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A Simple Schiff Base as Fluorescent Probe for Detection of Al3+ in Aqueous Media and its Application in Cells Imaging

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Abstract

A novel fluorescence probe for the detection of Al3+ was developed based on methionine protected gold nanoclusters (Met-AuNCs). A fluorescent Schiff base (an aldimine) is formed between the aldehyde group of salicylaldehyde (SA) and the amino groups of Met on the AuNCs, and developed for selective detection of Al3+ in aqueous solution. Al3+ can strongly bind with the Schiff base ligands, accompanied by the blue-shift and an obvious fluorescence emission enhancement at 455 nm. The limits of detection (LODs) of the probe are 2 pmol L−1 for Al3+. Moreover, the probe can successfully be used in fluorescence imaging of Al3+ in living cells (SHSY5Y cells), suggesting that the simple fluorescent probe has great potential use in biological imaging.

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References

  1. Zhao Y, Lin Z, Liao H, Duan C, Meng Q (2006) A highly selective fluorescent chemosensor for Al3+ derivated from 8-Hydroxyquinoline. Inorg Chem Commun 9:966–968

    Article  CAS  Google Scholar 

  2. Li Y, Niu Q, Wei T, Li T (2019) Novel thiophene-based colorimetric and fluorescent turn-on sensor for highly sensitive and selective simultaneous detection of Al3+ and Zn2+ in water and food samples and its application in bioimaging. Anal Chim Acta 1049:196–212

    Article  CAS  Google Scholar 

  3. Fasman GD (1996) Aluminum and Alzheimer’s Disease: Model studies. Coord Chem Rev 149:125–165

    Article  CAS  Google Scholar 

  4. Perl DP, Gajdusek DC, Garruto RM, Yanagihara RT, Gibbs CJ (1982) Intraneuronal aluminum accumulation in amyotrophic lateral sclerosis and parkinsonism-dementia of guam. Science 217:1053–1055

    Article  CAS  Google Scholar 

  5. Wen X, Fan Z (2016) Linear schiff-base fluorescence probe with aggregation-induced emission characteristics for Al3+ detection and its application in live cell imaging. Anal Chim Acta 945:75–84

    Article  CAS  Google Scholar 

  6. Faller P, Hureau C (2012) A bioinorganic view of alzheimer’s disease: When misplaced metal ions (Re) direct the electrons to the wrong target. Chem A Eur J 18:15910–15920

    Article  CAS  Google Scholar 

  7. Liu B, Wang P, Chai J, Hu X, Gao T, Chao J, Chen T, Yang B (2016) Naphthol-based fluorescent sensors for aluminium ion and application to bioimaging. Acta A Mol Biomol Spectrosc 168:98–103

    Article  CAS  Google Scholar 

  8. Xing B, Zhu W, Zheng X, Zhu Y, Wei Q, Wu D (2018) Electrochemiluminescence immunosensor based on quenching effect of SiO2@PDA on SnO2/rGO/Au Nps-luminol for insulin detection. Sens Actuators B Chem 265:403–411

    Article  CAS  Google Scholar 

  9. Yang L, Li Y, Zhang Y, Fan D, Pang X, Wei Q, Du B (2017) 3D nanostructured palladium-functionalized graphene-aerogel-supported Fe3O4 for enhanced Ru(bpy)32+-based electrochemiluminescent immunosensing of prostate specific antigen. ACS Appl Mater Interfaces 9:35260–35267

    Article  CAS  Google Scholar 

  10. Ren X, Zhang T, Wu D, Yan T, Pang X, Du B, Lou W, Wei Q (2017) Increased electrocatalyzed performance through high content potassium doped graphene matrix and aptamer tri infinite amplification labels strategy: Highly sensitive for matrix metalloproteinases-2 detection. Biosens Bioelectron 94:694–700

    Article  CAS  Google Scholar 

  11. Maity D, Govindaraju T (2012) A differentially selective sensor with fluorescence turn-on response to Zn2+ and dual-mode ratiometric response to Al3+ in aqueous media. Chem Commun Camb 48:1039–1041

