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Volumn 2, Issue 5, 2007, Pages 679-690

α-substituted phosphonate analogues of lysophosphatidic acid (LPA) selectively inhibit production and action of LPA

Author keywords

Autotaxin; Lysophospholipase D; Phosphonates; PPAR ; Receptors

Indexed keywords

LYSOPHOSPHATIDIC ACID; LYSOPHOSPHOLIPID; PHOSPHONIC ACID DERIVATIVE;

EID: 35448975763     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200600280     Document Type: Article
Times cited : (89)

References (55)
  • 1
    • 0030907226 scopus 로고    scopus 로고
    • Lysophosphatidic acid: G-protein signalling and cellular responses: W. H. Moolenaar, O. Kranenburg, F. R. Postma, G. C. M. Zondag, Curr. Opin. Cell Biol. 1997, 9, 168-173.
    • "Lysophosphatidic acid: G-protein signalling and cellular responses": W. H. Moolenaar, O. Kranenburg, F. R. Postma, G. C. M. Zondag, Curr. Opin. Cell Biol. 1997, 9, 168-173.
  • 2
    • 0035300534 scopus 로고    scopus 로고
    • Lysophosphatidic acid promotes matrix metalloproteinase (MMP) activation and MMP-dependent invasion in ovarian cancer cells: D. A. Fishman, Y. Y. Liu, S. M. Ellerbroek, M. S. Stack, Cancer Res. 2001, 61, 3194-3199.
    • "Lysophosphatidic acid promotes matrix metalloproteinase (MMP) activation and MMP-dependent invasion in ovarian cancer cells": D. A. Fishman, Y. Y. Liu, S. M. Ellerbroek, M. S. Stack, Cancer Res. 2001, 61, 3194-3199.
  • 3
    • 0242339246 scopus 로고    scopus 로고
    • Lysophosphatidic acid is a bioactive mediator in ovarian cancer: X. Fang, M. Schummer, M. Mao, S. Yu, F. H. Tabassam, R. Swaby, Y. Hasegawa, J. L. Tanyi, R. LaPushin, A. Eder, R. Jaffe, J. Erickson, G. B. Mills, Biochim. Biophys. Acta Mol. Cell Biol. Lipids 2002, 1582, 257-264.
    • "Lysophosphatidic acid is a bioactive mediator in ovarian cancer": X. Fang, M. Schummer, M. Mao, S. Yu, F. H. Tabassam, R. Swaby, Y. Hasegawa, J. L. Tanyi, R. LaPushin, A. Eder, R. Jaffe, J. Erickson, G. B. Mills, Biochim. Biophys. Acta Mol. Cell Biol. Lipids 2002, 1582, 257-264.
  • 4
    • 0042471532 scopus 로고    scopus 로고
    • Unfolding the pathophysiological role of bioactive lysophospholipids: Y. Xu, Y.-J. Xiao, K. Zhu, L. M. Baudhuin, J. Lu, G. Hong, K.-S. Kim, K. L. Cristina, L. Song, F. S. Williams, P. Elson, M. Markman, J. Belinson, Curr. Drug Targets Immune Endocr. Metab. Disord. 2003, 3, 23-32.
    • "Unfolding the pathophysiological role of bioactive lysophospholipids": Y. Xu, Y.-J. Xiao, K. Zhu, L. M. Baudhuin, J. Lu, G. Hong, K.-S. Kim, K. L. Cristina, L. Song, F. S. Williams, P. Elson, M. Markman, J. Belinson, Curr. Drug Targets Immune Endocr. Metab. Disord. 2003, 3, 23-32.
  • 5
    • 0034668925 scopus 로고    scopus 로고
    • Lysophosphatidic acid prevents apoptosis in fibroblasts via G(i)-protein-mediated activation of mitogen-activated protein kinase: X. Fang, S. Yu, R. LaPushin, Y. Lu, T. Furui, L. Z. Penn, D. Stokoe, J. R. Erickson, R. C. Bast, Jr., G. B. Mills, Biochem. J. 2000, 352, 135-143.
    • "Lysophosphatidic acid prevents apoptosis in fibroblasts via G(i)-protein-mediated activation of mitogen-activated protein kinase": X. Fang, S. Yu, R. LaPushin, Y. Lu, T. Furui, L. Z. Penn, D. Stokoe, J. R. Erickson, R. C. Bast, Jr., G. B. Mills, Biochem. J. 2000, 352, 135-143.
  • 6
    • 17144460494 scopus 로고    scopus 로고
    • Critical role of lysophospholipids in the pathophysiology, diagnosis, and management of ovarian cancer: G. B. Mills, A. Eder, X. Fang, Y. Hasegawa, M. Mao, Y. Lu, J. Tanyi, F. H. Tabassam, J. Wiener, R. Lapushin, S. Yu, J. A. Parrott, T. Compton, W. Tribley, D. Fishman, M. S. Stack, D. Gaudette, R. Jaffe, T. Furui, J. Aoki, J. R. Erickson, Cancer Treat. Res. 2002, 107, 259-283.
