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Volumn 49, Issue 17, 2006, Pages 5309-5315

Phosphonothioate and fluoromethylene phosphonate analogues of cyclic phosphatidic acid: Novel antagonists of lysophosphatidic acid receptors

Author keywords

[No Author keywords available]

Indexed keywords

1 FLUOROHYDROXYL 4 OLEOYLOXYLBUTANE 1,3 CYCLIC PHOSPHONATE; 1,1 DIFLUORO 3 HYDROXYL 4 OLEOYLOXYLBUTANE 1,3 CYCLIC PHOSPHONATE; 3 HYDROXYL 4 OLEOYLOXYLBUTANE 1,3 CYCLIC PHOSPHONOTHIOATE; 3 HYDROXYL 4 PALMITOYLOXYLBUTANE 1,3 CYCLIC PHOSPHONOTHIOATE; AMPHOPHILE; CALCIUM ION; CARBENE; FLUORINE DERIVATIVE; G PROTEIN COUPLED RECEPTOR; LYSOPHOSPHATIDIC ACID; LYSOPHOSPHATIDIC ACID RECEPTOR; LYSOPHOSPHATIDIC ACID RECEPTOR 1; LYSOPHOSPHATIDIC ACID RECEPTOR 2; LYSOPHOSPHATIDIC ACID RECEPTOR 3; LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONIST; PHOSPHATIDIC ACID; PHOSPHOLIPID; PHOSPHONIC ACID DERIVATIVE; RECEPTOR BLOCKING AGENT; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

EID: 33747593309     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060351+     Document Type: Article
Times cited : (38)

References (52)
  • 1
    • 0026793004 scopus 로고
    • Inhibition of eukaryotic DNA polymerase a with a novel lysophosphatidic acid (PHYLPA) isolated from myxoamebae of Physarum polycephalum
    • Murakami-Murofushi, K.; Shioda, M.; Kaji, K.; Yoshida, S.; Murofushi, H. Inhibition of eukaryotic DNA polymerase a with a novel lysophosphatidic acid (PHYLPA) isolated from myxoamebae of Physarum polycephalum. J. Biol. Chem. 1992, 267, 21512-21517.
    • (1992) J. Biol. Chem. , vol.267 , pp. 21512-21517
    • Murakami-Murofushi, K.1    Shioda, M.2    Kaji, K.3    Yoshida, S.4    Murofushi, H.5
  • 2
    • 0027491442 scopus 로고
    • Isolation of a new species of Physarum lysophosphatidic acid, PHYLPA, and its effect on DNA polymerase activity
    • Takahashi, Y.; Shimada, Y.; Shioda, M.; Yoshida, S.; Murofushi, H. et al. Isolation of a new species of Physarum lysophosphatidic acid, PHYLPA, and its effect on DNA polymerase activity. Cell Struct. Funct. 1993, 18, 135-138.
    • (1993) Cell Struct. Funct. , vol.18 , pp. 135-138
    • Takahashi, Y.1    Shimada, Y.2    Shioda, M.3    Yoshida, S.4    Murofushi, H.5
  • 3
    • 0027751832 scopus 로고
    • Inhibition of cell proliferation by a unique lysophosphatidic acid, PHYLPA, isolated from Physarum polycephalum: Signaling events of antiproliferative action by PHYLPA
    • Murakami-Murofushi, K.; Kaji, K.; Kano, K.; Fukuda, M.; Shioda, M. et al. Inhibition of cell proliferation by a unique lysophosphatidic acid, PHYLPA, isolated from Physarum polycephalum: Signaling events of antiproliferative action by PHYLPA. Cell Struct. Funct. 1993, 18, 363-370.
