Novel bioactive glycerol-based lysophospholipids: New data-New insight into their function

Biochimie

Volumn 95, Issue 4, 2013, Pages 667-679

  Grzelczyk, Anna ^a   Gendaszewska Darmach, Edyta ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

G protein coupled receptors; Lysophospholipids; Membranes fluidity; Phospholipases

Indexed keywords

EDELFOSINE; FAS ANTIGEN; G PROTEIN COUPLED RECEPTOR; G PROTEIN COUPLED RECEPTOR 119; G PROTEIN COUPLED RECEPTOR 34; G PROTEIN COUPLED RECEPTOR 4; G PROTEIN COUPLED RECEPTOR 55; GLYCEROL; HISTAMINE; INTERLEUKIN 10; INTERLEUKIN 4; INTERLEUKIN 5; INTERLEUKIN 6; LYSOPHOSPHATIDIC ACID; LYSOPHOSPHATIDYLCHOLINE; LYSOPHOSPHATIDYLETHANOLAMINE; LYSOPHOSPHATIDYLGLYCEROL; LYSOPHOSPHATIDYLINOSITOL; LYSOPHOSPHATIDYLSERINE; LYSOPHOSPHOLIPID; NITRIC OXIDE; PROSTAGLANDIN E2; SPHINGOSINE 1 PHOSPHATE; UNCLASSIFIED DRUG;

CANCER INHIBITION; CARCINOGENESIS; CELL INVASION; CELL MEMBRANE; CELL PROLIFERATION; HUMAN; LIPID MEMBRANE; LIPID RAFT; LIPOGENESIS; METABOLIC DISORDER; NERVOUS SYSTEM DEVELOPMENT; NONHUMAN; PROTEIN FUNCTION; PROTEIN STRUCTURE; REVIEW; SIGNAL TRANSDUCTION;

ANIMALS; CELL MEMBRANE; GLYCEROL; HUMANS; ION CHANNELS; LYSOPHOSPHOLIPIDS; RECEPTORS, G-PROTEIN-COUPLED;

EID: 84874648526     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2012.10.009     Document Type: Review

References (161)

1. H. Hosono, J. Aoki, Y. Nagai, K. Bandoh, M. Ishida, R. Taguchi, H. Arai, and K. Inoue Phosphatidylserine-specific phospholipase A1 stimulates histamine release from rat peritoneal mast cells through production of 2-acyl-1-lysophosphatidylserine J. Biol. Chem. 276 2001 29664 29670
2. F. Mollinedo, J.L. Fernandez-Luna, C. Gajate, B. Martin-Martin, A. Benito, R. Martinez-Dalmau, and M. Modolell Selective induction of apoptosis in cancer cells by the ether lipid ET-18-OCH3 (Edelfosine): molecular structure requirements, cellular uptake, and protection by Bcl-2 and Bcl-X(L) Cancer Res. 57 1997 1320 1328
3. M. Iwashita, K. Makide, T. Nonomura, Y. Misumi, Y. Otani, M. Ishida, R. Taguchi, M. Tsujimoto, J. Aoki, H. Arai, and T. Ohwada Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative J. Med. Chem. 52 2009 5837 5863
4. M. Gotoh, Y. Fujiwara, J. Yue, J. Liu, S. Lee, J. Fells, A. Uchiyama, K. Murakami-Murofushi, S. Kennel, J. Wall, R. Patil, R. Gupte, L. Balazs, D.D. Miller, and G.J. Tigyi Controlling cancer through the autotaxin-lysophosphatidic acid receptor axis Biochem. Soc. Trans. 40 2012 31 36
5. N.J. Pyne, F. Tonelli, K.G. Lim, J.S. Long, J. Edwards, and S. Pyne Sphingosine 1-phosphate signalling in cancer Biochem. Soc. Trans. 40 2012 94 100
6. H.J. Pownall, Q. Pao, and J.B. Massey Acyl chain and headgroup specificity of human plasma lecithin:cholesterol acyltransferase. Separation of matrix and molecular specificities J. Biol. Chem. 260 1985 2146 2152
7. J. Aoki, A. Taira, Y. Takanezawa, Y. Kishi, K. Hama, T. Kishimoto, K. Mizuno, K. Saku, R. Taguchi, and H. Arai Serum lysophosphatidic acid is produced through diverse phospholipase pathways J. Biol. Chem. 277 2002 48737 48744
8. G. Schmitz, and K. Ruebsaamen Metabolism and atherogenic disease association of lysophosphatidylcholine Atherosclerosis 208 2010 10 18
9. J.G. Bollinger, H. Ii, M. Sadilek, and M.H. Gelb Improved method for the quantification of lysophospholipids including enol ether species by liquid chromatography-tandem mass spectrometry J. Lipid Res. 51 2010 440 447
10. J.Y. Lee, H.K. Min, and M.H. Moon Simultaneous profiling of lysophospholipids and phospholipids from human plasma by nanoflow liquid chromatography-tandem mass spectrometry Anal. Bioanal. Chem. 400 2011 2953 2961
11. B. Christiaens, B. Vanloo, C. Gouyette, I. van Vynckt, H. Caster, J. Taveirne, A. Verhee, C. Labeur, F. Peelman, J. Vandekerckhove, J. Tavernier, and M. Rosseneu Headgroup specificity of lecithin cholesterol acyltransferase for monomeric and vesicular phospholipids Biochim. Biophys. Acta 1486 2000 321 327
12. E. Kitsiouli, G. Nakos, and M.E. Lekka Phospholipase A2 subclasses in acute respiratory distress syndrome Biochim. Biophys. Acta 1792 2009 941 953
13. W. Yan, C.M. Jenkins, X. Han, D.J. Mancuso, H.F. Sims, K. Yang, and R.W. Gross The highly selective production of 2-arachidonoyl lysophosphatidylcholine catalyzed by purified calcium-independent phospholipase A2gamma: identification of a novel enzymatic mediator for the generation of a key branch point intermediate in eicosanoid signaling J. Biol. Chem. 280 2005 26669 26679
14. M. Murakami, Y. Taketomi, Y. Miki, H. Sato, T. Hirabayashi, and K. Yamamoto Recent progress in phospholipase A research: from cells to animals to humans Prog. Lipid Res. 50 2011 152 192