    • "Critical role of lysophospholipids in the pathophysiology, diagnosis, and management of ovarian cancer": G. B. Mills, A. Eder, X. Fang, Y. Hasegawa, M. Mao, Y. Lu, J. Tanyi, F. H. Tabassam, J. Wiener, R. Lapushin, S. Yu, J. A. Parrott, T. Compton, W. Tribley, D. Fishman, M. S. Stack, D. Gaudette, R. Jaffe, T. Furui, J. Aoki, J. R. Erickson, Cancer Treat. Res. 2002, 107, 259-283.
  • 7
    • 0042887042 scopus 로고    scopus 로고
    • The emerging role of lysophosphatidic acid in cancer: G. B. Mills, W. H. Moolenaar, Nat. Rev. Cancer 2003, 3, 582-591.
    • "The emerging role of lysophosphatidic acid in cancer": G. B. Mills, W. H. Moolenaar, Nat. Rev. Cancer 2003, 3, 582-591.
  • 8
    • 0037077199 scopus 로고    scopus 로고
    • Multiple mechanisms linked to platelet activation result in lysophosphatidic acid and sphingosine 1-phosphate generation in blood: T. Sano, D. Baker, T. Virag, A. Wada, Y. Yatomi, T. Kobayashi, Y. Igarashi, G. Tigyi, J. Biol. Chem. 2002, 277, 21197-21206.
    • "Multiple mechanisms linked to platelet activation result in lysophosphatidic acid and sphingosine 1-phosphate generation in blood": T. Sano, D. Baker, T. Virag, A. Wada, Y. Yatomi, T. Kobayashi, Y. Igarashi, G. Tigyi, J. Biol. Chem. 2002, 277, 21197-21206.
  • 9
    • 20444386550 scopus 로고    scopus 로고
    • Inhibition of autotaxin by lysophosphatidic acid and sphingosine 1-phosphate: L. A. van Meeteren, P. Ruurs, E. Christodoulou, J. W. Goding, H. Takakusa, K. Kikuchi, A. Perrakis, T. Nagano, W. H. Moolenaar, J. Biol. Chem. 2005, 280, 21155-21161.
    • "Inhibition of autotaxin by lysophosphatidic acid and sphingosine 1-phosphate": L. A. van Meeteren, P. Ruurs, E. Christodoulou, J. W. Goding, H. Takakusa, K. Kikuchi, A. Perrakis, T. Nagano, W. H. Moolenaar, J. Biol. Chem. 2005, 280, 21155-21161.
  • 10
    • 2342437623 scopus 로고    scopus 로고
    • Lysophosphatidic acid and autotaxin stimulate cell motility of neoplastic and non-neoplastic cells through LPA1: K. Hama, J. Aoki, M. Fukaya, Y. Kishi, T. Sakai, R. Suzuki, H. Ohta, T. Yamori, M. Watanabe, J. Chun, H. Arai, J. Biol. Chem. 2004, 279, 17634-17639.
    • "Lysophosphatidic acid and autotaxin stimulate cell motility of neoplastic and non-neoplastic cells through LPA1": K. Hama, J. Aoki, M. Fukaya, Y. Kishi, T. Sakai, R. Suzuki, H. Ohta, T. Yamori, M. Watanabe, J. Chun, H. Arai, J. Biol. Chem. 2004, 279, 17634-17639.
  • 11
    • 0036244390 scopus 로고    scopus 로고
    • Identification of genes associated with metastasis of mammary carcinoma in metastatic versus non-metastatic cell lines: N. Euer, M. Schwirzke, V. Evtimova, H. Burscher, M. Jarsch, D. Tarin, U. H. Weidle, Anticancer Res. 2002, 22, 733-740.
    • "Identification of genes associated with metastasis of mammary carcinoma in metastatic versus non-metastatic cell lines": N. Euer, M. Schwirzke, V. Evtimova, H. Burscher, M. Jarsch, D. Tarin, U. H. Weidle, Anticancer Res. 2002, 22, 733-740.
  • 12
    • 0038487319 scopus 로고    scopus 로고
    • Lysophosphatidic acid signaling: how a small lipid does big things: C. Luquain, V. A. Sciorra, A. J. Morris, Trends Biochem. Sci. 2003, 28, 377-383.
    • "Lysophosphatidic acid signaling: how a small lipid does big things": C. Luquain, V. A. Sciorra, A. J. Morris, Trends Biochem. Sci. 2003, 28, 377-383.
