Skip to main content

Advertisement

Springer Nature Link
Log in

Two highly sensitive fluorescent probes based on cinnamaldehyde with large Stokes shift for sensing of HSO3− in pure water and living cells

  • Research Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

Two simple and novel fluorescent probes (CDC1 and CDC2) have been designed and prepared here for sensing HSO3− with large Stokes shifts (about 250 nm). The synthesized probes can react with HSO3− just in 2 min, followed by the obvious color change from blue to colorless. The colorimetric and ratiometric absorbance response of the probes to HSO3− is due to the addition of HSO3− to the electron-deficient C=C double bond group, which prevents significant intramolecular charge transfer (ICT). Besides, CDC1 and CDC2 can detect HSO3− in pure water and detection limits of CDC1 and CDC2 reached 4.59 nM and 8.19 nM, respectively. Considering the delicate difference in the two prepared probes’ molecular structures, CDC1 containing the carboxyl group has a more significant fluorescence intensity change response to HSO3− in pure water than CDC2 (with sulfinyl group). Beyond better response characteristics, CDC1 also has lower cytotoxicity and better biocompatibility compared with CDC2, which could be chosen to detect HSO3− in living cells. With these superior properties, probe CDC1 could have a potential application in the fields of environmental and biological detection.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

Explore related subjects

Discover the latest articles and news from researchers in related subjects, suggested using machine learning.

References

  1. Wang W, Han X-J, Liu J-T, Miao J-Y, Zhao B-X. A novel lipid droplets-targeted ratiometric fluorescence probe for HSO3−/SO32− in living cells. Dyes Pigments. 2020;173:107892.

    Article  CAS  Google Scholar 

  2. Zou L, Zhang G, Zhou M, Xin X, Chen S, Duan X, et al. Two reaction-based fluorescent sensors with cationic group enable high-selective detection of HSO3− in the environment. Ind Eng Chem Res. 2019;58(22):9231–8.

    Article  CAS  Google Scholar 

  3. Zou L, Xu J, Liu X, Zhang X, Gao Y, Zhang G et al. A colorimetric-fluorescent HSO3− sensor with high-selectivity enables rapid screening and accurate analysis of environmental samples. Microchem J. 2019:104461.

  4. Yin G, Gan Y, Yu T, Niu T, Yin P, Chen H, et al. A dual-emission and mitochondria-targeted fluorescent probe for rapid detection of SO2 derivatives and its imaging in living cells. Talanta. 2019;191:428–34.

    Article  CAS  Google Scholar 

  5. Wei T, Wang F, Chen Y, Qiang J, Zhang Z, Chen T, et al. A fluorescence probe for bisulfite sensing based on the bisulfite-induced binding site transfer between Zn2+ and an aminoquinoline derivate. Dyes Pigments. 2018;159:322–30.

    Article  CAS  Google Scholar 

  6. He L, Liu X, Zhang Y, Yang L, Fang Q, Geng Y, et al. A mitochondria-targeting ratiometric fluorescent probe for imaging hydrogen peroxide with long-wavelength emission and large Stokes shift. Sensors Actuators B Chem. 2018;276:247–53.

    Article  CAS  Google Scholar 

  7. Yang B, Xu J, Zhu H-L. Recent progress in the small-molecule fluorescent probes for the detection of sulfur dioxide derivatives (HSO3−/SO32−). Free Radical Bio Med. 2019;145:42–60.

    Article  CAS  Google Scholar 

  8. Ma Y, Tang Y, Zhao Y, Lin W. Rational design of a reversible fluorescent probe for sensing sulfur dioxide/formaldehyde in living cells, zebrafish, and living mice. Anal Chem. 2019;91(16):10723–30.

    Article  CAS  Google Scholar 

  9. Li J, Gao Y, Guo H, Li X, Tang H, Li J, et al. A novel colorimetric and ratiometric fluorescent probe for selective detection of bisulfite in real samples and living cells. Dyes Pigments. 2019;163:285–90.

    Article  CAS  Google Scholar 

  10. Karmakar A, Samanta P, Dutta S, Ghosh SK. Fluorescent “turn-on” sensing based on metal-organic frameworks (MOFs). Chem Asian J. 2019;14(24):4506–19.

    Article  CAS  Google Scholar 

  11. Feng G, Luo X, Lu X, Xie S, Deng L, Kang W, et al. Engineering of nucleic acids and synthetic cofactors as Holo sensors for probing signaling molecules in the cellular membrane microenvironment. Angew Chem Int Edit. 2019;58(20):6590–4.

