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A Highly Selective “Turn-on” Fluorescent Probe for Detection of Fe3+ in Cells

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Abstract

A new “turn-on” fluorescent probe Py based on rhodamine and piperonaldehyde was designed and synthesized for detecting Fe3+ in cells. The free probe Py was non-fluorescent. While only upon addition of Fe3+, the significant increase of the fluorescence and color were observed which could be visible directly by “naked-eye”. The probe Py shows high selectivity and sensitivity for Fe3+ over other common metal ions in EtOH-H2O (3/2, v/v) mixed solution. The association constant and the detection limit were calculated to be 4.81 × 104 M−1 and 1.18 × 10−8 mol/L respectively. The introduction of piperonaldehyde unit could increase probe rigidity which could enhance its optical properties. Meanwhile, the binding mode between Py and Fe3+ was found to be a 1:1 complex formation. The density functional theory (DFT) calculations were performed which would further confirm the recognition mechanism between probe Py and Fe3+. In addition, the probe has been proved to be reversible for detecting Fe3+. Moreover, the probe Py was used to detect Fe3+ in cells successfully.

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References

  1. Zhang Y, Wang Y-T, Kang X-X, Ge M, Feng H-Y, Han J, Wang D-H, Zhao D-Z (2018) Azobenzene disperse dye-based colorimetric probe for naked eye detection of Cu2+ in aqueous media: spectral properties, theoretical insights, and applications. J Photoch Photobio A 356:652–660

    Article  CAS  Google Scholar 

  2. Ozdemir M, Zhang Y, Guo M (2018) A highly selective “off-on” fluorescent sensor for subcellular visualization of labile iron(III) in living cells. Inorg Chem Commun 90:73–77

    Article  CAS  Google Scholar 

  3. Wang J, Zhang D, Liu Y, Ding P, Wang C, Ye Y, Zhao Y (2014) A N-stablization rhodamine-based fluorescent chemosensor for Fe3+ in aqueous solution and its application in bioimaging. Sensors Actuators B Chem 191:344–350

    Article  CAS  Google Scholar 

  4. Zhu C, Wang M, Qiu L, Hao S, Li K, Guo Z, He W (2018) A mitochondria-targeting fluorescent Fe3+ probe and its application in labile Fe3+ monitoring via imaging and flow cytometry. Dyes Pigments 157:328–333

    Article  CAS  Google Scholar 

  5. Yang Z, Bai X, Ma S, Liu X, Zhao S, Yang Z (2017) A benzoxazole functionalized fluorescent probe for selective Fe3+ detection and intracellular imaging in living cells. Anal Methods 9:18–22

    Article  CAS  Google Scholar 

  6. Sen S, Sarkar S, Chattopadhyay B, Moirangthem A, Basu A, Dhara K, Chattopadhyay P (2012) A ratiometric fluorescent chemosensor for iron: discrimination of Fe2+ and Fe3+ and living cell application. Analyst 137:3335–3342

    Article  CAS  PubMed  Google Scholar 

  7. Long L, Zhou L, Lin W, Meng S, Gong A, Chi Z (2014) A ratiometric fluorescent probe for iron(III) and its application for detection of iron(III) in human blood serum. Anal Chim Acta 812:145–151

    Article  CAS  PubMed  Google Scholar 

  8. Bao X, Shi J, Nie X, Zhou B, Wang X, Zhang L, Liao H, Pang T (2014) A new rhodamine B-based 'on-off' chemical sensor with high selectivity and sensitivity toward Fe(3+) and its imaging in living cells. Bioorg Med Chem 22:4826–4835

    Article  CAS  PubMed  Google Scholar 

  9. Jeong Y, Yoon J (2012) Recent progress on fluorescent chemosensors for metal ions. Inorg Chim Acta 381:2–14

    Article  CAS  Google Scholar 

  10. Xu H, Ding H, Li G, Fan C, Liu G, Pu S (2017) A highly selective fluorescent chemosensor for Fe3+ based on a new diarylethene with a rhodamine 6G unit. RSC Adv 7:29827–29834

    Article  CAS  Google Scholar 

  11. Yang Y, Wang X, Cui Q, Cao Q, Li L (2016) Self-assembly of fluorescent organic nanoparticles for Iron(III) sensing and cellular imaging. ACS Appl Mater Interfaces 8:7440–7448

    Article  CAS  PubMed  Google Scholar 

  12. Zheng M, Tan H, Xie Z, Zhang L, Jing X, Sun Z (2013) Fast response and high sensitivity europium metal organic framework fluorescent probe with chelating Terpyridine sites for Fe3+. ACS Appl Mater Interfaces 5:1078–1083

    Article  CAS  PubMed  Google Scholar 

  13. Pires MM, Chmielewski J (2008) Fluorescence imaging of cellular glutathione using a latent rhodamine. Org Lett 10:837–840