    • (1993) Cell Struct. Funct. , vol.18 , pp. 363-370
    • Murakami-Murofushi, K.1    Kaji, K.2    Kano, K.3    Fukuda, M.4    Shioda, M.5
  • 4
    • 0027281134 scopus 로고
    • Synthesis of 1-O-acylglycerol 2,3-cyclic phosphate: Determination of the absolute structure of PHYLPA, a specific inhibitor of DNA polymerase a
    • Kobayashi, S.; Tokunoh, R.; Shibasaki, M.; Shinagawa, R.; Murakami-Murofushi, K. Synthesis of 1-O-acylglycerol 2,3-cyclic phosphate: determination of the absolute structure of PHYLPA, a specific inhibitor of DNA polymerase a. Tetrahedron Lett. 1993, 34, 4047-4050.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4047-4050
    • Kobayashi, S.1    Tokunoh, R.2    Shibasaki, M.3    Shinagawa, R.4    Murakami-Murofushi, K.5
  • 5
    • 58149325700 scopus 로고
    • Selective inhibition of DNA polymerase-α family with chemically synthesized derivatives of PHYLPA, a unique Physarum lysophosphatidic acid
    • Murakami-Murofushi, K.; Kobayashi, S.; Onimura, K.; Maysumoto, M.; Shioda, M. et al. Selective inhibition of DNA polymerase-α family with chemically synthesized derivatives of PHYLPA, a unique Physarum lysophosphatidic acid. Biochim. Biophys. Acta 1995, 1258, 57-60.
    • (1995) Biochim. Biophys. Acta , vol.1258 , pp. 57-60
    • Murakami-Murofushi, K.1    Kobayashi, S.2    Onimura, K.3    Maysumoto, M.4    Shioda, M.5
  • 6
    • 0032426908 scopus 로고    scopus 로고
    • Naturally occurring analogs of lysophosphatidic acid elicit different cellular responses through selective activation of multiple receptor subtypes
    • Fischer, D. J.; Liliom, K.; Guo, H.; Nusser, N.; Virag, T. et al. Naturally occurring analogs of lysophosphatidic acid elicit different cellular responses through selective activation of multiple receptor subtypes. Mol. Pharmacol 1998, 54, 979-988.
    • (1998) Mol. Pharmacol. , vol.54 , pp. 979-988
    • Fischer, D.J.1    Liliom, K.2    Guo, H.3    Nusser, N.4    Virag, T.5
  • 7
    • 0033043251 scopus 로고    scopus 로고
    • Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA)
    • Mukai, M.; Imamura, F.; Ayaki, M.; Shinkai, K.; Iwasaki, T. et al. Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA). Int. J. Cancer 1999, 81, 918-922.
    • (1999) Int. J. Cancer , vol.81 , pp. 918-922
    • Mukai, M.1    Imamura, F.2    Ayaki, M.3    Shinkai, K.4    Iwasaki, T.5
  • 8
    • 0033614847 scopus 로고    scopus 로고
    • Structure-activity analysis of the effects of lysophosphatidic acid on platelet aggregation
    • Gueguen, G.; Gaige, B.; Grevy, J.; Rogalle, P.; Bellan, J. et al. Structure-activity analysis of the effects of lysophosphatidic acid on platelet aggregation. Biochemistry 1999, 38, 8440-8450.
    • (1999) Biochemistry , vol.38 , pp. 8440-8450
    • Gueguen, G.1    Gaige, B.2    Grevy, J.3    Rogalle, P.4    Bellan, J.5
  • 10
    • 0033569330 scopus 로고    scopus 로고
    • Existence of a bioactive lipid, cyclic phosphatidic acid, bound to human serum albumin
    • Kobayashi, T.; Tanaka-Ishii, R.; Taguchi, R.; Ikezawa, H.; Murakami-Murofushi, K. Existence of a bioactive lipid, cyclic phosphatidic acid, bound to human serum albumin. Life Sci. 1999, 65, 2185-2191.
    • (1999) Life Sci. , vol.65 , pp. 2185-2191
    • Kobayashi, T.1    Tanaka-Ishii, R.2    Taguchi, R.3    Ikezawa, H.4    Murakami-Murofushi, K.5
  • 11
    • 2342533007 scopus 로고    scopus 로고
    • Attenuation by cyclic phosphatidic acid of peritoneal metastasis of azoxymethane-induced intestinal cancers in Wistar rats
    • Ishihara, R.; Tatsuta, M.; Iishi, H.; Baba, M.; Uedo, N. et al. Attenuation by cyclic phosphatidic acid of peritoneal metastasis of azoxymethane-induced intestinal cancers in Wistar rats. Int. J. Cancer 2004, 110, 188-193.
