An efficient approach to the discovery of potent inhibitors against glycosyltransferases

Journal of Medicinal Chemistry

Volumn 53, Issue 15, 2010, Pages 5607-5619

  Hosoguchi, Kensaku ^a   Maeda, Takahiro ^a   Furukawa, Jun Ichi ^a   Shinohara, Yasuro ^a   Hinou, Hiroshi ^a   Sekiguchi, Mitsuaki ^a   Togame, Hiroko ^a   Takemoto, Hiroshi ^a   Kondo, Hirosato Shin Ichiro ^b   Nishimura, Shin Ichiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; FUCOSYLTRANSFERASE; GLYCOSYLTRANSFERASE; GLYCOSYLTRANSFERASE INHIBITOR; ISOTOPE; OLIGOSACCHARIDE; RECOMBINANT ENZYME; SIALYLTRANSFERASE; STABLE ISOTOPE; SUGAR NUCLEOTIDE;

ARTICLE; CYCLOADDITION; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SUBSTRATE; GLYCOSYLATION; HIGH THROUGHPUT SCREENING; IONIZATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; QUANTITATIVE ANALYSIS;

ALKYNES; ANIMALS; AZIDES; DATABASES, FACTUAL; FUCOSYLTRANSFERASES; GLYCOPEPTIDES; GLYCOSYLTRANSFERASES; HUMANS; NUCLEOTIDES; OLIGOSACCHARIDES; RATS; RECOMBINANT PROTEINS; SIALYLTRANSFERASES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77955343889     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100612r     Document Type: Article

References (66)

