메뉴 건너뛰기




Volumn 57, Issue 21, 2014, Pages 9096-9104

Identification and development of biphenyl substituted iminosugars as improved dual glucosylceramide synthase/neutral glucosylceramidase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYNOJIRIMYCIN DERIVATIVE; ALPHA GLUCOSIDASE; ANTIDIABETIC AGENT; BENZYL DERIVATIVE; BETA GLUCOSIDASE; BETA GLUCOSIDASE 2; BIPHENYL DERIVATIVE; CERAMIDE GLUCOSYLTRANSFERASE INHIBITOR; GLUCOSIDASE 2 INHIBITOR; GLUCOSYLCERAMIDASE; GLUCOSYLCERAMIDASE 1; GLYCOSIDASE; IMINOSUGAR; INTESTINAL GLYCOSIDASE INHIBITOR; LACTASE; SUCRASE; UNCLASSIFIED DRUG; 1 DEOXYNOJIRIMYCIN; CERAMIDE GLUCOSYLTRANSFERASE; ENZYME INHIBITOR; GBA2 PROTEIN, HUMAN; GLUCOSYLTRANSFERASE;

EID: 84923831699     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501181z     Document Type: Article
Times cited : (42)

References (44)
  • 2
    • 0038170055 scopus 로고    scopus 로고
    • Therapeutic applications of imino sugars in lysosomal storage disorders
    • Butters, T. D.; Dwek, R. A.; Platt, F. M. Therapeutic applications of imino sugars in lysosomal storage disorders Curr. Top. Med. Chem. 2003, 3, 561-574
    • (2003) Curr. Top. Med. Chem. , vol.3 , pp. 561-574
    • Butters, T.D.1    Dwek, R.A.2    Platt, F.M.3
  • 3
    • 84923790068 scopus 로고
    • Efficacy and tolerability of a 3-month treatment with the glucosidase inhibitor Miglitol (Bay +M 1099)
    • Hillebrand, I.; Englert, R.; Schulz, H. Efficacy and tolerability of a 3-month treatment with the glucosidase inhibitor Miglitol (Bay +M 1099) Diabetes 1986, 35, A93-A93
    • (1986) Diabetes , vol.35 , pp. 93-A93
    • Hillebrand, I.1    Englert, R.2    Schulz, H.3
  • 4
    • 0034006999 scopus 로고    scopus 로고
    • Miglitol. A review of its therapeutic potential in type 2 diabetes mellitus
    • Scott, L. J.; Spencer, C. M. Miglitol. A review of its therapeutic potential in type 2 diabetes mellitus Drugs 2000, 59, 521-549
    • (2000) Drugs , vol.59 , pp. 521-549
    • Scott, L.J.1    Spencer, C.M.2
  • 5
    • 0028176432 scopus 로고
    • N-butyldeoxynojirimycin is a novel inhibitor of glycolipid biosynthsis
    • Platt, F. M.; Neises, G. R.; Dwek, R. A.; Butters, T. D. N-butyldeoxynojirimycin is a novel inhibitor of glycolipid biosynthsis J. Biol. Chem. 1994, 269, 8362-8365
    • (1994) J. Biol. Chem. , vol.269 , pp. 8362-8365
    • Platt, F.M.1    Neises, G.R.2    Dwek, R.A.3    Butters, T.D.4
  • 7
    • 80054112943 scopus 로고    scopus 로고
    • Amphiphilic 1-deoxynojirimycin derivatives through click strategies for chemical chaperoning in N370S Gaucher cells
    • Diot, J. D.; Moreno, I. G.; Twigg, G.; Mellet, C. O.; Haupt, C. O.; Butters, T. D.; Kovensky, J.; Gouin, S. G. Amphiphilic 1-deoxynojirimycin derivatives through click strategies for chemical chaperoning in N370S Gaucher cells J. Org. Chem. 2011, 76, 7757-7768
    • (2011) J. Org. Chem. , vol.76 , pp. 7757-7768
    • Diot, J.D.1    Moreno, I.G.2    Twigg, G.3    Mellet, C.O.4    Haupt, C.O.5    Butters, T.D.6    Kovensky, J.7    Gouin, S.G.8
  • 8
    • 84863852895 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of N -alkylated deoxynojirimycin (DNJ) derivatives for the treatment of dengue virus infection
    • Yu, W.; Gill, T.; Du, Y.; Ye, H.; Qu, X.; Guo, J.-T.; Cuconati, A.; Zhao, K.; Block, T. M.; Xu, X.; Chang, J. Design, synthesis and biological evaluation of N -alkylated deoxynojirimycin (DNJ) derivatives for the treatment of dengue virus infection J. Med. Chem. 2012, 55, 6061-6075
    • (2012) J. Med. Chem. , vol.55 , pp. 6061-6075
    • Yu, W.1    Gill, T.2    Du, Y.3    Ye, H.4    Qu, X.5    Guo, J.-T.6    Cuconati, A.7    Zhao, K.8    Block, T.M.9    Xu, X.10    Chang, J.11
  • 9
    • 19344375262 scopus 로고    scopus 로고
    • Design and synthesis of iminosugar-based inhibitors of glucosylceramide synthase: The search for new therapeutic agents against Gaucher disease