  • 13
    • 5344266925 scopus 로고    scopus 로고
    • Lysophosphatidic acid production and action: validated targets in cancer?: M. Umezu-Goto, J. Tanyi, J. Lahad, S. Liu, S. Yu, R. Lapushin, Y. Hasegawa, Y. Lu, R. Trost, T. Bevers, E. Jonasch, K. Aldape, J. Liu, R. D. James, C. G. Ferguson, Y. Xu, G. D. Prestwich, G. B. Mills, J. Cell. Biochem. 2004, 92, 1115-1140.
    • "Lysophosphatidic acid production and action: validated targets in cancer?": M. Umezu-Goto, J. Tanyi, J. Lahad, S. Liu, S. Yu, R. Lapushin, Y. Hasegawa, Y. Lu, R. Trost, T. Bevers, E. Jonasch, K. Aldape, J. Liu, R. D. James, C. G. Ferguson, Y. Xu, G. D. Prestwich, G. B. Mills, J. Cell. Biochem. 2004, 92, 1115-1140.
  • 14
    • 0038152846 scopus 로고    scopus 로고
    • Identification of p2y9/GPR23 as a novel G-protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family: K. Noguchi, S. Ishii, T. Shimizu, J. Biol. Chem. 2003, 278, 25600-25606.
    • "Identification of p2y9/GPR23 as a novel G-protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family": K. Noguchi, S. Ishii, T. Shimizu, J. Biol. Chem. 2003, 278, 25600-25606.
  • 15
    • 33745957774 scopus 로고    scopus 로고
    • Lysophosphatidic acid binds to and activates GPR92, a G-protein-coupled receptor highly expressed in gastrointestinal lymphocytes: K. Kotarsky, A. Boketoft, J. Bristulf, N. E. Nilsson, A. Norberg, S. Hansson, R. Sillard, C. Owman, F. L. M. Leeb-Lundberg, B. Olde, J. Pharmacol. Exp. Ther. 2006, 318, 619-628.
    • "Lysophosphatidic acid binds to and activates GPR92, a G-protein-coupled receptor highly expressed in gastrointestinal lymphocytes": K. Kotarsky, A. Boketoft, J. Bristulf, N. E. Nilsson, A. Norberg, S. Hansson, R. Sillard, C. Owman, F. L. M. Leeb-Lundberg, B. Olde, J. Pharmacol. Exp. Ther. 2006, 318, 619-628.
  • 16
    • 33747685338 scopus 로고    scopus 로고
    • GPR92 as a new G12/13 and Gq coupled lysophosphatidic acid receptor that increases cAMP: LPA5: C.-W. Lee, R. Rivera, S. Gardell, A. Dubin, J. Chun, J. Biol. Chem. 2006, 281, 23589-23597.
    • "GPR92 as a new G12/13 and Gq coupled lysophosphatidic acid receptor that increases cAMP: LPA5": C.-W. Lee, R. Rivera, S. Gardell, A. Dubin, J. Chun, J. Biol. Chem. 2006, 281, 23589-23597.
  • 17
    • 0037134949 scopus 로고    scopus 로고
    • Plasma lysophosphatidic acid concentration and ovarian cancer: D. L. Baker, P. Morrison, B. Miller, C. A. Riely, B. Tolley, A. M. Westermann, J. M. G. Bonfrer, E. Bais, W. H. Moolenaar, G. Tigyi, JAMA J. Am. Med. Assoc. 2002, 287, 3081-3082.
    • "Plasma lysophosphatidic acid concentration and ovarian cancer": D. L. Baker, P. Morrison, B. Miller, C. A. Riely, B. Tolley, A. M. Westermann, J. M. G. Bonfrer, E. Bais, W. H. Moolenaar, G. Tigyi, JAMA J. Am. Med. Assoc. 2002, 287, 3081-3082.
  • 18
    • 0037422595 scopus 로고    scopus 로고
    • Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARγ agonist: T. M. McIntyre, A. V. Pontsler, A. R. Silva, A. St Hilaire, Y. Xu, J. C. Hinshaw, G. A. Zimmerman, K. Hama, J. Aoki, H. Arai, G. D. Prestwich, Proc. Natl. Acad. Sci. USA 2003, 100, 131-136.
    • "Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARγ agonist": T. M. McIntyre, A. V. Pontsler, A. R. Silva, A. St Hilaire, Y. Xu, J. C. Hinshaw, G. A. Zimmerman, K. Hama, J. Aoki, H. Arai, G. D. Prestwich, Proc. Natl. Acad. Sci. USA 2003, 100, 131-136.
