Skip to main content
Log in

A novel quinoline-based turn-on fluorescent probe for the highly selective detection of Al (III) and its bioimaging in living cells, plants tissues and zebrafish

  • Original Paper
  • Published:
JBIC Journal of Biological Inorganic Chemistry Aims and scope Submit manuscript

Abstract

A novel quinoline fluorescent probe QNP ((E)-N′-(5-chloro-2-hydroxybenzylidene) quinoline-2-carbohydrazide) for detection of Al3+ ion was designed, synthesized and characterized. QNP displayed a high fluorescence enhancement in the presence of Al3+ ion in DMF:PBS (99:1, v/v) solution and the detection limit was as low as 1.25 μM with high selectivity and excellent sensitivity from 0 to 3 μM. The sensing ability of QNP towards Al3+ ion is attributed to the synergistic effect of PET and ICT. Furthermore, the binding stoichiometry between QNP and Al3+ ion is of 1:1 by Job’s plot and mass spectrum, and the calculated binding constant is 4.29 × 108 M−1. The detection of Al3+ ion in water samples illustrates that QNP could be applied to the detection of practical samples in the environment. Bioimaging experiments on Hela cells, zebrafish and soybean root tissues demonstrate that it has potential application to investigate biological processes involving Al3+ ion within living cells.

Graphic abstract

A quinoline-based turn-on fluorescence probe for the detection of Al3+ and its bioimaging in living cells, plant, and zebrafish.

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.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Scheme 2
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Das S, Duttab M, Das D (2013) Fluorescent probes for selective determination of trace level Al3+: recent developments and future prospects. Anal Methods 5:6262–6285

    Article  CAS  Google Scholar 

  2. Zhang JJ, Chai XZ, He XP, Kim HJ, Yoon J, Tian H (2019) Fluorogenic probes for diseaserelevant enzymes. Chem Soc Rev 48:683–722

    Article  CAS  PubMed  Google Scholar 

  3. Wang GQ, Zhao YH, Hao YF (2018) Friction stir welding of high-strength aerospace aluminum alloy and application in rocket tank manufacturing. J Mater Sci Technol 34:73–91

    Article  CAS  Google Scholar 

  4. Wang CX, Wu B, Zhou W, Wang Q, Yu H, Deng K, Li JM, Zhuo RX, Huang SW (2018) Turn-on fluorescent probe-encapsulated micelle as colloidally stable nano-chemosensor for highly selective detection of Al3+ in aqueous solution and living cell imaging. Sens Actuator B Chem 271:225–238

    Article  CAS  Google Scholar 

  5. Goswami S, Paul S, Manna A (2013) Selective “naked eye” detection of Al (III) and PPi in aqueous media on a rhodamine–isatin hybrid moiety. RSC Adv 3:10639–10643

    Article  CAS  Google Scholar 

  6. Zhu Q, Li L, Mu L, Zeng X, Wei G (2016) A ratiometric Al3+ ion probe based on the coumarin-quinoline FRET system. J Photochem Photobiol A 328:217–224

    Article  CAS  Google Scholar 

  7. Walton JR (2006) Aluminum in hippocampal neurons from humans with Alzheimer’s disease. Neurotoxicology 27:385–394

    Article  CAS  PubMed  Google Scholar 

  8. Wang R, Jiang GQ, Li XH (2017) Two 5,5’-methylenebis(salicylaldehyde)-based Schiff base fluorescent sensors for selective sensing of Al3+ in DMSO/H2O solution. Inorg Chim Acta 455:247–253

    Article  CAS  Google Scholar 

  9. Chen S, Fang YM, Xiao Q, Li J, Song BL, Chen HJ, Sun JJ, Yang HH (2012) Rapid visual detection of aluminium ion using citrate capped gold nanoparticle. Analyst 137:2021–2023

    Article  CAS  PubMed  Google Scholar 

  10. Tang L, Ding S, Zhong K, Hou S, Bian Y, Yan X (2017) A new 2-(2’-hydroxyphenyl) quinazolin-4(3H)-one derived acylhydrazone for fluorescence recognition of Al3+. Spectrochim Acta A 174:70–74

