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Bi-8-carboxamidoquinoline Derivatives for the Fluorescent Recognition of Zn2+

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Abstract

Three fluorescent sensors which were composed of a phendiol (o-, m-, p-isomers) and two carboxamidoquinolines have been synthesized and characterized. Research on the Zn2+-sensing properties of the three sensors was carried out, and the results showed a significant difference in the recognition performance for Zn2+. The fluorescence intensity (I510 nm) of ortho isomeric sensor binding to Zn2+ was enhanced 23-fold, the meta 15-fold, the para 8-fold. As the distance between two carboxamidoquinolines became longer, the fluorescence enhancement decreased. In addition, the selectivity of sensors got poor and the detection limit became higher with rising the distance between two receptors.

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References

  1. Andreini C, Banci L, Bertini I, Rosato A (2006) Zinc through the three domains of life. J Proteome Res 5:3173–3178

    Article  CAS  PubMed  Google Scholar 

  2. Frassinetti S, Bronzetti G, Caltavuturo L, Cini M, Croce CD (2006) The role of zinc in life: a review. J Environ Pathol Toxicol Oncol 25:597–610

    Article  CAS  PubMed  Google Scholar 

  3. Cuajungco MP, Lees GJ (1997) Zinc metabolism in the brain: relevance to human neurodegenerative disorders. Neurobiol Dis 4:137–169

    Article  CAS  PubMed  Google Scholar 

  4. Wong LS, Khan F, Micklefield J (2009) Selective covalent protein immobilization: strategies and applications. Chem Rev 109:4025–4053

    Article  CAS  PubMed  Google Scholar 

  5. Yang Y, Zhao Q, Feng W, Li F (2013) Luminescent chemodosimeters for bioimaging. Chem Rev 113:192–270

    Article  CAS  PubMed  Google Scholar 

  6. Kobayashi H, Ogawa M, Alford R, Choyke PL, Urano Y (2010) New strategies for fluorescent probe design in medical diagnostic imaging. Chem Rev 110:2620–2640

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  7. Tomat E, Lippard SJ (2010) Imaging mobile zinc in biology. Curr Opin Chem Biol 14:225–230

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  8. Li X, Gao X, Shi W, Ma H (2014) Design strategies for water-soluble small molecular chromogenic and fluorogenic probes. Chem Rev 114:590–659

    Article  CAS  PubMed  Google Scholar 

  9. Xu ZC, Yoon JY, Spring DR (2010) Fluorescent chemosensors for Zn2+. Chem Soc Rev 39:1996–2006

    Article  CAS  PubMed  Google Scholar 

  10. Carter KP, Young AM, Palmer AE (2014) Fluorescent sensors for measuring metal ions in living systems. Chem Rev 114:4564–4601

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  11. Simmons JT, Allen JR, Morris DR, Clark RJ, Levenson CW, Davidson MW, Zhu L (2013) Integrated and passive 1, 2, 3-triazolyl groups in fluorescent indicators for Zinc (II) ions: thermodynamic and kinetic evaluations. Inorg Chem 52:5838–5850

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  12. Sumiya S, Shiraishi Y, Hirai T (2013) Mechanism for different fluorescence response of a coumarin–amide–dipicolylamine linkage to Zn (II) and Cd (II) in water. J Phys Chem A 117:1474–1482

    Article  CAS  PubMed  Google Scholar 

  13. Zhang JF, Kim S, Han JH, Lee SJ, Pradhan T, Cao QY, Lee SJ, Kang C, Kim JS (2011) Pyrophosphate-selective fluorescent chemosensor based on 1, 8-naphthalimide–DPA–Zn (II) complex and its application for cell imaging. Org Lett 13:5294–5297

    Article  CAS  PubMed  Google Scholar 

  14. Meeusen JW, Tomasiewicz H, Nowakowski A, Petering DH (2011) TSQ (6-methoxy- 8-p-toluenesulfonamido-quinoline), a common fluorescent sensor for cellular zinc, images zinc proteins. Inorg Chem 50:7563–7573

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  15. Ravikumar I, Ghosh P (2011) Zinc (II) and PPi selective fluorescence OFF–ON–OFF functionality of a chemosensor in physiological conditions. Inorg Chem 50:4229–4231

    Article  CAS  PubMed  Google Scholar 

  16. Fernández-Lodeiro J, Núñez C, de Castro CS, Bértolo E, Seixas de Melo JS, Capelo JL, Lodeiro C (2013) Steady-state and time-resolved investigations on pyrene-based chemosensors. Inorg Chem 52:121–129

    Article  PubMed  Google Scholar 

  17. Basa PN, Bhowmick A, Horn LM, Sykes AG (2012) Zinc (II) mediated imine–enamine tautomerization. Org Lett 14:2698–2701

    Article  CAS  PubMed  Google Scholar 

  18. Ingale SA, Seela F (2012) A ratiometric fluorescent on–off Zn2+ chemosensor based on a tripropargylamine pyrene azide click adduct. J Org Chem 77:9352–9356

