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A Novel 2-Phenyl-1,2,3-Triazole Derived Fluorescent Probe for Recyclable Detection of Al3+ in Aqueous Medium and Its Application

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—A novel 2-phenyl-1,2,3-triazole derived fluorescent probe HPTC ((2-hydroxybenzylidene)-2-phenyl-2H-1,2,3-triazole-4-carbohydrazide) has been designed and synthesized for recyclable detection of Al3+ in DMSO/Tris-HCl (pH 7.4) 1 : 100 v/v with high sensitivity and selectivity. A fluorescence enhancement of 97 folds at 457 nm can be realized upon addition of 10.0 equiv. Al3+ with excitation at 375 nm. The binding constant of HPTC with Al3+ and the detection limit of HPTC toward Al3+ were 1.67 × 105 M–1 and 8.875 × 10–8 M, respectively. In addition, the probe HPTC can detect Al3+ repeatedly in DMSO/Tris-HCl (pH 7.4) 1 : 100 v/v and the detection effect is not changed. The probe HPTC showed an excellent detection ability in a wide pH range from 3 to 10 and also in living cells. Furthermore, the Al3+ sensing mechanism was confirmed based on Job’s plot, 1H NMR titration, HR-MS, and DFT studies. Finally, HPTC-doped agarose hydrogel experiment suggests that the HPTC can recognize the Al3+ in solid state.

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REFERENCES

  1. Rao, V.K., Rao, A.J., Reddy, S.S., Raju, C.N., Rao, P.V., and Ghosh, S.K., Eur. J. Med. Chem., 2010, vol. 45, pp. 203–209. https://doi.org/10.1016/j.ejmech.2009.09.045

    CAS  Article  Google Scholar 

  2. Lee,Y.J., Lim, C., Suh, H., Song, E.J., and Kim, C., Sens. Actuators. B Chem., 2014, vol. 201, pp. 535–544. https://doi.org/10.1016/j.snb.2014.05.035

    CAS  Article  Google Scholar 

  3. Li, C.R., Qin, J.C., Wang, G.Q., Wang, B.D., Fu, A.K., and Yang, Z.Y., Inorg. Chim., Acta. 2015, vol. 430, pp. 91–95. https://doi.org/10.1016/j.ica.2015.02.004

    CAS  Article  Google Scholar 

  4. Liu, C., Yang, Z., and Yan, M., J. Coord. Chem., 2012, vol. 65, pp. 3845–3850. https://doi.org/10.1080/00958972.2012.726987

    CAS  Article  Google Scholar 

  5. Lu, C.Y., Liu, Y.W., Hung, P.J., Wan, C.F., and Wu, A.T., Inorg. Chem. Commun., 2013, vol. 35, pp. 273–275. https://doi.org/10.1016/j.inoche.2013.06.005

    CAS  Article  Google Scholar 

  6. Maity, D. and Govindaraju, T., Inorg. Chem., 2010, vol. 49, pp. 7229–7231. https://doi.org/10.1021/ic1009994

    CAS  Article  PubMed  Google Scholar 

  7. Malkondu, S., Tetrahedron, 2014, vol. 70, pp. 5580–5584. https://doi.org/10.1016/j.tet.2014.06.094

    CAS  Article  Google Scholar 

  8. Qin, J.C., Li, T.R., Wang, B.D., Yang, Z.Y., and Fan, L., Synth. Met., 2014, vol.195, pp. 141–146. https://doi.org/10.1016/j.synthmet.2014.06.002

    CAS  Article  Google Scholar 

  9. Chen, Y., Shi, W., Hui, Y., Sun, X., Xu, L., Feng, L., and Xie, Z., Talanta, 2015, vol. 137, pp. 38–42. https://doi.org/10.1016/j.talanta.2015.01.018

    CAS  Article  PubMed  Google Scholar 

  10. Ding, W.H., Wang, D., Zheng, X.J., Ding, W.J., Zheng, J.Q., Mu, W.H., Cao, W., and Jin, L.P., Sens. Actuators. B Chem., 2015, vol. 209, pp. 359–367. https://doi.org/10.1016/j.snb.2014.11.144

    CAS  Article  Google Scholar 

  11. Hu, S., Song, Wu, J.G., Cheng, C., and Gao, Q., Spectrochim. Acta. A Mol. Biomol. Spectrosc., 2015, vol. 136, pp. 1188–1194. https://doi.org/10.1016/j.saa.2014.10.005