    Article  CAS  Google Scholar 

  11. Guo CH, Hsu GSW, Chuang CJ, Chen PC (2009) Aluminum accumulation induced testicular oxidative stress and altered selenium metabolism in mice. Environ Toxicol Pharmacol 27:176–181

    Article  CAS  PubMed  Google Scholar 

  12. Sargazi M, Roberts NB, Shenkin A (2001) In-vitro studies of aluminium-induced toxicity on kidney proximal tubular cells. J Inorg Biochem 87:37–43

    Article  CAS  PubMed  Google Scholar 

  13. Kim YJ, Jang G, Lee TS (2017) Carbon nanodots functionalized with rhodamine and poly(ethylene glycol) for ratiometric sensing of Al ions in aqueous solution. Sens Actuator B Chem 249:59–65

    Article  CAS  Google Scholar 

  14. Silva AFD, Aguiar MSS, Carvalho OSD, Santana LDNS, Franco EC, Lima RR, Siqueira NVMD, Frio RA, Faro LRF, Walace GL (2013) Hippocampal neuronal loss, decreased GFAP immunoreactivity and cognitive impairment following experimental intoxication of rats with aluminum citrate. Brain Res 1491:23–33

    Article  CAS  PubMed  Google Scholar 

  15. Carvalho LL, Rodrigo P, Ivanise G (2018) Butan-1-ol as an extractant solvent in dispersive liquid-liquid microextraction in the spectrophotometric determination of aluminium. J Trace Elem Med Bio 50:175–181

    Article  Google Scholar 

  16. Lv R, Chen ZHY, Fu X, Yang BY, Li H, Su J, Gu W, Liu X (2018) A highly selective and fast-response fluorescent probe based on Cd-MOF for the visual detection of Al3+ ion and quantitative detection of Fe3+ ion. J Solid State Chem 259:67–72

    Article  CAS  Google Scholar 

  17. Guzin A, Dinc ZS (2017) A new dispersive liquid-liquid microextraction method for preconcentration and determination of aluminum, iron, copper, and lead in real water samples by HPLC. J AOAC Int 100:1524–1530

    Article  Google Scholar 

  18. Zeng S, Li SJ, Sun XJ, Li MQ, Ma YQ, Xing ZY, Li JL (2018) A naphthalenequinoline based chemosensor for fluorescent “turn-on” and absorbanceratiometric detection of Al3+ and its application in cells imaging. Spectrochim Acta A 205:276–286

    Article  CAS  Google Scholar 

  19. Hu X, Mao X, Zhang X, Huang Y (2017) One-step synthesis of orange fluorescent copper nanoclusters for sensitive and selective sensing of Al3+ ions in food samples. Sens Actuator B Chem 247:312–318

    Article  CAS  Google Scholar 

  20. Haouas M, Taulelle F, Martineau C (2016) Recent advances in application of 27Al NMR spectroscopy to materials science. Prog Nucl Magn Reson Spectrosc 94:11–36

    Article  PubMed  Google Scholar 

  21. Gao LX, Deng CC, Xiong J, Zhu PP, Chen Q, Tan KJ (2019) A sensitive ratiometric fluorescence method for visual detection of aluminum ion based on chelation-enhanced photoluminescence. Microchem J 150:104096–104104

    Article  CAS  Google Scholar 

  22. Zeng S, Li SJ, Liu TT, Sun XJ, Xing ZY (2019) A significant fluorescent “turn-on” chemosensor for Al3+ detection and application in real sample, logic gate and bioimaging. Inorg Chim Acta 495:118962–118970

    Article  CAS  Google Scholar 

  23. Nejad HH, Ordoee B, Khanmohammadi M (2019) A first principle photo-induced electron transfer study on a quinolin schiff base as Al3+ chemosensor using TD-DFT method. J Mol Struct 1196:861–865