    • Boucheron, C.; Desvergnes, V.; Compain, P.; Martin, O. R.; Lavi, A.; Mackeen, M.; Wormald, M.; Dwek, R.; Butters, T. D. Design and synthesis of iminosugar-based inhibitors of glucosylceramide synthase: The search for new therapeutic agents against Gaucher disease Tetrahedron: Asymmetry 2005, 16, 1747-1756
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1747-1756
    • Boucheron, C.1    Desvergnes, V.2    Compain, P.3    Martin, O.R.4    Lavi, A.5    Mackeen, M.6    Wormald, M.7    Dwek, R.8    Butters, T.D.9
  • 13
    • 0038100163 scopus 로고    scopus 로고
    • Biochemistry of glycosphingolipid storage disorders: Implications for therapeutic intervention
    • Aerts, J. M.; Hollak, C.; Boot, R.; Groener, A. Biochemistry of glycosphingolipid storage disorders: implications for therapeutic intervention Philos. Trans. R. Soc., B 2003, 358, 905-914
    • (2003) Philos. Trans. R. Soc., B , vol.358 , pp. 905-914
    • Aerts, J.M.1    Hollak, C.2    Boot, R.3    Groener, A.4
  • 16
    • 84923777601 scopus 로고    scopus 로고
    • Mirzaian, M.; Gaspar, P.; Blommaart, E.; Boot, R. G.; Margues, A.; Wisse, P.; Overkleeft, H. S.; Aerts, J. M. F. G. manuscript in preparation
    • Mirzaian, M.; Gaspar, P.; Blommaart, E.; Boot, R. G.; Margues, A.; Wisse, P.; Overkleeft, H. S.; Aerts, J. M. F. G. manuscript in preparation.
  • 18
    • 84862585334 scopus 로고    scopus 로고
    • Pharmacological chaperones facilitate the post-ER transport of recombinant N370S mutant beta-glucocerebrosidase in plant cells: Evidence that N370S is a folding mutant
    • Babajani, G.; Tropak, M. B.; Mahuran, D. J.; Kermode, A. R. Pharmacological chaperones facilitate the post-ER transport of recombinant N370S mutant beta-glucocerebrosidase in plant cells: evidence that N370S is a folding mutant Mol. Genet. Metab. 2012, 106, 323-329
    • (2012) Mol. Genet. Metab. , vol.106 , pp. 323-329
    • Babajani, G.1    Tropak, M.B.2    Mahuran, D.J.3    Kermode, A.R.4
  • 19
    • 35348989145 scopus 로고    scopus 로고
    • Crystal structures of complexes of N-butyl- and N-nonyl-deoxynojirimycin bound to acid beta-glucosidase - Insights into the mechanism of chemical chaperone action in Gaucher disease
    • Brumshtein, B.; Greenblatt, H. M.; Butters, T. D.; Shaaltiel, Y.; Aviezer, D.; Silman, I.; Futerman, A. H.; Sussman, J. L. Crystal structures of complexes of N-butyl- and N-nonyl-deoxynojirimycin bound to acid beta-glucosidase-Insights into the mechanism of chemical chaperone action in Gaucher disease J. Biol. Chem. 2007, 282, 29052-29058
    • (2007) J. Biol. Chem. , vol.282 , pp. 29052-29058
    • Brumshtein, B.1    Greenblatt, H.M.2    Butters, T.D.3    Shaaltiel, Y.4    Aviezer, D.5    Silman, I.6    Futerman, A.H.7    Sussman, J.L.8
  • 23
    • 13444251524 scopus 로고    scopus 로고
    • TNFalpha-induced insulin resistance in adipocytes as a membrane microdomain disorder: Involvement of ganglioside GM3
    • Kabayama, K.; Sato, T.; Kitamura, F.; Uemura, S.; Kang, B. W.; Igarashi, Y.; Inokuchi, J. TNFalpha-induced insulin resistance in adipocytes as a membrane microdomain disorder: involvement of ganglioside GM3 Glycobiology 2005, 15, 21-29
    • (2005) Glycobiology , vol.15 , pp. 21-29
    • Kabayama, K.1    Sato, T.2    Kitamura, F.3    Uemura, S.4    Kang, B.W.5    Igarashi, Y.6    Inokuchi, J.7
  • 28
    • 33846964923 scopus 로고    scopus 로고
    • Development of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives as selective inhibitors of glucosylceramide metabolism in man
    • Wennekes, T.; van den Berg, R. J. B. H. N.; Donker, W.; van der Marel, G. A.; Strijland, A.; Aerts, J. M. F. G.; Overkleeft, H. S. Development of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives as selective inhibitors of glucosylceramide metabolism in man J. Org. Chem. 2007, 72, 1088-1097
    • (2007) J. Org. Chem. , vol.72 , pp. 1088-1097