  • 19
    • 12144288490 scopus 로고    scopus 로고
    • Lysophosphatidic acid induces neointima formation through PPARγ activation: C. Zhang, D. L. Baker, S. Yasuda, N. Makarova, L. Balazs, L. R. Johnson, G. K. Marathe, T. M. McIntyre, Y. Xu, G. D. Prestwich, H. S. Byun, R. Bittman, G. Tigyi, J. Exp. Med. 2004, 199, 763-774.
    • "Lysophosphatidic acid induces neointima formation through PPARγ activation": C. Zhang, D. L. Baker, S. Yasuda, N. Makarova, L. Balazs, L. R. Johnson, G. K. Marathe, T. M. McIntyre, Y. Xu, G. D. Prestwich, H. S. Byun, R. Bittman, G. Tigyi, J. Exp. Med. 2004, 199, 763-774.
  • 20
    • 2942532893 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid: W. L. Santos, B. H. Heasley, R. Jarosz, K. M. Carter, K. R. Lynch, T. L. Macdonald, Bioorg. Med. Chem. Lett. 2004, 14, 3473-3476.
    • "Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid": W. L. Santos, B. H. Heasley, R. Jarosz, K. M. Carter, K. R. Lynch, T. L. Macdonald, Bioorg. Med. Chem. Lett. 2004, 14, 3473-3476.
  • 21
    • 0035206909 scopus 로고    scopus 로고
    • Activity of 2-substituted lysophosphatidic acid (LPA) analogues at LPA receptors: discovery of a LPA1/LPA3 receptor antagonist: C. E. Heise, W. L. Santos, A. M. Schreihofer, B. H. Heasley, Y. V. Mukhin, T. L. Macdonald, K. R. Lynch, Mol. Pharmacol. 2001, 60, 1173-1180.
    • "Activity of 2-substituted lysophosphatidic acid (LPA) analogues at LPA receptors: discovery of a LPA1/LPA3 receptor antagonist": C. E. Heise, W. L. Santos, A. M. Schreihofer, B. H. Heasley, Y. V. Mukhin, T. L. Macdonald, K. R. Lynch, Mol. Pharmacol. 2001, 60, 1173-1180.
  • 22
    • 0141570981 scopus 로고    scopus 로고
    • Ki16425, a subtype-selective antagonist for EDG-family lysophosphatidic acid receptors: H. Ohta, K. Sato, N. Murata, A. Damirin, E. Malchinkhuu, J. Kon, T. Kimura, M. Tobo, Y. Yamazaki, T. Watanabe, M. Yagi, M. Sato, R. Suzuki, H. Murooka, T. Sakai, T. Nishitoba, D. S. Im, H. Nochi, K. Tamoto, H. Tomura, F. Okajima, Mol. Pharmacol. 2003, 64, 994-1005.
    • "Ki16425, a subtype-selective antagonist for EDG-family lysophosphatidic acid receptors": H. Ohta, K. Sato, N. Murata, A. Damirin, E. Malchinkhuu, J. Kon, T. Kimura, M. Tobo, Y. Yamazaki, T. Watanabe, M. Yagi, M. Sato, R. Suzuki, H. Murooka, T. Sakai, T. Nishitoba, D. S. Im, H. Nochi, K. Tamoto, H. Tomura, F. Okajima, Mol. Pharmacol. 2003, 64, 994-1005.
  • 23
    • 2342626086 scopus 로고    scopus 로고
    • Initial structure-activity relationships of lysophosphatidic acid receptor antagonists: discovery of a high-affinity LPA1/LPA3 receptor antagonist: R. H. Heasley, R. Jarosz, K. R. Lynch, T. L. Macdonald, Bioorg. Med. Chem. Lett. 2004, 14, 2735-2740.
    • "Initial structure-activity relationships of lysophosphatidic acid receptor antagonists: discovery of a high-affinity LPA1/LPA3 receptor antagonist": R. H. Heasley, R. Jarosz, K. R. Lynch, T. L. Macdonald, Bioorg. Med. Chem. Lett. 2004, 14, 2735-2740.
  • 24
    • 0038069067 scopus 로고    scopus 로고
    • Fatty alcohol phosphates are subtype-selective agonists and antagonists of lysophosphatidic acid receptors: T. Virag, D. B. Elrod, K. Liliom, V. M. Sardar, A. L. Parrill, K. Yokoyama, G. Durgam, W. Deng, D. D. Miller, G. Tigyi, Mol. Pharmacol. 2003, 63, 1032-1042.
    • "Fatty alcohol phosphates are subtype-selective agonists and antagonists of lysophosphatidic acid receptors": T. Virag, D. B. Elrod, K. Liliom, V. M. Sardar, A. L. Parrill, K. Yokoyama, G. Durgam, W. Deng, D. D. Miller, G. Tigyi, Mol. Pharmacol. 2003, 63, 1032-1042.
