Selective antiproliferative activity of hydroxynaphthyl-β-D-xylosides

Journal of Medicinal Chemistry

Volumn 49, Issue 6, 2006, Pages 1932-1938

  Jacobsson, Mårten ^a   Ellervik, Ulf ^a   Belting, Mattias ^a   Mani, Katrin ^b  

^a LUND UNIVERSITY   (Sweden)

^b LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2 (6 HYDROXYNAPHTHYL) BETA DEXTRO XYLOPYRANOSIDE; 2 NAPHTHYL BETA DEXTRO XYLOPYRANOSIDE; AGLYCONE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NICK END LABELING; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARBOHYDRATE SEQUENCE; CELL LINE; CELL LINE, TRANSFORMED; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; GLYCOSIDES; HUMANS; MICE; MOLECULAR SEQUENCE DATA; NAPHTHOLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33645453618     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0512488     Document Type: Article

References (20)

1. Zhang, L.; David, G.; Esko, J. D. Repetitive Ser-Gly sequences enhance heparan sulfate assembly in proteoglycans. J. Biol. Chem. 1995, 270, 27127-27135.
2. Miao, H. Q.; Fritz, T. A.; Esko, J. D.; Zimmermann, J.; Yayon, A.; Vlodavsky, I. Heparan sulfate primed on β-D-xylosides restores binding of basic fibroblast growth factor. J. Cell Biochem. 1995, 57, 173-184.
3. Martin, N. B.; Masson, P.; Sepulchre, C.; Theveniaux, J.; Millet, J.; Bellamy, F. Pharmacologic and biochemical profiles of new venous antithrombotic β-D-xyloside derivatives: potential antiathero/thrombotic drugs. Semin. Thromb. Hemostasis 1996, 22, 247-254.
4. Mani, K.; Havsmark, B.; Persson, S.; Kaneda, Y.; Yamamoto, H.; Sakurai, K.; Ashikari, S.; Habuchi, H.; Suzuki, S.; Kimata, K.; Malmström, A.; Westergren-Thorsson, G.; Fransson, L.-Å. Heparan/ chondroitin/dermatan sulfate primer 2-(6-hydroxynaphthyl)-O-β-D-xylopyranoside preferentially inhibits growth of transformed cells. Cancer Res. 1998, 58, 1099-1104.
5. Mani, K.; Belting, M.; Ellervik, U.; Falk, N.; Svensson, G.; Sandgren, S.; Fransson, L.-Å. Tumor attenuation by 2-(6-hydroxynaphthyl)-β-D- xylopyranoside requires priming of heparan sulfate and nuclear targeting of the products. Glycobiology 2004, 5, 387-397.
6. Belting, M.; Borsig, L.; Fuster, M. M.; Brown, J. R.; Persson, L.; Fransson, L.-Å.; Esko, J. D. Tumor attenuation by combined heparan sulfate and polyamine depletion. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 371-376.
7. Jacobsson, M.; Ellervik, U. Synthesis of naphthoxylosides on solid support. Tetrahedron Lett. 2002, 43, 6549-6552.
8. a values of phenolic and nitrogen-containing compounds by computational chemical analysis as compared to those measured by liquid chromatography. J. Chromatogr. A 1997, 762, 55-61.
9. Valkó, K.; Plass, M.; Bevan, C.; Reynolds, D.; Abraham, M. H. Relationships between the Chromatographie hydrophobicity indices and solute descriptors obtained by using several reversed-phase, diol, nitrile, cyclodextrin, and immobilized artificial membrane-bonded high-performance liquid chromatography columns. J. Chromatogr. A 1998, 797, 41-55.
10. Foti, M. C.; Johnsson, E. R.; Vinqvist, M. R.; Wright, J. S.; Barclay, L. R. C.; Ingold, K. U. Naphthalene diols: A new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals. J. Org. Chem. 2002, 67, 5190-5196.
11. Flueraru, M.; Chichirau, A.; Chepelev, L. L.; Willmore, W. G.; Durst, T.; Charron, M.; Barclay, L. R. C.; Wright, J. S. Cytotoxicity and cytoprotective activity in naphthalenediols depends on their tendency to form naphthoquinones. Free Radical Biol. Med. 2005, 39, 1368-1377.
12. Thomsen, L. L.; Miles, D. W. Role of nitric oxide in tumor progression: lessons from human tumours. Cancer Metastasis Rev. 1998, 17, 107-118.
13. Bernfield, M.; Götte, M.; Park, P. W.; Reizes, O.; Fitzgerald, M. L.; Lincecum, J.; Zako, M. Functions of cell surface heparan sulfate proteoglycans. Annu. Rev. Biochem. 1999, 68, 729-777.
14. Liu, W.; Litwack, E. D.; Stanley, M. J.; Langford, J. K.; Lander, A. D.; Sanderson, R. D. Heparan sulfate proteoglycans as adhesive and antiinvasive molecules. Syndecans and glypican have distinct functions. J. Biol. Chem., 1998, 273, 22825-22832.
15. Kleeff, J.; Wildi, S.; Kumbasar, A.; Friess, H.; Lander, A. D.; Korc, M. Stable transfection of a glypican-1 antisense construct decreases tumorigenicity in PANC-1 pancreatic carcinoma cells. Pancreas 1999, 19, 281-288.
16. Liu, D.; Shriver, Z.; Venkataraman, G.; El Shabrawi, Y.; Sasisekharan, R. Tumor cell surface heparan sulfate as cryptic promoters or inhibitors of tumor growth and metastasis. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 568-573.
17. O'Brien, P. J. Molecular mechanisms of quinone cytotoxicity. Chem.-Biol. Interact. 1991, 80, 1-41.
18. Scott, L. T.; Rozeboom, M. D.; Houk, K. N.; Fukunaga, T.; Lindler, H. J.; Hafner, K. The quinones of azulene. A theoretical prognosis. J. Am. Chem. Soc. 1980, 102, 5169-5176.
19. Huang, P.; Feng, L.; Oldham, E. A.; Keating, M. J.; Plinkett, W. Superoxide dismutase as a target for the selective killing of cancer cells. Nature 2000, 407, 390-395.
20. Fransson, L.-Å.; Belting, M.; Cheng, F.; Jönsson, M.; Mani, K.; Sandgren, S. Novel aspects of glypican glycobiology. Cell. Mol. Life Sci. 2004, 9, 1016-1024.