1. Gabius, H.-J. The Sugar Code-Fundamentals of Glycosciences. Wiley-Blackwell: Weinheim, 2009.
2. Zachara, N. E.; Hart, G. W. The emerging significance of O -GlcNAc in cellular regulation Chem. Rev. 2002, 102, 431-438
3. Ohtsubo, K.; Marth, J. D. Glycosylation in cellular mechanisms of health and disease Cell 2006, 126, 855-867
4. Molinari, M. N -Glycan structure dictates extension of protein folding or onset of disposal Nature Chem. Biol. 2007, 3, 313-320
5. Arnold, J. N.; Wormald, M. R.; Sim, R. B.; Rudd, P. M.; Dwek, R. A. The impact of glycosylation on the biological function and structure of human immunoglobulins Annu. Rev. Immunol. 2007, 25, 21-50
6. Lau, K. S.; Partridge, E. A.; Grigorian, A.; Silvescu, C. I.; Reinhold, V. N.; Demetriou, M.; Dennis, J. W. Complex N -glycan number and degree of branching cooperate to regulate cell proliferation and differentiation Cell 2007, 129, 123-134
7. Taniguchi, N.; Honke, K.; Fukuda, M. Handbook of Glycosyltransferase and Related Genes; Springer: Tokyo, 2002.
8. Breton, C.; Snajdrova, L.; Jeanneau, C.; Koca, J.; Imberty, A. Structures and mechanisms of glycosyltransferases Glycobiology 2006, 16, 29R-37R
9. Pratt, M. R.; Hang, H. C.; Ten Hagen, K. G.; Rarick, J.; Gerken, T. A.; Tabak, L. A.; Bertozzi, C. R. Deconvoluting the functions of polypeptide N -a-acetylgalactosaminyltransferase family members by glycopeptide substrate profiling Chem. Biol. 2004, 11, 1009-1016
10. Countinho, P. M.; Deleury, E.; Davies, G. J.; Henrissat, B. An evolving hierarchical family classification for glycosyltransferases J. Mol. Biol. 2003, 328, 307-317
11. Davies, G. J.; Henrissat, B. Structures and mechanisms of glycosyl hydrolases Structure 1995, 3, 853-859
12. Hollingsworth, M. A.; Swanson, B. J. Mucins in cancer: protection and control of the cell surface Nature Rev. Cancer 2004, 4, 45-60
13. Shriver, Z.; Raguram, S.; Sasisekharan, R. Glycomics: A pathway to a class of new and improved therapeutics Nature Rev. Drug Discovery 2004, 3, 863-873
14. Ludwig, J. A.; Weinstein, J. N. Biomarkers in cancer staging, prognosis and treatment selection Nature Rev. Cancer 2005, 5, 845-856
15. Dube, D. H.; Bertozzi, C. R. Glycans in cancer and inflammation - potential for therapeutics and diagnostics Nature Rev. Drug Discovery 2005, 4, 477-488
16. Schaub, C.; Muller, B.; Schmidt, R. R. New sialyltransferase inhibitors based on CMP-quinic acid: development of a new sialyltransferase assay Glycoconjgate J. 1998, 15, 345-354
17. Amann, F.; Schaub, C.; Muller, B.; Schmidt, R. R. New potent sialyltransferase inhibitors: synthesis of donor and of transition-state analogues of sialyl donor CMP-Neu5Ac Chem. - Eur. J. 1998, 4, 1106-1115 (Pubitemid 28295438)
18. Kajihara, Y.; Kodama, H.; Wakabayashi, T.; Sato, K.-I.; Hashimoto, H. Characterization of inhibitory activities and binding mode of synthetic 6'-modified methyl N -acetyl-β-lactosaminide toward rat liver CMP-D-Neu5Ac: d -galactoside-(2?6)-a- d -sialyltransferase Carbohydr. Res. 1993, 247, 179-193
19. Wu, C. Y.; Hus, C. C.; Chen, S. T.; Tsai, Y. C. Soyasaponin I, a potent and specific sialyltransferase inhibitor Biochem. Biophys. Res. Commun. 2001, 284, 466-469
20. Hinou, H.; Sun, X.-L.; Ito, Y. Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases J. Org. Chem. 2003, 68, 5602-5613
21. Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. A potent and highly selective inhibitor of human a1,3-fucosyltransferase via click chemistry J. Am. Chem. Soc. 2003, 125, 9588-9589
22. Izumi, M.; Wada, K.; Yuasa, H.; Hashimoto, H. Synthesis of bisubstrate and donor analogues of sialyltransferase and their inhibitory activities J. Org. Chem. 2005, 70, 8817-8824
23. Lin, T. W.; Chang, W. W.; Chen, C. C.; Tsai, Y. C. Stachybotrydial, a potent inhibitor of fucosyltransferase and sialyltransferase Biochem. Biophys. Res. Commun. 2005, 331, 953-957
24. Takaya, K.; Nagahori, N.; Kurogochi, M.; Furuike, T.; Miura, N.; Monde, K.; Lee, Y. C.; Nishimura, S.-I. Rational design, synthesis, and characterization of novel inhibitors for human β1,4-galactosyltransferase J. Med. Chem. 2005, 341, 6054-6065