    • Wennekes, T.1    Van Den Berg, R.J.B.H.N.2    Donker, W.3    Van Der Marel, G.A.4    Strijland, A.5    Aerts, J.M.F.G.6    Overkleeft, H.S.7
  • 29
    • 27744459735 scopus 로고    scopus 로고
    • Gaucher disease-associated glucocerebrosidases show mutation-dependent chemical chaperone profiles
    • Compound 8 has been proposed as a pharmacological GBA1 chaperone: see
    • Compound 8 has been proposed as a pharmacological GBA1 chaperone: see: Sawkar, A. R.; Adamski-Werner, S. L.; Cheng, W. C.; Wong, C. H.; Beutler, E.; Zimmer, K. P.; Kelly, J. W. Gaucher disease-associated glucocerebrosidases show mutation-dependent chemical chaperone profiles Chem. Biol. 2005, 11, 1235-1244
    • (2005) Chem. Biol. , vol.11 , pp. 1235-1244
    • Sawkar, A.R.1    Adamski-Werner, S.L.2    Cheng, W.C.3    Wong, C.H.4    Beutler, E.5    Zimmer, K.P.6    Kelly, J.W.7
  • 30
    • 84885172160 scopus 로고    scopus 로고
    • Setting expectations in molecular optimizations: Strengths and limitations of commonly used composite parameters
    • Shultz, M. D. Setting expectations in molecular optimizations: strengths and limitations of commonly used composite parameters Bioorg. Med. Chem. Lett. 2013, 23, 5980-5991
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 5980-5991
    • Shultz, M.D.1
  • 32
    • 0019003203 scopus 로고
    • Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain
    • Vunnan, R. R.; Radin, N. S. Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain Chem. Phys. Lipids 1980, 26, 265-278
    • (1980) Chem. Phys. Lipids , vol.26 , pp. 265-278
    • Vunnan, R.R.1    Radin, N.S.2
  • 33
    • 34248228704 scopus 로고    scopus 로고
    • Inhibiting glycosphingolipid synthesis improves glycemic control and insulin sensitivity in animal models of type 2 diabetes
    • Zhao, H. M.; Przybylska, M.; Wu, I. H.; Zhang, J. H.; Siegel, C.; Komarnitsky, S.; Yew, N. S.; Cheng, S. H. Inhibiting glycosphingolipid synthesis improves glycemic control and insulin sensitivity in animal models of type 2 diabetes Diabetes 2007, 56, 1210-1218
    • (2007) Diabetes , vol.56 , pp. 1210-1218
    • Zhao, H.M.1    Przybylska, M.2    Wu, I.H.3    Zhang, J.H.4    Siegel, C.5    Komarnitsky, S.6    Yew, N.S.7    Cheng, S.H.8
  • 39
    • 0028171083 scopus 로고
    • N -Butyldeoxygalactonojirimycin inhibits glycolipid biosynthesis but does not affect N -linked oligosaccharide processing
    • Platt, F. M.; Neises, G. R.; Karlsson, G. B.; Dwek, R. A.; Butters, T. D. N -Butyldeoxygalactonojirimycin inhibits glycolipid biosynthesis but does not affect N -linked oligosaccharide processing J. Biol. Chem. 1994, 269, 27108-27144
    • (1994) J. Biol. Chem. , vol.269 , pp. 27108-27144
    • Platt, F.M.1    Neises, G.R.2    Karlsson, G.B.3    Dwek, R.A.4    Butters, T.D.5
  • 41
    • 0033952264 scopus 로고    scopus 로고
    • N-Butyldeoxygalactonojirimycin: A more selective inhibitor of glycosphingolipid biosynthesis than N-butyldeoxynojirimycin, in vitro and in vivo
    • Andersson, U.; Butters, T. B.; Dwek, R. A.; Platt, F. M. N-Butyldeoxygalactonojirimycin: a more selective inhibitor of glycosphingolipid biosynthesis than N-butyldeoxynojirimycin, in vitro and in vivo Biochem. Pharmacol. 2000, 59, 821-829
    • (2000) Biochem. Pharmacol. , vol.59 , pp. 821-829
    • Andersson, U.1    Butters, T.B.2    Dwek, R.A.3    Platt, F.M.4
  • 44
    • 0027532181 scopus 로고
    • Demonstration of the existence of a second, nonlysosomal glucocerebrosidase that is not deficient in Gaucher disease
    • van Weely, S.; Brandsma, M.; Strijland, A.; Tager, J. M.; Aerts, J. M. F. G. Demonstration of the existence of a second, nonlysosomal glucocerebrosidase that is not deficient in Gaucher disease Biochim. Biophys. Acta 1993, 1181, 55-62
    • (1993) Biochim. Biophys. Acta , vol.1181 , pp. 55-62
    • Van Weely, S.1    Brandsma, M.2    Strijland, A.3    Tager, J.M.4    Aerts, J.M.F.G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.