Hexose keto-C-glycoside conjugates: Design, synthesis, cytotoxicity, and evaluation of their affinity for the glucose transporter glut-1

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 12, 1996, Pages 2081-2090

  Uriel, Clara ^a   Egron, Marie José ^a   Santarromana, Monique ^b   Scherman, Daniel ^b   Antonakis, Kostas ^a   Herscovici, Jean ^a  

^a Lab de Chim Organique/S   (France)

^b Ctr de Biotech UMR 133 CNRS Rhone   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORAMBUCIL; FLOXURIDINE; GLUCOSE TRANSPORTER; GLYCOSIDE;

ARTICLE; BINDING AFFINITY; CANCER CELL; CELL CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAJI CELL; STRUCTURE ACTIVITY RELATION;

ERYTHROCYTES; GLUCOSE; GLUCOSE TRANSPORTER TYPE 1; GLUCOSIDES; GLYCOSIDES; HEXOSES; HUMANS; LYMPHOMA; MONOSACCHARIDE TRANSPORT PROTEINS; PYRONES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0030482714     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(96)00224-6     Document Type: Article

References (27)

1. 1. Herscovici, J.; Bennani-Baiti, M. I.; Frayssinet, C.; Antonakis. Bioorg. Med. Chem. Lett. 1991, 1, 395.
2. 2. Herscovici, J.; Bennani-Baiti, M. I.; Montserret, R.; Frayssinet, C.; Antonakis, K. Bioorg. Med. Chem. Lett, 1991, 1, 721.
3. 3. Herscovici, J.; Uriel, C.; Uriel, J.; Antonakis, K. Bioorg. Med. Chem. Lett. 1994, 4, 421.
4. 4. Fisher, J. F.; Harrison, A. W.; Bundy, G. L.; Wilkinson, K. F.; Rush, B. D.; Ruwart, M. J. J. Med. Chem. 1991, 34, 3140.
5. 5. Rodriguez, R. E.; Rodriguez, F. D.; Sacristan, M. P.; Torres, J. L.; Valencia, G.; Garcia Anton, J. M. Neurosci. Lett. 1989, 101, 89.
6. 6. Bardaji, E.; Torres, J. L.; Clapes, P.; Albericio, F.; Barany, G.; Rodriguez, R. E.; Sacristan, M. P.; Valencia, G. J. Chem. Soc., Perkin Trans, 1 1991, 1755.
7. 7. Polt, R.; Porecca, F.; Szabo, L.; Hruby, V. J. Glycoconj. J. 1993, 10, 261.
8. 8. Polt, R.; Porecca, F.; Szabo, L.; Bilsky, E. J.; Davis, P.; Abbruscato, T. J.; Davis, T. P.: Horvath, R.; Yamamura, H. I.; Hruby, V. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7114.
9. 9. Bell, G. I.; Burant, C. F.; Takeda, J.; Gould, G. W. J. Biol Chem. 1993, 268, 19161.
10. 10. Yamamoto, I.; Sekine, M.; Hata, T. J. Chem. Soc., Perkin 1. 1980, 306.
11. 11. Hatanaka, M. Biochim. Biophys. Acta 1974, 355, 77.
12. 12. Brown, R. S.; Wahl, R. I. Cancer 1993, 72, 2979.
13. 13. Drak, J.; Iwasawa, N.; Danishefsky, S. J.; Crothers, D. M. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 7464. Ajyar, J.; Danishefsky, S. J.; Crothers, D. M. J. Am. Chem. Soc. 1992, 114, 7552.
14. 13. Drak, J.; Iwasawa, N.; Danishefsky, S. J.; Crothers, D. M. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 7464. Ajyar, J.; Danishefsky, S. J.; Crothers, D. M. J. Am. Chem. Soc. 1992, 114, 7552.
15. 14. Nicolaou, K. C.; Tsay, S.-C.; Suzuki, T.; Joyce, G. F. J. Am. Chem. Soc. 1992,114, 7555.
16. 15. Silva, D. J.; Kahne, D. E. J. Am. Chem. Soc. 1993, 115, 7962. Silva, D. J.; Goodnow, R.; Kahne, D. Biochemistry 1993, 32, 463.
17. 15. Silva, D. J.; Kahne, D. E. J. Am. Chem. Soc. 1993, 115, 7962. Silva, D. J.; Goodnow, R.; Kahne, D. Biochemistry 1993, 32, 463.
18. 16. Barnett, G. E.; Holrnan, G. D.; Munday, K. A. Biochem. J. 1973, 131, 211.
19. 17. Schmidt, R. R.; Kinzy. W. Adv. Carbohyd. Chem. Biochem. 1994, 50, 21.
20. 18. Herscovici, J.; Egron, M. J.; Antonakis, K. J. Chem. Soc., Perkin Trans, 1 1982, 1697.
21. 19. Bessodes, M.; Komiotis, D.; Antonakis, K. Tetrahedron Lett. 1986, 27, 579.
22. 20. Halmos, T.; Antonakis, K.; Santarrromana, M.; Scherman, D. Eur. J. Pharmacol., 1997, in press.
23. 21. Pulvertaft, R. J. V. Lancet 1964, 238.
24. 22. Jarvis, S. Biochem. J. 1988, 249, 383.
25. 23. Brahm J.; Gasbjerg, P. K. Tenth School on Biophysics of Membrane Transport, Proceedings, Poland; Poland, 1990; p 26.
26. 24. Jarvis, S. M. Biochem. J. 1988, 249, 383.
27. 25. Lowe, A. G.; Walmsley, A. R. Biochim. Biophvs. Acta 1986, 857, 146.