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A multi-analyte selective dansyl derivative for the fluorescence detection of Cu(ii) and cysteine

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Abstract

A new multi-analyte selective fluorescence chemosensor DA was synthesized by a simple one pot reaction between dansyl chloride and 2-aminobenzohydrazide in the presence of a base. In DMSO: H2O(1: 1, v/v), the fluorescence of DA at 483 nm was blue shifted and enhanced at 474 nm along with a new shoulder peak appearing at 411 nm selectively in the presence of Cu2+ among the other tested metal ions due to the chelation enhanced fluorescence (CHEF) effect. Without any noticeable interference from potentially competitive metal ions, sensor DA can detect Cu2+ down to 9.79 x 10−7 M. Sensor DA gives satisfactory results for the quantification of Cu2+ in real water samples. Sequentially, the resultant in situ generated DA-Cu2+ complex is applied for the selective sensing of bioactive cysteine with a detection limit down to 1.76 x 10−6 M.

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References

  1. M. Gupta, A. Balamurugan and H.-i. Lee, Sens. Actuators, B, 2015, 211, 531–536.

    Article  CAS  Google Scholar 

  2. X. Chen, T. Pradhan, F. Wang, J. S. Kim and J. Yoon, Chem. Rev., 2012, 112, 1910–1956.

    Article  CAS  PubMed  Google Scholar 

  3. L. Gai, J. Mack, H. Lu, T. Nyokong, Z. Li, N. Kobayashi and Z. Shen, Coord. Chem. Rev., 2015, 285, 24–51.

    Article  CAS  Google Scholar 

  4. H. N. Kim, W. X. Ren, J. S. Kim and J. Yoon, Chem. Soc. Rev., 2012, 41, 3210–3244.

    Article  CAS  PubMed  Google Scholar 

  5. L. E. Santos-Figueroa, M. E. Moragues, E. Climent, A. Agostini, R. Martinez-Manez and F. Sancenon, Chem. Soc. Rev., 2013, 42, 3489–3613.

    Article  CAS  PubMed  Google Scholar 

  6. D. Sareen, P. Kaur and K. Singh, Coord. Chem. Rev., 2014, 265, 125–154.

    Article  CAS  Google Scholar 

  7. Y. Fu, Q.-C. Feng, X.-J. Jiang, H. Xu, M. Li and S.-Q. Zang, Dalton Trans., 2014, 43, 5815–5822.

    Article  CAS  PubMed  Google Scholar 

  8. A. Hens and K. K. Rajak, RSC Adv., 2015, 5, 44764–44777.

    Article  CAS  Google Scholar 

  9. K. B. Kim, H. Kim, E. J. Song, S. Kim, I. Noh and C. Kim, Dalton Trans., 2013, 42, 16569–16577.

    CAS  PubMed  Google Scholar 

  10. B. K. Rani and S. A. John, J. Hazard. Mater., 2018, 343, 98–106.

    Article  CAS  PubMed  Google Scholar 

  11. D. G. Barceloux and D. Barceloux, J. Toxicol., Clin. Toxicol., 1999, 37, 217–230.

    Article  CAS  Google Scholar 

  12. K. P. Carter, A. M. Young and A. E. Palmer, Chem. Rev., 2014, 114, 4564–4601.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. J. R. Prohaska and A. A. Gybina, J. Nutr., 2004, 134, 1003–1006.

    Article  CAS  PubMed  Google Scholar 

  14. S. Ferguson-Miller and G. T. Babcock, Chem. Rev., 1996, 96, 2889–2908.

    Article  CAS  PubMed  Google Scholar 

  15. N. E. Hellman and J. D. Gitlin, Annu. Rev. Nutr., 2002, 22, 439–458.

    Article  CAS  PubMed  Google Scholar 

  16. S. K. Sahoo, D. Sharma, A. Moirangthem, A. Kuba, R. Thomas, R. Kumar, A. Kuwar and H.-J. Choi, J. Lumin., 2016, 172, 297–303.

