α- and β-Substituted phosphonate analogs of LPA as autotaxin inhibitors

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 5, 2008, Pages 2212-2225

  Cui, Peng ^a   McCalmont, William F ^a   Tomsig, Jose L ^b   Lynch, Kevin R ^b   Macdonald, Timothy L ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

ATX; Autotaxin; LPA; Phosphonates

Indexed keywords

ALPHA HYDROXY PHOSPHONIC ACID DERIVATIVE; ANTINEOPLASTIC AGENT; AUTOTAXIN; AUTOTAXIN INHIBITOR; BETA HYDROXY PHOSPHONIC ACID DERIVATIVE; ENZYME INHIBITOR; LYSOPHOSPHATIDIC ACID; LYSOPHOSPHOLIPASE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG INHIBITION; DRUG SYNTHESIS; DRUG TARGETING; STEREOCHEMISTRY;

LYSOPHOSPHOLIPIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHOSPHODIESTERASE INHIBITORS; PHOSPHONIC ACIDS; PHOSPHORIC DIESTER HYDROLASES; PYROPHOSPHATASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 40749104578     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.11.078     Document Type: Article

References (40)

1. Bollen M., Gijsbers R., Ceulemans H., Stalmans W., and Stefan C. Crit. Rev. Biochem. Mol. Biol. 35 (2000) 393-432
2. Goding J. J. Leukoc. Biol. 67 (2000) 285-311
3. Stracke M., Krutzsch H., Unsworth E., Arestad A., Cioce V., Schiffmann E., and Liotta L. J. Biol. Chem. 267 (1992) 2524-2529
4. Lee H., Murata J., Clair T., Polymeropoulos M., Torres R., Manrow R., Liotta L., and Stracke M. Biochem. Biophys. Res. Commun. 218 (1996) 714-719
5. Narita M., Goji J., Nakamura H., and Sano K. J. Biol. Chem. 269 (1994) 28235-28242
6. Kawagoe H., Soma O., Goji J., Nishimura N., Narita M., Iinzawa J., Nakamura H., and Sano K. Genomics 30 (1995) 380-384
7. Fuss B., Baba H., Phan T., Tuohy V., and Macklin W. J. Neurosci. 17 (1997) 9095-9103
8. Stefan C., Gijsbers R., Stalmans W., and Bollen M. Biochim. Biophys. Acta 1450 (1999) 45-52
9. Yang S., Lee J., Park C., Kim S., Hong S., Chung H., Min S., Han J., Lee H., and Lee H. Clin. Exp. Metastasis 19 (2002) 603-608
10. Kishi Y., Okudaira S., Tanaka M., Hama K., Dai S., Kitayama J., Yamori T., Aoki J., Fujimaki T., and Arai H. J. Biol. Chem. 281 (2006) 17492-17500
11. Nam S., Clair T., Kim Y., McMarlin A., Schiffmann E., Liotta L., and Stracke M. Cancer Res. 61 (2001) 6938-6944
12. Kehlen A., Englert N., Seifert A., Klonisch T., Dralle H., Langner J., and Hoang-Vu C. Int. J. Cancer 109 (2004) 833-838
13. Ferry G., Tellier E., Try A., Gres S., Naime I., Simon M., Rodriguez M., Boucher J., Tack I., Gesta S., Chomarat P., Dieu M., Raes M., Galizzi J., Valet P., Boutin J., and Saulnier-Blache J. J. Biol. Chem. 278 (2003) 18162-18169
14. Song J., Clair T., Noh J., Eun J., Ryu S., Lee S., Ahn Y., Kim S., Lee S., Park W., Yoo N., Lee J., and Nam S. Biochem. Biophys. Res. Commun. 337 (2005) 967-975
15. Umezu-Goto M., Kishi Y., Taira A., Hama K., Dohmae N., Takio K., Yamori T., Mills G., Inoue K., Aoki J., and Arai H. J. Cell Biol. 158 (2002) 227-233
16. Tokumura A., Majima E., Kariya Y., Tominaga K., Kogure K., Yasuda K., and Fukuzawa K. J. Biol. Chem. 277 (2002) 39436-39442