    Article  CAS  PubMed  Google Scholar 

  19. Lin W, Buccella D, Lippard SJ (2013) Visualization of peroxynitrite-induced changes of labile Zn2+ in the endoplasmic reticulum with benzoresorufin-based fluorescent probes. J Am Chem Soc 135:13512–13520

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  20. Zhou Y, Li ZX, Zang SQ, Zhu YY, Zhang HY, Hou HW, Mak TCW (2012) A novel sensitive turn-on fluorescent Zn2+ chemosensor based on an easy to prepare C3-symmetric schiff-base derivative in 100% aqueous solution. Org Lett 14:1214–1217

    Article  CAS  PubMed  Google Scholar 

  21. Wang L, Qin W, Tang X, Dou W, Liu W (2011) Development and applications of fluorescent indicators for Mg2+ and Zn2+. J Phys Chem A 115:1609–1616

    Article  CAS  PubMed  Google Scholar 

  22. Pathak RK, Hinge VK, Mondal M, Rao CP (2011) Triazole-linked-thiophene conjugate of calix [4] arene: its selective recognition of Zn2+ and as biomimetic model in supporting the events of the metal detoxification and oxidative stress involving metallothionein. J Org Chem 76:10039–10049

    Article  CAS  PubMed  Google Scholar 

  23. Pathak RK, Tabbasum K, Rai A, Panda D, Rao CP (2012) Pyrophosphate sensing by a fluorescent Zn2+ bound triazole linked imino-thiophenyl conjugate of calix [4] arene in HEPES buffer medium: spectroscopy, microscopy, and cellular studies. Anal Chem 84:5117–5123

    Article  CAS  PubMed  Google Scholar 

  24. Song EJ, Kang J, You GR, Park GJ, Kim Y, Kim SJ, Kim C, Harrison RG (2013) A single molecule that acts as a fluorescence sensor for zinc and cadmium and a colorimetric sensor for cobalt. Dalton Trans 42:15514–15520

    Article  CAS  PubMed  Google Scholar 

  25. Pal P, Rastogi SK, Gibson CM, Aston DE, Branen AL, Bitterwolf TE (2011) Fluorescence sensing of zinc (II) using ordered mesoporous silica material (MCM-41) functionalized with N-(quinolin-8-yl)-2-[3-(triethoxysilyl) propylamino] acetamide. ACS Appl Mater Interfaces 3:279–286

    Article  CAS  PubMed  Google Scholar 

  26. Rastogi SK, Pal P, Aston DE, Bitterwolf TE, Branen AL (2011) 8-Aminoquinoline functionalized silica nanoparticles: a fluorescent nanosensor for detection of divalent zinc in aqueous and in yeast cell suspension. ACS Appl Mater Interfaces 3:1731–1739

    Article  CAS  PubMed  Google Scholar 

  27. Zhang Y, Guo XF, Jia LH, Xu SC, Xu ZH, Zheng LB, Qian XH (2012) Substituent-dependent fluorescent sensors for zinc ions based on carboxamidoquinoline. Dalton Trans 41:11776–11782

    Article  CAS  PubMed  Google Scholar 

  28. Mummidivarapu VSS, Tabbasum K, Chinta JP, Rao CP (2012) 1, 3-Di-amidoquinoline conjugate of calix [4] arene (L) as a ratiometric and colorimetric sensor for Zn2+: Spectroscopy, microscopy and computational studies. Dalton Trans 41:1671–1674

    Article  CAS  PubMed  Google Scholar 

  29. Tang LJ, Zhao J, Cai MJ, Zhou P, Zhong KL, Hou SH, Bian YJ (2013) An efficient sensor for relay recognition of Zn2+ and Cu2+ through fluorescence ‘off–on–off’ functionality. Tetrahedron Lett 54:6105–6109

    Article  CAS  Google Scholar 

  30. Callan JF, de Silva AP, Magri DC (2005) Luminescent sensors and switches in the early 21st century. Tetrahedron 61:8551–8588

    Article  CAS  Google Scholar 

  31. Zhang Y, Guo XF, Si WX, Jia LH, Qian XH (2008) Ratiometric and water-soluble fluorescent zinc sensor of carboxamidoquinoline with an alkoxyethylamino chain as receptor. Org Lett 10:473–476

    Article  CAS  PubMed  Google Scholar 

  32. Du JJ, Fan JL, Peng XJ, Li HL, Sun SG (2010) The quinoline derivative of ratiometric and sensitive fluorescent zinc probe based on deprotonation. Sensors Actuators B 144:337–341

    Article  CAS  Google Scholar 

  33. Goswami S, Das AK, Aich K, Manna A, Maity S, Khanra K, Bhattacharyya N (2013) Ratiometric and absolute water-soluble fluorescent tripodal zinc sensor and its application in killing human lung cancer cells. Analyst 138:4593–4598

    Article  CAS  PubMed  Google Scholar 

  34. Yu H, