Table of Contents
International Journal of Carbohydrate Chemistry
Volume 2014 (2014), Article ID 941059, 8 pages
http://dx.doi.org/10.1155/2014/941059
Research Article

Thio-β-D-glucosides: Synthesis and Evaluation as Glycosidase Inhibitors and Activators

Department of Chemistry, University of the Pacific, Stockton, CA 95211, USA

Received 4 June 2014; Revised 1 August 2014; Accepted 2 August 2014; Published 21 August 2014

Academic Editor: Francesco Nicotra

Copyright © 2014 Andrey V. Samoshin et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. K. H. Kinne and F. Castaneda, “SGLT inhibitors as new therapeutic tools in the treatment of diabetes,” Handbook of Experimental Pharmacology, vol. 203, pp. 105–126, 2011. View at Publisher · View at Google Scholar · View at Scopus
  2. A. Dondoni and A. Marra, “Calixarene and calixresorcarene glycosides: their synthesis and biological applications,” Chemical Reviews, vol. 110, no. 9, pp. 4949–4977, 2010. View at Publisher · View at Google Scholar · View at Scopus
  3. F. Castaneda, A. Burse, W. Boland, and R. K. H. Kinne, “Thioglycosides as inhibitors of hSGLT1 and hSGLT2: potential therapeutic agents for the control of hyperglycemia in diabetes,” International Journal of Medical Sciences, vol. 4, no. 3, pp. 131–139, 2007. View at Google Scholar · View at Scopus
  4. Q. V. Vo, C. Trenerry, S. Rochfort, J. Wadeson, C. Leyton, and A. B. Hughes, “Synthesis and anti-inflammatory activity of aromatic glucosinolates,” Bioorganic and Medicinal Chemistry, vol. 21, no. 19, pp. 5945–5954, 2013. View at Publisher · View at Google Scholar · View at Scopus
  5. J. Rodrigue, G. Ganne, B. Blanchard et al., “Aromatic thioglycoside inhibitors against the virulence factor LecA from Pseudomonas aeruginosa,” Organic and Biomolecular Chemistry, vol. 11, no. 40, pp. 6906–6918, 2013. View at Google Scholar
  6. E. S. H. El Ashry, E. S. H. El Tamany, M. E. D. A. El Fattah, A. T. A. Boraei, and H. M. Abd El-Nabi, “Regioselective synthesis, characterization and antimicrobial evaluation of S-glycosides and S,N-diglycosides of 1,2-Dihydro-5-(1H-indol-2-yl)-1,2,4-triazole-3-thione,” European Journal of Medicinal Chemistry, vol. 66, pp. 106–113, 2013. View at Publisher · View at Google Scholar · View at Scopus
  7. H. A. El-Sayed, A. H. Moustafa, and A. E. Z. Haikal, “Synthesis, antiviral, and antimicrobial activity of 1,2,4-triazole thioglycoside derivatives,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 188, no. 5, pp. 649–662, 2013. View at Publisher · View at Google Scholar · View at Scopus
  8. A. J. Cagnoni, O. Varela, J. Kovensky, and M. L. Uhrig, “Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose,” Organic and Biomolecular Chemistry, vol. 11, no. 33, pp. 5500–5511, 2013. View at Publisher · View at Google Scholar · View at Scopus
  9. E. Repetto, C. Marino, and O. Varela, “Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: inhibitory activity against a β-galactofuranosidase,” Bioorganic and Medicinal Chemistry, vol. 21, no. 11, pp. 3327–3333, 2013. View at Publisher · View at Google Scholar · View at Scopus
  10. I. L. Rogers, D. W. Gammon, and K. J. Naidoo, “Conformational preferences of plumbagin with phenyl-1-thioglucoside conjugates in solution and bound to MshB determined by aromatic association,” Carbohydrate Research, vol. 371, pp. 52–60, 2013. View at Publisher · View at Google Scholar · View at Scopus
  11. S. V. Pestova, D. V. Sudarikov, S. A. Rubtsova, and A. V. Kutchin, “Synthesis and asymmetric oxidation of thioglycosides derived from neomenthanethiol and α-D-galactose,” Russian Journal of Organic Chemistry, vol. 49, no. 3, pp. 366–373, 2013. View at Google Scholar
  12. T. Terauchi, Y. Koyama, S. Machida, T. Kasumi, and S. Komba, “Synthesis of novel thioglycoside analogs as the substrates and/or the inhibitors of cellobiohydrolases,” Journal of Applied Glycoscience, vol. 59, no. 1, pp. 11–19, 2012. View at Google Scholar