    • (2004) Int. J. Cancer , vol.110 , pp. 188-193
    • Ishihara, R.1    Tatsuta, M.2    Iishi, H.3    Baba, M.4    Uedo, N.5
  • 12
    • 33747588366 scopus 로고    scopus 로고
    • Cancerous metastasis inhibitors containing carbacyclic phosphatidic acid derivatives. PCT Int., 2002; pp WO 0294286
    • Mukai, M.; Kobayashi, S.; Murofushi, H.; Murofushi, K. Cancerous metastasis inhibitors containing carbacyclic phosphatidic acid derivatives. PCT Int., 2002; pp WO 0294286.
    • Mukai, M.1    Kobayashi, S.2    Murofushi, H.3    Murofushi, K.4
  • 13
    • 28844456029 scopus 로고    scopus 로고
    • New metabolically stabilized analogues of lysophosphatidic acid: Agonists, antagonists, and enzyme inhibitors
    • Prestwich, G. D.; Xu, Y.; Qian, L.; Gajewiak, J.; Jiang, G. New metabolically stabilized analogues of lysophosphatidic acid: Agonists, antagonists, and enzyme inhibitors. Biochem. Soc. Trans. 2005, 33, 1357-1361.
    • (2005) Biochem. Soc. Trans. , vol.33 , pp. 1357-1361
    • Prestwich, G.D.1    Xu, Y.2    Qian, L.3    Gajewiak, J.4    Jiang, G.5
  • 14
    • 0346366461 scopus 로고    scopus 로고
    • Enantioselective responses to OMPT, a phosphorothioate analogue of lysophosphatidic acid with LPA3 receptor-selective agonist activity
    • Qian, L.; Xu, Y.; Hasegawa, Y.; Aoki, J.; Mills, G. B. et al. Enantioselective responses to OMPT, a phosphorothioate analogue of lysophosphatidic acid with LPA3 receptor-selective agonist activity. J. Med. Chem. 2003, 46, 5575-5578.
    • (2003) J. Med. Chem. , vol.46 , pp. 5575-5578
    • Qian, L.1    Xu, Y.2    Hasegawa, Y.3    Aoki, J.4    Mills, G.B.5
  • 15
    • 33646536386 scopus 로고    scopus 로고
    • Synthesis of novel alkyl thiophosphate LPA analogues as potential antagonists and agonists for lysophosphatidic acid (LPA) receptors
    • Qian, L.; Xu, Y.; Simper, T. D.; Jiang, G.; Aoki, J. et al. Synthesis of novel alkyl thiophosphate LPA analogues as potential antagonists and agonists for lysophosphatidic acid (LPA) receptors. ChemMedChem. 2006, 1, 376-383.
    • (2006) ChemMedChem. , vol.1 , pp. 376-383
    • Qian, L.1    Xu, Y.2    Simper, T.D.3    Jiang, G.4    Aoki, J.5
  • 16
    • 20944435206 scopus 로고    scopus 로고
    • Structure-activity relationships of fluorinated lysophosphatidic acid analogues
    • Xu, Y.; Aoki, J.; Shimizu, K.; Umezu-Goto, M.; Hama, K. et al. Structure-activity relationships of fluorinated lysophosphatidic acid analogues. J. Med. Chem. 2005, 48, 3319-3327.
    • (2005) J. Med. Chem. , vol.48 , pp. 3319-3327
    • Xu, Y.1    Aoki, J.2    Shimizu, K.3    Umezu-Goto, M.4    Hama, K.5
  • 17
    • 0038208387 scopus 로고    scopus 로고
    • Synthesis of monofluorinated analogues of lysophosphatidic acid
    • Xu, Y.; Qian, L.; Prestwich, G. D. Synthesis of monofluorinated analogues of lysophosphatidic acid. J. Org. Chem. 2003, 68, 5320-5330.
    • (2003) J. Org. Chem. , vol.68 , pp. 5320-5330
    • Xu, Y.1    Qian, L.2    Prestwich, G.D.3
  • 18
    • 0035169222 scopus 로고    scopus 로고
    • (α-Monofluoroalkyl)phosphonates: A class of isoacidic and tunable mimics of biological phosphates
    • Berkowitz, D. B.; Bose, M. (α-Monofluoroalkyl)phosphonates: a class of isoacidic and tunable mimics of biological phosphates. J. Fluorine Chem. 2001, 112, 13-33.
    • (2001) J. Fluorine Chem. , vol.112 , pp. 13-33
    • Berkowitz, D.B.1    Bose, M.2
  • 19
    • 28844435760 scopus 로고    scopus 로고
    • Structural characteristics of lysophosphatidic acid biological targets
    • Parrill, A. L. Structural characteristics of lysophosphatidic acid biological targets. Biochem. Soc. Trans. 2005, 33, 1366-1369.
