Specific, uncompetitive inhibition of β-galactosidases by a 5,6- isopropylidenedioxyfuro[2,3-d]isoxazole-3-methanol derivative

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 2, 1999, Pages 277-278

  Schaller, Christophe ^a   Demange, Raynald ^a   Picasso, Sylviane ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

galactosidases; Acetonide; Inhibitors; Isoxazoles

Indexed keywords

BETA GALACTOSIDASE; GLYCOSIDASE; ISOXAZOLE DERIVATIVE; METHANOL DERIVATIVE;

ARTICLE; ASPERGILLUS NIGER; ASPERGILLUS ORYZAE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; HYDROLYSIS; NONHUMAN;

ASPERGILLUS; BETA-GALACTOSIDASE; DOSE-RESPONSE RELATIONSHIP, DRUG; FURANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; INHIBITORY CONCENTRATION 50; ISOXAZOLES; MAGNETIC RESONANCE SPECTROSCOPY;

ASPERGILLUS NIGER; ASPERGILLUS ORIZAE; ASPERGILLUS ORYZAE; STAPHYLOCOCCUS PHAGE 3A;

EID: 0033579851     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00722-7     Document Type: Article

References (16)

1. See e.g.: Hendrix, M.; Wong, C.-H. Pure & Appl. Chem. 1996, 68, 2081-2087; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365-19372; Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955-1959.
2. See e.g.: Hendrix, M.; Wong, C.-H. Pure & Appl. Chem. 1996, 68, 2081-2087; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365-19372; Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955-1959.
3. See e.g.: Hendrix, M.; Wong, C.-H. Pure & Appl. Chem. 1996, 68, 2081-2087; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365-19372; Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955-1959.
4. See e.g.: Hendrix, M.; Wong, C.-H. Pure & Appl. Chem. 1996, 68, 2081-2087; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365-19372; Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955-1959.
5. See e.g.: Bols, M. Acc. Chem. Res. 1998, 31, 1-8; Kraehenbuehl, K.; Picasso, S.; Vogel, P. Helv. Chim. Acta 1998, 81, 1439-1479 and ref. cited therein.
6. See e.g.: Bols, M. Acc. Chem. Res. 1998, 31, 1-8; Kraehenbuehl, K.; Picasso, S.; Vogel, P. Helv. Chim. Acta 1998, 81, 1439-1479 and ref. cited therein.
7. Schaller, C; Vogel, P.; Jäger, V. Carbohydr. Res. in print.
8. Appropriate p-nitrophenyl glycoside substrates buffered to the optimum pH of the enzymes were used, for details see: Brandi, A.; Cicchi, S.; Cordero, F.M.; Frignoli, B.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 195, 60, 6806-6812.
9. For other inhibitors of this β-galactosidase, see: Lee, Y. C. Biochem. Biophys. Res. Commun. 1981, 35, 161-167; Miyake, Y.; Ebata, M. J. Antibiot. 1987, 40, 122-123; Miyake, Y.; Ebata, M. Agric. Biol. Chem. 1988, 52, 153-158; Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259-264; Qian, X.; Moris, V. F.; Wong, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 1117-1122; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1994, 1, 1-8.
10. For other inhibitors of this β-galactosidase, see: Lee, Y. C. Biochem. Biophys. Res. Commun. 1981, 35, 161-167; Miyake, Y.; Ebata, M. J. Antibiot. 1987, 40, 122-123; Miyake, Y.; Ebata, M. Agric. Biol. Chem. 1988, 52, 153-158; Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259-264; Qian, X.; Moris, V. F.; Wong, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 1117-1122; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1994, 1, 1-8.
11. For other inhibitors of this β-galactosidase, see: Lee, Y. C. Biochem. Biophys. Res. Commun. 1981, 35, 161-167; Miyake, Y.; Ebata, M. J. Antibiot. 1987, 40, 122-123; Miyake, Y.; Ebata, M. Agric. Biol. Chem. 1988, 52, 153-158; Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259-264; Qian, X.; Moris, V. F.; Wong, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 1117-1122; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1994, 1, 1-8.
12. For other inhibitors of this β-galactosidase, see: Lee, Y. C. Biochem. Biophys. Res. Commun. 1981, 35, 161-167; Miyake, Y.; Ebata, M. J. Antibiot. 1987, 40, 122-123; Miyake, Y.; Ebata, M. Agric. Biol. Chem. 1988, 52, 153-158; Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259-264; Qian, X.; Moris, V. F.; Wong, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 1117-1122; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1994, 1, 1-8.
13. For other inhibitors of this β-galactosidase, see: Lee, Y. C. Biochem. Biophys. Res. Commun. 1981, 35, 161-167; Miyake, Y.; Ebata, M. J. Antibiot. 1987, 40, 122-123; Miyake, Y.; Ebata, M. Agric. Biol. Chem. 1988, 52, 153-158; Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259-264; Qian, X.; Moris, V. F.; Wong, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 1117-1122; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1994, 1, 1-8.
14. For other inhibitors of this β-galactosidase, see: Lee, Y. C. Biochem. Biophys. Res. Commun. 1981, 35, 161-167; Miyake, Y.; Ebata, M. J. Antibiot. 1987, 40, 122-123; Miyake, Y.; Ebata, M. Agric. Biol. Chem. 1988, 52, 153-158; Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259-264; Qian, X.; Moris, V. F.; Wong, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 1117-1122; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1994, 1, 1-8.
15. Glucosidases are inhibited by imidazoles, see: Li, Y. K.; Byers, L. D. Biochim. Biophys. Acta. 1989, 999, 227-232; Field, R. A.; Haines, A. H.; Chrystal, E. J.; Luszniak, M. C. Biochem. J. 1991, 274, 885-889.
16. Glucosidases are inhibited by imidazoles, see: Li, Y. K.; Byers, L. D. Biochim. Biophys. Acta. 1989, 999, 227-232; Field, R. A.; Haines, A. H.; Chrystal, E. J.; Luszniak, M. C. Biochem. J. 1991, 274, 885-889.