    CAS  Article  PubMed  Google Scholar 

  12. Lu, Y., Huang, S., Liu, Y., He, S., Zhao, L., and Zeng, X., Org. Lett., 2011, vol. 13, pp. 5274–5277. https://doi.org/10.1021/ol202054v

    CAS  Article  PubMed  Google Scholar 

  13. Kang, L., Liu, Y.T., Li, N.N., Dang, Q.X., Xing, Z.Y., Li, J.L., and Zhang, Y., J. Lumin., 2017, vol. 186, pp. 48–52. https://doi.org/10.1016/j.jlumin.2016.12.056

    CAS  Article  Google Scholar 

  14. Kaur, B., Kaur, N., and Kumar, S., Coord. Chem. Rev., 2018, vol. 358, pp. 13–69. https://doi.org/10.1016/j.ccr.2017.12.002

    CAS  Article  Google Scholar 

  15. Lee, J.J., Park, G.J., Kim, Y.S., Lee, S.Y., Lee, H.J., Noh, I., and Kim, C., Biosens. Bioelectron., 2015, vol. 69, pp. 226–229. https://doi.org/10.1016/j.bios.2015.02.038

    CAS  Article  Google Scholar 

  16. Kumar, M., Kumar, A., Faizi, Md.S.H., Kumar, S., Singh, M.K., Sahu, S.K., Kishor, S., and John, R.P., Sens. Actuators. B Chem., 2018, vol. 260, pp. 888–899. https://doi.org/10.1016/j.snb.2018.01.098

    CAS  Article  Google Scholar 

  17. Selvan, G.T., Kumaresan, M., Sivaraj, R., Enoch, I.V.M.V., and Selvakumar, P.M., Sens. Actuators. B Chem., 2016, vol. 229, pp. 181–189. https://doi.org/10.1016/j.snb.2016.01.097

    CAS  Article  Google Scholar 

  18. Jo, T.G., Bok, K.H., Han, J., Lim, M.H., and Kim, C., Dyes pigm., 2017, vol. 139, pp. 136–147. https://doi.org/10.1016/j.dyepig.2016.11.052

  19. Sarma, S., Bhowmik, A., Sarma, M.J., Banu, S., Phukan, P., and Das, D.K., Inorg. Chim. Acta, 2018, vol. 469, pp. 202–208. https://doi.org/10.1016/j.ica.2017.09.025

    CAS  Article  Google Scholar 

  20. Purkait, R., Patra, C., Mahapatra, A.D., Chattopadhyay, D., and Sinha, C., Sens. Actuators. B Chem., 2018, vol. 257, pp. 545–552. https://doi.org/10.1016/j.snb.2017.10.168

    CAS  Article  Google Scholar 

  21. Sooksin, S., Promarak, V., Ittisanronnachai, S., and Ngeontae, W., Sens. Actuators. B Chem., 2018, vol. 262, pp. 720–732. https://doi.org/10.1016/j.snb.2018.01.239

    CAS  Article  Google Scholar 

  22. Lv, R., Chen, Z., Fu, X., Yang, B., Li, H., Su, J., Gu, W., and Liu, X., J. Solid State Chem., 2018, vol. 259, pp. 67–72. https://doi.org/10.1016/j.jssc.2017.12.033

    CAS  Article  Google Scholar 

  23. Wang, N., Wang, R., Tu, Y., Pu, S., and Liu, G., Spectrochim. Acta A, 2018, vol. 196, pp. 303–310. https://doi.org/10.1016/j.saa.2018.02.018

    CAS  Article  Google Scholar 

  24. Lee, S.A., You, G.R., Choi, Y.W., Jo, H.Y., Kim, A.R., Noh, I., Kim, S.J., Kim, Y., and Kim, C., Dalton Trans., 2014, vol. 43, pp. 6650–6659. https://doi.org/10.1039/C4DT00361F

    CAS  Article  PubMed  Google Scholar 

  25. Liu, L.M. and Yang, Z.Y., Inorg. Chim. Acta, 2018, vol. 469, pp. 588–592. https://doi.org/10.1016/j.ica.2017.09.051

    CAS  Article  Google Scholar 

  26. Feng, E., Fan, C., Wang, N., Liu, G., and Pu, S., Dyes Pigm., 2018, vol. 151, pp. 22–27. https://doi.org/10.1016/j.dyepig.2017.12.041