    • (2005) Biochem. Soc. Trans. , vol.33 , pp. 1366-1369
    • Parrill, A.L.1
  • 20
    • 0141996371 scopus 로고    scopus 로고
    • Molecular mechanisms of lysophosphatidic acid action
    • Tigyi, G.; Parrill, A. L. Molecular mechanisms of lysophosphatidic acid action. Prog. Lipid. Res. 2003, 42, 498-526.
    • (2003) Prog. Lipid. Res. , vol.42 , pp. 498-526
    • Tigyi, G.1    Parrill, A.L.2
  • 22
    • 0042887042 scopus 로고    scopus 로고
    • The emerging role of lysophosphatidic acid in cancer
    • Mills, G. B.; Moolenaar, W. H. The emerging role of lysophosphatidic acid in cancer. Nat. Rev. Cancer 2003, 3, 582-591.
    • (2003) Nat. Rev. Cancer , vol.3 , pp. 582-591
    • Mills, G.B.1    Moolenaar, W.H.2
  • 23
    • 0035084540 scopus 로고    scopus 로고
    • Stereoselective inhibition of glutamate carboxypeptidase by chiral phosphonothioic acids
    • Lu, H.; Berkman, C. E. Stereoselective inhibition of glutamate carboxypeptidase by chiral phosphonothioic acids. Bioorg. Med. Chem. 2001, 9, 395-402.
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 395-402
    • Lu, H.1    Berkman, C.E.2
  • 24
    • 0001397262 scopus 로고    scopus 로고
    • A convenient triflate displacement approach to (α-monofluoroalkyl) phosphonates
    • Berkowitz, D. B.; Bose, M.; Asher, N. G. A convenient triflate displacement approach to (α-monofluoroalkyl)phosphonates. Org. Lett. 2001, 3, 2009-2012.
    • (2001) Org. Lett. , vol.3 , pp. 2009-2012
    • Berkowitz, D.B.1    Bose, M.2    Asher, N.G.3
  • 25
    • 0029975902 scopus 로고    scopus 로고
    • Stannyl radical mediated ceavage of p-deficient heterocyclic sulfones. Synthesis of α-fluoro esters and the first homonucleoside a-fluoromethylene phosphonate
    • Wnuk, S. F.; Robins, M. J. Stannyl radical mediated ceavage of p-deficient heterocyclic sulfones. Synthesis of α-fluoro esters and the first homonucleoside a-fluoromethylene phosphonate. J. Am. Chem. Soc. 1996, 118, 2519-2520.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2519-2520
    • Wnuk, S.F.1    Robins, M.J.2
  • 26
    • 0141629758 scopus 로고    scopus 로고
    • Synthesis of α-fluorinated phosphonates from α- fluorovinylphosphonates: A new route to analogues of lysophosphatidic acid
    • Xu, Y.; Qian, L.; Prestwich, G. D. Synthesis of α-fluorinated phosphonates from α-fluorovinylphosphonates: a new route to analogues of lysophosphatidic acid. Org. Lett. 2003, 5, 2267-2270.
    • (2003) Org. Lett. , vol.5 , pp. 2267-2270
    • Xu, Y.1    Qian, L.2    Prestwich, G.D.3
  • 27
    • 0037078853 scopus 로고    scopus 로고
    • Synthesis of chiral (α, α-difluoroalkyl)-phosphonate analogues of (lyso)phosphatidic acid via hydrolytic kinetic resolution
    • Xu, Y.; Prestwich, G. D. Synthesis of chiral (α, α-difluoroalkyl)-phosphonate analogues of (lyso)phosphatidic acid via hydrolytic kinetic resolution. Org. Lett. 2002, 4, 4021-4024.
    • (2002) Org. Lett. , vol.4 , pp. 4021-4024
    • Xu, Y.1    Prestwich, G.D.2
  • 28
    • 0002999181 scopus 로고
    • Synthetic and mechanistic aspects of the reaction of trialkylsilyl halides with thio and seleno esters of phosphorus
    • Borecka, B.; Chojnowski, J.; Cypryk, M.; Michalski, J.; Zielinska, J. Synthetic and mechanistic aspects of the reaction of trialkylsilyl halides with thio and seleno esters of phosphorus. J. Organomet. Chem. 1979, 171, 17-34.
