β-secretase inhibitory activity of phenolic acid conjugated chitooligosaccharides

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 28, Issue 1, 2013, Pages 214-217

  Eom, Tae Kil ^a   Ryu, BoMi ^b   Lee, Jung Kwon ^c   Byun, Hee Guk ^c   Park, Sun Joo ^b   Kim, Se Kwon ^b  

^a Hongcheon Institute of Medicinal Herb   (South Korea)

^b Pukyong National University   (South Korea)

^c Gangneung Wonju National University   (South Korea)

Author keywords

secretase; Alzheimer's disease; Chitooligosaccharides; Phenolic acids

Indexed keywords

BETA SECRETASE INHIBITOR; OLIGOSACCHARIDE; PHENOLIC ACID CONJUGATED CHITOOLIGOSACCHARIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME STRUCTURE; ENZYME SYNTHESIS; IC 50; PRIORITY JOURNAL;

AMYLOID PRECURSOR PROTEIN SECRETASES; ASPARTIC ACID ENDOPEPTIDASES; CAFFEIC ACIDS; CHEMISTRY TECHNIQUES, SYNTHETIC; ENZYME INHIBITORS; HUMANS; HYDROXYBENZOATES; INHIBITORY CONCENTRATION 50; OLIGOSACCHARIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84873266593     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.629197     Document Type: Article

References (21)

1. Haass C, Selkoe DJ. Cellular processing of β-amyloid precursor protein and the genesis of amyloid β-peptide. Cell 1993;75:1039-1042
2. LaFerla FM, Green KN, Oddo S. Intracellular amyloid-β in Alzheimer's disease. Nat Rev Neurosci 2007;8:499-509
3. Vassar R, Bennett BD, Babu-Khan S, Kahn S, Mendiaz EA, Denis P et al. β-secretase cleavage of Alzheimer's amyloid precursor protein by the transmembrane aspartic protease BACE. Science 1999;286:735-741
4. Seubert P, Oltersdorf T, Lee MG, Barbour R, Blomquist C, Davis DL et al. Secretion of β-amyloid precursor protein cleaved at the amino terminus of the β-amyloid peptide. Nature 1993;361:260-263 (Pubitemid 23034476)
5. Nunan J, Shearman MS, Checler F, Cappai R, Evin G, Beyreuther K et al. The C-terminal fragment of the Alzheimer's disease amyloid protein precursor is degraded by a proteasome-dependent mechanism distinct from γ-secretase. Eur J Biochem 2001;268:5329-533
6. Nunan J, Williamson NA, Hill AF, Sernee MF, Masters CL, Small DH. Proteasome-mediated degradation of the C-terminus of the Alzheimer's disease β-amyloid protein precursor: Effect of C-terminal truncation on production of β-amyloid protein. J Neurosci Res 2003;74:378-385 (Pubitemid 37362814)
7. Nguyen TV, Galvan V, Huang W, Banwait S, Tang H, Zhang J et al. Signal transduction in Alzheimer disease: P21-activated kinase signaling requires C-terminal cleavage of APP at Asp664. J Neurochem 2008;104:1065-1080 (Pubitemid 351143641)
8. Ravi Kumar MNV. A review of chitin and chitosan applications. React Funct Polym 2000;46:1-27 (Pubitemid 33763425)
9. Kim SK, Rajapakse N. Enzymatic production and biological activities of chitosan oligosaccharides (COS): Review. Carbohydr Polym 2005; 62:357-368 (Pubitemid 41745217)
10. Jeon YJ, Kim SK. Antitumor activity of chitosan oligosaccharides produced in ultrafilteration membrane system. J Microbiol Biotechnol 2002;12:503-507
11. Lee SH, Senevirathne M, Ahn CB, Kim SK, Je JY. Factors affecting anti-inflammatory effect of chitooligosaccharides in lipopolysaccharides-induced RAW264.7 macrophage cells. Bioorg Med Chem Lett 2009;19:6655-6658
12. Je JY, Park PJ, Kim SK. Free radical scavenging properties of heterochitooligosaccharides using an ESR spectroscopy. Food Chem Toxicol 2004;42:381-387
13. Park PJ, Je JY, Byun HG, Moon SH, Kim SK. Antimicrobial activity of hetero-chitosan and their oligosaccharides with different molecular weights. J Microbiol Biotechnol 2004;14: 317-323
14. Van Ta Q, Kim MM, Kim SK. Inhibitory effect of chitooligosaccharides on matrix metalloproteinase-9 in human fibrosarcoma cells (HT1080). Mar Biotechnol 2006;8:593-599 (Pubitemid 46106885)
15. Kumar SG, Rahman MA, Lee SH, Hwang HS, Kim HA, Yun JW. Plasma proteome analysis for anti-obesity and anti-diabetic potentials of chitosan oligosaccharides in ob/ob mice. Proteomics 2009;9:2149-2162
16. Park PJ, Je JY, Kim SK. Angiotensin I converting enzyme (ACE) inhibitory activity of hetero-chitooligosaccharides prepared from partially different deacetylated chitosans. J Agric Food Chem 2003;51:4930-4934
17. Byun HG, Kim YT, Park PJ, Lin X, Kim SK. Chitooligosaccharides as a novel β-secretase inhibitor. Carbohydr Polym 2005;61:198-202
18. Pasanphan W, Chirachanchai S. Conjugation of gallic acid onto chitosan: An approach for green and water-based antioxidant. Carbohydr Polym 2008;72:169-177
19. Je JY, Kim SK. Water-soluble chitosan derivatives as a BACE1 inhibitor. Bioorg Med Chem 2005;13:6551-6555
20. Dixon M. The determination of enzyme inhibitor constants. Biochem J 1953;55:170-171
21. Larson RA. (1997). Naturally occurring antioxidants: Boca Raton, USA: Lewis Publishers. 22. Bittner S. When quinones meet amino acids: Chemical, physical and biological consequences. Amino Acids 2006;30:205-224