    Article  CAS  PubMed  Google Scholar 

  14. Zhang JF, Zhou Y, Yoon J, Kim Y, Kim SJ, Kim JS (2010) Naphthalimide modified rhodamine derivative: Ratiometric and selective fluorescent sensor for Cu2+ based on two different approaches. Org Lett 12:3852–3855

    Article  CAS  PubMed  Google Scholar 

  15. Kang H, Fan C, Xu H, Liu G, Pu S (2018) A highly selective fluorescence switch for Cu2+ and Fe3+ based on a new diarylethene with a triazole-linked rhodamine 6G unit. Tetrahedron 74:4390–4399

    Article  CAS  Google Scholar 

  16. Qin JC, Yang ZY, Wang GQ, Li CR (2015) FRET-based rhodamine–coumarin conjugate as a Fe3+ selective ratiometric fluorescent sensor in aqueous media. Tetrahedron Lett 56:5024–5029

    Article  CAS  Google Scholar 

  17. You Q-H, Huang H-B, Zhuang Z-X, Wang X-R, Chan W-H (2016) A new rhodamine-based fluorescent probe for the discrimination of Fe3+ from Fe2+. Bull Kor Chem Soc 37:1772–1777

    Article  CAS  Google Scholar 

  18. Ge F, Ye H, Zhang H, Zhao B-X (2013) A novel ratiometric probe based on rhodamine B and coumarin for selective recognition of Fe(III) in aqueous solution. Dyes Pigments 99:661–665

    Article  CAS  Google Scholar 

  19. Zhao J, Gao Q, Zhang F, Sun W, Bai Y (2016) Two colorimetric fluorescent probes for detection Fe3+: synthesis, characterization and theoretical calculations. J Lumin 180:278–286

    Article  CAS  Google Scholar 

  20. Chen X, Sun W, Bai Y, Zhang F, Zhao J, Ding X (2018) Novel rhodamine Schiff base type naked-eye fluorescent probe for sensing Fe(3+) and the application in cell. Spectrochim Acta A Mol Biomol Spectrosc 191:566–572

    Article  CAS  PubMed  Google Scholar 

  21. Zhang J, Zhang L, Wei Y, Chao J, Shuang S, Cai Z, Dong C (2014) A selectively rhodamine-based colorimetric probe for detecting copper(II) ion. Spectrochim Acta A Mol Biomol Spectrosc 122:191–197

    Article  CAS  Google Scholar 

  22. Hao Z, Fan J, Jing L, Hu M, Cao J, Jing W, Li H, Liu X, Peng X (2012) Optical Cu2+ probe bearing an 8-hydroxyquinoline subunit: high sensitivity and large fluorescence enhancement. Talanta 93:55

    Article  CAS  Google Scholar 

  23. Bao X, Cao X, Nie X, Xu Y, Guo W, Zhou B, Zhang L, Liao H, Pang T (2015) A new selective fluorescent chemical sensor for Fe3+ based on rhodamine B and a 1,4,7,10-tetraoxa-13-azacyclopentadecane conjugate and its imaging in living cells. Sensors Actuators B Chem 208:54–66

    Article  CAS  Google Scholar 

  24. Li Z, Zhao JL, Wu YT, Mu L, Zeng X, Jin Z, Wei G, Xie N, Redshaw C (2017) Highly selective recognition of Al(3+) and I(−) ions using a bi-functional fluorescent probe. Org Biomol Chem 15:8627–8633

    Article  CAS  PubMed  Google Scholar 

  25. Ruan Q, Mu L, Zeng X, Zhao JL, Zeng L, Chen ZM, Yang C, Wei G, Redshaw C (2018) A three-dimensional (time, wavelength and intensity) functioning fluorescent probe for the selective recognition/discrimination of cu(2+), hg(2+), Fe(3+) and F(−) ions. Dalton Trans 47:3674–3678

    Article  CAS  PubMed  Google Scholar 

  26. Li X, Yin Y, Deng J, Zhong H, Tang J, Chen Z, Yang L, Ma LJ (2016) A solvent-dependent fluorescent detection method for Fe(3+) and hg(2+) based on a rhodamine B derivative. Talanta 154:329–334

    Article  CAS  PubMed  Google Scholar 

  27. OuYang H, Gao Y, Yuan Y (2013) A highly selective rhodamine-based optical–electrochemical multichannel chemosensor for Fe3+. Tetrahedron Lett 54:2964–2966 26

    Article  CAS  Google Scholar 

  28. Chai M, Zhang D, Wang M, Hong H, Ye Y, Zhao Y (2012) Four rhodamine B-based fluorescent chemosensor for Fe3+ in aqueous solution. Sensors Actuators B Chem 174:231–236

    Article  CAS  Google Scholar 

  29. Liu Y, Shen R, Ru J, Yao X, Yang Y, Liu H, Tang X, Bai D, Zhang G, Liu W (2016) A reversible rhodamine 6G-based fluorescence turn-on probe for Fe3+ in water and its application in living cell imaging. RSC Adv 6:111754–111759