    • (1979) J. Organomet. Chem. , vol.171 , pp. 17-34
    • Borecka, B.1    Chojnowski, J.2    Cypryk, M.3    Michalski, J.4    Zielinska, J.5
  • 29
    • 0029878638 scopus 로고    scopus 로고
    • Easy and general access to α, α- difluoromethylenephosphonothioic acids. A new class of compounds
    • Piettre, S. R.; Raboisson, P. Easy and general access to α, α-difluoromethylenephosphonothioic acids. A new class of compounds. Tetrahedron Lett. 1996, 37, 2229-2232.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2229-2232
    • Piettre, S.R.1    Raboisson, P.2
  • 30
    • 0000240075 scopus 로고
    • A general and facile synthesis of β- and γ-hydroxy phosphonates
    • Li, Z.; Racha, S.; Dan, L.; El-Subbagh, H.; Abushanab, E. A general and facile synthesis of β- and γ-hydroxy phosphonates. J. Org. Chem. 1993, 58, 5779-5783.
    • (1993) J. Org. Chem. , vol.58 , pp. 5779-5783
    • Li, Z.1    Racha, S.2    Dan, L.3    El-Subbagh, H.4    Abushanab, E.5
  • 31
    • 0033305986 scopus 로고    scopus 로고
    • Stereospecific thionation of 2-ethoxy-1,2-oxaphosphorinane 2-oxide and its derivatives with Lawesson's reagent
    • Polozov, A. M.; Cremer, S. E.; Fanwick, P. E. Stereospecific thionation of 2-ethoxy-1,2-oxaphosphorinane 2-oxide and its derivatives with Lawesson's reagent. Can. J. Chem. 1999, 77, 1274-1280.
    • (1999) Can. J. Chem. , vol.77 , pp. 1274-1280
    • Polozov, A.M.1    Cremer, S.E.2    Fanwick, P.E.3
  • 32
    • 33747622404 scopus 로고
    • Stereospecific synthesis and reactions of optically active isopropyl methylphosphinate
    • Reiff, L. P.; H. S., A. Stereospecific synthesis and reactions of optically active isopropyl methylphosphinate. J. Am. Chem. Soc. 1970, 92, 6391-6392.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 6391-6392
    • Reiff, L.P.1
  • 34
    • 0024559949 scopus 로고
    • Phospholipids chiral at phosphorus. 18. Stereochemistry of phosphatidylinositide-specific phospholipase C
    • Lin, G.; Tsai, M. D. Phospholipids chiral at phosphorus. 18. Stereochemistry of phosphatidylinositide-specific phospholipase C. J. Am. Chem. Soc. 1989, 111, 3099-3101.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3099-3101
    • Lin, G.1    Tsai, M.D.2
  • 35
    • 0000468774 scopus 로고    scopus 로고
    • Electrophilic NF fluorinating agents
    • Lal, G. S.; Pez, G. P.; Syvret, R. G. Electrophilic NF fluorinating agents. Chem. Rev. 1996, 96, 1737-1755.
    • (1996) Chem. Rev. , vol.96 , pp. 1737-1755
    • Lal, G.S.1    Pez, G.P.2    Syvret, R.G.3
  • 36
    • 0030110808 scopus 로고    scopus 로고
    • Inhibition of phosphatidylinositol-specific phospholipase C: Studies on synthetic substrates, inhibitors and a synthetic enzyme
    • Viztiu, D.; Kriste, A. G.; Campbell, A. S.; Thatcher, G. R. J. Inhibition of phosphatidylinositol-specific phospholipase C: studies on synthetic substrates, inhibitors and a synthetic enzyme. J. Mol. Recogn. 1996, 9, 197-209.
    • (1996) J. Mol. Recogn. , vol.9 , pp. 197-209
    • Viztiu, D.1    Kriste, A.G.2    Campbell, A.S.3    Thatcher, G.R.J.4
  • 37
    • 0013664555 scopus 로고
    • Studies on the alkaline hydrolysis of lecithin: Synthesis of cyclic 1,2-glycerophosphate
    • Ukita, T.; Bates, N. A.; Carter, H. E. Studies on the alkaline hydrolysis of lecithin: synthesis of cyclic 1,2-glycerophosphate. J. Biol. Chem. 1955, 216, 867-874.
