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Highly sensitive fluorescent probe based on a novel phenothiazine dye for detection of thiophenols in real water samples and living cells

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Abstract

Based on an excited-state intramolecular proton transfer (ESIPT) fluorophore, a novel fluorescent off-on probe for detection of thiophenols was designed and synthesized. This probe (λex = 401 nm, λem = 527 nm) displayed high specificity for sensing thiophenols over other biologically related species. Besides, this probe possessed capabilities of monitoring thiophenols with rapid response rate (3 min), a large Stokes shift (126 nm), and high sensitivity (2.7 nM). The sensing mechanism was considered to be that thiophenols triggered thiolysis of the probe and the ESIPT fluorophore was released, as confirmed by means of HPLC and HRMS. Most notably, this probe was successfully applied to monitor levels of thiophenols in realistic samples and MDA-MB-231 cells.

A novel phenothiazine-based fluorescent probe was developed for sensitively sensing thiophenols in both aqueous medium and living cells.

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References

  1. Eychmuller A, Rogach AL. Chemistry and photophysics of thiol-stabilized II–VI semiconductor nanocrystals. Pure Appl Chem. 2000;72:179–88.

    Article  CAS  Google Scholar 

  2. Love JC, Estroff LA, Kriebel JK, Nuzzo RG, Whitesides GM. Self-assembled monolayers of thiolates on metals as a form of nanotechnology. Chem Rev. 2005;105:1103–70.

    Article  CAS  PubMed  Google Scholar 

  3. Liu XL, Duan XY, Du XJ, Song QH. Quinolinium-based fluorescent probes for the detection of thiophenols in environmental samples and living cells. Chem Asian J. 2012;7:2696–702.

    Article  CAS  PubMed  Google Scholar 

  4. Shimada K, Mitamura K. Derivatization of thiol-containing compounds. J Chromatogr B. 1994;659:227–41.

    Article  CAS  Google Scholar 

  5. Heil TP, Lindsay RC. Toxicological properties of thio-and alkylphenolscausing flavor tainting in fish from the upper Wisconsin River. J Environ Sci Health B. 1989;24:349–60.

    Article  CAS  PubMed  Google Scholar 

  6. Amrolia P, Sullivan SG, Stern A, Munday R. Toxicity of aromatic thiols in the human red bloos cell. J Appl Toxicol. 1989;9:113–8.

    Article  CAS  PubMed  Google Scholar 

  7. Munday R. Toxicity of aromatic disulphides. II. Intra-erythrocytic hydrogen peroxide formation and oxidative damage by aromatic disulphides. J Appl Toxicol. 1985;5:409–13.

    Article  CAS  PubMed  Google Scholar 

  8. Juneja TR, Gupta RL, Samanta S. Activation of monocrotaline, fulvine and their derivatives to toxic pyrroles by some thiols. Toxicol Lett. 1984;21:185–9.

    Article  CAS  PubMed  Google Scholar 

  9. Wang K, Zhao CX, Leng TH, Wang CY, Lu YX, Shen YJ, et al. Dual quenching strategy for sensitive detection of toxic thiolphenols based on a NIR-illuminant platform with a large stokes shift. Dyes Pigments. 2018;151:194–201.

    Article  CAS  Google Scholar 

  10. Munday R, Manns E. Toxicity of aromatic disulphides. III. In vivo haemolytic activity of aromatic disulphides. J Appl Toxicol. 1985;5:414–7.

    Article  CAS  PubMed  Google Scholar 

  11. Munday R. Toxicity of aromatic disulphides. I. Generation of superoxide radical and hydrogen peroxide by aromatic disulphides in vivo. J Appl Toxicol. 1985;5:402–8.

    Article  CAS  PubMed  Google Scholar 

  12. Chitre SA, Lobo GAM, Rathod SM, Smith RB, Leslie R, Livingstone C, et al. Bromide–sulfur interchange: ion chromatographic determination of total reduced thiol levels in plasma. J Chromatogr B. 2008;864:173–7.

    Article  CAS  Google Scholar 

  13. Sun Y, Lv Z, Sun Z, Wu C, Ji Z, You J. Determination of thiophenols with a novel fluorescence labelling reagent: analysis of industrial wastewater samples with SPE extraction coupled with HPLC. Anal Bioanal Chem. 2016;408:3527–36.

    Article  CAS  PubMed  Google Scholar 

  14. Cheng D, Pan Y, Wang L, Zeng Z, Yuan L, Zhang X, et al. Selective visualization of the endogenous peroxynitrite in an inflamed mouse model by a mitochondria-targetable two-photon ratiometric fluorescent probe. J Am Chem Soc. 2017;139:285–92.