15. J.E. Burke, and E.A. Dennis Phospholipase A2 biochemistry Cardiovasc. Drugs Ther. 23 2009 49 59
16. B.B. Boyanovsky, and N.R. Webb Biology of secretory phospholipase A2 Cardiovasc. Drugs Ther. 23 2009 61 72
17. Y. Xu Sphingosylphosphorylcholine and lysophosphatidylcholine: G protein-coupled receptors and receptor-mediated signal transduction Biochim. Biophys. Acta 1582 2002 81 88
18. C. Stock, T. Schilling, A. Schwab, and C. Eder Lysophosphatidylcholine stimulates IL-1beta release from microglia via a P2X7 receptor-independent mechanism J. Immunol. 177 2006 8560 8568
19. E. Nishi, N. Kume, Y. Ueno, H. Ochi, H. Moriwaki, and T. Kita Lysophosphatidylcholine enhances cytokine-induced interferon gamma expression in human T lymphocytes Circ. Res. 83 1998 508 515
20. H. Hasegawa, J. Lei, T. Matsumoto, S. Onishi, K. Suemori, and M. Yasukawa Lysophosphatidylcholine enhances the suppressive function of human naturally occurring regulatory T cells through TGF-beta production Biochem. Biophys. Res. Commun. 415 2011 526 531
21. T. Schilling, and C. Eder Importance of lipid rafts for lysophosphatidylcholine-induced caspase-1 activation and reactive oxygen species generation Cell. Immunol. 265 2010 87 90
22. M. Riederer, P.J. Ojala, A. Hrzenjak, W.F. Graier, R. Malli, M. Tritscher, M. Hermansson, B. Watzer, H. Schweer, G. Desoye, A. Heinemann, and S. Frank Acyl chain-dependent effect of lysophosphatidylcholine on endothelial prostacyclin production J. Lipid Res. 51 2010 2957 2966
23. N.D. Hung, D.E. Sok, and M.R. Kim Prevention of 1-palmitoyl lysophosphatidylcholine-induced inflammation by polyunsaturated acyl lysophosphatidylcholine Inflamm. Res. 61 2012 473 483
24. M. Takahashi, H. Okazaki, Y. Ogata, K. Takeuchi, U. Ikeda, and K. Shimada Lysophosphatidylcholine induces apoptosis in human endothelial cells through a p38-mitogen-activated protein kinase-dependent mechanism Atherosclerosis 161 2002 387 394
25. C.C. Hsieh, M.H. Yen, H.W. Liu, and Y.T. Lau Lysophosphatidylcholine induces apoptotic and non-apoptotic death in vascular smooth muscle cells: in comparison with oxidized LDL Atherosclerosis 151 2000 481 491
26. T. Soga, T. Ohishi, T. Matsui, T. Saito, M. Matsumoto, J. Takasaki, S. Matsumoto, M. Kamohara, H. Hiyama, S. Yoshida, K. Momose, Y. Ueda, H. Matsushime, M. Kobori, and K. Furuichi Lysophosphatidylcholine enhances glucose-dependent insulin secretion via an orphan G-protein-coupled receptor Biochem. Biophys. Res. Commun. 326 2005 744 751
27. S.A. Metz Ether-linked lysophospholipids initiate insulin secretion. Lysophospholipids may mediate effects of phospholipase A2 activation on hormone release Diabetes 35 1986 808 817
28. K. Liliom, Z. Guan, J.L. Tseng, D.M. Desiderio, G. Tigyi, and M.A. Watsky Growth factor-like phospholipids generated after corneal injury Am. J. Physiol. 274 1998 C1065 C1074
29. S.C. Frasch, K.Z. Berry, R. Fernandez-Boyanapalli, H.S. Jin, C. Leslie, P.M. Henson, R.C. Murphy, and D.L. Bratton NADPH oxidase-dependent generation of lysophosphatidylserine enhances clearance of activated and dying neutrophils via G2A J. Biol. Chem. 283 2008 33736 33749
30. T. Sato, J. Aoki, Y. Nagai, N. Dohmae, K. Takio, T. Doi, H. Arai, and K. Inoue Serine phospholipid-specific phospholipase A that is secreted from activated platelets. A new member of the lipase family J. Biol. Chem. 272 1997 2192 2198
31. R.F. Zwaal, and A.J. Schroit Pathophysiologic implications of membrane phospholipid asymmetry in blood cells Blood 89 1997 1121 1132
32. N. Arima, A. Inoue, K. Makide, T. Nonaka, and J. Aoki Surface loops of extracellular phospholipase A(1) determine both substrate specificity and preference for lysophospholipids J. Lipid Res. 53 2012 513 521
33. S. Courtney Frasch, and D.L. Bratton Emerging roles for lysophosphatidylserine in resolution of inflammation Prog. Lipid Res. 51 2012 199 207
34. G.A. Smith, T.R. Hesketh, R.W. Plumb, and J.C. Metcalfe The exogenous lipid requirement for histamine release from rat peritoneal mast cells stimulated by concanavalin A FEBS Lett. 105 1979 58 62
35. K. Kawamoto, J. Aoki, A. Tanaka, A. Itakura, H. Hosono, H. Arai, Y. Kiso, and H. Matsuda Nerve growth factor activates mast cells through the collaborative interaction with lysophosphatidylserine expressed on the membrane surface of activated platelets J. Immunol. 168 2002 2002 6412 6419
36. S. Lourenssen, and M.G. Blennerhassett Lysophosphatidylserine potentiates nerve growth factor-induced differentiation of PC12 cells Neurosci. Lett. 248 1998 77 80
37. K. Yea, J. Kim, S. Lim, T. Kwon, H.S. Park, K.S. Park, P.G. Suh, and S.H. Ryu Lysophosphatidylserine regulates blood glucose by enhancing glucose transport in myotubes and adipocytes Biochem. Biophys. Res. Commun. 378 2009 783 788