    • (1955) J. Biol. Chem. , vol.216 , pp. 867-874
    • Ukita, T.1    Bates, N.A.2    Carter, H.E.3
  • 38
    • 0000669015 scopus 로고
    • Cyclic phosphates. III. Some general observations on the formation and properties of five-, six- and seven-membered cyclic phosphate esters
    • Khorana, H. G.; Tener, G. M.; Wright, R. S.; Moffatt, J. G. Cyclic phosphates. III. Some general observations on the formation and properties of five-, six- and seven-membered cyclic phosphate esters. J. Am. Chem. Soc. 1957, 79, 430-436.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 430-436
    • Khorana, H.G.1    Tener, G.M.2    Wright, R.S.3    Moffatt, J.G.4
  • 39
    • 0024426154 scopus 로고
    • Fluorine in enzyme chemistry. Part 2. The preparation of difluoromethylenephosphonate analogues of glycolytic phosphates approaching an isosteric and isoelectronic phosphate mimic
    • Chambers, R. D.; Jaouhar, R.; O'Hagan, D. Fluorine in enzyme chemistry. Part 2. The preparation of difluoromethylenephosphonate analogues of glycolytic phosphates approaching an isosteric and isoelectronic phosphate mimic. Tetrahedron 1989, 45, 5101-5108.
    • (1989) Tetrahedron , vol.45 , pp. 5101-5108
    • Chambers, R.D.1    Jaouhar, R.2    O'Hagan, D.3
  • 40
    • 0029655735 scopus 로고    scopus 로고
    • Synthesis of monofluor- and difluoro-methylenephosphonate analogues of sn-glycero-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X-ray structure of the fluoromethylenephosphonate moiety
    • Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Synthesis of monofluor- and difluoro-methylenephosphonate analogues of sn-glycero-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X-ray structure of the fluoromethylenephosphonate moiety. Tetrahedron 1996, 52, 165-176.
    • (1996) Tetrahedron , vol.52 , pp. 165-176
    • Nieschalk, J.1    Batsanov, A.S.2    O'Hagan, D.3    Howard, J.A.K.4
  • 43
    • 0034812654 scopus 로고    scopus 로고
    • Short-chain phosphatidates are subtype-selective antagonists of lysophosphatidic acid receptors
    • Fischer, D. J.; Nusser, N.; Virag, T.; Yokoyama, K.; Wang, D. A. et al. Short-chain phosphatidates are subtype-selective antagonists of lysophosphatidic acid receptors. Mol. Pharmacol. 2001, 60, 776-784.
    • (2001) Mol. Pharmacol. , vol.60 , pp. 776-784
    • Fischer, D.J.1    Nusser, N.2    Virag, T.3    Yokoyama, K.4    Wang, D.A.5
  • 44
    • 0038069067 scopus 로고    scopus 로고
    • Fatty alcohol phosphates are subtype-selective agonists and antagonists of lysophosphatidic acid receptors
    • Virag, T.; Elrod, D. B.; Liliom, K.; Sardar. V. M.; Parrill, A. L. et al. Fatty alcohol phosphates are subtype-selective agonists and antagonists of lysophosphatidic acid receptors. Mol. Pharmacol. 2003, 63, 1032-1042.
    • (2003) Mol. Pharmacol. , vol.63 , pp. 1032-1042
    • Virag, T.1    Elrod, D.B.2    Liliom, K.3    Sardar, V.M.4    Parrill, A.L.5
  • 45
    • 27144538692 scopus 로고    scopus 로고
    • Identification of residues responsible for ligand recognition and regioisomeric selectivity of lysophosphatidic acid receptors expressed in mammalian cells
    • Fujiwara, Y.; Sardar, V.; Tokumura, A.; Baker, D.; MurakamiMurofushi, K. et al. Identification of residues responsible for ligand recognition and regioisomeric selectivity of lysophosphatidic acid receptors expressed in mammalian cells. J. Biol. Chem. 2005, 280, 35038-35050.
    • (2005) J. Biol. Chem. , vol.280 , pp. 35038-35050
    • Fujiwara, Y.1    Sardar, V.2    Tokumura, A.3    Baker, D.4    Murakamimurofushi, K.5
  • 46
    • 0037073806 scopus 로고    scopus 로고
    • Serum lysophosphatidic acid is produced through diverse phospholipase pathways
    • Aoki, J.; Taira, A.; Takanezawa, Y.; Kishi, Y.; Hama, K. et al. Serum lysophosphatidic acid is produced through diverse phospholipase pathways. J. Biol. Chem. 2002, 277, 48737-48744.