    Article  CAS  Google Scholar 

  17. C. Vulpe, B. Levinson, S. Whitney, S. Packman and J. Gitschier, Nat. Genet., 1993, 3, 7–13.

    Article  CAS  PubMed  Google Scholar 

  18. K. J. Barnham, C. L. Masters and A. I. Bush, Nat. Rev. Drug Discovery, 2004, 3, 205–214.

    Article  CAS  PubMed  Google Scholar 

  19. D. J. Waggoner, T. B. Bartnikas and J. D. Gitlin, Neurobiol. Dis., 1999, 6, 221–230.

    Article  CAS  PubMed  Google Scholar 

  20. P. C. Bull, G. R. Thomas, J. M. Rommens, J. R. Forbes and D. W. Cox, Nat. Genet., 1993, 5, 327–337.

    Article  CAS  PubMed  Google Scholar 

  21. D. R. Brown and H. Kozlowski, Dalton Trans., 2004, 1907–1917.

    Google Scholar 

  22. J. S. Valentine and P. J. Hart, Proc. Natl. Acad. Sci. U. S. A., 2003, 100, 3617–3622.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. L. I. Bruijn, T. M. Miller and D. W. Cleveland, Annu. Rev. Neurosci., 2004, 27, 723–749.

    Article  CAS  PubMed  Google Scholar 

  24. E. Gaggelli, H. Kozlowski, D. Valensin and G. Valensin, Chem. Rev., 2006, 106, 1995–2044.

    Article  CAS  PubMed  Google Scholar 

  25. Z. A. Wood, E. Schröder, J. R. Harris and L. B. Poole, Trends Biochem. Sci., 2003, 28, 32–40.

    Article  CAS  PubMed  Google Scholar 

  26. Y. Zhou and J. Yoon, Chem. Soc. Rev., 2012, 41, 52–67.

    Article  CAS  PubMed  Google Scholar 

  27. J. W. Miller, S. A. Beresford, M. L. Neuhouser, T.-Y. D. Cheng, X. Song, E. C. Brown, Y. Zheng, B. Rodriguez, R. Green and C. M. Ulrich, Am. J. Clin. Nutr., 2013, 97, 827–834.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. T. P. Dalton, H. G. Shertzer and A. Puga, Annu. Rev. Pharmacol. Toxicol., 1999, 39, 67–101.

    Article  CAS  PubMed  Google Scholar 

  29. S. A. Lipton, Y.-B. Choi, H. Takahashi, D. Zhang, W. Li, A. Godzik and L. A. Bankston, Trends Neurosci., 2002, 25, 474–480.

    Article  CAS  PubMed  Google Scholar 

  30. G. A. Petsko and D. Ringe, Protein structure and function, New Science Press, 2004.

    Google Scholar 

  31. S. Shahrokhian, Anal. Chem., 2001, 73, 5972–5978.

    Article  CAS  PubMed  Google Scholar 

  32. W. G. Haynes, Cleve. Clin. J. Med., 2004, 71, 729.

    Article  PubMed  Google Scholar 

  33. M.-Y. Jia, L.-Y. Niu, Y. Zhang, Q.-Z. Yang, C.-H. Tung, Y.-F. Guan and L. Feng, ACS Appl. Mater. Interfaces, 2015, 7, 5907–5914.

    Article  CAS  PubMed  Google Scholar 

  34. D. Zhang, Z. Yang, H. Li, Z. Pei, S. Sun and Y. Xu, Chem. Commun., 2016, 52, 749–752.

    Article  CAS  Google Scholar 

  35. H. Agarwalla, H. Anila, F. Ali, S. R. Pradhan, B. Ganguly, S. K. Pramanik and A. Das, Chem. Commun., 2018, 54, 9079–9082.