    CAS  Article  Google Scholar 

  27. Li, C.R., Qin, J.C., Wang, G.Q., Wang, B.D., and Yang, Z.Y., Anal. Methods, 2015, vol. 7, pp. 3500–3505. https://doi.org/10.1039/C5AY00200A

    CAS  Article  Google Scholar 

  28. Li, C.R., Liao, Z.C., Qin, J.C., Wang, B.D., and Yang, Z.Y., J. Lumin., 2015, vol. 168, pp. 330–333. https://doi.org/10.1016/j.jlumin.2015.07.055

    CAS  Article  Google Scholar 

  29. Liu, Y.J., Tian, F.F., Fan, X.Y., Jiang, F.L., and Liu, Y., Sens. Actuators. B Chem., 2017, vol. 240, pp. 916–925. https://doi.org/10.1016/j.snb.2016.09.051

    CAS  Article  Google Scholar 

  30. Chen, Y., Wei, T., Zhang, Z., Chen, T., Li, J., Qiang, J., Lv, J., Wang, F., and Chen, X., Ind. Eng. Chem. Res., 2017, vol. 56, pp. 12 267–12 275. https://doi.org/10.1021/acs.iecr.7b02979

    CAS  Article  Google Scholar 

  31. Liu, T., Wan, X., and Yao, Y., Sens. Actuators. B Chem., 2018, vol. 254, pp.1094–1100. https://doi.org/10.1016/j.snb.2017.07.114

    CAS  Article  Google Scholar 

  32. Sen, B., Mukherjee, M., Banerjee, S., Pal, S., and Chattopadhyay, P., Dalton Trans., 2015, vol. 44, pp. 8708–8717. https://doi.org/10.1039/C5DT00315F

    CAS  Article  PubMed  Google Scholar 

  33. Li, M.X., Zhang, X., Fan, Y.H., and Bi, C.F., Luminescence, 2016, vol. 31, pp. 851–855. https://doi.org/10.1002/bio.3041

    CAS  Article  PubMed  Google Scholar 

  34. Mergu, N., Singh, A.K., and Gupta, V.K., Sensors, 2015, vol. 15, pp. 9097–9111. https://doi.org/10.3390/s150409097

    CAS  Article  PubMed  Google Scholar 

  35. Liao, Z., Liu, Y., Han, S.F., Wang, D., Zheng, J.Q., Zheng, X.J., and Jin, L.P., Sens. Actuators. B Chem., 2017, vol. 244, pp. 914–921. https://doi.org/10.1016/j.snb.2017.01.074

    CAS  Article  Google Scholar 

  36. Alam, R., Mistri, T., Bhowmick, R., Katarkar, A., Chaudhuri, K., and Ali, M., RSC Adv., 2016, vol. 6, pp. 1268–1278. https://doi.org/10.1039/C5RA18424J

    CAS  Article  Google Scholar 

  37. Cui, S., Tang, Y., and Pu, S., RSC Adv., 2016, vol. 6, pp. 84 592–84 598. https://doi.org/10.1039/C6RA18068J

    CAS  Article  Google Scholar 

  38. Gupta, S.R., Singh, P., Koch, B., and Singh, V.P., J. Photoch. Photobio. A, 2017, vol. 348, pp. 246–254. https://doi.org/10.1016/j.jphotochem.2017.08.055

    CAS  Article  Google Scholar 

  39. Zhu, Z.X., Yu, D.D., Liu, Z.G., Huang, Y.W., Zhou, A.Y., Chen, Z.W., Sun, J., Wang, X., Jin, L.T., and Cong, W.T., Luminescence, 2017, vol. 32, pp. 1307–1312. https://doi.org/10.1002/bio.3326

    CAS  Article  PubMed  Google Scholar 

  40. Liu, Z.C., Zhu, W.P., Chen, Y.H., Li, Y.X., Ding, Y.J., Yang, W.J., and Li, K., Dalton Trans., 2015, vol. 44, pp. 16 528–16 533. https://doi.org/10.1039/C5DT02220G

    CAS  Article  Google Scholar 

  41. Wang, J. and Peng, Y., RSC Adv., 2014, vol. 4, pp. 5845–5848. https://doi.org/10.1039/C3RA47104G

    CAS  Article  Google Scholar 

  42. Liu, Z., Ren, K., Chen, Y., Li, Y., Xie, J., Ding, Y., Li, L., Li, K., Zhu, W., Yang, W., and Xu, Z., RSC Adv., 2017, vol. 7, pp. 38 160–38 165. https://doi.org/10.1039/C7RA06915D

