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A Pyrene-based Highly Selective Turn-on Fluorescent Sensor for Copper(II) Ion and its Application in Live Cell Imaging

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Abstract

A new pyrene derivative (chemosensor 1) containing a picolinohydrazide moiety exhibits high selectivity for Cu2+ ion detection in mixed aqueous media (CH3OH:H2O = 7:3). Significant fluorescence enhancement was observed with chemosensor 1 in the presence of Cu2+. However, the metal ions Ag+, Ca2+, Cd2+, Co2+, Cu2+, Fe2+, Fe3+, Hg2+, K+, Mg2+, Mn2+, Ni2+, Pb2+, and Zn2+ produced only minor changes in fluorescence for the system. The apparent association constant (K a) of Cu2+ binding in chemosensor 1 was found to be 2.75*103 M−1. The maximum fluorescence enhancement caused by Cu2+ binding in chemosensor 1 was observed over the pH range 5–8. Moreover, by means of fluorescence microscopy experiments, it is demonstrated that 1 can be used as a fluorescent probe for detecting Cu2+ in living cells.

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References

  1. Bull PC, Thomas GR, Rommens JM, Forbes JR, Cox DW (1993) The Wilson disease gene is a putative copper transporting P-type ATPase similar to the Menkes gene. Nat Genet 5:327–337

    Article  PubMed  CAS  Google Scholar 

  2. Hahn SH, Tanner MS, Danke DM, Gahl WA (1995) Normal metallothionein synthesis in fibroblasts obtained from children with indian childhood cirrhosis or copper-associated childhood cirrhosis. Biochem Mol Med 54:142–145

    Article  PubMed  CAS  Google Scholar 

  3. Barnham KJ, Masters CL, Bush AI (2004) Neurodegenerative diseases and oxidatives stress. Nat Rev Drug Discov 3:205–214

    Article  PubMed  CAS  Google Scholar 

  4. Waggoner DJ, Bartnikas TB, Gitlin JD (1999) The role of copper in neurodegenerative disease. Neurobiol Disease 6:221–230

    Article  CAS  Google Scholar 

  5. Vulpe C, Levinson B, Whitney S, Packman S, Gitschier J (1993) Isolation of a candidate gene for Menkes disease and evidence that it encodes a copper-transporting ATPase. Nat Genet 3:7–13

    Article  PubMed  CAS  Google Scholar 

  6. Gonzales APS, Firmino MA, Nomura CS, Rocha FRP, Oliveira PV, Gaubeur I (2009) Peat as a natural solid-phase for copper preconcentration and determination in a multicommuted flow system coupled to flame atomic absorption spectrometry. Anal Chim Acta 636:198–204

    Article  PubMed  CAS  Google Scholar 

  7. Becker JS, Matusch A, Depboylu C, Dobrowolska J, Zoriy MV (2007) Quantitative imaging of selenium, copper, and zinc in thin sections of biological tissues (slugs-genus arion) measured by laser ablation inductively coupled plasma mass spectrometry. Anal Chem 79:6074–6080

    Article  PubMed  CAS  Google Scholar 

  8. Liu Y, Liang P, Guo L (2005) Nanometer titanium dioxide immobilized on silica gel as sorbent for preconcentration of metal ions prior to their determination by inductively coupled plasma atomic emission spectrometry. Talanta 68:25–30

    Article  PubMed  CAS  Google Scholar 

  9. Ensafi AA, Khayamian T, Benvidi A (2006) Simultaneous determination of copper, lead and cadmium by cathodic adsorptive stripping voltammetry using artificial neural network. Anal Chim Acta 561:225–232

    Article  CAS  Google Scholar 

  10. Zheng Y, Huo Q, Kele P, Andreopoulos FM, Pham SM, Leblanc RM (2001) A new fluorescent chemosensor for copper ions based on tripeptide glycyl−histidyl−lysine (GHK). Org Lett 3:3277–3280

    Article  PubMed  CAS  Google Scholar 

  11. Zeng L, Miller EW, Pralle A, Isacoff EY, Chang CJ (2006) A selective turn-on fluorescent sensor for imaging copper in living cells. J Am Chem Soc 128:10–11

    Article  PubMed  CAS  Google Scholar 

  12. Qi X, Jun EJ, Xu L, Kim S, Hong JSJ, Yoon YJ, Yoon J (2006) New BODIPY derivatives as off-on fluorescent chemosensor and fluorescent chemodosimeter for Cu2+: cooperative selectivity enhancement toward Cu2+. J Org Chem 71:2881–2884

    Article  PubMed  CAS  Google Scholar 

  13. Xiang Y, Tong A, Jin P, Ju Y (2006) New fluorescent rhodamine hydrazone chemosensor for Cu(II) with high selectivity and sensitivity. Org Lett 8:2863–2866

    Article  PubMed  CAS  Google Scholar 

  14. Yang H, Liu Z, Zhou Z, Shi E, Li F, Du Y, Yi T, Huang C (2006) Highly selective ratiometric fluorescent sensor for Cu(II) with two urea groups. Tetrahedron Lett 47:2911–2914

