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A colorimetric method for α-glucosidase activity assay and its inhibitor screening based on aggregation of gold nanoparticles induced by specific recognition between phenylenediboronic acid and 4-aminophenyl-α-D-glucopyranoside
Genxi Li1,2(
)
)Abstract
A colorimetric method has been established for α-glucosidase activity assay and its inhibitor screening. The method is based on the specific recognition between 1, 4-phenylenediboronic acid (PDBA) and 4-aminophenyl-α-D-glucopyranoside (pAPG), which may induce aggregation of pAPG-functionalized gold nanoparticles (AuNPs) to achieve color change of the test solution. Because pAPG is the substrate of α-glucosidase, the aggregation of AuNPs will be influenced by α-glucosidase since there is no coordination reactivity between PDBA and 4-aminobenzene, the hydrolyzed product of pAPG catalyzed by the enzyme. Therefore, a simple and easily-operated colorimetric method for the assay of α-glucosidase activity can be developed. Under the optimized experimental conditions, the ratios of absorbance at a wavelength of 650 nm to that at 520 nm vary linearly with the α-glucosidase activity within a range from 0.05 to 1.1 U/mL with a lowest detection limit of 0.004 U/mL. Moreover, using the proposed method, the inhibition effect of gallic acid and quercetin on α-glucosidase activity can be tested with IC50 values of 1.16 mM and 1.82 μM, respectively. Thus, the method has a great potential not only for the detection of α-glucosidase activity, but also for the screening of its inhibitors.
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1
Zhang, B.; Chen, T.; Chen, Z.; Wang, M.; Zheng, D.; Wu, J.; Jiang, X.; Li, X. Synthesis and anti-hyperglycemic activity of hesperidin derivatives. Bioorg. Med. Chem. Lett. 2012, 22, 7194-7197.
2
Shimodaira, M.; Muroya, Y.; Kumagai, N.; Tsuzawa, K.; Honda, K. Effects of short-term intensive glycemic control on insulin, glucagon, and glucagon-like peptide-1 secretion in patients with type 2 diabetes. J. Endocrinol. Invest. 2013, 36, 734-738.
3
Huang, X. C.; Tanaka, K. S. E.; Bennet, A. J. Glucosidase-catalyzed hydrolysis of α-D-glucopyranosyl pyridinium salts: Kinetic evidence for nucleophilic involvement at the glucosidation transition state. J. Am. Chem. Soc. 1997, 119, 11147-11154.
4
Hansawasdi, C.; Kawabata, J. Alpha-glucosidase inhibitory effect of mulberry (morus alba) leaves on CaCo-2. Fitoterapia 2006, 77, 568-573.
5
Puls, W.; Keup, U.; Krause, H. P.; Thomas, G.; Hoffmeister, F. Glucosidase inhibition. A new approach to the treatment of diabetes, obesity, and hyperlipoproteinaemia. Naturwissenschaften 1977, 64, 536-537.
6
Kim, J. H.; Ryu, Y. B.; Kang, N. S.; Lee, B. W.; Heo, J. S.; Jeong, I. Y.; Park, K. H. Glycosidase inhibitory flavonoids from Sophora flavescens. Biol. Pharm. Bull. 2006, 29, 302-305.
7
Li, Y. H.; Wen, S. P.; Kota, B. P.; Peng, G.; Li, G. Q.; Yamahara, J.; Roufogalis, B. D. Punica granatum flower extract, a potent α-glucosidase inhibitor, improves postprandial hyperglycemia in Zucker diabetic fatty rats. J. Ethnopharmacol. 2005, 99, 239-244.
8
Oki, T.; Matsui, T.; Osajima, Y. Inhibitory effect of α-glucosidase inhibitors varies according to its origin. J. Agric. Food Chem. 1999, 47, 550-553.
9
Matsui, T.; Yoshimoto, C.; Osajima, K.; Oki, T.; Osajima, Y. In vitro survey of α-glucosidase inhibitory food components. Biosci. Biotechnol. Biochem. 1996, 60, 2019-2022.
10
Sawada, Y.; Tsuno, T.; Ueki, T.; Yamamoto, H.; Fukagawa, Y.; Oki, T. Pradimicin Q, a new pradimicin aglycone, with α-glucosidase inhibitory activity. J. Antibiot. 1993, 46, 507-510.