38. K. Yea, J. Kim, J.H. Yoon, T. Kwon, J.H. Kim, B.D. Lee, H.J. Lee, S.J. Lee, J.I. Kim, T.G. Lee, M.C. Baek, H.S. Park, K.S. Park, M. Ohba, P.G. Suh, and S.H. Ryu Lysophosphatidylcholine activates adipocyte glucose uptake and lowers blood glucose levels in murine models of diabetes J. Biol. Chem. 284 2009 33833 33840
39. K.S. Park, H.Y. Lee, M.K. Kim, E.H. Shin, and Y.S. Bae Lysophosphatidylserine stimulates leukemic cells but not normal leukocytes Biochem. Biophys. Res. Commun. 333 2005 353 358
40. S.Y. Lee, H.Y. Lee, S.D. Kim, S.H. Jo, J.W. Shim, H.J. Lee, J. Yun, and Y.S. Bae Lysophosphatidylserine stimulates chemotactic migration in U87 human glioma cells Biochem. Biophys. Res. Commun. 374 2008 147 151
41. K.S. Park, H.Y. Lee, M.K. Kim, E.H. Shin, S.H. Jo, S.D. Kim, D.S. Im, and Y.S. Bae Lysophosphatidylserine stimulates L2071 mouse fibroblast chemotactic migration via a process involving pertussis toxin-sensitive trimeric G-proteins Mol. Pharmacol. 69 2006 1066 1073
42. Y. Xu, X.J. Fang, G. Casey, and G.B. Mills Lysophospholipids activate ovarian and breast cancer cells Biochem. J. 309 1995 933 940
43. Y. Xu, G. Casey, and G.B. Mills Effect of lysophospholipids on signaling in the human Jurkat T cell line J. Cell. Physiol. 163 1995 441 450
44. S. Cho, H.H. Kim, M.J. Lee, S. Lee, C.S. Park, S.J. Nam, J.J. Han, J.W. Kim, and J.H. Chung Phosphatidylserine prevents UV-induced decrease of type I procollagen and increase of MMP-1 in dermal fibroblasts and human skin in vivo J. Lipid Res. 49 2008 1235 1245
45. D. van der Kleij, E. Latz, J.F. Brouwers, Y.C. Kruize, M. Schmitz, E.A. Kurt-Jones, T. Espevik, E.C. de Jong, M.L. Kapsenberg, D.T. Golenbock, A.G. Tielens, and M. Yazdanbakhsh A novel host-parasite lipid cross-talk. Schistosomal lyso-phosphatidylserine activates toll-like receptor 2 and affects immune polarization J. Biol. Chem. 277 2002 48122 48129
46. K. Retra, E. van Riet, A.A. Adegnika, B. Everts, S. van Geest, P.G. Kremsner, J.J. van Hellemond, D. van der Kleij, A.G. Tielens, and M. Yazdanbakhsh Immunologic activity of schistosomal and bacterial TLR2 ligands in Gabonese children Parasite Immunol. 30 2008 39 46
47. S. Oka, T. Toshida, K. Maruyama, K. Nakajima, A. Yamashita, and T. Sugiura 2-Arachidonoyl-sn-glycero-3-phosphoinositol: a possible natural ligand for GPR55 J. Biochem. 145 2009 13 20
48. R. Sutphen, Y. Xu, G.D. Wilbanks, J. Fiorica, E.C. Grendys Jr., J.P. LaPolla, H. Arango, M.S. Hoffman, M. Martino, K. Wakeley, D. Griffin, R.W. Blanco, A.B. Cantor, Y.J. Xiao, and J.P. Krischer Lysophospholipids are potential biomarkers of ovarian cancer Cancer Epidemiol. Biomarkers Prev. 13 2004 1185 1191
49. M.M. Billah, and E.G. Lapetina Formation of lysophosphatidylinositol in platelets stimulated with thrombin or ionophore A23187 J. Biol. Chem. 257 1982 5196 5200
50. M. Falasca, C. Iurisci, A. Carvelli, A. Sacchetti, and D. Corda Release of the mitogen lysophosphatidylinositol from H-Ras-transformed fibroblasts; a possible mechanism of autocrine control of cell proliferation Oncogene 16 1998 2357 2365
51. M. Falasca, and D. Corda Elevated levels and mitogenic activity of lysophosphatidylinositol in k-ras-transformed epithelial cells Eur. J. Biochem. 221 1994 383 389
52. R. Pineiro, and M. Falasca Lysophosphatidylinositol signalling: new wine from an old bottle Biochim. Biophys. Acta 1821 2012 694 705
53. F. Ghomashchi, G.S. Naika, J.G. Bollinger, A. Aloulou, M. Lehr, C.C. Leslie, and M.H. Gelb Interfacial kinetic and binding properties of mammalian group IVB phospholipase A2 (cPLA2beta) and comparison with the other cPLA2 isoforms J. Biol. Chem. 285 2010 36100 36111
54. A. Yamashita, T. Kumazawa, H. Koga, N. Suzuki, S. Oka, and T. Sugiura Generation of lysophosphatidylinositol by DDHD domain containing 1 (DDHD1): possible involvement of phospholipase D/phosphatidic acid in the activation of DDHD1 Biochim. Biophys. Acta 1801 2010 711 720
55. R.A. Ross L-alpha-lysophosphatidylinositol meets GPR55: a deadly relationship Trends Pharmacol. Sci. 32 2011 265 269
56. L.A. Ford, A.J. Roelofs, S. Anavi-Goffer, L. Mowat, D.G. Simpson, A.J. Irving, M.J. Rogers, A.M. Rajnicek, and R.A. Ross A role for L-alpha-lysophosphatidylinositol and GPR55 in the modulation of migration, orientation and polarization of human breast cancer cells Br. J. Pharmacol. 160 2010 762 771
57. M. Monet, D. Gkika, V. Lehen'kyi, A. Pourtier, F. Vanden Abeele, G. Bidaux, V. Juvin, F. Rassendren, S. Humez, and N. Prevarsakaya Lysophospholipids stimulate prostate cancer cell migration via TRPV2 channel activation Biochim. Biophys. Acta 1793 2009 528 539
