Abstract
The authors describe a rationally designed nanoprobe for the fluorometric determination of lysine. It is based on a ternary complex consisting of graphene oxide, aluminum ions (acting as a bridging agent), and alizarin red (GO-Al-AR). The fluorescence of the complex (with excitation/emission maxima at 440/512 nm) is weak but significantly enhanced upon the addition of lysine, probably due to a photoinduced electron transfer signalling mechanism. The method has a detection limit of 2 mg L−1 of lysine and a linear range from 25 mg L−1 to 250 mg L−1. It was applied to image lysine in human retinal pigment epithelium cells.
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Qian X, Gong W, Wang F, Lin Y, Ning G (2015) A pyrylium-based colorimetric and fluorimetric chemosensor for the selective detection of lysine in aqueous environment and real sample. Tetrahedron Lett 56:2764–2767
Lohar S, Safin DA, Sengupta A et al (2015) Ratiometric sensing of lysine through the formation of the pyrene excimer: experimental and computational studies. Chem Commun 51:8536–8539
Felig P (1975) Amino acid metabolism in man. Annu Rev Biochem 44:933–955
Hirayama C, Suyama K, Horie Y, Tanimoto K, Kato S (1987) Plasma amino acid patterns in hepatocellular carcinoma. Biochem Med Metab Biol 38:127–133
Chwatko G, Bald E (2000) Determination of cysteine in human plasma by high-performance liquid chromatography and ultraviolet detection after pre-column derivatization with 2-chloro-1-methylpyridinium iodide. Talanta 52:509–515
Tcherkas YV, Denisenko AD (2001) Simultaneous determination of several amino acids, including homocysteine, cysteine and glutamic acid, in human plasma by isocratic reversed-phase high-performance liquid chromatography with fluorimetric detection. J Chromatogr A 913:309–313
Inoue T, Kirchhoff JR (2000) Electrochemical detection of thiols with a coenzyme pyrroloquinoline quinone modified electrode. Anal Chem 72:5755–5760
Kiba N, Miwa T, Tachibana M, Tani K, Koizumi H (2002) Chemiluminometric sensor for simultaneous determination of L-glutamate and L-lysine with immobilized oxidases in a flow injection system. Anal Chem 74:1269–1274
Wang S, Yu J, Wan F, Ge S, Yan M, Zhang M (2011) Flow injection electrochemiluminescence determination of L-lysine using tris (2,2′-bipyridyl) ruthenium(II) (Ru(bpy)(3)(2+)) on indium tin oxide (ITO) glass. Anal Methods 3:1163–1167
Douša M, Břicháč J, Gibala P, Lehnert P (2011) Rapid hydrophilic interaction chromatography determination of lysine in pharmaceutical preparations with fluorescence detection after postcolumn derivatization with o-phtaldialdehyde. J Pharm Biomed Anal 54:972–978
Shibata K, Yasui M, Sano M, Fukuwatari T (2011) Fluorometric determination of 2-oxoadipic acid, a common metabolite of tryptophan and lysine, by high-performance liquid chromatography with pre-chemical derivatization. Biosci Biotechnol Biochem 75:185–187
Razi SS, Ali R, Srivastava P, Shahid M, Misra A (2014) An azo based colorimetric probe for the detection of cysteine and lysine amino acids and its real application in human blood plasma. RSC Adv 4:16999–17007
Minami T, Esipenko NA, Zhang B, Isaacs L, Jr PA (2014) "turn-on" fluorescent sensor array for basic amino acids in water. Chem Commun 50:61–63
Zhou Y, Won J, Lee JY, Yoon JY (2011) Studies leading to the development of a highly selective colorimetric and fluorescent chemosensor for lysine. Chem Commun 47:1997–1999
Volkert AA, Haes AJ (2014) Advancements in nanosensors using plastic antibodies. Analyst 139:21–31
Kerr CA, Rica RDL (2015) Photoluminescent nanosensors for intracellular detection. Anal Methods 7:7067–7075
Liu J, Liu Z, Barrow CJ, Yang W (2015) Molecularly engineered graphene surfaces for sensing applications: a review. Anal Chim Acta 859:1–19
Xuan W, He X, Chen J, Wang W, Wang X, Xu Y, Xu Z, Fu YQ, Luo JK (2015) High sensitivity flexible lamb-vave humidity sensors with a graphene oxide sensing layer. Nanoscale 7:7430–7436
