1-Deoxy-d-galactonojirimycins with dansyl capped N-substituents as β-galactosidase inhibitors and potential probes for GM1 gangliosidosis affected cell lines

Carbohydrate Research

Volumn 346, Issue 12, 2011, Pages 1592-1598

  Fröhlich, Richard F G ^a   Furneaux, Richard H ^a   Mahuran, Don J ^b   Saf, Robert ^e   Stütz, Arnold E ^c   Tropak, Michael B ^b   Wicki, Jacqueline ^d   Withers, Stephen G ^d   Wrodnigg, Tanja M ^c  

^a CALLAGHAN INNOVATION   (New Zealand)

^b HOSPITAL FOR SICK CHILDREN   (Canada)

^c GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^d UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^e GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Galactosidase inhibitor; GM1 gangliosidosis; Iminoalditol; Molecular chaperone; N Alkylation

Indexed keywords

GALACTOSIDASES; GM1-GANGLIOSIDOSIS; IMINOALDITOL; MOLECULAR CHAPERONE; N-ALKYLATION;

CARBOXYLIC ACIDS; FLUORESCENCE; SYNTHESIS (CHEMICAL);

CELL CULTURE;

BETA GALACTOSIDASE; BETA GLUCOSIDASE; CHAPERONE; FLUORESCENT DYE; GLYCOSIDASE INHIBITOR; N (DANSYLAMINO)HEXYLAMINOCARBONYLPENTYL 1,5 DIDEOXY 1,5 IMINO DEXTRO GALACTITOL; N (DANSYLAMINOHEXYLAMINO)HEXYL 3,4 O ISOPROPYLIDENE 1,5 DIDEOXY 1,5 IMINO DEXTRO GALACTITOL; N [(DANSYLAMINOHEXYL) N OCTANOYLAMINO]HEXYL 1,5 DIDEOXY 1,5 IMINO DEXTRO GALACTITOL; N [(DANSYLAMINOHEXYL) N OCTANOYLAMINO]HEXYL 3,4 O ISOPROPYLIDENE 1,5 DIDEOXY 1,5 IMINO DEXTRO GALACTITOL; N AMINOHEXYL 1 DEOXY DEXTRO GALACTONOJIRIMYCIN; N BIS(DANSYLAMINOHEXYL)AMINOCARBONYLPENTYL 1,5 DIDEOXY 1,5 IMINO DEXTRO GALACTITOL; N BIS(DANSYLAMINOHEXYL)AMINOHEXYL 1,5 DIDEOXY 1,5 IMINO DEXTRO GALACTITOL; N BIS(DANSYLAMINOHEXYL)AMINOHEXYL 3,4 O ISOPROPYLIDENE 1,5 DIDEOXY 1,5 IMINO DEXTRO GALACTITOL; N CARBOXYPENTYL 1 DEOXY DEXTRO GALACTONOJIRIMYCIN; N DANSYL 1,6 DIAMINOHEXANE; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ARTICLE; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; FIBROBLAST; GM1 GANGLIOSIDOSIS; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; SUBSTITUTION REACTION;

1-DEOXYNOJIRIMYCIN; ANIMALS; BACTERIAL PROTEINS; BETA-GALACTOSIDASE; CATS; CELL LINE; DANSYL COMPOUNDS; DIAMINES; ENZYME INHIBITORS; FLUORESCENT DYES; GANGLIOSIDOSIS, GM1; HUMANS; IMINES; KINETICS; LYSOSOMES; MOLECULAR CHAPERONES; MOLECULAR PROBES; MOLECULAR TARGETED THERAPY; PHOSPHATIDYLCHOLINES; PLANT PROTEINS; SUGAR ALCOHOLS;

EID: 79959980422     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2011.05.010     Document Type: Article

References (27)