    Article  Google Scholar 

  43. Yue, Y., Xie, Z., Chu, Y., and Shi, W., Russ. J. Org. Chem., 2019, vol. 55, pp. 866–873. https://doi.org/10.1134/S1070428019060186

    CAS  Article  Google Scholar 

  44. Chu, Y., Xie, Z., Yue, Y., Yue, Y., Kong, X., Shi, W., and Feng, S., ACS Omega, 2019, vol. 4, pp. 5367–5373. https://doi.org/10.1021/acsomega.9b00290

    CAS  Article  Google Scholar 

  45. Xie, Z., Kong, X., Feng, L., Ma, J., Li, Y., Wang, X., Bao, W., Shi, W., and Hui, Y., Sens. Actuators. B Chem., 2018, vol. 257, pp. 154–165. https://doi.org/10.1016/j.snb.2017.10.167

    CAS  Article  Google Scholar 

  46. Hao, Y., Xie, Z., Bao, W., Wang, X., and Shi, W., Chin. J. Org. Chem., 2018, vol. 38, pp. 2109–2115. http://sioc-journal.cn/10.6023/cjoc201804034

    CAS  Article  Google Scholar 

  47. Wang, X., Shi, W., Feng, L., Ma, J., Li, Y., Kong, X., Chen, Y., Hui, Y., and Xie, Z., Inorg. Chem. Commun., 2017, vol. 79, pp. 50–54. https://doi.org/10.1016/j.inoche.2017.03.006

    CAS  Article  Google Scholar 

  48. Li, Y., Shi, W., Ma, J., Wang, X., Kong, X., Zhang, Y., Feng, L., Hui, Y., and Xie, Z., J. Photochem. Photobiol. A, 2017, vol. 338, pp. 1–7. https://doi.org/10.1016/j.jphotochem.2017.01.026

    CAS  Article  Google Scholar 

  49. Lei, F., Shi, W., Ma, J., Chen, Y., Fan, K., Hui, Y., and Xie, Z., Sens. Actuators. B Chem., 2016, vol. 237, pp. 563–569. https://doi.org/10.1016/j.snb.2016.06.129

    CAS  Article  Google Scholar 

  50. Lin, H., Shi, W., Tian, Y., Ma, F., Xu, L., Ma, J., Hui, Y., and Xie, Z., J. Lumin., 2015, vol. 157, pp. 280–284. https://doi.org/10.1016/j.jlumin.2014.09.004

    CAS  Article  Google Scholar 

  51. Yan, W., Wang, Q., Lin, Q., Li, M., Petersen, J.L., and Shi, X., Chem. Eur. J., 2011, vol. 17, pp. 5011–5018. https://doi.org/10.1002/chem.201002937

    CAS  Article  PubMed  Google Scholar 

  52. Zhang, Y., Ye, X., Petersen, J.L., Li, M., and Shi, X., J. Org. Chem., 2015, vol. 80, pp. 3664–3669. https://doi.org/10.1021/acs.joc.5b00006

    CAS  Article  PubMed  Google Scholar 

  53. Ma, J., Shi, W., Feng, L., Chen, Y., Fan, K., Hao, Y., Hui, Y., and Xie, Z., RSC Adv., 2016, vol. 6, pp. 28 034–28 037. https://doi.org/10.1039/C6RA01589A

    CAS  Article  Google Scholar 

  54. Safaeian, M., Solomon, D., and Castle, P.E., Spectroscopy, 2003, vol. 18, pp. 112–114. https://www.researchgate.net/publication/279903095_Limits_of_detection_ in_spectroscopy.

    Google Scholar 

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The authors thank Youth Science and Technology Innovation Team of SWPU (project no. 2017CXTD05).

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Correspondence to Zhengfeng Xie or Shun Feng.

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Corresponding author: phone: +86 28 83037306; fax: +86 28 83037305; e-mail: xiezhf@swpu.edu.cn.

Corresponding author: e-mail: fengshunxd@hotmail.com.

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Zhengfeng Xie, Hao, Y., Li, Z. et al. A Novel 2-Phenyl-1,2,3-Triazole Derived Fluorescent Probe for Recyclable Detection of Al3+ in Aqueous Medium and Its Application. Russ J Bioorg Chem 46, 627–641 (2020). https://doi.org/10.1134/S1068162020040214

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Keywords:

  • fluorescent probe
  • 2-phenyl-1,2,3-triazole
  • aluminum ion
  • bioimaging