Dreyer DR, Park S, Bielawski CW, Ruoff RS (2010) The chemistry of graphene oxide. Chem Soc Rev 39:228–240
Xu J, Wang Y, Hu S (2017) Nanocomposites of graphene and graphene oxides: synthesis, molecular functionalization and application in electrochemical sensors and biosensors. A review. Microchim Acta 184:1–44
Lin Y, Tao Y, Pu F, Ren J, Qu X (2011) Combination of graphene oxide and thiol-activated DNA metallization for sensitive fluorescence turn-on detection of cysteine and their use for logic gate operations. Adv Funct Mater 21:4565–4572
Wang L, Pu K, Li J, Qi X, Li H, Zhang H, Fan C, Liu B (2011) Graphene-conjugated oligomer hybrid probe for light-up sensing of lectin and Escherichia coli. Adv Mater 23:4386–4391
Cheng R, Liu Y, Ou S, Pan Y, Zhang S, Chen H, Dai L, Qu J (2012) Optical turn-on sensor based on graphene oxide for selective detection of D-glucosamine. Anal Chem 84:5641–5644
Seth RL, Dey AK (1963) Composition and stability of the chelate between aluminium (III) and sodium alizarin 3-sulphonate: spectrophotometric and electrical conductance studies. J Parkt Chem 19:229–237
Hummers WSJ, Offeman RE (1958) Preparation of graphitic oxide. J Am Chem Soc 80:1339
Fain VY, Zaitsev BE, Ryabov MA (2004) Metal complexes with alizarin and alizarin red S: electronic absorption spectra and structure of ligands. Russ J Coord Chem 30:365–370
Cheng R, Ou S, Bu Y, Li X, Liu X, Wang Y, Guo R, Shi B, Jin D, Liu Y (2015) Starch–borate–graphene oxide nanocomposites as highly efficient targeted antitumor drugs. RSC Adv 5:94855–94858
Zhou M, Zhai YM, Dong SJ (2009) Electrochemical sensing and biosensing platform based on chemically reduced graphene oxide. Anal Chem 81:5603–5613
Malard LM, Pimenta MA, Dresselhaus G, Dresselhaus MS (2009) Raman spectroscopy in graphene. Phys Rep 473:51–87
Ferrari AC, Meyer JC, Scardaci V et al (2006) Raman spectrum of graphene and graphene layers. Phys Rev Lett 97:187401
Sathish RS, Kumar MR, Rao GN, Kumar KA, Janardhana CA (2007) Water-soluble fluorescent fluoride ion probe based on alizarin red S-al(III) complex. Spectrochim Acta part A 66:457–461
Shen J, Hu Y, Shi M, Lu X, Qin C, Li C, Ye M (2009) Fast and facile preparation of graphene oxide and reduced graphene oxide nanoplatelets. Chem Mater 31:3514–3520
Gong K, Du F, Xia Z, Durstock M, Dai L (2009) Nitrogen-doped carbon nanotube arrays with high electrocatalytic activity for oxygen reduction. Science 323:760–764
Kim HN, Lee MH, Kim HJ, Kim JS, Yoon JY (2008) A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions. Chem Soc Rev 37:1465–1472
Turfan B, Akkaya EU (2008) Modulation of boradiazaindacene emission by cation-mediated oxidative PET. Org Lett 4:2857–2859
Veerapandian M, Lévaray N, Lee MH, Giasson S, Zhu X (2015) Glucosamine-anchored graphene oxide nanosheets: fabrication, ultraviolet irradiation, and electrochemical properties. ACS Appl Mater Interfaces 7:14552–14556
Sahin OG, Gulce H, Gulce A (2013) Polyvinylferrocenium based platinum electrodeposited amperometric biosensors for lysine detection. J Electroanal Chem 690:1–7
Rawat KA, Kailas SK (2014) Visual detection of arginine, histidine and lysine using quercetin-functionalized gold nanoparticles. Microchim Acta 181:1917–1929
Acknowledgements
The National Natural Science Foundation of China (21405115, 51202167), the National “Thousand Talents Program”, the Wenzhou Bureau of Science and Technology (Y20120218), the technology project of Zhejiang Province Medical and Health Project (2015KYB254, 2017KY492) and Ophthalmology & Optometry of Wenzhou Medical University (YNCX201408) are acknowledged.
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Cheng, R., Peng, Y., Ge, C. et al. A turn-on fluorescent lysine nanoprobe based on the use of the Alizarin Red aluminum(III) complex conjugated to graphene oxide, and its application to cellular imaging of lysine. Microchim Acta 184, 3521–3528 (2017). https://doi.org/10.1007/s00604-017-2375-0
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DOI: https://doi.org/10.1007/s00604-017-2375-0