Inhibitory effects and specificity of synthetic sialyldendrimers toward recombinant human cytosolic sialidase 2 (NEU2)

Glycobiology

Volumn 23, Issue 4, 2013, Pages 495-504

  Rahman, M Motiur ^a   Kitao, Satoshi ^a   Tsuji, Daisuke ^a,b   Suzuki, Kaori ^c   Sakamoto, Jun Ichi ^c   Matsuoka, Koji ^c   Matsuzawa, Fumiko ^d   Aikawa, Sei Ichi ^d   Itoh, Kohji ^a,b  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b NATIONAL VETERINARY ASSAY LABORATORY   (Japan)

^c SAITAMA UNIVERSITY   (Japan)

^d Altif Laboratories Inc   (Japan)

Author keywords

docking model; inhibitor; sialidase 2; sialyldendrimers; thiosialyloligosaccharides

Indexed keywords

CARBOHYDRATE DERIVATIVE; DENDRIMER; GALACTOSE; GLUCOSE; HYDROGEN; SIALIDASE; SIALIDASE 2; SIALYLDENDRIMER; THIOSIALYLDISACCHARIDE; THIOSIALYLOLIGOSACCHARIDE; THIOSIALYLTRISACCHARIDE; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CATALYSIS; HYDROGEN BOND; IC 50; IN VITRO STUDY; MOLECULAR DOCKING; PREDICTION; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS; WILD TYPE;

AMINO ACID SEQUENCE; BINDING SITES; CARBOHYDRATE SEQUENCE; DENDRIMERS; ENZYME INHIBITORS; GALACTOSE; GLUCOSE; HYDROGEN BONDING; MOLECULAR DOCKING SIMULATION; MOLECULAR SEQUENCE DATA; MUTATION, MISSENSE; N-ACETYLNEURAMINIC ACID; NEURAMINIDASE; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY; TRISACCHARIDES;

EID: 84874690469     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cws221     Document Type: Article

References (28)

