Anthraquinonyl glycoside facilitates the standardization of graphene electrodes for the impedance detection of lectins

Chemistry Central Journal

Bi-Wen Zhu¹  Liang Cai¹  Xiao-Peng He¹  Guo-Rong Chen¹  Yi-Tao Long¹ 

[1] Key Laboratory for Advanced Materials & Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, PR China

关键词: Standardization;    EIS;    Electrochemistry;    Lectin;    Glycoside;    Graphene;    Anthraquinone;   

Others  :  1082273
DOI  :  10.1186/s13065-014-0067-y

 received in 2014-07-09, accepted in 2014-10-30,  发布年份 2014

【 摘 要 】

Background

Construction of electrochemical impedance sensors by the self-assembly technique has become a promising strategy for the ‘label-free’ detection of protein-ligand interactions. However, previous impedance sensors are devoid of an inherent electrochemical signal, which limits the standardization of the sensors for protein recognition in a reproducible manner.

Results

We designed and synthesized an anthraquinonyl glycoside (AG) where the anthraquinone (AQ) moiety can bind to the surface of a graphene-based working electrode while the glycoside serving as a ligand for lectin. By measuring the inherent voltammetric signal of AQ, the glycosides decorated on the working electrode could be simply quantified to obtain electrodes with a unified signal window. Subsequently, impedance analysis showed that the ‘standardized’ electrodes gave a reproducible electrochemical response to a selective lectin with no signal variation in the presence of unselective proteins.

Conclusion

Anthraquinone-modified ligands could be used to facilitate the standardization of electrochemical impedance sensors for the reproducible, selective analysis of ligand-protein interactions.

【 授权许可】

   
2014 Zhu et al.; licensee Springer.

【 图 表 】

Figure 1.

Figure 2.

Figure 3.

Figure 4.

【 参考文献 】

• [1]Chen Y, Star A, Vidal S: Sweet carbon nanostructures: carbohydrate conjugates with carbon nanotubes and graphene and their applications. Chem Soc Rev 2013, 42:4532-4552.
• [2]Vedala H, Chen Y, Cecioni S, Imberty A, Vidal S, Star A: Nanoelectronic detection of lectin-carbohydrate interactions using carbon nanotubes. Nano Lett 2011, 11:170-175.
• [3]He XP, Wang XW, Jin XP, Zhou H, Shi XX, Chen GR, Long YT: Epimeric monosaccharide-quinone hybrids on gold electrodes toward the electrochemical probing of specific carbohydrate-protein recognitions. J Am Chem Soc 2011, 133:3649-3657.
• [4]Zhang HL, Wei XL, Zang Y, Cao JY, Liu S, He XP, Chen Q, Long YT, Li J, Chen GR, Chen K: Fluorogenic probing of specific recognitions between sugar ligands and glycoprotein receptors on cancer cells by an economic graphene nanocomposite. Adv Mater 2013, 25:4097-4101.
• [5]Li Z, Deng SS, Zang Y, Gu Z, He XP, Chen GR, Chen K, James TD, Li J, Long YT: Capturing intercellular sugar-mediated ligand-receptor recognitions via a simple yet highly biospecific interfacial system.Sci Rep 2013, 3:2293.
• [6]Bertók T, Katrlík J, Gemeiner P, Tkac J: Electrochemical lectin based biosensors as a label-free tool in glycomics. Microchim Acta 2013, 180:1-13.
• [7]Min IM, Choi L, Ahn KS, Kim BK, Lee BY, Kim KS, Choi HN, Lee WY: Electrochemical determination of carbohydrate-binding proteins using carbohydrate-stabilized gold nanoparticles and silver enhancement. Biosens Bioelectron 2010, 26:1326-1331.
• [8]Bertok T, Sediva A, Katrlik J, Gemeiner P, Mikula M, Nosko M, Tkac J: Label-free detection of glycoproteins by the lectin biosensor down to attomolar level using gold nanoparticles. Talanta 2013, 108:11-18.
• [9]Hu Y, Zuo P, Ye BC: Label-free electrochemical impedance spectroscopy biosensor for direct detection of cancer cells based on the interaction between carbohydrate and lectin. Biosens Bioelectron 2013, 43:79-83.
• [10]Oliveira MDL, Andrade CAS, Correia MTS, Coelho LCBB, Singh PR, Zeng X: Impedimetric biosensor based on self-assembled hybrid cystein-gold nanoparticles and CramoLL lectin for bacterial lipopolysaccharide recognition. J Colloid Interface Sci 2011, 362:194-201.
• [11]Loaiza OA, Lamas-Ardisana PJ, Jubete E, Ochoteco E, Loinaz I, Cabañero G, García I, Penadés S: Nanostructured disposable impedimetric sensors as tools for specific bimolecular interactions: sensitive recognition of concanavalin A. Anal Chem 2011, 83:2987-2995.
• [12]Bertok T, Gemeiner P, Mikula M, Gemeiner P, Tkac J: Ultrasensitive impedimetric based biosensor for glycoproteins containing sialic acid. Microchim Acta 2013, 180:151-159.
• [13]Zhang X, Teng Y, Fu Y, Zhang S, Wang T, Wang C, Jin L, Zhang W: Lectin-based electrochemical biosensor constructed by functionalized carbon nanotubes for the competitive assay of glycan expression on living cancer cells. Chem Sci 2011, 2:2353-2360.
• [14]Chen H, Xi F, Gao X, Chen Z, Lin X: Bienzyme bionanomultilayer electrode for glucose biosensing on functional carbon nanotubes and sugar-lectin biospecific interaction. Anal Biochem 2010, 403:36-42.
• [15]Zhang Y, Luo S, Tang Y, Yu L, Hou KY, Cheng JP, Zeng X, Wang PG: Carbohydrate-protein interactions by “clicked” carbohydrate self-assembled monolayers. Anal Chem 2006, 78:2001-2008.
• [16]Otaman O, Boullanger P, Lafont D, Hamaide T: New amphiphilic glycopolymers based on a polycaprolactone-maleic anhydride copolymer backbone: characterization by 15N NMR and application to colloidal stabilization of nanoparticles. Macromol Chem Phys 2008, 209:2410-2422.
• [17]Song W, Li DW, Li YT, Li Y, Long YT: Disposable biosensor based on graphene oxide conjugated with tyrosinase assembled gold nanoparticles. Biosens Bioelectron 2011, 26:3181-3186.
• [18]Huang X, Zeng Z, Fan Z, Liu J, Zhang H: Graphene-based electrodes. Adv Mater 2012, 24:5979-6004.
• [19]Cai L, Fu Q, Shi R, Tang Y, Long TY, He XP, Jin Y, Liu G, Chen GR, Chen K: ‘Pungent’ copper surface resists acid corrosion in strong HCl solutions. Ind Eng Chem Res 2014, 53:64-69.
• [20]He XP, Deng Q, Cai L, Wang CZ, Zang Y, Li J, Chen GR, Tian H: Fluorogenic resveratrol-confined graphene oxide for economic and rapid detection of Alzheimer’s disease. ACS Appl Mater Interfaces 2014, 6:5379-5382.
• [21]Sun X, Zhu B, Ji DK, Chen Q, He XP, Chen GR, James TD: Selective fluorescence detection of monosaccharides using a material composite formed between graphene oxide and boronate-based receptors. ACS Appl Mater Interfaces 2014, 6:10078-10082.