  • 25
    • 0346366461 scopus 로고    scopus 로고
    • 3 receptor-selective agonist activity: L. Qian, Y. Xu, Y. Hasegawa, J. Aoki, G. B. Mills, G. D. Prestwich, J. Med. Chem. 2003, 46, 5575-5578.
    • 3 receptor-selective agonist activity": L. Qian, Y. Xu, Y. Hasegawa, J. Aoki, G. B. Mills, G. D. Prestwich, J. Med. Chem. 2003, 46, 5575-5578.
  • 26
    • 0141629758 scopus 로고    scopus 로고
    • Synthesis of α-fluorinated phosphonates from α-fluorovinylphosphonates: a new route to analogues of lysophosphatidic acid: Y. Xu, L. Qian, G. D. Prestwich, Org. Lett. 2003, 5, 2267-2270.
    • "Synthesis of α-fluorinated phosphonates from α-fluorovinylphosphonates: a new route to analogues of lysophosphatidic acid": Y. Xu, L. Qian, G. D. Prestwich, Org. Lett. 2003, 5, 2267-2270.
  • 27
    • 20944435206 scopus 로고    scopus 로고
    • Structure-activity relationships of fluorinated lysophosphatidic acid analogues: Y. Xu, J. Aoki, K. Shimizu, M. Umezu-Goto, K. Hama, Y. Takanezawa, S. Yu, G. B. Mills, H. Arai, L. Qian, G. D. Prestwich, J. Med. Chem. 2005, 48, 3319-3327.
    • "Structure-activity relationships of fluorinated lysophosphatidic acid analogues": Y. Xu, J. Aoki, K. Shimizu, M. Umezu-Goto, K. Hama, Y. Takanezawa, S. Yu, G. B. Mills, H. Arai, L. Qian, G. D. Prestwich, J. Med. Chem. 2005, 48, 3319-3327.
  • 28
    • 54849439903 scopus 로고    scopus 로고
    • Identifying specific conformations by using a carbohydrate scaffold: discovery of subtype-selective LPA-receptor agonists and an antagonist: Y. Tamaruya, M. Suzuki, G. Kamura, M. Kanai, K. Hama, K. Shimizu, J. Aoki, H. Arai, M. Shibasaki, Angew. Chem. 2004, 116, 2894-2897;
    • "Identifying specific conformations by using a carbohydrate scaffold: discovery of subtype-selective LPA-receptor agonists and an antagonist": Y. Tamaruya, M. Suzuki, G. Kamura, M. Kanai, K. Hama, K. Shimizu, J. Aoki, H. Arai, M. Shibasaki, Angew. Chem. 2004, 116, 2894-2897;
  • 29
    • 3242712299 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 2834-2837.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2834-2837
  • 30
    • 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: G. G. Durgam, T. Virag, M. D. Walker, R. Tsukahara, S. Yasuda, K. Liliom, L. A. van Meeteren, W. H. Moolenaar, N. Wilke, W. Siess, G. Tigyi, D. D. Miller, J. Med. Chem. 2005, 48, 4919-4930.
    • "Synthesis, structure-activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptor ligands, activators of PPARγ and inhibitors of autotaxin": G. G. Durgam, T. Virag, M. D. Walker, R. Tsukahara, S. Yasuda, K. Liliom, L. A. van Meeteren, W. H. Moolenaar, N. Wilke, W. Siess, G. Tigyi, D. D. Miller, J. Med. Chem. 2005, 48, 4919-4930.
  • 31
    • 28844456029 scopus 로고    scopus 로고
    • New metabolically stabilized analogues of lysophosphatidic acid: agonists, antagonists, and enzyme inhibitors: G. D. Prestwich, Y. Xu, L. Qian, J. Gajewiak, G. Jiang, Biochem. Soc. Trans. 2005, 33, 1357-1361.
    • "New metabolically stabilized analogues of lysophosphatidic acid: agonists, antagonists, and enzyme inhibitors": G. D. Prestwich, Y. Xu, L. Qian, J. Gajewiak, G. Jiang, Biochem. Soc. Trans. 2005, 33, 1357-1361.
  • 32
    • 0141996371 scopus 로고    scopus 로고
    • Molecular mechanisms of lysophosphatidic acid action: G. Tigyi, A. L. Parrill, Prog. Lipid Res. 2003, 42, 498-526.
    • "Molecular mechanisms of lysophosphatidic acid action": G. Tigyi, A. L. Parrill, Prog. Lipid Res. 2003, 42, 498-526.
  • 33
    • 0037809241 scopus 로고    scopus 로고
    • Identification of a phosphothionate analogue of lysophosphatidic acid (LPA) as a selective agonist of the LPA3 receptor: Y. Hasegawa, J. R. Erickson, G. J. Goddard, S. Yu, S. Liu, K. W. Cheng, A. Eder, K. Bandoh, J. Aoki, R. Jarosz, A. D. Schrier, K. R. Lynch, G. B. Mills, X. Fang, J. Biol. Chem. 2003, 278, 11962-11969.