11
Song, G.; Chen, C.; Ren, J.; Qu, X. A simple, universal colorimetric assay for endonuclease/methyltransferase activity and inhibition based on an enzyme-responsive nanoparticle system. ACS Nano 2009, 3, 1183-1189.
12
Deng, J.; Jiang, Q.; Wang, Y.; Yang, L.; Yu, P.; Mao, L. Real-time colorimetric assay of inorganic pyrophosphatase activity based on reversibly competitive coordination of Cu2+ between cysteine and pyrophosphate ion. Anal. Chem. 2013, 85, 9409-9415.
13
Storhoff, J. J.; Lucas, A. D.; Garimella, V.; Bao, Y. P.; Muller, U. R. Homogeneous detection of unamplified genomic DNA sequences based on colorimetric scatter of gold nanoparticle probes. Nat. Biotechnol. 2004, 22, 883-887.
14
Storhoff, J. J.; Elghanian, R.; Mucic, R. C.; Mirkin, C. A.; Letsinger, R. L. One-pot colorimetric differentiation of polynucleotides with single base imperfections using gold nanoparticle probes. J. Am. Chem. Soc. 1998, 120, 1959-1964.
15
Chen, C.; Zhao, C.; Yang, X.; Ren, J.; Qu, X. Enzymatic manipulation of DNA-modified gold nanoparticles for screening G-quadruplex ligands and evaluating selectivities. Adv. Mater. 2010, 22, 389-393.
16
Pan, B. F.; Ao, L. M.; Gao, F.; Tian, H. Y.; He, R.; Cui, D. X. End-to-end self-assembly and colorimetric characterization of gold nanorods and nanospheres via oligonucleotide hybridization. Nanotechnology 2005, 16, 1776-1780.
17
Guarise, C.; Pasquato, L.; De Filippis, V.; Scrimin, P. Gold nanoparticles-based protease assay. Proc. Natl. Acad. Sci. USA 2006, 103, 3978-3982.
18
Wang, Z. X.; Levy, R.; Fernig, D. G.; Brust, M. Kinase-catalyzed modification of gold nanoparticles: A new approach to colorimetric kinase activity screening. J. Am. Chem. Soc. 2006, 128, 2214-2215.
19
Xu, X.; Han, M. S.; Mirkin, C. A. A gold-nanoparticle-based real-time colorimetric screening method for endonuclease activity and inhibition. Angew. Chem. Int. Ed. 2007, 46, 3468-3470.
20
Lee, J. S.; Han, M. S.; Mirkin, C. A. Colorimetric detection of mercuric ion (Hg2+) in aqueous media using DNA-functionalized gold nanoparticles. Angew. Chem. Int. Ed. 2007, 46, 4093-4096.
21
Li, W.; Feng, L.; Ren, J.; Wu, L.; Qu, X. Visual detection of glucose using conformational switch of i-motif DNA and non-crosslinking gold nanoparticles. Chem. Eur. J. 2012, 18, 12637-12642.
22
Yum, K.; Ahn, J. H.; McNicholas, T. P.; Barone, P. W.; Mu, B.; Kim, J. H.; Jain, R. M.; Strano, M. S. Boronic acid library for selective, reversible near-infrared fluorescence quenching of surfactant suspended single-walled carbon nanotubes in response to glucose. ACS Nano 2012, 6, 819-830.
23
Shoji, E.; Freund, M. S. Potentiometric saccharide detection based on the pKa changes of poly(aniline boronic acid). J. Am. Chem. Soc. 2002, 124, 12486-12493.
24
Deng, J.; Yu, P.; Yang, L.; Mao, L. Competitive coordination of Cu2+ between cysteine and pyrophosphate ion: Toward sensitive and selective sensing of pyrophosphate ion in synovial fluid of arthritis patients. Anal. Chem. 2013, 85, 2516-2522.
25
Gu, Y. J.; Cheng, J.; Lin, C. C.; Lam, Y. W.; Cheng, S. H.; Wong, W. T. Nuclear penetration of surface functionalized gold nanoparticles. Toxicol. Appl. Pharmacol. 2009, 237, 196-204.