    Article  CAS  Google Scholar 

  12. Zhou S, Rong Y, Wang H, Liu X, Wei L, Song X. A naphthalimide-indole fused chromophore-based fluorescent probe for instantaneous detection of thiophenol with a red emission and a large Stokes shift. Sensors Actuators B Chem. 2018;276:136–41.

    Article  CAS  Google Scholar 

  13. Liu X-L, Niu L-Y, Chen Y-Z, Yang Y, Yang Q-Z. A ratiometric fluorescent probe based on monochlorinated BODIPY for the discrimination of thiophenols over aliphatic thiols in water samples and in living cells. Sensors Actuators B Chem. 2017;252:470–6.

    Article  CAS  Google Scholar 

  14. Han J, Li Y, Wang Y, Bao X, Wang L, Ren L, et al. A water-soluble fluorescent probe for monitoring hypochlorite in water and in living cells. Sensors Actuators B Chem. 2018;273:778–83.

    Article  CAS  Google Scholar 

  15. Hong J, Xia Q, Feng W, Feng G. A dicyanoisophorone-based near-infrared fluorescent probe and its application for detecting thiophenols in water and living cells. Dyes Pigments. 2018;159:604–9.

    Article  CAS  Google Scholar 

  16. Zhu B, Wu L, Zhang M, Wang Y, Zhao Z, Wang Z, et al. A fast-response, highly specific fluorescent probe for the detection of picomolar hypochlorous acid and its bioimaging applications. Sensors Actuators B Chem. 2018;263:103–8.

    Article  CAS  Google Scholar 

  17. Zhu B, Wu L, Zhu H, Wang Z, Duan Q, Fang Z, et al. A highly specific and ultrasensitive two-photon fluorescent probe for imaging native hypochlorous acid in living cells. Sensors Actuators B Chem. 2018;269:1–7.

    Article  CAS  Google Scholar 

  18. Chen L-D, Ding H-L, Wang N, An Y, Lü C-W. Two highly selective and sensitive fluorescent probes design and apply to specific detection of hypochlorite. Dyes Pigments. 2019;161:510–8.

    Article  CAS  Google Scholar 

  19. Zheng Y, Sun S, Xu L, Ni S, Liu W, Huang B, et al. Arylamine-coumarin based donor-acceptor dyads: unveiling the relationship between two-photon absorption cross-section and lifetime of singlet excited state intramolecular charge separation. Dyes Pigments. 2019;165:301–7.

    Article  CAS  Google Scholar 

  20. Zeng L, Yuan Y, Jiang C, Mu J, Li F, Wan Y, et al. A near-infrared turn-on probe for in vivo chemoselective photoacoustic detection of fluoride ion. Dyes Pigments. 2019;165:408–14.

    Article  CAS  Google Scholar 

  21. Song F, Yang C, Shao X, Du L, Zhu J, Kan C. A reversible “turn-off-on” fluorescent probe for real-time visualization of mercury (II) in environmental samples and its biological applications. Dyes Pigments. 2019;165:444–50.

    Article  CAS  Google Scholar 

  22. Ma J, Feng G, Liu F, Yang F, Guo Y, Wu Y, et al. A conjugated polymer based on alkylthio-substituted benzo[1,2-c:4,5-c’]dithiophene-4,8-dione acceptor for polymer solar cells. Dyes Pigments. 2019;165:335–40.

    Article  CAS  Google Scholar 

  23. George J, Sajan D, Alex J, Vinitha G. Proton-induced intermolecular charge transfer in picolinium tartrate monohydrate crystal for OLED and nonlinear optical applications: a combined experimental and computational study. Dyes Pigments. 2019;165:239–48.

    Article  CAS  Google Scholar 

  24. Miltsov S, Karavan V, Misharev A, Starova G, Alonso-Chamarro J, Puyol M. Unprecedented acid-catalyzed Wurtz-type coupling of meso -bromoindodicarbocyanine dyes. Tetrahedron Lett. 2017;58(34):3353–7.

    Article  CAS  Google Scholar 

  25. Wani MY, Ahmad A, Aqlan FM, Al-Bogami AS. Azole based acetohydrazide derivatives of cinnamaldehyde target and kill Candida albicans by causing cellular apoptosis. ACS Med Chem Lett. 2020;11(4):566–74.