58. N.A. Balenga, E. Aflaki, J. Kargl, W. Platzer, R. Schröder, S. Blättermann, E. Kostenis, A.J. Brown, A. Heinemann, and M. Waldhoer GPR55 regulates cannabinoid 2 receptor-mediated responses in human neutrophils Cell Res. 21 2011 1452 1469
59. J.M. Moreno-Navarrete, V. Catalan, L. Whyte, A. Diaz-Arteaga, R. Vazquez-Martinez, F. Rotellar, R. Guzman, J. Gomez-Ambrosi, M.R. Pulido, W.R. Russell, M. Imbernon, R.A. Ross, M.M. Malagon, C. Dieguez, J.M. Fernandez-Real, G. Fruhbeck, and R. Nogueiras The L-α-lysophosphatidylinositol/GPR55 system and its potential role in human obesity Diabetes 61 2012 281 291
60. T.E. Merchant, J.H. Lass, P. Meneses, J.V. Greiner, and T. Glonek Human crystalline lens phospholipid analysis with age Invest. Ophthalmol. Vis. Sci. 32 1991 549 555
61. S.Y. Lee, H.Y. Lee, S.D. Kim, J.W. Shim, and Y.S. Bae Lysophosphatidylglycerol stimulates chemotactic migration and tube formation in human umbilical vein endothelial cells Biochem. Biophys. Res. Commun. 363 2007 490 494
62. G. Murugesan, and P.L. Fox Role of lysophosphatidylcholine in the inhibition of endothelial cell motility by oxidized low density lipoprotein J. Clin. Invest. 97 1996 2736 2744
63. S.H. Jo, S.D. Kim, J.M. Kim, H.Y. Lee, S.Y. Lee, J.W. Shim, J. Yun, D.S. Im, and Y.S. Bae Lysophosphatidylglycerol stimulates chemotactic migration in human natural killer cells Biochem. Biophys. Res. Commun. 372 2008 147 151
64. J.W. Shim, S.H. Jo, S.D. Kim, H.Y. Lee, J. Yun, and Y.S. Bae Lysophosphatidylglycerol inhibits formyl peptide receptorlike-1-stimulated chemotactic migration and IL-1beta production from human phagocytes Exp. Mol. Med. 41 2009 584 591
65. S.A. Metz Lysophosphatidylinositol, but not lysophosphatidic acid, stimulates insulin release. A possible role for phospholipase A2 but not de novo synthesis of lysophospholipid in pancreatic islet function Biochem. Biophys. Res. Commun. 138 1986 720 727
66. U.K. Misra Isolation of lysophosphatidylethanolamine from human serum Biochim. Biophys. Acta 106 1965 371 378
67. P.B. Corr, D.W. Snyder, B.I. Lee, R.W. Gross, C.R. Keim, and B.E. Sobel Pathophysiological concentrations of lysophosphatides and the slow response Am. J. Physiol. 243 1982 H187 H195
68. C. Schober, J. Schiller, F. Pinker, J.G. Hengstler, and B. Fuchs Lysophosphatidylethanolamine is - in contrast to - choline - generated under in vivo conditions exclusively by phospholipase A2 but not by hypochlorous acid Bioorg. Chem. 37 2009 202 210
69. S. Chen, and P.V. Subbaiah Phospholipid and fatty acid specificity of endothelial lipase: potential role of the enzyme in the delivery of docosahexaenoic acid (DHA) to tissues Biochim. Biophys. Acta 1771 2007 1319 1328
70. Y. Tan, P. Yin, L. Tang, W. Xing, Q. Huang, D. Cao, X. Zhao, W. Wang, X. Lu, Z. Xu, H. Wang, and G. Xu Metabolomics study of stepwise hepatocarcinogenesis from the model rats to patients: potential biomarkers effective for small hepatocellular carcinoma diagnosis Mol. Cell. Proteomics 11 2012 M111.010694
71. K.S. Park, H.Y. Lee, S.Y. Lee, M.K. Kim, S.D. Kim, J.M. Kim, J. Yun, D.S. Im, and Y.S. Bae Lysophosphatidylethanolamine stimulates chemotactic migration and cellular invasion in SK-OV3 human ovarian cancer cells: involvement of pertussis toxin-sensitive G-protein coupled receptor FEBS Lett. 581 2007 4411 4416
72. A. Nishina, H. Kimura, A. Sekiguchi, R.H. Fukumoto, S. Nakajima, and S. Furukawa Lysophosphatidylethanolamine in Grifola frondosa as a neurotrophic activator via activation of MAPK J. Lipid Res. 47 2006 1434 1443
73. N.D. Hung, M.R. Kim, and D.E. Sok 2-Polyunsaturated acyl lysophosphatidylethanolamine attenuates inflammatory response in zymosan A-induced peritonitis in mice Lipids 46 2011 893 906
74. I. Gay, Z. Schwartz, V.L. Sylvia, and B.D. Boyan Lysophospholipid regulates release and activation of latent TGF-beta1 from chondrocyte extracellular matrix Biochim. Biophys. Acta 1684 2004 18 28
75. N. Mohandas, J. Wyatt, S.F. Mel, M.E. Rossi, and S.B. Shohet Lipid translocation across the human erythrocyte membrane. Regulatory factors J. Biol. Chem. 257 1982 6537 6543
76. L. Saunders Molecular aggregation in aqueous dispersions of phosphatidyl and lysophosphatidyl cholines Biochim. Biophys. Acta 125 1966 70 74
77. A.I. Bondarenko, R. Malli, and W.F. Graier The GPR55 agonist lysophosphatidylinositol directly activates intermediate-conductance Ca2+ -activated K+ channels Pflugers Arch. 462 2011 245 255
78. B.A. Silverman, P.F. Weller, and M.L. Shin Effect of erythrocyte membrane modulation by lysolecithin on complement-mediated lysis J. Immunol. 132 1984 386 391
79. R.E. Stafford, T. Fanni, and E.A. Dennis Interfacial properties and critical micelle concentration of lysophospholipids Biochemistry 28 1989 5113 5120