1. Achyuthan KE, Achyuthan AM. 2001. Comparative enzymology, biochemistry and pathophysiology of human exo-alpha-sialidases (neuraminidases). Comp Biochem Physiol. 129:29-64. (Pubitemid 32401124)
2. Albohy A, Li MD, Zheng RB, Zou C, Cairo CW. 2010. Insight into substrate recognition and catalysis by the human neuraminidase 3 (NEU3) through molecular modeling and site-directed mutagenesis. Glycobiology. 20:1127-1138.
3. Amaya MF, Watts AG, Damager I, Wehenkel A, Nguyen T, Buschiazzo A, Paris G, Frasch AC, Withers SG, Alzari PM. 2004. Structural insights into the catalytic mechanism of Trypanosoma cruzi trans-sialidase. Structure. 12:775-784. (Pubitemid 38595766)
4. Burk D, Lineweaver H. 1930. The influence of fixed nitrogen on Azotobacter. J Bacteriol. 19:389-414.
5. Buschiazzo A, Alzari PM. 2008. Structural insights into sialic acid enzymology. Curr Opin Chem Biol. 12:565-572.
6. Cabezas JA. 1991. Some questions and suggestions on the type references of the official nomenclature (IUB) for sialidase(s) and endosialidase. Biochem J. 278:311-312.
7. Chavas LMG, Kato R, Suzuki N, Itzstein MV, Mann MC, Thomson RJ, Dyason JC, Breschkin JM, Fusi P, Tringali C, et al. 2010. Complexity in influenza virus targeted drug design: Interaction with human sialidases. J Med Chem. 53(7):2998-3002.
8. Chavas LMG, Tringali C, Fusi P, Venerando B, Tettamanti G, Kato R, Monti E, Wakatsuki S. 2005. Crystal structure of the human cytosolic sialidase Neu2. J Biol Chem. 280:469-475.
9. Comelli EM, Amado M, Lustig SR, Paulson JC. 2003. Identification and expression of NEU4, a novel murine sialidase. Gene. 321:155-161. (Pubitemid 37421406)
10. Guex N, Peitsch MC. 1997. SWISS-MODEL and the Swiss-PdbViewer: An environment for comparative protein modeling. Electrophoresis. 18:2714-2723. (Pubitemid 28059943)
11. Hata K, Koseki K, Yamaguchi K, Moriya S, Suzuki Y, Yingsakmongkon S, Hirai G, Sodeoka M, Itzstein MV, Miyagi T. 2008. Limited inhibitory effects of oseltamivir and zanamivir on human sialidases. Antimicrob Agents Chemother. 52:3484-3491.
12. Itzstein VM. 2007. The war against influenza: Discovery and development of sialidase inhibitors. Nat Rev. 6:967-974.
13. Itzstein VM, Thomson R. 2009. Anti-influenza drugs: The development of sialidase inhibitors. Handb Exp Pharmacol. 189:111-154.
14. Laemmli UK. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 227:680-685.
15. Li CY, Yu Q, Ye ZQ, Sun Y, He Q, Li XM, Zhang W, Luo J, Gu X, Zheng X, et al. 2007. A nonsynonymous SNP in human cytosolic sialidase in a small Asian population results in reduced enzyme activity: Potential link with severe adverse reactions to oseltamivir. Cell Res. 17:357-362. (Pubitemid 46639940)
16. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. 1951. Protein measurement with the folin-phenol reagents. J Biol Chem. 193:265-275.
17. Magesh S, Savita V, Moriya S, Suzuki T, Miyagi T, Ishida H, Kiso M. 2009. Human sialidase inhibitors: Design, synthesis, and biological evaluation of 4-acetamido-5-acylamido-2-fluoro benzoic acids. Bioorg Med Chem. 17:4595-4603.
18. Magesh S, Suzuki T, Miyagi T, Ishida H, Kiso M. 2006. Homology modeling of human sialidase enzymes NEU1, NEU3 and NEU4 based on the crystal structure of NEU2: Hints for the design of selective NEU3 inhibitors. J Mol Graph. 25:196-207. (Pubitemid 44345275)
19. Miyagi T, Hata K, Hasegawa A, Aoyagi T. 1993. Differential effect of various inhibitors on four types of rat sialidase. Glycoconj J. 10:45-49. (Pubitemid 23168570)
20. Miyagi T, Yamaguchi K. 2012. Mammalian sialidases: Physiological and pathological roles in cellular functions. Glycobiology. 22:880-896.
21. Monti E, Bassi MT, Bresciani R, Civini S, Croci GL, Papini N, Riboni M, Zanchetti G, Ballabio A, Preti A, et al. 2004. Molecular cloning and characterization of NEU4, the fourth member of the human sialidase gene family. Genomics. 83:445-453. (Pubitemid 38220849)
22. Monti E, Bonten E, D' Azzo A, Bresciani R, Venerando B, Borsani G, Schauer R, Tettamanti G. 2010. Sialidases in vertebrates: A family of enzymes tailored for several cell functions. Adv Carbohydr Chem Biochem. 64:403-479.
23. Mozzi A, Mazzacuva P, Zampella G, Forcella ME, Fusi PA, Monti E. 2012. Molecular insight into substrate recognition by human cytosolic sialidase NEU2. Proteins. 80:1123-1132.
24. Oka H, Onaga T, Koyama T, Guo CT, Suzuki Y, Esumi Y, Hatano K, Terunuma D, Matsuoka K. 2009. Synthesis and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses. Bioorg Med Chem Lett. 17:5465-5475.
25. Saito M, Yu RK. 1995. Biochemistry and function of sialidases. In: Rosenberg A, editor. Biology of the Sialic Acids. New York (NY): Plenum Press. p. 261-313.
26. Sakamoto JI, Koyama T, Miyamoto D, Yingsakmongkon S, Hidari KIPJ, Jampangern W, Suzuki T, Suzuki Y, Esumi Y, Nakamura T, et al. 2009. Systematic synthesis of influenza neuraminidase inhibitors: A series of carbosilane dendrimers uniformly functionalized with thioglycoside-type sialic acid moieties. Bioorg Med Chem Lett. 17:5451-5464.
27. Tringali C, Papini N, Fusi P, Croci G, Borsani G, Preti A, Tortora P, Tettamanti G, Venerando B, Monti E. 2004. Properties of recombinant human cytosolic sialidase HsNEU2. The enzyme hydrolyzes monomerically dispersed GM1 ganglioside molecules. J Biol Chem. 279: 3169-3179. (Pubitemid 38140549)
28. Wang Q, Wolff M, Polat T, Du Y, Linhardt RJ. 2000. Inhibition of neuraminidase with neuraminic acid C-glycosides. Bioorg Med Chem Lett. 10: 941-944. (Pubitemid 30301598)