25. Chang, K. H.; Lee, L.; Chen, J.; Li, W. S. Lithocholic acid analogues, new and potent alpha-2,3-sialyltransferase inhibitors Chem. Commun. 2006, 629-631
26. Taylor, G. Sialidases: structures, biological significance and therapeutic potential Curr. Opin. Struct. Biol. 1996, 6, 830-837
27. Taylor, N. R.; Itzstein, M. Molecular modeling studies on ligand binding to sialidase from influenza virus and the mechanism of catalysis J. Med. Chem. 1994, 37, 616-624
28. Chiu, C. P.; Watts, A. G.; Lairson, L. L.; Gilbert, M.; Lim, D.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. Structural analysis of the sialyltransferase CstII from Campylobacter jejuni in complex with a substrate analog Nature Struct. Mol. Biol. 2004, 11, 163-170
29. Fritz, T. A.; Hurley, J. H.; Trinh, L.-B.; Shiloach, J.; Tabak, L. A. The beginnings of mucin biosynthesis: the crystal structure of UDP-GalNAc: polypeptide a- N -acetylgalactosaminyltransferase-T1 Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 15307-15312
30. Qasba, P. K.; Ramakrishnan, B.; Boeggeman, E. Substrate-induced conformational changes in glycosyltransferases Trends Biochem. Sci. 2005, 30, 53-62
31. Fritz, T. A.; Raman, J.; Tabak, T. A. Dynamic association between the catalytic and lectin domains of human UDP-GalNAc: polypeptide a- N -acetylgalactosaminyltransferase-2 J. Biol. Chem. 2006, 281, 8613-8619
32. Chiu, C. P.; Lairson, L. L.; Gilbert, M.; Wakarchuk, W. W.; Withers, S. G.; Strynadka, N. C. Structural analysis of the alpha-2,3-sialyltransferase Cst-I from Campylobacter jejuni in apo and substrate-analogue bound forms Biochemistry 2007, 46, 7196-7204
33. Ni, L.; Chokhawala, H. A.; Cao, H.; Henning, R.; Ng, L.; Huang, S.; Yu, H.; Chen, X.; Fisher, A. J. Crystal structures of Pasteurella multocida sialyltransferase complexes with acceptor and donor analogues reveal substrate binding sites and catalytic mechanism Biochemistry 2007, 46, 6288-6298
34. Rao, F. V.; Rich, J. R.; Rakic, B.; Buddai, S.; Schwartz, M. F.; Johnson, K.; Bowe, C.; Wakarchuk, W. W.; DeFrees, S.; Withers, S. G.; Strynadka, N. C. J. Structural insight into mammalian sialyltransferases Nature Struct. Mol. Biol. 2009, 16, 1186-1188
35. Pesnot, T.; Jørgensen, R.; Palcic, M. M.; Wagner, G. K. Structure and mechanistic basis for a new mode of glycosyltransferases inhibition Nature Chem. Biol. 2010, 6, 321-323
36. Schindler, T.; Bornmann, W.; Pellicena, P.; Miller, W. T.; Clarkson, B.; Kuriyan, J. Structural mechanism for STI-571 inhibition of Abelson tyrosine kinase Science 2000, 289, 1938-1942
37. Liu, Y.; Gray, N. S. Rational design of inhibitors that bind to inactive kinase conformations Nature Chem. Biol. 2006, 2, 358-364
38. Klebl, B. M.; Müller, G. Second-generation kinase inhibitors Expert Opin. Ther. Targets 2005, 9, 975-993
39. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
40. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 2002, 67, 3057-3064
41. Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery Drug Discovery Today 2003, 8, 1128-1137
42. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Polytriazoles as Copper(I)-Stabilizing Ligands in Catalysis Org. Lett. 2004, 6, 2853-2855
43. Meldal, M.; Tornøe, C. W. Cu-Catalyzed azide-alkyne cycloaddition Chem. Rev. 2008, 108, 2952-3015
44. Kondo, N.; Nishimura, S.-I. MALDI-TOF Mass spectrometry-based versatile method for the characterization of protein kinases Chem. - Eur. J. 2009, 15, 1413-1421
45. Amano, M.; Yamaguchi, M.; Takegawa, Y.; Yamashita, T.; Terashima, M.; Furukawa, J.-I; Miura, Y.; Shinohara, Y.; Iwasaki, N.; Minami, A.; Nishimura, S.-I. Threshold in stage-specific embryonic glycotypes uncovered by a full portrait of dynamic N -glycan expression during cell differentiation Mol. Cell. Proteomics 2010, 9, 523-537
46. Shinohara, Y.; Furukawa, J-i.; Niikura, K.; Miura, N.; Nishimura, S. -I. Direct N -glycan profiling in the presence of tryptic peptides on MALDI-TOF by controlled ion enhancement and suppression upon glycan-selective derivatization Anal. Chem. 2004, 76, 6989-6997
47. Furukawa, J.; Shinohara, Y.; Kuramoto, H.; Miura, Y.; Shimaoka, H.; Kurogochi, M.; Nakano, M.; Nishimura, S.-I. Comprehensive approach to structural and functional glycomics based on chemoselective glycoblotting and sequential tag conversion Anal. Chem. 2008, 80, 1094-1101