    Article  CAS  PubMed  Google Scholar 

  15. Cheng D, Xu W, Yuan L, Zhang X. Investigation of drug-induced hepatotoxicity and its remediation pathway with reaction-based fluorescent probes. Anal Chem. 2017;89:7693–700.

    Article  CAS  PubMed  Google Scholar 

  16. Ren T, Xu W, Jin F, Cheng D, Zhang L, Yuan L, et al. Rational engineering of bioinspired anthocyanidin fluorophores with excellent two-photon properties for sensing and imaging. Anal Chem. 2017;89:11427–34.

    Article  CAS  PubMed  Google Scholar 

  17. Ren M, Zhou K, Wang L, Liu K. Construction of a ratiometric two-photon fluorescent probe to monitor the changes of mitochondrial viscosity. Sensor Actuators B Chem. 2018;262:452–9.

    Article  CAS  Google Scholar 

  18. Deng B, Ren M, Kong X, Zhou K, Lin W. Development of an enhanced turn-on fluorescent HOCl probe with a large stokes shift and its use for imaging HOCl in cells and zebrafish. Sensor Actuators B Chem. 2018;255:963–9.

    Article  CAS  Google Scholar 

  19. Liu C, Wang F, Xiao T, Chi B, Wu Y, Zhu D, et al. The ESIPT fluorescent probes for N2H4 based on benzothiazol and their application for gas sensing and bioimaging. Sensor Actuators B Chem. 2018;256:55–62.

    Article  CAS  Google Scholar 

  20. Chang C, Wang F, Qiang J, Zhang Z, Chen Y, Zhang W, et al. Benzothiazole-based fluorescent sensor for hypochlorite detection and its application for biological imaging. Sensor Actuators B Chem. 2017;243:22–8.

    Article  CAS  Google Scholar 

  21. Jin X, Wu S, She M, Jia Y, Hao L, Yin B, et al. Novel fluorescein-based fluorescent probe for detecting H2S and its real applications in blood plasma and biological imaging. Anal Chem. 2016;88:11253–60.

    Article  CAS  PubMed  Google Scholar 

  22. Zhang D, Xu N, Li H, Yao Q, Xu F, Fan J, et al. Probing thiophenol pollutant in solutions and cells with BODIPY-based fluorescent probe. Ind Eng Chem Res. 2017;56:9303–9.

    Article  CAS  Google Scholar 

  23. Xiong L, Ma J, Huang Y, Wang Z, Lu Z. Highly sensitive squaraine-based water-soluble far-red/near-infrared chromofluorogenic thiophenol probe. ACS Sens. 2017;2:599–605.

    Article  CAS  PubMed  Google Scholar 

  24. Sun Q, Yang SH, Wu L, Yang WC, Yang GF. A highly sensitive and selective fluorescent probe for thiophenol designed via a twist-blockage strategy. Anal Chem. 2016;88:2266–72.

    Article  CAS  PubMed  Google Scholar 

  25. Khandare DG, Banerjee M, Gupta R, Kumar N, Ganguly A, Singh D, et al. Green synthesis of a benzothiazole based “turn-on” type fluorimetric probe and its use for the selective detection of thiophenols in environmental samples and living cells. RSC Adv. 2016;6:52790–7.

    Article  CAS  Google Scholar 

  26. Yuan M, Ma X, Jiang T, Zhang C, Chen H, Gao Y, et al. A novel coelenterate luciferin-based luminescent probe for selective and sensitive detection of thiophenols. Org Biomol Chem. 2016;14:10267–74.

    Article  CAS  PubMed  Google Scholar 

  27. Zhai Q, Yang S, Fang Y, Zhang H, Feng G. A new ratiometric fluorescent probe for the detection of thiophenols. RSC Adv. 2015;5:94216–21.

    Article  CAS  Google Scholar 

  28. Liu XJ, Qi FP, Su YN, Chen WQ, Yang L, Song XZ. A red emitting fluorescent probe for instantaneous sensing of thiophenol in both aqueous medium and living cells with a large Stokes shift. J Mater Chem C. 2016;4:4320–6.

    Article  CAS  Google Scholar 

  29. Pan Y, Ren T, Cheng D, Zeng Z, Yuan L, Zhang X. A selective near-infrared fluorescent probe for in vivo imaging of thiophenols from a focused library. Chem Asian J. 2016;11:3575–82.

    Article  CAS  PubMed  Google Scholar 

  30. Liu XJ, Yang L, Gao L, Chen WQ, Qi FP, Song XZ. A phthalimide-based fluorescent probe for thiophenol detection in water samples and living cells with a large stokes shift. Tetrahedron. 2015;71:8285–9.