    Article  CAS  Google Scholar 

  36. F. Ali, S. Kushwaha, N. Taye, S. Chattopadhyay and A. Das, Anal. Chem., 2016, 88, 12161–12168.

    Article  PubMed  CAS  Google Scholar 

  37. F. Ali, H. Anila, N. Taye, R. G. Gonnade, S. Chattopadhyay and A. Das, Chem. Commun., 2015, 51, 16932–16935.

    Article  CAS  Google Scholar 

  38. H. Anila, F. Ali, N. Taye, S. Chattopadhyay and A. Das, Chem. Commun., 2015, 51, 15592–15595.

    Article  CAS  Google Scholar 

  39. P. Das, A. K. Mandal, N. B. Chandar, M. Baidya, H. B. Bhatt, B. Ganguly, S. K. Ghosh and A. Das, Chem. -Eur. J., 2012, 18, 15382–15393.

    Article  CAS  PubMed  Google Scholar 

  40. H. Agarwalla, N. Taye, S. Ghorai, S. Chattopadhyay and A. Das, Chem. Commun., 2014, 50, 9899–9902.

    Article  CAS  Google Scholar 

  41. C.-C. Zhao, Y. Chen, H.-Y. Zhang, B.-J. Zhou, X.-J. Lv and W.-F. Fu, J. Photochem. Photobiol., A, 2014, 282, 41–46.

    Article  CAS  Google Scholar 

  42. K.-S. Lee, J. Park, H.-J. Park, Y. K. Chung, S. B. Park, H.-J. Kim, I.-S. Shin and J.-I. Hong, Sens. Actuators, B, 2016, 237, 256–261.

    Article  CAS  Google Scholar 

  43. X.-X. Zhao, J.-F. Zhang, W. Liu, S. Zhou, Z.-Q. Zhou, Y.-H. Xiao, G. Xi, J.-Y. Miao and B.-X. Zhao, J. Mater. Chem. B, 2014, 2, 7344–7350.

    Article  CAS  Google Scholar 

  44. D. S. McClure, J. Chem. Phys., 1952, 20, 682–686.

    Article  CAS  Google Scholar 

  45. S.-Y. Yu and S.-P. Wu, Sens. Actuators, B, 2014, 201, 25–30.

    Article  CAS  Google Scholar 

  46. C. R. Lohani, L. N. Neupane, J.-M. Kim and K.-H. Lee, Sens. Actuators, B, 2012, 161, 1088–1096.

    Article  CAS  Google Scholar 

  47. Y.-J. Chang, S.-S. Wu, C.-H. Hu, C. Cho, M. X. Kao and A.-T. Wu, Inorg. Chim. Acta, 2015, 432, 25–31.

    Article  CAS  Google Scholar 

  48. W. Nasomphan, P. Tangboriboonrat and S. Smanmoo, J. Fluoresc., 2017, 27, 2201–2212.

    Article  CAS  PubMed  Google Scholar 

  49. K. M. Dokken, J. G. Parsons, J. McClure and J. L. Gardea-Torresdey, Inorg. Chim. Acta, 2009, 362, 395–401.

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are thankful to The Director, SVNIT for necessary lab facilities and instrumental facilities. ThangarajAnand and Dr Sahoo thank DST-SERB National postdoctoral fellowship (PDF/2016/000804) for the research grant with the fellowship.

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Authors and Affiliations

  1. Department of Applied Chemistry, SV National Institute of Technology (SVNIT), Surat, 395007, Gujarat, India

    Anand Thangaraj, Vinita Bhardwaj & Suban K. Sahoo

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  1. Anand Thangaraj
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  2. Vinita Bhardwaj
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  3. Suban K. Sahoo
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Correspondence to Suban K. Sahoo.

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Thangaraj, A., Bhardwaj, V. & Sahoo, S.K. A multi-analyte selective dansyl derivative for the fluorescence detection of Cu(ii) and cysteine. Photochem Photobiol Sci 18, 1533–1539 (2019). https://doi.org/10.1039/c9pp00080a

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  • DOI: https://doi.org/10.1039/c9pp00080a

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