    Article  CAS  Google Scholar 

  30. Kagit R, Yildirim M, Ozay O, Yesilot S, Ozay H (2014) Phosphazene based multicentered naked-eye fluorescent sensor with high selectivity for Fe3+ ions. Inorg Chem 53:2144–2151

    Article  CAS  PubMed  Google Scholar 

  31. Yan L, Yang M, Leng X, Zhang M, Long Y, Yang B (2016) A new dual-function fluorescent probe of Fe3+ for bioimaging and probe-Fe3+ complex for selective detection of CN−. Tetrahedron 72:4361–4367

    Article  CAS  Google Scholar 

  32. Senthil Murugan A, Vidhyalakshmi N, Ramesh U, Annaraj J (2018) In vivo bio-imaging studies of highly selective, sensitive rhodamine based fluorescent chemosensor for the detection of Cu2+/Fe3+ ions. Sensors Actuators B Chem 274:22–29

    Article  CAS  Google Scholar 

  33. Wang Y, Song F, Zhu J, Zhang Y, Du L, Kan C (2018) Highly selective fluorescent probe based on a rhodamine B and furan-2-carbonyl chloride conjugate for detection of Fe3+ in cells. Tetrahedron Lett 59:3756–3762

    Article  CAS  Google Scholar 

  34. Sharma N, Reja SI, Gupta N, Bhalla V, Kaur D, Arora S, Kumar M (2017) A highly selective fluorescent probe for Fe3+ in living cells: a stress induced cell based model study. Org Biomol Chem 15:1006–1012

    Article  CAS  PubMed  Google Scholar 

  35. Weerasinghe AJ, Schmiesing C, Varaganti S, Ramakrishna G, Sinn E (2010) Single- and multiphoton turn-on fluorescent Fe3+ sensors based on Bis(rhodamine). J Phys Chem B 114:9413–9419

    Article  CAS  PubMed  Google Scholar 

  36. Liu P, Luo A, Wang Y, Hu J, Huang Q, Wang H (2018) A bis-(rhodamine)-based off–on colorimetric and fluorescent probe for Fe3+ ion detection in serum and bioimaging. Chem Pap 72:2575–2587

    Article  CAS  Google Scholar 

  37. Zhao N, Xuan S, Fronczek FR, Smith KM, Vicente MGH (2017) Enhanced Hypsochromic shifts, quantum yield, and π–π interactions in a meso,β-Heteroaryl-fused BODIPY. J Organomet Chem 82:3880–3885

    Article  CAS  Google Scholar 

  38. Kaewtong C, Noiseephum J, Uppa Y, Morakot N, Morakot N, Wanno B, Tuntulani T, Pulpoka B (2010) A reversible Em-FRET rhodamine-based chemosensor for carboxylate anions using a ditopic receptor strategy. New J Chem 34:1104–1108

    Article  CAS  Google Scholar 

  39. Thordarson P (2011) Determining association constants from titration experiments in supramolecular chemistry. Chem Soc Rev 40:1305–1323

    Article  CAS  PubMed  Google Scholar 

  40. Reed AE, Curtiss LA, Weinhold F (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 88:899–926

    Article  CAS  Google Scholar 

  41. Pandith A, Kumar A, Kim HS (2015) 9-N-Alkylaminomethylanthracene probes for selective fluorescence sensing of pentafluorophenol. RSC Adv 5:81808–81816

    Article  CAS  Google Scholar 

  42. Zhang Q, Liu X-J, He R-C, Guo C-B, Zhao W-Z, Zeng C-C, Yin L-P (2018) Development of a fluorescent-type sensor based on rhodamine B for Fe(III) determination. Chem Lett 47:122–125

    Article  CAS  Google Scholar 

  43. Zhou T, Chen X, Hua Q, Lei W, Hao Q, Zhou B, Su C, Bao X (2017) Synthesis and evaluation of a new furfuran-based rhodamine B fluorescent chemosensor for selective detection of Fe3+ and its application in living-cell imaging. Sensors Actuators B Chem 253:292–301

    Article  CAS  Google Scholar 

  44. Mallick D, Biswal B, Thirunavoukkarasu M, Mohanty R, Bag B (2017) Signalling probes appended with two rhodamine derivatives: inter-component preferences, Fe(III)-ion selective fluorescence responses and bio-imaging in plant species. New J Chem 41:15144–15156

    Article  CAS  Google Scholar 

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Acknowledgements

We gratefully acknowledge financial support from the National Natural Science Foundation of China (Grant no.21042002).

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Authors and Affiliations

  1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi’an, Shaanxi, 710127, People’s Republic of China

    Xiaorui Cao, Feifei Zhang, Yinjuan Bai & Xiaohu Ding

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  1. Xiaorui Cao
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Correspondence to Yinjuan Bai.

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Cao, X., Zhang, F., Bai, Y. et al. A Highly Selective “Turn-on” Fluorescent Probe for Detection of Fe3+ in Cells. J Fluoresc 29, 425–434 (2019). https://doi.org/10.1007/s10895-019-02351-x

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  • DOI: https://doi.org/10.1007/s10895-019-02351-x

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