    Article  CAS  Google Scholar 

  26. Nieres PD, Trasarti AF, Apesteguía CR. Valorisation of plant oil derivatives via metathesis reactions: study of the cross-metathesis of methyl oleate with cinnamaldehyde. Mol Catal. 2020;481.

  27. Cao X, Li Y, Han Q, Gao A, Wang B, Chang X, et al. Design of large π-conjugated α-cyanostilbene derivatives as colorimetric sensors for volatile acids and organic amine gases. J Mater Chem C. 2020;8(12):4058–64.

    Article  CAS  Google Scholar 

  28. Chen T, Chen Z, Liu R, Zheng S. A NIR fluorescent probe for detection of viscosity and lysosome imaging in live cells. Org Biomol Chem. 2019;17(26):6398–403.

    Article  CAS  Google Scholar 

  29. Bhattacharyya A, Makhal SC, Guchhait N. Comparative photophysical study of differently substituted cinnamaldehyde-based chalcones: from intramolecular charge transfer to fluorogenic solvent selectivity. J Phys Chem A. 2019;123(30):6411–9.

    Article  CAS  Google Scholar 

  30. Reja SI, Gupta N, Bhalla V, Kaur D, Arora S, Kumar M. A charge transfer based ratiometric fluorescent probe for detection of hydrazine in aqueous medium and living cells. Sensors Actuators B Chem. 2016;222:923–9.

    Article  CAS  Google Scholar 

  31. Cheng S, Pan X, Shi M, Zuo G, Su T, Zhang C, et al. Naphthalene-benzoindole derived two novel fluorometric pH-responsive probes for environmental systems and bioimaging. Talanta. 2019;203:90–8.

    Article  CAS  Google Scholar 

  32. Liu S, Yang M, Liu Y, Chen H, Li H. A novel “turn-on” fluorescent probe based on triphenylimidazole-hemicyanine dyad for colorimetric detection of CN– in 100% aqueous solution. J Hazard Mater. 2018;344:875–82.

    Article  CAS  Google Scholar 

  33. Niu W, Wei Z, Jia J, Shuang S, Dong C, Yun K. A ratiometric emission NIR-fluorescent probe for sensing and imaging pH changes in live cells. Dyes Pigments. 2018;152:155–60.

    Article  CAS  Google Scholar 

  34. Awual MR, Khraisheh M, Alharthi NH, Luqman M, Islam A, Rezaul Karim M, et al. Efficient detection and adsorption of cadmium (II) ions using innovative nano-composite materials. Chem Eng J. 2018;343:118–27.

    Article  CAS  Google Scholar 

  35. Awual MR, Alharthi NH, Okamoto Y, Karim MR, Halim ME, Hasan MM, et al. Ligand field effect for dysprosium (III) and lutetium (III) adsorption and EXAFS coordination with novel composite nanomaterials. Chem Eng J. 2017;320:427–35.

    Article  CAS  Google Scholar 

Download references

Funding

We acknowledge the financial support by the Wenzhou Medical University (89220006, KYYW201906, and KYQD20190513).

Author information

Authors and Affiliations

  1. State Key Laboratory of Ophthalmology, Optometry and Vision Science, School of Ophthalmology and Optometry, School of Biomedical Engineering, Wenzhou Medical University, Wenzhou, 325027, Zhejiang, China

    Xihao Pan & Xiaoliang Qi

  2. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, Jiangsu, China

    Xihao Pan, Siyao Cheng & Cheng Zhang

Authors
  1. Xihao Pan
    View author publications

    Search author on:PubMed Google Scholar

  2. Siyao Cheng
    View author publications

    Search author on:PubMed Google Scholar

  3. Cheng Zhang
    View author publications

    Search author on:PubMed Google Scholar

  4. Xiaoliang Qi
    View author publications

    Search author on:PubMed Google Scholar

Corresponding author

Correspondence to Xiaoliang Qi.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Research involving human participants and/or animals

This article does not contain any studies with human participants or animals performed by any of the authors.

Additional information

Publisher’s note

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

Electronic supplementary material

ESM 1

(PDF 824 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pan, X., Cheng, S., Zhang, C. et al. Two highly sensitive fluorescent probes based on cinnamaldehyde with large Stokes shift for sensing of HSO3− in pure water and living cells. Anal Bioanal Chem 412, 6959–6968 (2020). https://doi.org/10.1007/s00216-020-02827-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-020-02827-x

Keywords