80. H. Heerklotz, and R.M. Epand The enthalpy of acyl chain packing and the apparent water-accessible apolar surface area of phospholipids Biophys. J. 80 2001 271 279
81. J.A. Lundbaek, and O.S. Andersen Lysophospholipids modulate channel function by altering the mechanical properties of lipid bilayers J. Gen. Physiol. 104 1994 645 673
82. G. Ben-Zeev, M. Telias, and I. Nussinovitch Lysophospholipids modulate voltage-gated calcium channel currents in pituitary cells; effects of lipid stress Cell Calcium 47 2010 514 524
83. S.C. Frasch, K. Zemski-Berry, R.C. Murphy, N. Borregaard, P.M. Henson, and D.L. Bratton Lysophospholipids of different classes mobilize neutrophil secretory vesicles and induce redundant signaling through G2A J. Immunol. 178 2007 6540 6548
84. S.Y. Khan, N.J. McLaughlin, M.R. Kelher, P. Eckels, F. Gamboni-Robertson, A. Banerjee, and C.C. Silliman Lysophosphatidylcholines activate G2A inducing G(alphai)-/G(alphaq/)- Ca(2)(+) flux, G(betagamma)-Hck activation and clathrin/beta-arrestin-1/GRK6 recruitment in PMNs Biochem. J. 432 2010 35 45
85. P.K. Flemming, A.M. Dedman, S.Z. Xu, J. Li, F. Zeng, J. Naylor, C.D. Benham, A.N. Bateson, K. Muraki, and D.J. Beech Sensing of lysophospholipids by TRPC5 calcium channel J. Biol. Chem. 281 2006 4977 4982
86. F. Vanden Abeele, A. Zholos, G. Bidaux, Y. Shuba, S. Thebault, B. Beck, M. Flourakis, Y. Panchin, R. Skryma, and N. Prevarskaya Ca2+-independent phospholipase A2-dependent gating of TRPM8 by lysophospholipids J. Biol. Chem. 281 2006 40174 40182
87. D.A. Andersson, M. Nash, and S. Bevan Modulation of the cold-activated channel TRPM8 by lysophospholipids and polyunsaturated fatty acids J. Neurosci. 27 2007 3347 3355
88. A.I. Bondarenko, R. Malli, and W.F. Graier The GPR55 agonist lysophosphatidylinositol acts as an intracellular messenger and bidirectionally modulates Ca2+ -activated large-conductance K+ channels in endothelial cells Pflugers Arch. 461 2011 177 189
89. F. Maingret, A.J. Patel, F. Lesage, M. Lazdunski, and E. Honore Lysophospholipids open the two-pore domain mechano-gated K(+) channels TREK-1 and TRAAK J. Biol. Chem. 275 2000 10128 10133
90. S. Danthi, J.A. Enyeart, and J.J. Enyeart Modulation of native TREK-1 and Kv1.4 K+ channels by polyunsaturated fatty acids and lysophospholipids J. Membr. Biol. 195 2003 147 164
91. Y.L. Kim, Y.J. Im, N.C. Ha, and D.S. Im Albumin inhibits cytotoxic activity of lysophosphatidylcholine by direct binding Prostaglandins Other Lipid Mediat. 83 2007 130 138
92. K. Kogure, S. Nakashima, A. Tsuchie, A. Tokumura, and K. Fukuzawa Temporary membrane distortion of vascular smooth muscle cells is responsible for their apoptosis induced by platelet-activating factor-like oxidized phospholipids and their degradation product, lysophosphatidylcholine Chem. Phys. Lipids 126 2003 29 38
93. L. Zhou, M. Shi, Z. Guo, W. Brisbon, R. Hoover, and H. Yang Different cytotoxic injuries induced by lysophosphatidylcholine and 7-ketocholesterol in mouse endothelial cells Endothelium 13 2006 213 226
94. M. Mochizuki, J.S. Zigler Jr., P. Russell, and I. Gery Serum proteins neutralize the toxic effect of lysophosphatidyl choline Curr. Eye Res. 2 1982 621 624
95. C. Gajate, R.I. Fonteriz, C. Cabaner, G. Alvarez-Noves, Y. Alvarez-Rodriguez, M. Modolell, and F. Mollinedo Intracellular triggering of Fas, independently of FasL, as a new mechanism of antitumor ether lipid-induced apoptosis Int. J. Cancer 85 2000 674 682
96. M. Potier, A. Chantome, V. Joulin, A. Girault, S. Roger, P. Besson, M.L. Jourdan, J.Y. LeGuennec, P. Bougnoux, and C. Vandier The SK3/K(Ca)2.3 potassium channel is a new cellular target for edelfosine Br. J. Pharmacol. 162 2011 464 479
97. C. Gajate, and F. Mollinedo Lipid rafts and Fas/CD95 signaling in cancer chemotherapy Recent Pat. Anticancer Drug Discov. 6 2011 274 283
98. A.H. van der Luit, M. Budde, S. Zerp, W. Caan, J.B. Klarenbeek, M. Verheij, and W.J. van Blitterswijk Resistance to alkyl-lysophospholipid-induced apoptosis due to downregulated sphingomyelin synthase 1 expression with consequent sphingomyelin- and cholesterol-deficiency in lipid rafts Biochem. J. 401 2007 541 549
99. A. Ausili, A. Torrecillas, F.J. Aranda, F. Mollinedo, C. Gajate, S. Corbalan-Garcia, A. de Godos, and J.C. Gomez-Fernandez Edelfosine is incorporated into rafts and alters their organization J. Phys. Chem. B 112 2008 11643 11654
100. T. Nakano, I. Inoue, R. Shinozaki, M. Matsui, T. Akatsuka, S. Takahashi, K. Tanaka, M. Akita, M. Seo, S. Hokari, S. Katayama, and T. Komoda A possible role of lysophospholipids produced by calcium-independent phospholipase A(2) in membrane-raft budding and fission Biochim. Biophys. Acta 1788 2009 2222 2228