    Article  CAS  Google Scholar 

  24. Jiang Q, Li MX, Song J, Yang YQ, Xu X, Xu HJ, Wang SF (2019) A highly sensitive and selective fluorescent probe for quantitative detection of Al3+ in food, water, and living cells. RSC Adv 9:10414–10419

    Article  CAS  Google Scholar 

  25. Jin L, Wang WL, Shen ZY, Xu JH, Wang QM, Zhao CY (2019) A new coumarin-based fluorescence “turn-on” sensor for Al(III) ions and its bioimaging in cell. J Mol Struct 1197:73–79

    Article  CAS  Google Scholar 

  26. Wang JH, Gao DR, Wang XY, Lu YM, Shen WX, Lv YY (2019) Near-infrared fluorescent probe for ratiometric Al3+ signaling and imaging through combined PET and ICT mechanisms. Sens Actuator B Chem 294:14–23

    Article  CAS  Google Scholar 

  27. Tian LM, Xue J, Li SL, Yang ZY (2019) A novel chromone derivative as dual probe for selective sensing of Al(III) by fluorescent and Cu(II) by colorimetric methods in aqueous solution. J Photochem Photobiol A 382:111955–111962

    Article  CAS  Google Scholar 

  28. Zhang Q, Ma RF, Li ZY, Liu ZZ (2020) A multi-responsive crown ether-based colorimetric/fluorescent chemosensor for highly selective detection of Al3+, Cu2+ and Mg2+. Spectrochim Acta A 228:117857–117869

    Article  CAS  Google Scholar 

  29. Wang JH, Feng LH, Chao JB, Wang Y, Shuang SM (2019) A new ‘turn-on’ and reversible fluorescent sensor for Al3+ detection and live cell imaging. Anal Methods 11:5598–5606

    Article  Google Scholar 

  30. Tian ZN, Wu DQ, Sun XJ, Liu TT, Xing ZY (2019) A benzothiazole-based fluorescent probe for ratiometric detection of Al3+ and its application in water samples and cell imaging. Int J Mol Sci 20:5993–6004

    Article  CAS  PubMed Central  Google Scholar 

  31. Li L, Chen Q, Niu ZG, Zhou XH, Yang T, Huang W (2016) Lanthanide metal–organic frameworks assembled from a fluorene-based ligand: selective sensing of Pb2+ and Fe3+ ions. J Mater Chem C 4:1900–1905

    Article  CAS  Google Scholar 

  32. Song F, Yang C, Shao XT, Du L, Zhu J, Kan C (2019) A reversible “turn-off-on” fluorescent probe for real-time visualization of mercury(II) in environmental samples and its biological applications. Dyes Pigm 165:444–450

    Article  CAS  Google Scholar 

  33. Huang MX, Lai JP, Sun H, Wu WZ (2019) A simple, highly selective and ultra-sensitive “off-on-off” fluorescent chemosensor for successive detection of aluminum ion and phosphate in water samples. Microchem J 151:104195–104202

    Article  CAS  Google Scholar 

  34. Suman GR, Bubbly SG, Gudennavar SB (2019) Benzimidazole and benzothiazole fluorophores with large Stokes shift and intense sky-blue emission in aggregation as Al3+ and Pb2+ sensors. J Lumin 215:116688–116697

    Article  CAS  Google Scholar 

  35. Peng HN, Han YJ, Lin N, Liu HH (2019) Two pyridine-derived Schiff-bases as turn-on fluorescent sensor for detection of aluminium ion. Opt Mater 95:109210–109216

    Article  CAS  Google Scholar 

  36. Fu JX, Yao K, Chang YX, Li B, Yang L, Xu KX (2019) A novel colorimetric-fluorescent probe for Al3+ and the resultant complex for F and its applications in cell imaging Spectrochim. Acta A 222:117234–117244

    Article  CAS  Google Scholar 

  37. Mukherjee S, Betal S, Chattopadhyay AP (2020) Dual sensing and synchronous fluorescence spectroscopic monitoring of Cr3+ and Al3+ using a luminescent Schiff base: extraction and DFT studies. Spectrochim Acta A 228:117837–117846