    • "Identification of a phosphothionate analogue of lysophosphatidic acid (LPA) as a selective agonist of the LPA3 receptor": Y. Hasegawa, J. R. Erickson, G. J. Goddard, S. Yu, S. Liu, K. W. Cheng, A. Eder, K. Bandoh, J. Aoki, R. Jarosz, A. D. Schrier, K. R. Lynch, G. B. Mills, X. Fang, J. Biol. Chem. 2003, 278, 11962-11969.
  • 34
    • 0019473828 scopus 로고    scopus 로고
    • Phosphonates as analogues of biological phosphates: G. M. Blackburn, Chem. Ind. 1981, 5, 134-138.
    • "Phosphonates as analogues of biological phosphates": G. M. Blackburn, Chem. Ind. 1981, 5, 134-138.
  • 35
    • 1542690351 scopus 로고    scopus 로고
    • Phosphonates as analogues of natural phosphates: R. Engel, Chem. Rev. 1977, 77, 349-367.
    • "Phosphonates as analogues of natural phosphates": R. Engel, Chem. Rev. 1977, 77, 349-367.
  • 36
    • 0032477315 scopus 로고    scopus 로고
    • Phosphonate lipid tubules. 1: B. N. Thomas, R. C. Corcoran, C. L. Cotant, C. M. Lindemann, J. E. Kirsch, P. J. Persichini, J. Am. Chem. Soc. 1998, 120, 12178-12186.
    • "Phosphonate lipid tubules. 1": B. N. Thomas, R. C. Corcoran, C. L. Cotant, C. M. Lindemann, J. E. Kirsch, P. J. Persichini, J. Am. Chem. Soc. 1998, 120, 12178-12186.
  • 37
    • 0142184536 scopus 로고    scopus 로고
    • Synthesis and applications of C2-symmetric guanidine bases: M. T. Allingham, A. Howard-Jones, P. J. Murphy, D. A. Thomasa, P. W. R. Caulkett, Tetrahedron Lett. 2003, 44, 8677-8680.
    • "Synthesis and applications of C2-symmetric guanidine bases": M. T. Allingham, A. Howard-Jones, P. J. Murphy, D. A. Thomasa, P. W. R. Caulkett, Tetrahedron Lett. 2003, 44, 8677-8680.
  • 38
    • 0025612824 scopus 로고    scopus 로고
    • A convenient synthesis of (2R)-1-amino-1-deoxy-1- phosphinylglycerols: T. Hanaya, A. Miyoshi, A. Noguchi, H. Kawamoto, M. A. Armour, A. M. Hogg, H. Yamamoto, Bull. Chem. Soc. Jpn. 1990, 63, 3590-3594.
    • "A convenient synthesis of (2R)-1-amino-1-deoxy-1- phosphinylglycerols": T. Hanaya, A. Miyoshi, A. Noguchi, H. Kawamoto, M. A. Armour, A. M. Hogg, H. Yamamoto, Bull. Chem. Soc. Jpn. 1990, 63, 3590-3594.
  • 39
    • 84988121926 scopus 로고    scopus 로고
    • Addition reactions of esters of phosphorusACHTUNGTRENNUNG(III) acids with unsaturated systems: A. N. Pudovik, I. V. Konovalova, Synthesis 1979, 81-96.
    • "Addition reactions of esters of phosphorusACHTUNGTRENNUNG(III) acids with unsaturated systems": A. N. Pudovik, I. V. Konovalova, Synthesis 1979, 81-96.
  • 40
    • 84963451884 scopus 로고    scopus 로고
    • Preparation of diethyl 1-bromoalkylphosphonates: T. Gajda, Phosphorus Sulfur Silicon Relat. Elem. 1990, 53, 327-331.
    • "Preparation of diethyl 1-bromoalkylphosphonates": T. Gajda, Phosphorus Sulfur Silicon Relat. Elem. 1990, 53, 327-331.
  • 41
    • 0002243953 scopus 로고    scopus 로고
    • A convenient synthesis of diethyl 1-chloroalkylphosphonates: T. Gajda, Synthesis 1990, 717-718.
    • "A convenient synthesis of diethyl 1-chloroalkylphosphonates": T. Gajda, Synthesis 1990, 717-718.
  • 42
    • 0005680259 scopus 로고    scopus 로고
    • Synthesis of primary α-chlorophosphines by a chemoselective reduction of α-chlorophosphonates: J. L. Cabioch, B. Pellerin, J. M. Denis, Phosphorus Sulfur Silicon Relat. Elem. 1989, 44, 27-32.
