, Mol. Pharmacol., 63, 1032, 10.1124/mol.63.5.1032 Parrill, 2000, Identification of Edg1 receptor residues that recognize sphingosine 1-phosphate, J. Biol. Chem., 275, 39379, 10.1074/jbc.M007680200 Parrill AL, Baker DL, Wang D, Fischer DJ, Bautista DL, van Brocklyn J, et al. Structural features of EDG1 receptor–ligand complexes revealed by computational modeling and mutagenesis. In: Goetzl EJ, Lynch KR, editors. Lysophospholipids and eicosanoids in biology and pathophysiology. Ann N Y Acad Sci, vol. 905; 2000. p. 330–9. Bautista, 2000, Dynamic modeling of EDG1 receptor structural changes induced by site-directed mutations, J. Mol. Struct. THEOCHEM, 529, 219, 10.1016/S0166-1280(00)00549-2 Vaidehi, 2002, Prediction of structure and function of G protein-coupled receptors, Proc. Natl. Acad. Sci. U.S.A., 99, 12622, 10.1073/pnas.122357199 Ballesteros JA, Weinstein H. Integrated methods for the construction of three dimensional models and computational probing of structure–function relations in G-protein coupled receptors. In: Conn PM, Sealfon SC, editors. Methods in neurosciences, vol. 25. Academic Press; 1995. p. 366–428. Cronet, 2001, Structure of the PPARalpha and -gamma ligand binding domain in complex with AZ 242 ligand selectivity and agonist activation in the PPAR family, Structure (Camb), 9, 699, 10.1016/S0969-2126(01)00634-7 Xu, 2001, Structural determinants of ligand binding selectivity between the peroxisome proliferator-activated receptors, Proc. Natl. Acad. Sci. U.S.A., 98, 13919, 10.1073/pnas.241410198 Gampe, 2000, Asymmetry in the PPARgamma/RXRalpha crystal structure reveals the molecular basis of heterodimerization among nuclear receptors, Mol. Cell, 5, 545, 10.1016/S1097-2765(00)80448-7 Nolte, 1998, Ligand binding and co-activator assembly of the peroxisome proliferator-activated receptor-gamma, Nature, 395, 137, 10.1038/25931 Sauerberg, 2002, Novel tricyclic-alpha-alkyloxyphenylpropionic acids: dual PPARalpha/gamma agonists with hypolipidemic and antidiabetic activity, J. Med. Chem., 45, 789, 10.1021/jm010964g Ebdrup, 2003, Synthesis and biological and structural characterization of the dual-acting peroxisome proliferator-activated receptor alpha/gamma agonist ragaglitazar, J. Med. Chem., 46, 1306, 10.1021/jm021027r Oberfield, 1999, A peroxisome proliferator-activated receptor gamma ligand inhibits adipocyte differentiation, Proc. Natl. Acad. Sci. U.S.A., 96, 6102, 10.1073/pnas.96.11.6102 Yu, 2004, Binding analyses between Human PPARgamma-LBD and ligands, Eur. J. Biochem., 271, 386, 10.1046/j.1432-1033.2003.03937.x Kawasaki H, Ozawa K, Yamamoto K. Pyrazolopyridine compounds and use thereof as drugs. Patent 2001. WO 01/98301 A1. Osada, 2002, Enhancement of sphingosine 1-phosphate-induced migration of vascular endothelial cells and smooth muscle cells by an EDG-5 antagonist, Biochem. Biophys. Res. Commun., 299, 483, 10.1016/S0006-291X(02)02671-2 Koide, 2002, Development of novel EDG3 antagonists using a 3D database search and their structure-activity relationships, J. Med. Chem., 45, 4629, 10.1021/jm020080c Kahan, 2003, Pharmacodynamics, pharmacokinetics, and safety of multiple doses of FTY720 in stable renal transplant patients: a multicenter, randomized, placebo-controlled, phase I study, Transplantation, 76, 1079, 10.1097/01.TP.0000084822.01372.AC Graler, 2004, The