17. Siess W., Zangl K., Essler M., Bauer M., Brandl R., Corrinth C., Bittman R., Tigyi G., and Aepfelbacher M. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 6931-6936
18. Zhang C., Baker D., Yasuda S., Makarova N., Balazs L., Johnson L., Marathe G., McIntyre T., Xu Y., Prestwich G., Byun H., Bittman R., and Tigyi G. J. Exp. Med. 199 (2004) 763-774
19. Sugiura T., Nakane S., Kishimoto S., Waku K., Yoshioka Y., and Tokumura A. J. Lipid Res. 43 (2002) 2049-2055
20. Strum A., Sudermann T., Schulte K., Goebell H., and Dignass A. Gastroenterology 117 (1999) 368-377
21. Sturm A., and Dignass A. Biochim. Biophys. Acta 1582 (2002) 282-288
22. Deng W., Balazs L., Wang D., Van Middlesworth L., Tigyi G., and Johnson L. Gastroenterology 123 (2002) 206-216
23. Contos J., Ishii I., and Chun J. Mol. Pharm. 58 (2000) 1188-1196
24. Noguchi K., Ishii S., and Shimizu T. J. Biol. Chem. 278 (2003) 25600-25606
25. Lee C., Rivera R., Dubin A., and Chun J. J. Biol. Chem. 282 (2007) 4310-4317
26. Lee C., Rivera R., Gardell S., Dubin A., and Chun J. J. Biol. Chem. 281 (2003) 23589-23597
27. McIntyre T., Pontsler A., Silva A., St. Hilaire A., Xu Y., Hinshaw J., Zimmerman G., Hama K., Aoki J., Arai H., and Prestwich G. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 131-136
28. Durgam G., Virag T., Walker D., Tsukahara R., Yasuda S., Liliom K., van Meeteren A., Moolenaar H., Wilke N., Siess W., Tigyi G., and Miller D. J. Med. Chem. 48 (2005) 4919-4930
29. Durgam G., Tsukahara R., Makarova N., Walker D., Fujiwara Y., Pigg R., Baker L., Sardar M., Parrill L., Tigyi G., and Miller D. Bioorg. Med. Chem. Lett. 16 (2006) 633-640
30. Gududuru V., Zeng K., Tsukahara R., Makarova N., Fujiwara Y., Pigg K., Baker D., Tigyi G., and Miller D. Bioorg. Med. Chem. Lett. 16 (2006) 451-456
31. Baker L., Fujiwara Y., Pigg R., Tsukahara R., Kobayashi S., Murofushi H., Uchiyama A., Murakami-Murofushi K., Koh E., Bandle W., Byun H., Bittman R., Fan D., Murph M., Mills B., and Tigyi G. J. Biol. Chem. 281 (2006) 22786-22793
32. Uchiyama A., Mukai M., Fujiwara Y., Kobayashi S., Kawai N., Murofushi H., Inoue M., Enoki S., Tanaka Y., Niki T., Kobayashi T., Tigyi G., and Murakami-Murofushi K. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1771 (2007) 103-112
33. Cui P., Tomsig J., McCalmont W., Lee S., Becker C., Lynch K., and Macdonald T. Bioorg. Med. Chem. Lett. 17 (2007) 1634-1640
34. Nieschalk J., Batsanov A., O'Hagan D., and Howard J. Tetrahedron 52 (1992) 165-176
35. Adams P., and Harrison R. Biochem. J. 141 (1974) 729-732
36. Xu Y., Qian L., and Prestwich G. Org. Lett. 5 (2003) 2267-2270
37. Chakravarty P., Combs P., Roth A., and Greenlee W. Tetrahedron Lett. 28 (1987) 611-612
38. Karplus M. J. Am. Chem. Soc. 85 (1963) 2870-2871
39. Futagawa S., Inui T., and Shiba T. Bull. Chem. Soc. Jpn. 46 (1973) 3308-3310
40. Dufour M., Jouin P., Poncet J., Pantaloni A., and Castro B. J. Chem. Soc., Perkin Trans. 1 (1986) 1895-1899