    Article  CAS  Google Scholar 

  38. Fu JX, Chang YX, Li B, Mei HH, Yang L, Xu KX (2019) A novel fluorescent-colorimetric probe for Al3+ and Zn2+ ion detection with different response and applications in F- detection and cell imaging. Analyst 144:5706–5716

    Article  CAS  PubMed  Google Scholar 

  39. Roy A, Das S, Sacher S, Mandal SK, Roy P (2019) A rhodamine based biocompatible chemosensor for Al3+, Cr3+ and Fe3+ ions: extraordinary fluorescence enhancement and a precursor for future chemosensors. Dalton Trans 48:17594–17604

    Article  CAS  PubMed  Google Scholar 

  40. Yao K, Chang YX, Li B, Yang H, Xu KX (2019) A novel coumarin-based fluorescent sensor for Ca2+ and sequential detection of F- and its live cell imaging. Spectrochim Acta A 216:385–394

    Article  CAS  Google Scholar 

  41. Suresh M, Mandal AK, Saha S, Suresh E, Mandoli A, Liddo RD, Parnigotto PP, Das A (2010) Azine-based receptor for recognition of Hg2+ ion: crystallographic evidence and imaging application in live cells. Org Lett 12:5406–5409

    Article  CAS  PubMed  Google Scholar 

  42. Xue L, Liu Q, Jiang H (2009) Ratiometric Zn2+ fluorescent sensor and new approach for sensing Cd2+ by ratiometric displacement. Org Lett 11:3454–3457

    Article  CAS  PubMed  Google Scholar 

  43. Sun XJ, Liu TT, Li NN, Zeng S, Xing ZY (2020) A novel dual-function probe for recognition of Zn2+ and Al3+ and its application in real samples. Spectrochim Acta A 228:117786–117798

    Article  CAS  Google Scholar 

  44. Xu YK, Wang HY, Zhao JY, Yang XF, Pei MS, Zhang GY, Zhang YX (2019) A dual functional fluorescent sensor for the detection of Al3+ and Zn2+ in different solvents. New J Chem 43:14320–14326

    Article  CAS  Google Scholar 

  45. Wang GQ, Qin JC, Li CR, Yang ZY (2015) A highly selective fluorescent probe for Al3+ based on quinoline derivative. Spectrochim Acta A 150:21–25

    Article  CAS  Google Scholar 

  46. Tian L, Xue J, Yang ZY (2018) A simple quinoline derivative as fluorescent probe with high sensitivity and selectivity for Al3+ in aqueous solution. Tetrahedron Lett 59:4110–4115

    Article  CAS  Google Scholar 

  47. Hakonen A (2009) Plasmon enhancement and surface wave quenching for phase ratiometry in coextraction-based fluorosensors. Anal Chem 81:4555–4559

    Article  CAS  PubMed  Google Scholar 

  48. Facchiano A, Ragone R (2003) Modification of Job’s method for determining the stoichiometry of protein-protein complexes. Anal Biochem 313:170–172

    Article  CAS  PubMed  Google Scholar 

  49. Towari K, Mishra M, Singh VP (2013) A highly sensitive and selective fluorescent sensor for Al3+ ions based on thiophene-2-carboxylic acid hydrazide Schiff base. RSC Adv 3:12124–12132

    Article  Google Scholar 

  50. Qin JC, Li TR, Wang BD, Yang ZY, Fan L (2014) A sensor for selective detection of Al3+ based on quinoline Schiff-base in aqueous media. Synth Met 195:141–146

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Key Research and Development Program of China (2017YFD060070602), Innovation Fund for Young Scholars of Nanjing Forestry University (CX2017017) and the priority academic program development of Jiangsu higher education institutions.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Li Xu.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 453 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lu, W., Chen, J., Shi, J. et al. A novel quinoline-based turn-on fluorescent probe for the highly selective detection of Al (III) and its bioimaging in living cells, plants tissues and zebrafish. J Biol Inorg Chem 26, 57–66 (2021). https://doi.org/10.1007/s00775-020-01836-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00775-020-01836-6

Keywords

Navigation