immunosuppressant FTY720 down-regulates sphingosine 1-phosphate G protein-coupled receptors, Faseb J., 18, 551, 10.1096/fj.03-0910fje Billich, 2003, Phosphorylation of the immunomodulatory drug FTY720 by sphingosine kinases, J. Biol. Chem., 278, 47408, 10.1074/jbc.M307687200 Paugh, 2003, The immunosuppressant FTY720 is phosphorylated by sphingosine kinase type 2, FEBS Lett., 554, 189, 10.1016/S0014-5793(03)01168-2 Sanchez, 2003, Phosphorylation and action of the immunomodulator FTY720 inhibits vascular endothelial cell growth factor-induced vascular permeability, J. Biol. Chem., 278, 47281, 10.1074/jbc.M306896200 Bittman, 1996, Inhibitors of lipid phosphatidate receptors: N-palmitoyl-serine and N-palmitoyl-tyrosine phosphoric acids, J. Lipid Res., 37, 391, 10.1016/S0022-2275(20)37625-2 Liliom, 1996, N-palmitoyl-serine and N-palmitoyl-tyrosine phosphoric acids are selective competitive antagonists of the lysophosphatidic acid receptors, Mol. Pharmacol., 50, 616 Hooks, 1998, Characterization of a receptor subtype-selective lysophosphatidic acid mimetic, Mol. Pharmacol., 53, 188, 10.1124/mol.53.2.188 Fischer, 2001, Short-chain phosphatidates are subtype-selective antagonists of lysophosphatidic acid receptors, Mol. Pharmacol., 60, 776 Ohta, 2003, Ki16425, a subtype-selective antagonist for EDG-family lysophosphatidic acid receptors, Mol. Pharmacol., 64, 994, 10.1124/mol.64.4.994 Okusa, 2003, Selective blockade of lysophosphatidic acid LPA3 receptors reduces murine renal ischemia-reperfusion injury, Am. J. Physiol. Renal. Physiol., 285, F565, 10.1152/ajprenal.00023.2003 Yamada, 2004, Lysophosphatidic acid in malignant ascites stimulates motility of human pancreatic cancer cells through LPA1, J. Biol. Chem., 279, 6595, 10.1074/jbc.M308133200 Rother, 2003, Subtype-selective antagonists of lysophosphatidic acid receptors inhibit platelet activation triggered by the lipid core of atherosclerotic plaques, Circulation, 108, 741, 10.1161/01.CIR.0000083715.37658.C4 Zhang C, Baker DL, Yasuda S, Makarova N, Balazs L, Johnson LR, et al. Lysophosphatidic acid induces neointima formation through PPARg activation. J Exp Med 2004;199:763–74. Arikawa, 2003, Ligand-dependent inhibition of B16 melanoma cell migration and invasion via endogenous S1P2 G protein-coupled receptor. Requirement of inhibition of cellular RAC activity, J. Biol. Chem., 278, 32841, 10.1074/jbc.M305024200 Ikeda, 2003, Antiproliferative property of sphingosine 1-phosphate in rat hepatocytes involves activation of Rho via Edg-5, Gastroenterology, 124, 459, 10.1053/gast.2003.50049 Ohmori, 2003, Sphingosine 1-phosphate induces contraction of coronary artery smooth muscle cells via S1P2, Cardiovasc. Res., 58, 170, 10.1016/S0008-6363(03)00260-8 Kumar, 2001, MEGA2: molecular evolutionary genetics analysis software, Bioinformatics, 17, 1244, 10.1093/bioinformatics/17.12.1244 Morris, 1998, Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function, J. Comput. Chem., 19, 1639, 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B Berman, 2000, The Protein Data Bank, Nucleic Acids Res., 28, 235, 10.1093/nar/28.1.235 Halgren, 1996, Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94, J. Comp. Chem., 17, 490, 10.1002/(SICI)1096-987X(199604)17:5/6<490::AID-JCC1>3.0.CO;2-P MOE. edition 2003.02. Edited by Montreal Chemical Computing Group; 2002.