101. T. Nakano, I. Inoue, D.H. Alpers, Y. Akiba, S. Katayama, R. Shinozaki, J.D. Kaunitz, S. Ohshima, M. Akita, S. Takahashi, I. Koyama, M. Matsushita, and T. Komoda Role of lysophosphatidylcholine in brush-border intestinal alkaline phosphatase release and restoration Am. J. Physiol. Gastrointest. Liver Physiol. 297 2009 G207 G214
102. H.H. Chowdhury, K. Rebolj, M. Kreft, R. Zorec, P. Macek, and K. Sepcic Lysophospholipids prevent binding of a cytolytic protein ostreolysin to cholesterol-enriched membrane domains Toxicon 51 2008 1345 1356
103. M.T. Ma, J.F. Yeo, A.A. Farooqui, J. Zhang, P. Chen, and W.Y. Ong Differential effects of lysophospholipids on exocytosis in rat PC12 cells J. Neural Transm. 117 2010 301 308
104. T. Hla, M.J. Lee, N. Ancellin, J.H. Paik, and M.J. Kluk Lysophospholipids-receptor revelations Science 294 2001 1875 1878
105. E. Gendaszewska-Darmach Lysophosphatidic acids, cyclic phosphatidic acids and autotaxin as promising targets in therapies of cancer and other diseases Acta Biochim. Pol. 55 2008 227 240
106. W.C. Sin, Y. Zhang, W. Zhong, S. Adhikarakunnathu, S. Powers, T. Hoey, S. An, and J. Yang G protein-coupled receptors GPR4 and TDAG8 are oncogenic and overexpressed in human cancers Oncogene 23 2004 6299 6303
107. S. Oka, K. Nakajima, A. Yamashita, S. Kishimoto, and T. Sugiura Identification of GPR55 as a lysophosphatidylinositol receptor Biochem. Biophys. Res. Commun. 362 2007 928 934
108. T. Sugo, H. Tachimoto, T. Chikatsu, Y. Murakami, Y. Kikukawa, S. Sato, K. Kikuchi, T. Nagi, M. Harada, K. Ogi, M. Ebisawa, and M. Mori Identification of a lysophosphatidylserine receptor on mast cells Biochem. Biophys. Res. Commun. 341 2006 1078 1087
109. K. Kim, H.L. Kim, Y.K. Lee, M. Han, S.J. Sacket, J.Y. Jo, Y.L. Kim, and D.S. Im Lysophosphatidylserine induces calcium signaling through Ki16425/VPC32183-sensitive GPCR in bone marrow-derived mast cells and in C6 glioma and colon cancer cells Arch. Pharm. Res. 31 2008 310 317
110. R. Pineiro, T. Maffucci, and M. Falasca The putative cannabinoid receptor GPR55 defines a novel autocrine loop in cancer cell proliferation Oncogene 30 2011 142 152
111. K.S. Park, M.K. Kim, D.S. Im, and Y.S. Bae Effect of lysophosphatidylglycerol on several signaling molecules in OVCAR-3 human ovarian cancer cells: involvement of pertussis toxin-sensitive G-protein coupled receptor Biochem. Pharmacol. 73 2007 675 681
112. R.L. van der Bend, J. Brunner, K. Jalink, E.J. van Corven, W.H. Moolenaar, and W.J. van Blitterswijk Identification of a putative membrane receptor for the bioactive phospholipid, lysophosphatidic acid EMBO J. 11 1992 2495 2501
113. Z. Weng, A.C. Fluckiger, S. Nisitani, M.I. Wahl, L.Q. Le, C.A. Hunter, A.A. Fernal, M.M. Le Beau, and O.N. Witte A DNA damage and stress inducible G protein-coupled receptor blocks cells in G2/M Proc. Natl. Acad. Sci. U.S.A. 95 1998 12334 12339
114. S.C. Frasch, R.F. Fernandez-Boyanapalli, K.Z. Berry, C.C. Leslie, J.V. Bonventre, R.C. Murphy, P.M. Henson, and D.L. Bratton Signaling via macrophage G2A enhances efferocytosis of dying neutrophils by augmentation of Rac activity J. Biol. Chem. 286 2011 12108 12122
115. H. Obinata, T. Hattori, S. Nakane, K. Tatei, and T. Izumi Identification of 9-hydroxyoctadecadienoic acid and other oxidized free fatty acids as ligands of the G protein-coupled receptor G2A J. Biol. Chem. 280 2005 40676 40683
116. H. Yin, A. Chu, W. Li, B. Wang, F. Shelton, F. Otero, D.G. Nguyen, J.S. Caldwell, and Y.A. Chen Lipid G protein-coupled receptor ligand identification using beta-arrestin PathHunter assay J. Biol. Chem. 284 2009 12328 12338
117. N. Murakami, T. Yokomizo, T. Okuno, and T. Shimizu G2A is a proton-sensing G-protein-coupled receptor antagonized by lysophosphatidylcholine J. Biol. Chem. 279 2004 42484 42491
118. C.G. Radu, L.V. Yang, M. Riedinger, M. Au, and O.N. Witte T cell chemotaxis to lysophosphatidylcholine through the G2A receptor Proc. Natl. Acad. Sci. U.S.A. 101 2004 245 250
119. L. Wang, C.G. Radu, L.V. Yang, L.A. Bentolila, M. Riedinger, and O.N. Witte Lysophosphatidylcholine-induced surface redistribution regulates signaling of the murine G protein-coupled receptor G2A Mol. Biol. Cell 16 2005 2234 2247
120. P. Lin, and R.D. Ye The lysophospholipid receptor G2A activates a specific combination of G proteins and promotes apoptosis J. Biol. Chem. 278 2003 14379 14386
121. J.H. Kabarowski G2A and LPC: regulatory functions in immunity Prostaglandins Other Lipid Mediat. 89 2009 73 81
122. C. Peter, M. Waibel, C.G. Radu, L.V. Yang, O.N. Witte, K. Schulze-Osthoff, S. Wesselborg, and K. Lauber Migration to apoptotic "find-me" signals is mediated via the phagocyte receptor G2A J. Biol. Chem. 283 2008 5296 5305
