Structure-activity relationships of fluorinated lysophosphatidic acid analogues

Journal of Medicinal Chemistry

Volumn 48, Issue 9, 2005, Pages 3319-3327

  Xu, Yong ^a   Aoki, Junken ^b   Shimizu, Kumiko ^b   Umezu Goto, Makiko ^b   Hama, Kotaro ^b   Takanezawa, Yasukazu ^b   Yu, Shuangxing ^c   Mills, Gordon B ^c   Arai, Hiroyuki ^b   Qian, Lian ^a   Prestwich, Glenn D ^a  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF TOKYO   (Japan)

^c UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 OLEOYLLIPOPHOSPHATIDIC ACID; ALPHA DIFLUOROMETHYLENE; ALPHA FLUOROMETHYLENEPHOSPHONATE DERIVATIVE; ALPHA MONOFLUOROMETHYLENE; CALCIUM; CARBENE; FLUORINE; G PROTEIN COUPLED RECEPTOR; HYDROXYL GROUP; LIGAND; LYSOPHOSPHATIDIC ACID; LYSOPHOSPHATIDIC ACID DERIVATIVE; LYSOPHOSPHATIDIC ACID RECEPTOR 1; LYSOPHOSPHATIDIC ACID RECEPTOR 2; LYSOPHOSPHATIDIC ACID RECEPTOR 3; LYSOPHOSPHATIDIC ACID RECEPTOR 3 STIMULATING AGENT; MITOGEN ACTIVATED PROTEIN KINASE; OXYGEN; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PHOSPHATASE; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; PROTEIN KINASE B; RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CALCIUM TRANSPORT; CANCER CELL CULTURE; CELL CULTURE; CELL LINE; CELL STRAIN HT29; CONCENTRATION RESPONSE; DRUG EFFICACY; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVATION; FLUORINATION; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; INSECT CELL; NONHUMAN; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANIMALS; CALCIUM; CELL LINE; CELL LINE, TUMOR; CHEMOTAXIS; FLUORINE; HUMANS; INSECTS; LIGANDS; LYSOPHOSPHOLIPIDS; MITOGEN-ACTIVATED PROTEIN KINASE KINASES; PHOSPHONIC ACIDS; PHOSPHORIC MONOESTER HYDROLASES; PROTEIN-SERINE-THREONINE KINASES; PROTO-ONCOGENE PROTEINS; PROTO-ONCOGENE PROTEINS C-AKT; RECEPTORS, LYSOPHOSPHATIDIC ACID; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 20944435206     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049186t     Document Type: Article

References (32)