  13. C. Stanetty, A. Wolkerstorfer, H. Amer et al., “Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogs of glycyrrhizin,” Beilstein Journal of Organic Chemistry, vol. 8, pp. 705–711, 2012. View at Publisher · View at Google Scholar
  14. R. Dettmann and T. Ziegler, “Synthesis of octyl S-glycosides of tri- to pentasaccharide fragments related to the GPI anchor of Trypanosoma brucei,” Carbohydrate Research, vol. 346, no. 15, pp. 2348–2361, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. H. N. Hafez, H. A. R. Hussein, and A.-R. B. A. El-Gazzar, “Synthesis of substituted thieno[2,3-d]pyrimidine-2,4-dithiones and their S-glycoside analogues as potential antiviral and antibacterial agents,” European Journal of Medicinal Chemistry, vol. 45, no. 9, pp. 4026–4034, 2010. View at Publisher · View at Google Scholar · View at Scopus
  16. M. Poláková, M. Beláňová, L. Petruš, and K. Mikušová, “Synthesis of alkyl and cycloalkyl α-D-mannopyranosides and derivatives thereof and their evaluation in the mycobacterial mannosyltransferase assay,” Carbohydrate Research, vol. 345, no. 10, pp. 1339–1347, 2010. View at Publisher · View at Google Scholar · View at Scopus
  17. R. Caraballo, M. Sakulsombat, and O. Ramström, “Towards dynamic drug design: identification and optimization of β-galactosidase inhibitors from a dynamic hemithioacetal system,” ChemBioChem, vol. 11, no. 11, pp. 1600–1606, 2010. View at Publisher · View at Google Scholar · View at Scopus
  18. I. F. Nassar, “Synthesis and antitumor activity of new substituted mercapto-1,2,4-triazine derivatives, their thioglycosides, and acyclic thioglycoside analogs,” Journal of Heterocyclic Chemistry, vol. 50, no. 1, pp. 129–134, 2013. View at Publisher · View at Google Scholar · View at Scopus
  19. I. García-Álvarez, H. Groult, J. Casas et al., “Synthesis of antimitotic thioglycosides: in vitro and in vivo evaluation of their anticancer activity,” Journal of Medicinal Chemistry, vol. 54, no. 19, pp. 6949–6955, 2011. View at Publisher · View at Google Scholar · View at Scopus
  20. M. A. Abu-Zaied, E. M. El-Telbani, G. H. Elgemeie, and G. A. M. Nawwar, “Synthesis and in vitro anti-tumor activity of new oxadiazole thioglycosides,” European Journal of Medicinal Chemistry, vol. 46, no. 1, pp. 229–235, 2011. View at Publisher · View at Google Scholar · View at Scopus
  21. M. A. Jermyn, “Fungal cellulases. XV. Acceptor specificity of the aryl beta-glucosidase of Stachybotrys atra.,” Australian Journal of Biological Sciences, vol. 19, no. 5, pp. 903–917, 1966. View at Google Scholar · View at Scopus
  22. T. Kuntothom, M. Raab, I. Tvaroška et al., “Binding of β-d-glucosides and β-d-mannosides by rice and barley β-d-glycosidases with distinct substrate specificities,” Biochemistry, vol. 49, no. 40, pp. 8779–8793, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. M. Schnabelrauch, A. Vasella, and S. G. Withers, “Synthesis and evaluation as irreversible glycosidase inhibitors of mono- and oligo(glycosylthio)benzoquinones,” Helvetica Chimica Acta, vol. 77, no. 3, pp. 778–799, 1994. View at Publisher · View at Google Scholar · View at Scopus
  24. C.-S. Kuhn, J. Lehmann, and J. Steck, “Syntheses and properties of some photolabile β-thioglycosides: potential photoaffinity reagents for β-glycoside hydrolases,” Tetrahedron, vol. 46, no. 9, pp. 3129–3134, 1990. View at Publisher · View at Google Scholar · View at Scopus
  25. B. Brazdova, N. S. Tan, N. M. Samoshina, and V. V. Samoshin, “Novel easily accessible glucosidase inhibitors: 4-hydroxy-5-alkoxy-1,2-cyclohexanedicarboxylic acids,” Carbohydrate Research, vol. 344, no. 3, pp. 311–321, 2009. View at Publisher · View at Google Scholar · View at Scopus