26
Tian, Q.; Zhang, C. N.; Wang, X. H.; Wang, W.; Huang, W.; Cha, R. T.; Wang, C. H.; Yuan, Z.; Liu, M.; Wan, H. Y.; et al. Glycyrrhetinic acid-modified chitosan/poly(ethylene glycol) nanoparticles for liver-targeted delivery. Biomaterials 2010, 31, 4748-4756.
27
Grabar, K. C.; Freeman, R. G.; Hommer, M. B.; Natan, M. J. Preparation and characterization of Au colloid monolayers. Anal. Chem. 1995, 67, 735-743.
28
Li, H.; Rothberg, L. Colorimetric detection of DNA sequences based on electrostatic interactions with unmodified gold nanoparticles. Proc. Natl. Acad. Sci. USA 2004, 101, 14036-14039.
29
Mader, H. S.; Wolfbeis, O. S. Boronic acid based probes for microdetermination of saccharides and glycosylated biomolecules. Microchim. Acta 2008, 162, 1-34.
30
Zhu, K.; Zhang, Y.; He, S.; Chen, W.; Shen, J.; Wang, Z.; Jiang, X. Quantification of proteins by functionalized gold nanoparticles using click chemistry. Anal. Chem. 2012, 84, 4267-4270.
31
Liu, D.; Chen, W.; Wei, J.; Li, X.; Wang, Z.; Jiang, X. A highly sensitive, dual-readout assay based on gold nanoparticles for organophosphorus and carbamate pesticides. Anal. Chem. 2012, 84, 4185-4191.
32
Kong, B.; Zhu, A.; Luo, Y.; Tian, Y.; Yu, Y.; Shi, G. Sensitive and selective colorimetric visualization of cerebral dopamine based on double molecular recognition. Angew. Chem. Int. Ed. 2011, 50, 1837-1840.
33
Cao, A.; Tang, Y.; Liu, Y. Novel fluorescent biosensor for α-glucosidase inhibitor screening based on cationic conjugated polymers. ACS Appl. Mater. Interfaces 2012, 4, 3773-3778.
34
Wan, C.; Yuan, T.; Li, L.; Kandhi, V.; Cech, N. B.; Xie, M.; Seeram, N. P. Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems. Bioorg. Med. Chem. Lett. 2012, 22, 597-600.
35
Cirillo, G.; Kraemer, K.; Fuessel, S.; Puoci, F.; Curcio, M.; Spizzirri, U. G.; Altimari, I.; Iemma, F. Biological activity of a gallic acid-gelatin conjugate. Biomacromolecules 2010, 11, 3309-3315.
36
Liu, J.; Lu, J. F.; Kan, J.; Jin, C. H. Synthesis of chitosang-allic acid conjugate: Structure characterization and in vitro anti-diabetic potential. Int. J. Biol. Macromol. 2013, 62, 321-329.
37
Yu, Y.; Xu, Y.; Wu, J.; Xiao, G.; Fu, M.; Zhang, Y. Effect of ultra-high pressure homogenisation processing on phenolic compounds, antioxidant capacity and anti-glucosidase of mulberry juice. Food Chem. 2014, 153, 114-120.
38
Li, Y. Q.; Zhou, F. C.; Gao, F.; Bian, J. S.; Shan, F. Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of α-glucosidase. J. Agric. Food Chem. 2009, 57, 11463-11468.
39
Phan, M. A. T.; Wang, J.; Tang, J.; Lee, Y. Z.; Ng, K. Evaluation of α-glucosidase inhibition potential of some flavonoids from epimedium brevicornum. LWT-Food Sci. Technol. 2013, 53, 492-498.
40
Ito, M.; Yoshioka, A.; Imayoshi, Y.; Koriyama, C.; Moriyama, A. Effect of flavonoids on α-glucosidase and β-fructosidase from yeast. Agric. Biol. Chem. 1984, 48, 1559-1563.
Pages 920-930
Cite this article:
Zhang J, Liu Y, Lv J, et al. A colorimetric method for α-glucosidase activity assay and its inhibitor screening based on aggregation of gold nanoparticles induced by specific recognition between phenylenediboronic acid and 4-aminophenyl-α-D-glucopyranoside. Nano Research, 2015, 8(3): 920-930. https://doi.org/10.1007/s12274-014-0573-1
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