1. Mills, G. B.; Moolenaar, W. H. The emerging role of lysophosphatidic acid in cancer. Nat. Rev. Cancer 2003, 3, 582-591.
2. Feng, L.; Mills, G. B.; Prestwich, G. D. Modulators of lysophosphatidic acid signaling. Expert Opin. Ther. Pat. 2003, 13, 1619-1634.
3. Noguchi, K.; Ishii, S.; Shimizu, T. Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family. J. Biol. Chem. 2003, 278, 25600-25606.
4. Contos, J. J.; Ishii, I.; Chun, J. Lysophosphatidic acid receptors. Mol. Pharmacol. 2000, 58, 1188-1196.
5. 3/Edg7 lysophosphatidic acid receptor gene: genomic structure, chromosomal localization, and expression pattern. Gene 2001, 267, 243-253.
6. 2. Mol. Cell. Biol. 2002, 22, 6921-6929.
7. McIntyre, T. M.; Pontsler, A. V.; Silva, A. R.; St Hilaire, A.; Xu, Y.; Hinshaw, J. C.; Zimmerman, G. A.; Hama, K.; Aoki, J.; Arai, H.; Prestwich, G. D. Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARγ agonist. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 131-136.
8. Hooks, S. B.; Santos, W. L.; Im, D. S.; Heise, C. E.; Macdonald, T. L.; Lynch, K. R. Lysophosphatidic acid-induced mitogenesis is regulated by lipid phosphate phosphatases and is Edg-receptor independent. J. Biol. Chem. 2001, 276, 4611-4621.
9. Aoki, J.; Taira, A.; Takanezawa, Y.; Kishi, Y.; Kama, K.; Kishimoto, T.; Mizuno, K.; Baku, K.; Taguchi, R.; Arai, H. Serum lysophosphatidic acid is produced through diverse phospholipase pathways. J. Biol. Chem. 2002, 277, 48737-48744.
10. Baker, D. L.; Desiderio, D. M.; Miller, D. D.; Tolley, B.; Tigyi, G. J. Direct quantitative analysis of lysophosphatidic acid molecular species by stable isotope dilution electrospray ionization liquid chromatography-mass spectrometry. Anal. Biochem. 2001, 292, 287-295.
11. Gerrard, J. M.; Robinson, P. Identification of the molecular species of lysophosphatidic acid produced when platelets are stimulated by thrombin. Biochim. Biophys. Acta 1989, 1001, 282-285.
12. Bandoh, K.; Aoki, J.; Hosono, H.; Kobayashi, S.; Kobayashi, T.; Murakami-Murofushi, K.; Tsujimoto, M.; Arai, H.; Inoue, K. Molecular cloning and characterization of a novel human G-protein-coupled receptor, EDG7, for lysophosphatidic acid. J. Biol. Chem. 1999, 274, 27776-27785.
13. Bandoh, K.; Aoki, J.; Taira, A.; Tsujimoto, M.; Arai, H.; Inoue, K. Lysophosphatidic acid (LPA) receptors of the EDG family are differentially activated by LPA species. Structure-activity relationship of cloned LPA receptors. FEBS Lett. 2000, 478, 159-165.
14. 2+ mobilization in human A431 cells: structure-activity analysis. Biochem. J. 1995, 307, 609-616.
15. Tokumura, A.; Iimori, M.; Nishioka, Y.; Kitahara, M.; Sakashita, M.; Tanaka, S. Lysophosphatidic acids induce proliferation of cultured vascular smooth muscle cells from rat aorta. Am. J. Physiol. 1994, 267, C204-C210.
16. Hayashi, K.; Takahashi, M.; Nishida, W.; Yoshida, K.; Ohkawa, Y.; Kitabatake, A.; Aoki, J.; Arai, H.; Sobue, K. Phenotypic modulation of vascular smooth muscle cells induced by unsaturated lysophosphatidic acids. Circ. Res. 2001, 89, 251-258.
17. Patani, G. A.; LaVoie, E. J. Bioisosterism: A rational approach in drug design. Chem. Rev. 1996, 96, 3147-3176.
18. Xu, Y.; Qian, L.; Prestwich, G. D. Synthesis of monofluorinated analogues of lysophosphatidic acid. J. Org. Chem. 2003, 68, 5320-5330.
19. 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.
20. 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.
21. Xu, Y.; Prestwich, G. D. Concise synthesis of acyl migration-blocked 1,1-difluorinated analogues of lysophosphatidic acid. J. Org. Chem. 2002, 67, 7158-7161.
22. 1. J. Biol. Chem. 2004, 279, 17634-17639.
23. 3 receptor. J. Biol. Chem. 2003, 278, 11962-11969.
24. Chevallier, J.; Sakai, N.; Robert, F.; Kobayashi, T.; Gruenberg, J.; Matile, S. Rapid access to synthetic lysobisphosphatidic acids using P(III) chemistry. Org. Lett. 2000, 2, 1859-1861.
25. 3 receptor-selective agonist activity. J. Med. Chem. 2003, 46, 5575-5578.
26. 3 receptor antagonist. Mol. Pharmacol. 2001, 60, 1173-1180.
27. Yokoyama, K.; Baker, D. L.; Virag, T.; Liliom, K.; Byun, H. S.; Tigyi, G.; Bittman, R. Stereochemical properties of lysophosphatidic acid receptor activation and metabolism. Biochim. Biophys. Acta 2002, 1582, 295-308.
28. Tamaruya, Y.; Suzuki, M.; Kamura, G.; Kanai, M.; Kama, K.; Shimizu, K.; Aoki, J.; Arai, H.; Shibasaki, M. Identifying specific conformations by using a carbohydrate scaffold: discovery of subtype-selective LPA-receptor agonists and an antagonist. Angew Chem., Int. Ed. 2004, 43, 2834-2837.
29. Lynch, K. R.; Macdonald, T. L. Structure-activity relationships of lysophosphatidic acid analogs. Biochim. Biophys. Acta 2002, 1582, 289-294.
30. Tigyi, G.; Parrill, A. L. Molecular mechanisms of lysophosphatidic acid action. Prog. Lipid Res. 2003, 42, 498-526.
31. 3 receptor-selective antagonist. Bioorg. Med. Chem. Lett. 2004, 14, 4069-4074.
32. Santos, W. L.; Heasley, B. H.; Jarosz, R.; Carter, K. M.; Lynch, K. R.; Macdonald, T. L. Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid. Bioorg. Med. Chem. Lett. 2004, 14, 3473-3476.