    • "Synthesis of primary α-chlorophosphines by a chemoselective reduction of α-chlorophosphonates": J. L. Cabioch, B. Pellerin, J. M. Denis, Phosphorus Sulfur Silicon Relat. Elem. 1989, 44, 27-32.
  • 43
    • 54849405711 scopus 로고    scopus 로고
    • Reaction of dimethyl 1-hydroxyalkylphosphonates with some chlorides: M. Yamashita, T. Morizane, K. Fujita, K. Nakatani, S. Inokawa, Bull. Chem. Soc. Jpn. 1987, 60, 812-814.
    • "Reaction of dimethyl 1-hydroxyalkylphosphonates with some chlorides": M. Yamashita, T. Morizane, K. Fujita, K. Nakatani, S. Inokawa, Bull. Chem. Soc. Jpn. 1987, 60, 812-814.
  • 44
    • 54849404452 scopus 로고    scopus 로고
    • Synthesis of an optically active C1-symmetric Al(salalen) complex and its application to the catalytic hydrophosphonylation of aldehydes: B. Saito, T. Katsuki, Angew. Chem. 2005, 117, 4676-4678;
    • "Synthesis of an optically active C1-symmetric Al(salalen) complex and its application to the catalytic hydrophosphonylation of aldehydes": B. Saito, T. Katsuki, Angew. Chem. 2005, 117, 4676-4678;
  • 45
    • 22744433733 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4600-4602.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 4600-4602
  • 46
    • 0034812654 scopus 로고    scopus 로고
    • Short-chain phosphatidates are subtype-selective antagonists of lysophosphatidic acid receptors: D. J. Fischer, N. Nusser, T. Virag, K. Yokoyama, D. A. Wang, D. L. Baker, D. Bautista, A. L. Parrill, G. Tigyi, Mol. Pharmacol. 2001, 60, 776-784.
    • "Short-chain phosphatidates are subtype-selective antagonists of lysophosphatidic acid receptors": D. J. Fischer, N. Nusser, T. Virag, K. Yokoyama, D. A. Wang, D. L. Baker, D. Bautista, A. L. Parrill, G. Tigyi, Mol. Pharmacol. 2001, 60, 776-784.
  • 47
    • 33645640436 scopus 로고    scopus 로고
    • Different residues mediate recognition of 1-O- oleyllysohosphatidic acid and rosiglitazone in the ligand binding domain of peroxisome proliferator-activated receptor gamma: T. Tsukahara, R. Tsukahara, S. Yasuda, N. Makarova, W. J. Valentine, P. Allison, H. Yuan, D. L. Baker, Z. Li, R. Bittman, A. L. Parrill, G. Tigyi, J. Biol. Chem. 2005, 281, 3398-3407.
    • "Different residues mediate recognition of 1-O- oleyllysohosphatidic acid and rosiglitazone in the ligand binding domain of peroxisome proliferator-activated receptor gamma": T. Tsukahara, R. Tsukahara, S. Yasuda, N. Makarova, W. J. Valentine, P. Allison, H. Yuan, D. L. Baker, Z. Li, R. Bittman, A. L. Parrill, G. Tigyi, J. Biol. Chem. 2005, 281, 3398-3407.
  • 48
    • 0346965738 scopus 로고    scopus 로고
    • Synthesis of difluoromethyl substituted lysophosphatidic acid analogues: Y. Xu, L. Qian, A. V. Pontsler, T. M. McIntyre, G. D. Prestwich, Tetrahedron 2004, 60, 43-49.
    • "Synthesis of difluoromethyl substituted lysophosphatidic acid analogues": Y. Xu, L. Qian, A. V. Pontsler, T. M. McIntyre, G. D. Prestwich, Tetrahedron 2004, 60, 43-49.
  • 49
    • 0037073806 scopus 로고    scopus 로고
    • Serum lysophosphatidic acid is produced through diverse phospholipase pathways: J. Aoki, A. Taira, Y. Takanezawa, Y. Kishi, K. Hama, T. Kishimoto, K. Mizuno, K. Saku, R. Taguchi, H. Arai, J. Biol. Chem. 2002, 277, 48737-48744.
    • "Serum lysophosphatidic acid is produced through diverse phospholipase pathways": J. Aoki, A. Taira, Y. Takanezawa, Y. Kishi, K. Hama, T. Kishimoto, K. Mizuno, K. Saku, R. Taguchi, H. Arai, J. Biol. Chem. 2002, 277, 48737-48744.
  • 50
    • 0031466275 scopus 로고    scopus 로고
    • Lysophosphatidic acid induces threonine phosphorylation of Tiam1 in Swiss 3T3 fibroblasts via activation of protein kinase C: I. N. Fleming, C. M. Elliott, J. G. Collard, J. H. Exton, J. Biol. Chem. 1997, 272, 33105-33110.