123. H. Lum, J. Qiao, R.J. Walter, F. Huang, P.V. Subbaiah, K.S. Kim, and O. Holian Inflammatory stress increases receptor for lysophosphatidylcholine in human microvascular endothelial cells Am. J. Physiol. Heart Circ. Physiol. 285 2003 H1786 H1789
124. J. Qiao, F. Huang, R.P. Naikawadi, K.S. Kim, T. Said, and H. Lum Lysophosphatidylcholine impairs endothelial barrier function through the G protein-coupled receptor GPR4 Am. J. Physiol. Lung Cell. Mol. Physiol. 291 2006 L91 L101
125. F. Huang, D. Mehta, S. Predescu, K.S. Kim, and H. Lum A novel lysophospholipid- and pH-sensitive receptor, GPR4, in brain endothelial cells regulates monocyte transmigration Endothelium 14 2007 25 34
126. M.G. Ludwig, M. Vanek, D. Guerini, J.A. Gasser, C.E. Jones, U. Junker, H. Hofstetter, R.M. Wolf, and K. Seuwen Proton-sensing G-protein-coupled receptors Nature 425 2003 93 98
127. K. Seuwen, M.G. Ludwig, and R.M. Wolf Receptors for protons or lipid messengers or both? J. Recept. Signal. Transduct. Res. 26 2006 599 610
128. D.S. Im Two ligands for a GPCR, proton vs lysolipid Acta Pharmacol. Sin 26 2005 1435 1441
129. H. Tomura, C. Mogi, K. Sato, and F. Okajima Proton-sensing and lysolipid-sensitive G-protein-coupled receptors: a novel type of multi-functional receptors Cell Signal. 17 2005 1466 1476
130. S. An, C. Tsai, and E.J. Goetzl Cloning, sequencing and tissue distribution of two related G protein-coupled receptor candidates expressed prominently in human lung tissue FEBS Lett. 375 1995 121 124
131. K.S. Kim, J. Ren, Y. Jiang, Q. Ebrahem, R. Tipps, K. Cristina, Y.J. Xiao, J. Qiao, K.L. Taylor, H. Lum, B. Anand-Apte, and Y. Xu GPR4 plays a critical role in endothelial cell function and mediates the effects of sphingosylphosphorylcholine FASEB J. 19 2005 819 821
132. I. Liebscher, U. Muller, D. Teupser, E. Engemaier, K.M. Engel, L. Ritscher, D. Thor, K. Sangkuhl, A. Ricken, A. Wurm, D. Piehler, S. Schmutzler, H. Fuhrmann, F.W. Albert, A. Reichenbach, J. Thiery, T. Schoneberg, and A. Schulz Altered immune response in mice deficient for the G protein-coupled receptor GPR34 J. Biol. Chem. 286 2011 2101 2110
133. T. Schoneberg, A. Schulz, R. Grosse, R. Schade, P. Henklein, G. Schultz, and T. Gudermann A novel subgroup of class I G-protein-coupled receptors Biochim. Biophys. Acta 1446 1999 57 70
134. E. Engemaier, H. Rompler, T. Schoneberg, and A. Schulz Genomic and supragenomic structure of the nucleotide-like G-protein-coupled receptor GPR34 Genomics 87 2006 254 264
135. M. Baens, J. Finalet Ferreiro, T. Tousseyn, H. Urbankova, L. Michaux, L. de Leval, D. Dierickx, P. Wolter, X. Sagaert, P. Vandenberghe, C. De Wolf-Peeters, and I. Wlodarska t(X;14)(p11.4;q32.33) is recurrent in marginal zone lymphoma and up-regulates GPR34 Haematologica 97 2012 184 188
136. A. Bedard, P. Tremblay, A. Chernomoretz, and L. Vallieres Identification of genes preferentially expressed by microglia and upregulated during cuprizone-induced inflammation Glia 55 2007 777 789
137. K. Makide, H. Kitamura, Y. Sato, M. Okutani, and J. Aoki Emerging lysophospholipid mediators, lysophosphatidylserine, lysophosphatidylthreonine, lysophosphatidylethanolamine and lysophosphatidylglycerol Prostaglandins Other Lipid Mediat. 89 2009 135 139
138. J. Mitoma, T. Kasama, S. Furuya, and Y. Hirabayashi Occurrence of an unusual phospholipid, phosphatidyl-l-threonine, in cultured hippocampal neurons. Exogenous l-serine is required for the synthesis of neuronal phosphatidyl-l-serine and sphingolipids J. Biol. Chem. 273 1998 19363 19366
139. H. Kitamura, K. Makide, A. Shuto, M. Ikubo, A. Inoue, K. Suzuki, Y. Sato, S. Nakamura, Y. Otani, T. Ohwada, and J. Aoki GPR34 is a Receptor for Lysophosphatidylserine with a Fatty Acid at the sn-2 Position J. Biochem. 151 2012 511 518
140. L. Ritscher, E. Engemaier, C. Staubert, I. Liebscher, P. Schmidt, T. Hermsdorf, H. Rompler, A. Schulz, and T. Schoneberg The ligand specificity of the G-protein-coupled receptor GPR34 Biochem. J. 443 2012 841 850
141. G. Godlewski, L. Offertaler, J.A. Wagner, and G. Kunos Receptors for acylethanolamides-GPR55 and GPR119 Prostaglandins Other Lipid Mediat. 89 2009 105 111
142. H.A. Overton, A.J. Babbs, S.M. Doel, M.C. Fyfe, L.S. Gardner, G. Griffin, H.C. Jackson, M.J. Procter, C.M. Rasamison, M. Tang-Christensen, P.S. Widdowson, G.M. Williams, and C. Reynet Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents Cell Metab. 3 2006 167 175
143. Y. Sakamoto, H. Inoue, S. Kawakami, K. Miyawaki, T. Miyamoto, K. Mizuta, and M. Itakura Expression and distribution of Gpr119 in the pancreatic islets of mice and rats: predominant localization in pancreatic polypeptide-secreting PP-cells Biochem. Biophys. Res. Commun. 351 2006 474 480