1. P. Compain, and O.R. Martin Iminosugars - From Synthesis to Therapeutic Applications 2007 Wiley Chichester
2. O.R. Martin, and P. Compain Iminosugars: Recent Insights into their Bioactivity and Potential as Therapeutic Agents, Curr. Top. Med. Chem. 3 2003 471 591
3. T.M. Wrodnigg From Lianas to Glycobiology Tools: Twenty-Five Years of 2,5-Dideoxy-2,5-Imino-d-Mannitol W. Schmid, A.E. Stütz, Timely Research Perspectives in Carbohydrate Chemistry 2002 Springer Vienna, New York 43 76 (Pubitemid 37387283)
4. T.D. Heightman, and A.T. Vasella Angew. Chem., Int. Ed. 38 1999 750 770
5. A.E. Stütz Iminosugars as Glycosidase Inhibitors 1999 Wiley-VCH Weinheim
6. P. Compain, and O.R. Martin P. Compain, O.R. Martin, Iminosugars - From Synthesis to Therapeutic Applications 2007 Wiley Chichester 1 6
7. T. Wennekes, R.J.B.H.N. van den Berg, R.G. Boot, G.A. van der Marel, H.S. Overkleeft, and J.M.F.G. Aerts Angew. Chem., Int. Ed. 48 2009 8848 8869
8. J.-Q. Fan P. Compain, O.R. Martin, Iminosugars - From Synthesis to Therapeutic Applications 2007 Wiley Chichester 225 247
9. T. Butters P. Compain, O.R. Martin, Iminosugars - From Synthesis to Therapeutic Applications 2007 Wiley Chichester 249 268
10. Z. Luan, K. Higaki, M. Aguilar-Moncayo, L. Li, H. Ninomiya, E. Nanba, K. Ohno, M.I. Garcia-Moreno, C. Ortiz Mellet, J.M. Garcia Fernandez, and Y. Suzuki ChemBioChem 11 2010 2453 2464
11. Z. Luan, K. Higaki, M. Aguilar-Moncayo, H. Ninomiya, K. Ohno, M.I. Garcia-Moreno, C. Ortiz Mellet, J.M. Garcia Fernandez, and Y. Suzuki ChemBioChem 10 2009 2780 2792
12. B. Brumshtein, M. Aguilar-Moncayo, M.I. Garcia-Moreno, C. Ortiz Mellet, J.M. Garcia Fernandez, I. Silman, Y. Shaaltiel, D. Aviezer, J.L. Sussman, and A.H. Futerman ChemBioChem 10 2009 1480 1485
13. X.X. Zhu, K.A. Sheth, S. Li, H.H. Chang, and J.Q. Fan Angew. Chem., Int. Ed. 44 2005 7450 7453
14. A.R. Sawkar, S.L. Adamski-Werner, W.-C. Cheng, C.-H. Wong, E. Beutler, K.-P. Zimmer, and J.W. Kelly Chem. Biol. 12 2005 1235 1244
15. T. Wennekes, R.J.B.H.N. van den Berg, W. Donker, G.A. van der Marel, A. Strijland, M.F.G. Aerts, and H.S. Overkleeft J. Org. Chem. 72 2007 1088 1097
16. E. Elliot-Smith, A.O. Speak, E. Lloyd-Evans, D.A. Smith, A.C. van der Spoel, M. Jeyakumar, T.D. Butters, R.A. Dwek, A. d'Azzo, and F.M. Platt Mol. Gen. Metabol. 94 2008 204 211
17. Y. Suzuki, S. Ogawa, and Y. Sakakibara Perspect. Med. Chem. 3 2009 7 19
18. A.J. Steiner, A.E. Stütz, C.A. Tarling, S.G. Withers, and T.M. Wrodnigg Carbohydr. Res. 342 2007 1850 1858
19. A.J. Steiner, A.E. Stütz, T.M. Wrodnigg, C.A. Tarling, S.G. Withers, A. Hermetter, and H. Schmidinger Bioorg. Med. Chem. Lett. 18 2008 1922 1925
20. K. Fantur, D. Hofer, G. Schitter, A.J. Steiner, B.M. Pabst, T.M. Wrodnigg, A.E. Stütz, and E. Paschke Mol. Genet. Metab. 100 2010 262 268
21. R.F.G. Fröhlich, R.H. Furneaux, D. Mahuran, B. Rigat, A.E. Stütz, J. Wicki, S.G. Withers, and T.M. Wrodnigg Carbohydr. Res. 345 2010 1371 1376
22. G. Schitter, E. Scheucher, A.J. Steiner, A.E. Stütz, M. Thonhofer, C. Tarling, S.G. Withers, J. Wicki, K. Fantur, E. Paschke, D. Mahuran, B.A. Rigat, M. Tropak, and T.M. Wrodnigg Beilstein J. Org. Chem. 6 2010 21
23. D.R. Martin, B.A. Rigat, P. Foureman, G.S. Varadarajan, M. Hwang, B.K. Krum, B.F. Smith, J.W. Callahan, D.J. Mahuran, and H.J. Baker Mol. Genet. Metab. 94 2008 212 221
24. H. Prade, L.F. Mackenzie, and S.G. Withers Carbohydr. Res. 305 1998 371 381
25. J.B. Kempton, and S.G. Withers Biochemistry 31 1992 9961 9969
26. D.J. Mahuran, and J.A. Lowden Can. J. Biochem. 58 1980 287 294
27. M.B. Tropak, S.P. Reid, M. Guiral, S.G. Withers, and D.J. Mahuran J. Biol. Chem. 279 2004 13478 13487