    Article  CAS  Google Scholar 

  31. Chen S, Hou P, Wang J, Fu S, Liu L. A simple but effective fluorescent probe with large stokes shift for specific detection of cysteine in living cells. J Photochem Phoyobio A. 2018;363:7–12.

    Article  CAS  Google Scholar 

  32. Chen S, Li HM, Hou P. Imidazo[1,5-α]pyridine-derived fluorescent turn-on probe for cellular thiols imaging with a large stokes shift. Tetrahedron Lett. 2017;58:2654–7.

    Article  CAS  Google Scholar 

  33. Chen S, Li HM, Hou P. A novel cyanobiphenyl benzothiazole-based fluorescent probe for detection of biothiols with a large stokes shift and its application in cell imaging. Tetrahedron. 2017;73:589–3.

    Article  CAS  Google Scholar 

  34. Chen S, Li HM, Hou P. A novel imidazo[1,5-α]pyridine-based fluorescent probe with a large stokes shift for imaging hydrogen sulphide. Sensor Actuators B Chem. 2018;256:1086–92.

    Article  CAS  Google Scholar 

  35. Chen S, Li HM, Hou P. A large stokes shift fluorescent probe for sensing of thiophenols based on imidazo[1,5-α]pyridine in both aqueous medium and living cells. Anal Chim Acta. 2017;993:63–70.

    Article  CAS  PubMed  Google Scholar 

  36. Chen L, Park SJ, Wu D, Kim HM, Yoon J. A two-photo ESIPT based fluorescence probe for specific detection of hypochlorite. Dyes Pigments. 2018;158:526–32.

    Article  CAS  Google Scholar 

  37. Tian M, Sun J, Tang Y, Dong B, Lin W. Discriminating live and dead cells in dual-color mode with two-photo fluorescent probe based on ESIPT mechanism. Anal Chem. 2018;90:998–1005.

    Article  CAS  PubMed  Google Scholar 

  38. Liang C, Jiang S. Fluorescence light-up detection of cyanide in water based on cyclization reaction followed by ESIPT and AIEE. Analyst. 2017;142:4825–33.

    Article  CAS  PubMed  Google Scholar 

  39. Chen L, Wu D, Kim JM, Yoon J. An ESIPT-based fluorescence probe for colorimetric, ratiometric, and selective detection of phosgene in solution and the gas phase. Anal Chem. 2017;89:12596–601.

    Article  CAS  PubMed  Google Scholar 

  40. Wu D, Sedgwick AC, Gunnlaugsson T, Akkaya EU, Yoon J, James TD. Fluorescent chemosensors: the past, present and future. Chem Soc Rev. 2017;46:7105–23.

    Article  CAS  PubMed  Google Scholar 

  41. Chen W, Yue X, Li W, Hao Y, Zhang L, Zhu L, et al. A phenothiazine coumarin-based red emitting fluorescent probe for nanomolar detection of thiophenol with a large stokes shift. Sensor Actuators B Chem. 2017;245:702–10.

    Article  CAS  Google Scholar 

  42. Zeng R, Gao Q, Cheng F, Yang Y, Zhang P, Chen S, et al. A near-infrared fluorescent sensor with large stokes shift for rapid and highly selective detection of thiophenols in water samples and living cells. Anal Bioanal Chem. 2018;410:2001–9.

    Article  CAS  PubMed  Google Scholar 

  43. Frath D, Massue J, Ulrich G, Ziessel R. Luminescent materials: locking π-conjugated and heterocyclic ligands with boron (III). Angew Chem Int Ed. 2014;53:2290–310.

    Article  CAS  Google Scholar 

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Funding

The research was supported by University Nursing Program for Young Scholars with Creative Talents in Heilongjiang Province (No. UNPYSCT-2017167), China.

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Authors and Affiliations

  1. College of Pharmacy, Qiqihar Medical University, 333 Bukui Street, Qiqihar, 161006, Heilongjiang, China

    Peng Hou, Jing Wang, Shuang Fu, Lei Liu & Song Chen

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  1. Peng Hou
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  2. Jing Wang
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  3. Shuang Fu
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  4. Lei Liu
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  5. Song Chen
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Correspondence to Song Chen.

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Hou, P., Wang, J., Fu, S. et al. Highly sensitive fluorescent probe based on a novel phenothiazine dye for detection of thiophenols in real water samples and living cells. Anal Bioanal Chem 411, 935–942 (2019). https://doi.org/10.1007/s00216-018-1525-5

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  • DOI: https://doi.org/10.1007/s00216-018-1525-5

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