  26. N. S. Tan, B. Brazdova, N. M. Samoshina, and V. V. Samoshin, “Novel inhibitors for fungal glycosidases based on cyclohexane-1, 2-dicarboxylic acids,” Journal of Undergraduate Chemistry Research, vol. 6, no. 4, pp. 186–192, 2007. View at Google Scholar
  27. I. A. Dotsenko, M. Curtis, N. M. Samoshina, and V. V. Samoshin, “Convenient synthesis of 5-aryl(alkyl)sulfanyl-1,10-phenanthrolines from 5,6-epoxy-5,6-dihydro-1,10-phenanthroline, and their activity towards fungal β-d-glycosidases,” Tetrahedron, vol. 67, no. 39, pp. 7470–7478, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. M. M. Gomarteli, A. K. Kulikova, A. K. Tsereteli, A. M. Bezborodov, and G. I. Kvesitadze, “beta-Galactosidase from Penicillium canescens st. 20171,” Applied Biochemistry and Microbiology, vol. 24, no. 1, pp. 16–22, 1988. View at Google Scholar
  29. N. M. Samoshina, L. V. Yugova, P. H. Gross, G. B. Bravova, A. A. Shishkova, and V. V. Samoshin, “Partial purification and characterization of glycosidases from Aspergillus oryzae and Penicillium canescens,” in Proceedings of the 219th National Meeting of the American Chemical Society, p. 160, The American Chemical Society, San Francisco, Calif, USA, 2000.
  30. O. S. Korneeva, N. A. Zherebtsov, and I. V. Cheryomushkina, “Identification of catalytically active groups of Penicillium canescens F-436 beta-galactosidase,” Biochemistry, vol. 66, no. 3, pp. 334–339, 2001. View at Google Scholar
  31. O. A. Sinitsyna, F. E. Bukhtoyarov, A. V. Gusakov et al., “Isolation and properties of major components of Penicillium canescens extracellular enzyme complex,” Biochemistry, vol. 68, no. 11, pp. 1200–1209, 2003. View at Publisher · View at Google Scholar · View at Scopus
  32. I. M. Gracheva and A. Y. Krivova, The Technology of Enzyme Preparations, Elevar, Moscow, Russia, 2000.
  33. A. B. Pardee, F. Jacob, and J. Monod, “The genetic control and cytoplasmic expression of inducibility in the synthesis of β-galactosidase by Escherichia coli,” Journal of Molecular Biology, vol. 1, pp. 165–178, 1959. View at Google Scholar
  34. C. Riou, J. Salmon, M. Vallier, Z. Günata, and P. Barre, “Purification, characterization, and substrate specificity of a novel highly glucose-tolerant β-glucosidase from Aspergillus oryzae,” Applied and Environmental Microbiology, vol. 64, no. 10, pp. 3607–3614, 1998. View at Google Scholar · View at Scopus
  35. X. Bian, X. Fan, C. Ke, Y. Luan, G. Zhao, and A. Zeng, “Synthesis and α-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-β-d-glucopyranosides,” Bioorganic and Medicinal Chemistry, vol. 21, no. 17, pp. 5442–5450, 2013. View at Publisher · View at Google Scholar · View at Scopus
  36. K. Duskova, L. Gude, and M.-S. Arias-Pérez, “N-Phenanthroline glycosylamines: synthesis and copper(II) complexes,” Tetrahedron, vol. 70, no. 5, pp. 1071–1076, 2014. View at Google Scholar
  37. T. M. Wrodnigg and A. E. Stütz, “The two faces of iminoalditols: powerful inhibitors trigger glycosidase activation,” Current Enzyme Inhibition, vol. 8, no. 1, pp. 47–99, 2012. View at Publisher · View at Google Scholar · View at Scopus
  38. Y. Nakagawa, S. Sehata, S. Fujii, H. Yamamoto, A. Tsuda, and K. Koumoto, “Mechanistic study on the facilitation of enzymatic hydrolysis by α-glucosidase in the presence of betaine-type metabolite analogs,” Tetrahedron, vol. 70, no. 35, pp. 5895–5903, 2014. View at Google Scholar
  39. N. M. Samoshina and V. V. Samoshin, “The Michaelis constants ratio for two substrates with a series of fungal (mould and yeast) β-galactosidases,” Enzyme and Microbial Technology, vol. 36, no. 2-3, pp. 239–251, 2005. View at Publisher · View at Google Scholar · View at Scopus
  40. E. Alverson-Banks Avegno, S. J. Hasty, A. R. Parameswar, G. S. Howarth, A. V. Demchenko, and L. D. Byers, “Reactive thioglucoside substrates for β-glucosidase,” Archives of Biochemistry and Biophysics, vol. 537, no. 1, pp. 1–4, 2013. View at Google Scholar