    Article  CAS  Google Scholar 

  15. Martinez R, Zapata F, Caballero A, Espinosa A, Tarraga A, Molina P (2006) Rhodamine-diacetic acid conjugate 2-aza-1,3-butadiene derivatives featuring an anthracene or pyrene unit: highly selective colorimetric and fluorescent signaling of Cu2+ cation. Org Lett 8:3235–3238

    Article  PubMed  CAS  Google Scholar 

  16. Zhang X, Shiraishi Y, Hirai T (2007) Cu(II)-selective green fluorescence of a rhodamine-diacetic acid conjugate. Org Lett 9:5039–5042

    Article  PubMed  CAS  Google Scholar 

  17. Li G, Xu Z, Chen C, Huang Z (2008) A highly efficient and selective turn-on fluorescent sensor for Cu2+ ion based on calix[4]arene bearing four iminoquinoline subunits on the upper rim. Chem Comm 1774–1776

  18. Wu S, Liu S (2009) A new water-soluble fluorescent Cu(II) chemosensor based on tetrapeptide histidyl-glycyl-glycyl-glycine (HGGG). Sens Actuators B 141:187–191

    Article  Google Scholar 

  19. Ballesteros E, Moreno D, Gomez T, Rodriguez T, Rojo J, Garcia-Valverde M, Torroba T (2009) A new selective chromogenic and turn-on fluorogenic probe for copper(II) in water-acetonitrile 1:1 solution. Org Lett 11:1269–1272

    Article  PubMed  CAS  Google Scholar 

  20. Jung HS, Kwon PS, Lee JW, Kim J, Hong CS, Kim JW, Yan S, Lee JY, Lee JW, Joo T, Kim S (2009) Coumarin-derived Cu2+-selective fluorescence sensor:synthesis, mechanisms, and applications in living cells. J Am Chem Soc 131:2008–2012

    Article  PubMed  CAS  Google Scholar 

  21. Zhou Y, Wang F, Kim Y, Kim S, Yoon J (2009) Cu2+-selective ratiometric and “off-on” sensor based on the rhodamine derivative bearing pyrene group. Org Lett 11:4442–4445

    Article  PubMed  CAS  Google Scholar 

  22. He G, Zhao X, Zhang X, Fan H, Wu S, Li H, He C, Duan C (2010) A turn-on PET fluorescence sensor for imaging Cu2+ in living cells. New J Chem 34:1055–1058

    Article  CAS  Google Scholar 

  23. Goswami S, Sen D, Das NK (2010) A new highly selective, ratiometric and colorimetric fluorescence sensor for Cu2+ with a remarkable red shift in absorption and emission spectra based on internal charge transfer. Org Lett 12:856–859

    Article  PubMed  CAS  Google Scholar 

  24. Wu S, Wang T, Liu S (2010) A highly selective turn-on fluorescent sensor for copper(II) ion. Tetrahedron 66:9655–9658

    Article  CAS  Google Scholar 

  25. Senthilvelan A, Ho I, Chang K, Lee G, Liu Y, Chung W (2009) Cooperative recognition of a copper cation and anion by a calix[4]arene substituted at the lower rim by a ß-amino-a, ß-unsaturated ketone. Chem Eur J 15:6152–6160

    Article  PubMed  CAS  Google Scholar 

  26. Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707

    Article  CAS  Google Scholar 

  27. Singh RB, Mahanta S, Guchhait N (2010) Spectral modulation of charge transfer fluorescence probe encapsulated inside aqueous and non-aqueous β-cyclodextrin nanocavities. J Mol Struc 963:92–97

    Article  CAS  Google Scholar 

  28. Maeda H, Inoue Y, Ishida H, Mizuno K (2001) UV absorption and fluorescence properties of pyrene derivatives having trimethylsilyl, trimethylgermyl, and trimethylstannyl groups. Chem Lett 1224–1225

  29. Karpovich DS, Blanchard GJ (1995) Relating the polarity-dependent fluorescence response of pyrene to vibronic coupling. Achieving a fundamental understanding of the py polarity scale. J Phys Chem 99:3951–3958

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge the financial supports of the National Science Council (ROC) and National Chiao Tung University.

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Authors and Affiliations

  1. Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan, 300, Republic of China

    Shu-Pao Wu, Zhen-Ming Huang, Shi-Rong Liu & Peter Kun Chung

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  1. Shu-Pao Wu
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  2. Zhen-Ming Huang
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  3. Shi-Rong Liu
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  4. Peter Kun Chung
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Correspondence to Shu-Pao Wu.

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Wu, SP., Huang, ZM., Liu, SR. et al. A Pyrene-based Highly Selective Turn-on Fluorescent Sensor for Copper(II) Ion and its Application in Live Cell Imaging. J Fluoresc 22, 253–259 (2012). https://doi.org/10.1007/s10895-011-0955-7

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  • DOI: https://doi.org/10.1007/s10895-011-0955-7

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