144. Z.L. Chu, R.M. Jones, H. He, C. Carroll, V. Gutierrez, A. Lucman, M. Moloney, H. Gao, H. Mondala, D. Bagnol, D. Unett, Y. Liang, K. Demarest, G. Semple, D.P. Behan, and J. Leonard A role for beta-cell-expressed G protein-coupled receptor 119 in glycemic control by enhancing glucose-dependent insulin release Endocrinology 148 2007 2601 2609
145. L.M. Lauffer, R. Iakoubov, and P.L. Brubaker GPR119 is essential for oleoylethanolamide-induced glucagon-like peptide-1 secretion from the intestinal enteroendocrine L-cell Diabetes 58 2009 1058 1066
146. H. Lan, G. Vassileva, A. Corona, L. Liu, H. Baker, A. Golovko, S.J. Abbondanzo, W. Hu, S. Yang, Y. Ning, R.A. Del Vecchio, F. Poulet, M. Laverty, E.L. Gustafson, J.A. Hedrick, and T.J. Kowalski GPR119 is required for physiological regulation of glucagon-like peptide-1 secretion but not for metabolic homeostasis J. Endocrinol. 201 2009 219 230
147. Z.L. Chu, C. Carroll, R. Chen, J. Alfonso, V. Gutierrez, H. He, A. Lucman, C. Xing, K. Sebring, J. Zhou, B. Wagner, D. Unett, R.M. Jones, D.P. Behan, and J. Leonard N-oleoyldopamine enhances glucose homeostasis through the activation of GPR119 Mol. Endocrinol. 24 2010 161 170
148. E. Ryberg, N. Larsson, S. Sjogren, S. Hjorth, N.O. Hermansson, J. Leonova, T. Elebring, K. Nilsson, T. Drmota, and P.J. Greasley The orphan receptor GPR55 is a novel cannabinoid receptor Br. J. Pharmacol. 152 2007 1092 1101
149. J.E. Lauckner, J.B. Jensen, H.Y. Chen, H.C. Lu, B. Hille, and K. Mackie GPR55 is a cannabinoid receptor that increases intracellular calcium and inhibits M current Proc. Natl. Acad. Sci. U.S.A. 105 2008 2699 2704
150. D.G. Johns, D.J. Behm, D.J. Walker, Z. Ao, E.M. Shapland, D.A. Daniels, M. Riddick, S. Dowell, P.C. Staton, P. Green, U. Shabon, W. Bao, N. Aiyar, T.L. Yue, A.J. Brown, A.D. Morrison, and S.A. Douglas The novel endocannabinoid receptor GPR55 is activated by atypical cannabinoids but does not mediate their vasodilator effects Br. J. Pharmacol. 152 2007 825 831
151. F. Petitet, M. Donlan, and A. Michel GPR55 as a new cannabinoid receptor: still a long way to prove it Chem. Biol. Drug Des. 67 2006 252 253
152. E. Kotsikorou, D.L. Lynch, M.E. Abood, and P.H. Reggio Lipid bilayer molecular dynamics study of lipid-derived agonists of the putative cannabinoid receptor, GPR55 Chem. Phys. Lipids 164 2011 131 143
153. M. Sawzdargo, T. Nguyen, D.K. Lee, K.R. Lynch, R. Cheng, H.H. Heng, S.R. George, and B.F. O'Dowd Identification and cloning of three novel human G protein-coupled receptor genes GPR52, PsiGPR53 and GPR55: GPR55 is extensively expressed in human brain Brain Res. Mol. Brain Res. 64 1999 193 198
154. S. Oka, S. Kimura, T. Toshida, R. Ota, A. Yamashita, and T. Sugiura Lysophosphatidylinositol induces rapid phosphorylation of p38 mitogen-activated protein kinase and activating transcription factor 2 in HEK293 cells expressing GPR55 and IM-9 lymphoblastoid cells J. Biochem. 147 2010 671 678
155. M. Waldeck-Weiermair, C. Zoratti, K. Osibow, N. Balenga, E. Goessnitzer, M. Waldhoer, R. Malli, and W.F. Graier Integrin clustering enables anandamide-induced Ca2+ signaling in endothelial cells via GPR55 by protection against CB1-receptor-triggered repression J. Cell. Sci. 121 2008 1704 1717
156. C. Andradas, M.M. Caffarel, E. Perez-Gomez, M. Salazar, M. Lorente, G. Velasco, M. Guzman, and C. Sanchez The orphan G protein-coupled receptor GPR55 promotes cancer cell proliferation via ERK Oncogene 30 2011 245 252
157. T. Nevalainen, and A.J. Irving GPR55, a lysophosphatidylinositol receptor with cannabinoid sensitivity? Curr. Top. Med. Chem. 10 2010 799 813
158. C.M. Henstridge, N.A. Balenga, L.A. Ford, R.A. Ross, M. Waldhoer, and A.J. Irving The GPR55 ligand L-alpha-lysophosphatidylinositol promotes RhoA-dependent Ca2+ signaling and NFAT activation FASEB J. 23 2009 183 193
159. C.M. Henstridge, N.A. Balenga, R. Schroder, J.K. Kargl, W. Platzer, L. Martini, S. Arthur, J. Penman, J.L. Whistler, E. Kostenis, M. Waldhoer, and A.J. Irving GPR55 ligands promote receptor coupling to multiple signalling pathways Br. J. Pharmacol. 160 2010 604 614
160. L.S. Whyte, E. Ryberg, N.A. Sims, S.A. Ridge, K. Mackie, P.J. Greasley, R.A. Ross, and M.J. Rogers The putative cannabinoid receptor GPR55 affects osteoclast function in vitro and bone mass in vivo Proc. Natl. Acad. Sci. U.S.A. 106 2009 16511 16516
161. M. Pietr, E. Kozela, R. Levy, N. Rimmerman, Y.H. Lin, N. Stella, Z. Vogel, and A. Juknat Differential changes in GPR55 during microglial cell activation FEBS Lett. 583 2009 2071 2076