48. Srivastava, G.; Kaur, K. J.; Hindsgaul, O.; Palcic, M. M. Enzymatic transfer of a preassembled trisaccharide antigen to cell surfaces using a fucosyltransferase J. Biol. Chem. 1992, 267, 22356-22361
49. Washiya, K.; Furuike, T.; Nakajima, F.; Lee, Y. C.; Nishimura, S.-I. Design of fluorogenic substrates for continuous assay of sialyltransferase by resonance energy transfer Anal. Biochem. 2000, 283, 39-48
50. Sawa, M.; Hsu, T.-L.; Itoh, T.; Sugiyama, M.; Hanson, S. R.; Vogt, P. K; Wong, C.-H. Glycoproteomic probe for fluorescent imaging of fucosylated glycans in vivo Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12371-12376
51. Brossmer, R.; Rose, U.; Kasper, D.; Smith, T. L.; Grasmuk, H.; Unger, F. M. Enzymic synthesis of 5-acetamido-9-azido-3,5,9-trideoxy- d -glycero- d -galacto-2-nonulosonic acid, a 9-azido-9-deoxy derivative of N -acetylneuraminic acid Biochem. Biophys. Res. Commun. 1980, 96, 1282-1289
52. Liu, J. L.-C.; Shen, G.-J.; Ichikawa, Y.; Rutan, J. F.; Zapata, G.; Willie F. Vann, W. F. V.; Wong, C.-H. Overproduction of CMP-sialic acid synthetase J. Am. Chem. Soc. 1992, 114, 3901-3910
53. Yu, H.; Yu, H.; Karpel, R.; Chen, X. Chemoenzymatic synthesis of CMP-sialic acid derivatives by one-pot two-enzyme system: comparison of substrate flexibility of three microbial CMP-sialic acid synthetases Bioorg. Med. Chem. 2004, 12, 6427-6435
54. Luchansky, S. J.; Goon, S.; Bertozzi, C. R. Expanding the diversity of unnatural cell-surface sialic acids ChemBioChem 2004, 5, 371-374
55. Maeda, T.; Nishimura, S.-I. FRET-based direct and continuous monitoring of human fucosyltransferases activity: efficient synthesis of versatile GDP- l -fucose derivatives from abundant d -galactose Chem. - Eur. J. 2007, 14, 478-487
56. Nishimura, S.-I.; Niikura, K.; Kurogochi, M.; Matsushita, T.; Fumoto, M.; Hinou, H.; Kamitani, R.; Nakagawa, H.; Deguchi, K.; Miura, N.; Monde, K.; Kondo, H. High-throughput protein glycomics: combined use of chemoselective glycoblotting and MALDI-TOF/TOF mass spectrometry Angew. Chem., Int. Ed. 2004, 44, 91-96
57. Miura, Y.; Hato, M.; Shinohara, Y.; Kuramoto, H.; Furukawa, J.; Kurogochi, M.; Shimaoka, H.; Tada, M.; Nakanishi, K.; Ozaki, M.; Todo, S.; Nishimura, S.-I. BlotGlycoABC, an integrated glycoblotting technique for rapid and large scale clinical glycomics Mol. Cell. Proteomics 2008, 7, 370-377
58. Seko, A.; Koketsu, M.; Nishizono, M.; Enoki, Y.; Ibrahim, H. R.; Juneja, L. R.; Kim, M.; Yamamoto, T. Occurrence of a sialylglycopeptide and free sialylglycans in hen's egg yolk Biochim. Biophys. Acta 1997, 1335, 23-32
59. Jung, K.-H.; Schwörer, R.; Schmidt, R. R. Sialyltransferase inhibitors Trends Glycosci. Glycotechnol. 2003, 15, 275-289
60. Kleineidam, R. G.; Schmelter, T.; Schwarz, R. T.; Schauer, R. Studies on the inhibition of sialyl- and galactosyltransferases Glycoconjugate J. 1997, 14, 57-66
61. Whalen, L. J.; McEvoy, K. A.; Halcomb, R. L. Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases Bioorg. Med. Chem. Lett. 2003, 13, 301-304
62. Prieels, J. P.; Monnom, D.; Dolmans, M. Co-purification of the Lewis blood group N -acetylglucosaminide a1,4-fucosyltransferase and N -acetylglucosaminide a1,3-fucosyltransferase from human milk J. Biol. Chem. 1981, 256, 10456-10463
63. Wong, C.-H.; Dumas, D. P.; Ichikawa, Y.; Koseki, K.; Danishefsky, S. J.; Weston, B. W.; Lowe, J. B. Specificity, inhibition, and synthetic utility of a recombinant human a 1,3-fucosyltransferase J. Am. Chem. Soc. 1992, 114, 7321-7322
64. Ihara, H.; Ikeda, Y.; Taniguchi, N. Reaction mechanism and substrate specificity for nucleotide sugar of mammalian a1,6-fucosyltransferase: A large-scale preparation and characterization of recombinant human FUT8 Glycobiology 2006, 16, 333-342
65. Matsuoka, K.; Oka, H.; Terunuma, D.; Kuzuhara, H. Synthesis and reactivity of a 5-azido analogue of neuramic acid Carbohydr. Lett. 2001, 4, 123-130
66. Tanaka, H.; Nishiura, Y.; Adachi, M.; Takahashi, T. Synthetic study of a(2,8) oligosialoside using N -troc sialyl N -phenyltrifluoroimidate Heterocycles 2006, 67, 107-112