Skip to main content
Log in

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

  • Original Paper
  • Published:
Microchimica Acta Aims and scope Submit manuscript

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.

Schematic of a fluorescent nanosensor composed of graphene oxide, aluminum (III) ions and Alizarin Red to image lysine in human retinal pigment epithelium cells.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. 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

    Article  CAS  Google Scholar 

  2. 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

    Article  CAS  Google Scholar 

  3. Felig P (1975) Amino acid metabolism in man. Annu Rev Biochem 44:933–955

    Article  CAS  Google Scholar 

  4. 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

    Article  CAS  Google Scholar 

  5. 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

    Article  CAS  Google Scholar 

  6. 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

    Article  CAS  Google Scholar 

  7. Inoue T, Kirchhoff JR (2000) Electrochemical detection of thiols with a coenzyme pyrroloquinoline quinone modified electrode. Anal Chem 72:5755–5760

    Article  CAS  Google Scholar 

  8. 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

    Article  CAS  Google Scholar 

  9. 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

    Article  Google Scholar 

  10. 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

    Article  Google Scholar 

  11. 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

    Article  CAS  Google Scholar 

  12. 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

    Article  CAS  Google Scholar 

  13. 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

    Article  CAS  Google Scholar 

  14. 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

    Article  CAS  Google Scholar 

  15. Volkert AA, Haes AJ (2014) Advancements in nanosensors using plastic antibodies. Analyst 139:21–31

    Article  CAS  Google Scholar 

  16. Kerr CA, Rica RDL (2015) Photoluminescent nanosensors for intracellular detection. Anal Methods 7:7067–7075

    Article  CAS  Google Scholar 

  17. Liu J, Liu Z, Barrow CJ, Yang W (2015) Molecularly engineered graphene surfaces for sensing applications: a review. Anal Chim Acta 859:1–19

    Article  CAS  Google Scholar 

  18. 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

    Article  CAS  Google Scholar 

  19. Dreyer DR, Park S, Bielawski CW, Ruoff RS (2010) The chemistry of graphene oxide. Chem Soc Rev 39:228–240

  20. 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

    Article  CAS  Google Scholar 

  21. 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

    Article  CAS  Google Scholar 

  22. 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

    Article  CAS  Google Scholar 

  23. 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

    Article  CAS  Google Scholar 

  24. 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

    Article  CAS  Google Scholar 

  25. Hummers WSJ, Offeman RE (1958) Preparation of graphitic oxide. J Am Chem Soc 80:1339

    Article  CAS  Google Scholar 

  26. 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

    Article  CAS  Google Scholar 

  27. 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

    Article  CAS  Google Scholar 

  28. Zhou M, Zhai YM, Dong SJ (2009) Electrochemical sensing and biosensing platform based on chemically reduced graphene oxide. Anal Chem 81:5603–5613

    Article  CAS  Google Scholar 

  29. Malard LM, Pimenta MA, Dresselhaus G, Dresselhaus MS (2009) Raman spectroscopy in graphene. Phys Rep 473:51–87

    Article  CAS  Google Scholar 

  30. Ferrari AC, Meyer JC, Scardaci V et al (2006) Raman spectrum of graphene and graphene layers. Phys Rev Lett 97:187401

    Article  CAS  Google Scholar 

  31. 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

    Article  Google Scholar 

  32. 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

    Article  Google Scholar 

  33. 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

    Article  CAS  Google Scholar 

  34. 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

    Article  CAS  Google Scholar 

  35. Turfan B, Akkaya EU (2008) Modulation of boradiazaindacene emission by cation-mediated oxidative PET. Org Lett 4:2857–2859

    Article  Google Scholar 

  36. 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

    Article  CAS  Google Scholar 

  37. Sahin OG, Gulce H, Gulce A (2013) Polyvinylferrocenium based platinum electrodeposited amperometric biosensors for lysine detection. J Electroanal Chem 690:1–7

    Article  CAS  Google Scholar 

  38. Rawat KA, Kailas SK (2014) Visual detection of arginine, histidine and lysine using quercetin-functionalized gold nanoparticles. Microchim Acta 181:1917–1929

    Article  CAS  Google Scholar 

Download references

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.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yuhua Xue.

Ethics declarations

The author(s) declare that they have no competing interests.

Electronic supplementary material

ESM 1

(DOC 4569 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00604-017-2375-0

Keywords

Navigation