    Article  CAS  Google Scholar 

  12. Chandra R, Manna AK, Rout K, Mondal J, Patra GK (2018) A dipodal molecular probe for naked eye detection of trivalent cations (Al3+, Fe3+ and Cr3+) in aqueous medium and its applications in real sample analysis and molecular logic gates. RSC Adv 8:35946–35958

    Article  CAS  Google Scholar 

  13. Fan L, Qin J, Li T, Wang B, Yang Z (2014) A novel rhodamine chromone-based “off-on” chemosensor for the differential detection of Al(III) and Zn(II) in aqueous solutions. Sens Actuators B Chem 203:550–556

    Article  CAS  Google Scholar 

  14. Cao W, Zheng X, Sun J, Wong W, Fang D, Zhang J, Jin L (2014) A highly selective chemosensor for Al(III) and Zn(II) and its coordination with metal ions. Inorg Chem 53:3012–3021

    Article  CAS  Google Scholar 

  15. Jiang J, Jiang H, Tang X, Yang L, Dou W, Liu W, Fang R, Liu W (2011) An efficient sensor for Zn2+ and Cu2+ based on different binding modes. Dalton Trans 40:6367–6370

    Article  CAS  Google Scholar 

  16. Shellaiah M, Wu Y, Lin H (2013) Simple pyridyl-salicylimine-based fluorescence “turn-on” sensors for distinct detections of Zn2+, Al3+ and OH- ions in mixed aqueous media. Analyst 138:2931–2942

    Article  CAS  Google Scholar 

  17. Wang L, Qin W, Liu W (2010) A sensitive schiff-base fluorescent indicator for the detection of Zn2+. Inorg Chem Commun 13:1122–1125

    Article  CAS  Google Scholar 

  18. Udhayakumari D, Saravanamoorthy S, Ashok M, Velmathi S (2011) Simple imine linked colorimetric and fluorescent receptor for sensing Zn2+ ions in aqueous medium based on inhibition of ESIPT mechanism. Tetrahedron Lett 52:4631–4635

    Article  CAS  Google Scholar 

  19. Gupta VK, Singh AK, Ganjali MR, Norouzi P, Faridbod F, Mergu N (2013) Comparative study of colorimetric sensors based on newly synthesized schiff bases. Sens Actuators B Chem 182:642–651

    Article  CAS  Google Scholar 

  20. Al Zoubi W, Al Mohanna N (2014) Membrane sensors based on schiff bases as chelating ionophores - A review, Spectrochim. Acta A Mol Biomol Spectrosc 132:854–870

    Article  CAS  Google Scholar 

  21. Kumar A, Dubey M, Pandey R, Gupta RK, Kumar A, Kalita AC, Pandey DS (2014) A schiff base and its copper(II) complex as a highly selective chemodosimeter for mercury(II) involving preferential hydrolysis of aldimine over an ester group. Inorg Chem 53:4944–4955

    Article  CAS  Google Scholar 

  22. Manna AK, Chowdhury S, Patra GK (2020) Combined experimental and theoretical studies on a phenyl thiadiazole-based novel turn-on fluorescent colorimetric Schiff base chemosensor for the selective and sensitive detection of Al3+. New J Chem 44:10819–10832

    Article  CAS  Google Scholar 

  23. Li QR, Zhou R, Sun Y, Xiao D, Liu M, Zhao D, Peng S, Chen Y, Lin Y (2021) Synthesis and antitumor application of antiangiogenetic gold nanoclusters. ACS Appl Mater Interfaces 13:11708–11720

    Article  CAS  Google Scholar 

  24. Li D, Liu Q, Qi Q, Shi H, Hsu EC, Chen W, Yuan W, Wu Y, Lin S, Zeng Y, Xiao Z, Xu L, Zhang Y, Stoyanova T, Jia W, Cheng Z (2020) Gold nanoclusters for NIR-II fluorescence imaging of bones. Small 16:e2003851

  25. Yang X, Luo Y, Zhuo Y, Feng Y, Zhu S (2014) Novel synthesis of gold nanoclusters templated with L-tyrosine for selective analyzing tyrosinase. Anal Chim Acta 840:87–92