    • (2002) J. Biol. Chem. , vol.277 , pp. 48737-48744
    • Aoki, J.1    Taira, A.2    Takanezawa, Y.3    Kishi, Y.4    Hama, K.5
  • 47
    • 0031466275 scopus 로고    scopus 로고
    • Lysophosphatidic acid induces threonine phosphorylation of Tiam1 in Swiss 3T3 fibroblasts via activation of protein kinase C
    • Fleming, I. N.; Elliott, C. M.; Collard, J. G.; Exton, J. H. Lysophosphatidic acid induces threonine phosphorylation of Tiam1 in Swiss 3T3 fibroblasts via activation of protein kinase C. J. Biol. Chem. 1997, 272, 33105-33110.
    • (1997) J. Biol. Chem. , vol.272 , pp. 33105-33110
    • Fleming, I.N.1    Elliott, C.M.2    Collard, J.G.3    Exton, J.H.4
  • 48
    • 0036828287 scopus 로고    scopus 로고
    • Lysophosphatidic acid-induced squamous cell carcinoma cell proliferation and motility involves epidermal growth factor receptor signal transactivation
    • Gschwind, A.; Prenzel, N.; Ullrich, A. Lysophosphatidic acid-induced squamous cell carcinoma cell proliferation and motility involves epidermal growth factor receptor signal transactivation. Cancer Res. 2002, 62, 6329-6336.
    • (2002) Cancer Res. , vol.62 , pp. 6329-6336
    • Gschwind, A.1    Prenzel, N.2    Ullrich, A.3
  • 49
    • 0035206909 scopus 로고    scopus 로고
    • Activity of 2-substituted lysophosphatidic acid (LPA) analogues at LPA receptors: Discovery of a LPA1/LPA3 receptor antagonist
    • Heise, C. E.; Santos, W. L.; Schreihofer, A. M.; Heasley, B. H.; Mukhin, Y. V. et al. Activity of 2-substituted lysophosphatidic acid (LPA) analogues at LPA receptors: discovery of a LPA1/LPA3 receptor antagonist. Mol. Pharmacol. 2001, 60, 1173-1180.
    • (2001) Mol. Pharmacol. , vol.60 , pp. 1173-1180
    • Heise, C.E.1    Santos, W.L.2    Schreihofer, A.M.3    Heasley, B.H.4    Mukhin, Y.V.5
  • 50
    • 2942532893 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid
    • Santos, W. L.; Heasley, B. H.; Jarosz, R.; Carter, K. M.; Lynch, K. R. et al. Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid. Bioorg. Med. Chem. Lett. 2004, 14, 3473-3476.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 3473-3476
    • Santos, W.L.1    Heasley, B.H.2    Jarosz, R.3    Carter, K.M.4    Lynch, K.R.5
  • 51
    • 0141570981 scopus 로고    scopus 로고
    • Ki16425, a subtype-selective antagonist for EDG-family lysophosphatidic acid receptors
    • Ohta, H.; Sato, K.; Murata, N.; Damirin, A.; Malchinkhuu, E. et al. Ki16425, a subtype-selective antagonist for EDG-family lysophosphatidic acid receptors. Mol. Pharmacol. 2003, 64, 994-1005.
    • (2003) Mol. Pharmacol. , vol.64 , pp. 994-1005
    • Ohta, H.1    Sato, K.2    Murata, N.3    Damirin, A.4    Malchinkhuu, E.5
  • 52
    • 22744456880 scopus 로고    scopus 로고
    • Synthesis, structure-activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptor ligands, activators of PPARγ, and inhibitors of autotaxin
    • Durgam, G. G.; Virag, T.; Walker, M.; Tsukahara, R.; Yasuda, S. et al. Synthesis, structure-activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptor ligands, activators of PPARγ, and inhibitors of autotaxin. J. Med. Chem. 2005, 48, 4919-4930.
    • (2005) J. Med. Chem. , vol.48 , pp. 4919-4930
    • Durgam, G.G.1    Virag, T.2    Walker, M.3    Tsukahara, R.4    Yasuda, S.5


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