    • "Lysophosphatidic acid induces threonine phosphorylation of Tiam1 in Swiss 3T3 fibroblasts via activation of protein kinase C": I. N. Fleming, C. M. Elliott, J. G. Collard, J. H. Exton, J. Biol. Chem. 1997, 272, 33105-33110.
  • 51
    • 0036828287 scopus 로고    scopus 로고
    • Lysophosphatidic acid-induced squamous cell carcinoma cell proliferation and motility involves epidermal growth factor receptor signal transactivation: A. Gschwind, N. Prenzel, A. Ullrich, Cancer Res. 2002, 62, 6329-6336.
    • "Lysophosphatidic acid-induced squamous cell carcinoma cell proliferation and motility involves epidermal growth factor receptor signal transactivation": A. Gschwind, N. Prenzel, A. Ullrich, Cancer Res. 2002, 62, 6329-6336.
  • 52
    • 33744759598 scopus 로고    scopus 로고
    • Fluorogenic phospholipid substrate to detect lysophospholipase D/autotaxin activity: C. G. Ferguson, C. S. Bigman, R. D. Richardson, L. A. van Meeteren, W. H. Moolenaar, G. D. Prestwich, Org. Lett. 2006, 8, 2023-2026.
    • "Fluorogenic phospholipid substrate to detect lysophospholipase D/autotaxin activity": C. G. Ferguson, C. S. Bigman, R. D. Richardson, L. A. van Meeteren, W. H. Moolenaar, G. D. Prestwich, Org. Lett. 2006, 8, 2023-2026.
  • 53
    • 33746908110 scopus 로고    scopus 로고
    • Functional lipidomics: Lysophosphatidic acid as a target for molecular diagnosis and therapy of ovarian cancer: J. Tanyi, D. Croetzer, J. Wolf, S. Yu, Y. Hasegawa, J. Lahad, K. W. Cheng, M. Umezu-Goto, G. D. Prestwich, A. J. Morris, R. A. Newman, E. A. Felix, R. Lapis, G. B. Mills in Functional Lipidomics (Eds.: L. Feng, G. D. Prestwich), CRC Press/Taylor & Francis, New York, 2006, pp. 101-123.
    • "Functional lipidomics: Lysophosphatidic acid as a target for molecular diagnosis and therapy of ovarian cancer": J. Tanyi, D. Croetzer, J. Wolf, S. Yu, Y. Hasegawa, J. Lahad, K. W. Cheng, M. Umezu-Goto, G. D. Prestwich, A. J. Morris, R. A. Newman, E. A. Felix, R. Lapis, G. B. Mills in Functional Lipidomics (Eds.: L. Feng, G. D. Prestwich), CRC Press/Taylor & Francis, New York, 2006, pp. 101-123.
  • 54
    • 33747354637 scopus 로고    scopus 로고
    • Carba analogues of cyclic phosphatidic acid are selective inhibitors of autotaxin and cancer cell invasion and metastasis: D. Baker, Y. Fujiwara, K. R. Pigg, R. Tsukahara, S. Kobayashi, H. Murofushi, A. Uchiyama, K. Murakami-Murofushi, E. Koh, R. W. Bandle, H. S. Byun, R. Bittman, D. Fan, M. Murph, G. B. Mills, G. Tigyi, J. Biol. Chem. 2006, 281, 22786-22793.
    • "Carba analogues of cyclic phosphatidic acid are selective inhibitors of autotaxin and cancer cell invasion and metastasis": D. Baker, Y. Fujiwara, K. R. Pigg, R. Tsukahara, S. Kobayashi, H. Murofushi, A. Uchiyama, K. Murakami-Murofushi, E. Koh, R. W. Bandle, H. S. Byun, R. Bittman, D. Fan, M. Murph, G. B. Mills, G. Tigyi, J. Biol. Chem. 2006, 281, 22786-22793.
  • 55
    • 18444390571 scopus 로고    scopus 로고
    • Molecular basis for lysophosphatidic acid receptor antagonist selectivity: V. M. Sardar, D. L. Bautista, D. J. Fischer, K. Yokoyama, N. Nusser, T. Virag, D. Wang, D. L. Baker, G. Tigyi, A. L. Parrill, Biochim. Biophys. Acta Mol. Cell Biol. Lipids 2002, 1582, 309-317.
    • "Molecular basis for lysophosphatidic acid receptor antagonist selectivity": V. M. Sardar, D. L. Bautista, D. J. Fischer, K. Yokoyama, N. Nusser, T. Virag, D. Wang, D. L. Baker, G. Tigyi, A. L. Parrill, Biochim. Biophys. Acta Mol. Cell Biol. Lipids 2002, 1582, 309-317.


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