    Article  CAS  Google Scholar 

  26. Khan IM, Niazi S, Yu Y, Mohsin A, Mushtaq BS, Iqbal MW, Rehman A, Akhtar W, Wang Z (2019) Aptamer induced multicolored AuNCs-WS2 “turn on” FRET nano platform for dual-color simultaneous detection of aflatoxinB1 and zearalenone. Anal Chem 91:14085–14092

    Article  CAS  Google Scholar 

  27. Sang F, Li M, Yin S, Shi H, Zhao Y, Zhang Z (2021) Highly sensitive and selective detection and intracellular imaging of glutathione using MnO2 nanosheets assisted enhanced fluorescence of gold nanoclusters. Spectrochim Acta A Mol Biomol Spectrosc 256:119743

    Article  CAS  Google Scholar 

  28. Sang F, Zhang X, Shen F (2019) Fluorescent methionine-capped gold nanoclusters for ultra-sensitive determination of copper (II) and cobalt (II), and their use in a test strip. Microchim Acta 186:1–9

    Article  Google Scholar 

  29. Xiu L, Huang K, Zhu C, Zhang Q, Peng H, Xia X, Chen W, Deng H (2021) Rare-Earth Eu3+/gold nanocluster ensemble-based fluorescent photoinduced electron transfer sensor for biomarker dipicolinic acid detection. Langmuir 37:949–956

    Article  CAS  Google Scholar 

  30. Bilecka I, Niederberger M (2010) Microwave chemistry for inorganic nanomaterials synthesis. Nanoscale 2:1358–1374

    Article  CAS  Google Scholar 

  31. Larhed M, Moberg C, Hallberg A (2002) Microwave-accelerated homogeneous catalysis in organic chemistry. Acc Chem Res 35:717–727

    Article  CAS  Google Scholar 

  32. Shang L, Yang L, Stockmar F, Popescu R, Trouillet V, Bruns M, Gerthsen D, Nienhaus GU (2012) Microwave-assisted rapid synthesis of luminescent gold nanoclusters for sensing Hg2+ in living cells using fluorescence imaging. Nanoscale 4:4155–4160

    Article  CAS  Google Scholar 

  33. Gharagozlou M, Boghaei DM (2008) Interaction of water-soluble amino acid schiff base complexes with bovine serum albumin: Fluorescence and circular dichroism studies. Spectrochim Acta A Mol Biomol Spectrosc 71:1617–1622

    Article  Google Scholar 

  34. Faiz Ur R, Ali A, Guo R, Tian J, Wang H, Li Z, Zhang D (2015) Methionine-derived schiff base as selective fluorescent “turn-on” chemosensor for Zn2+ in aqueous medium and its application in living cells imaging. Sens Actuators B Chem 211:544–50

    Article  Google Scholar 

  35. Kumar A, Asthana SK, Upadhyay KK (2016) A dichloro-substituted salicylimine as a bright yellow emissive probe for Al3+. J Photochem Photobiol A 329:69e76

  36. Liu X, Fu C, Ren X, Liu H, Li L, Meng X (2015) Fluorescence switching method for cascade detection of salicylaldehyde and zinc(II) ion using protein protected gold nanoclusters. Biosens Bioelectron 74:322–328

    Article  CAS  Google Scholar 

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Funding

This work was funded by the Natural Science Foundation of China (NSFC) (No. 21407035), Shandong Provincial Natural Science Foundation (ZR2014BM021).

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All authors contributed to the study conception and design. Writing-original draft preparation, data collection and analysis were performed by [Fuming Sang]. Writing-original draft preparation, data collection and editing: [Tiedan Xiong]. Material preparation, data collection and analysis: [Weijie Wang]. Data collection and analysis: [Jianxin Pan]. Material preparation: [Huahua Shi]. Writing-review and editing: [Yan Zhao]. All authors read and approved the final manuscript.

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Correspondence to Fuming Sang.

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Sang, F., Xiong, T., Wang, W. et al. A Simple Schiff Base as Fluorescent Probe for Detection of Al3+ in Aqueous Media and its Application in Cells Imaging. J Fluoresc 33, 177–184 (2023). https://doi.org/10.1007/s10895-022-03047-5

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