  41. A. E. Stutz, Ed., Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond, Wiley-VCH, Weinheim, Germany, 1999.
  42. P. Compain and O. R. Martin, Eds., Iminosugars: From Synthesis to Therapeutic Applications, John Wiley & Sons, Chichester, UK, 2007.
  43. P. Compain, V. Chagnault, and O. R. Martin, “Tactics and strategies for the synthesis of iminosugar C-glycosides: a review,” Tetrahedron Asymmetry, vol. 20, no. 6-8, pp. 672–711, 2009. View at Publisher · View at Google Scholar · View at Scopus
  44. G. M. Aerts, O. van Opstal, and C. K. de Bruyne, “Mixed inhibition of β-d-glucosidase from Stachybotrys atra by substrate analogues,” Carbohydrate Research, vol. 138, pp. 127–134, 1985. View at Publisher · View at Google Scholar · View at Scopus
  45. V. Gopalan, L. B. Daniels, R. H. Glew, and M. Claeyssens, “Kinetic analysis of the interaction of alkyl glycosides with two human β-glucosidases,” Biochemical Journal, vol. 262, no. 2, pp. 541–548, 1989. View at Google Scholar · View at Scopus
  46. M. S. Cheng, Q. L. Wang, Q. Tian et al., “Total synthesis of methyl protodioscin: a potent agent with antitumor activity,” The Journal of Organic Chemistry, vol. 68, no. 9, pp. 3658–3662, 2003. View at Publisher · View at Google Scholar · View at Scopus
  47. S. Weng, “Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron,” Tetrahedron Letters, vol. 50, no. 46, pp. 6414–6417, 2009. View at Publisher · View at Google Scholar · View at Scopus
  48. J. Kuhn, E. M. Pettersson, B. K. Feld et al., “Sequestration of plant-derived phenolglucosides by larvae of the leaf beetle Chrysomela lapponica: thioglucosides as mechanistic probes,” Journal of Chemical Ecology, vol. 33, no. 1, pp. 5–24, 2007. View at Publisher · View at Google Scholar · View at Scopus
  49. E. M. Montgomery, N. K. Richtmyer, and C. S. Hudson, “Attempts to find new antimalarials. VIII. Phenyl β-D-glucothiosides, diphenyl disulfides, phenyl thiocyanates, and related compounds,” Journal of Organic Chemistry, vol. 11, no. 3, pp. 301–306, 1946. View at Google Scholar · View at Scopus
  50. W. T. Haskins, R. M. Hann, and C. S. Hudson, “Relations between rotatory power and structure in the sugar group. XXXV. Some 2′-naphthyl 1-thioglycopyranosides and their acetates,” Journal of the American Chemical Society, vol. 69, no. 7, pp. 1668–1672, 1947. View at Publisher · View at Google Scholar · View at Scopus
  51. S. A. Galema, J. B. F. N. Engberts, and H. A. van Doren, “Synthesis, purification and liquid-crystalline behaviour of several alkyl 1-thio-D-glycopyranosides,” Carbohydrate Research, vol. 303, no. 4, pp. 423–434, 1997. View at Publisher · View at Google Scholar · View at Scopus
  52. H. Lineweaver and D. Burk, “The determination of enzyme dissociation constants,” Journal of the American Chemical Society, vol. 56, no. 3, pp. 658–666, 1934. View at Publisher · View at Google Scholar · View at Scopus
  53. I. H. Segel, Biochemical Calculations, John Wiley & Sons, New York, NY, USA, 1976.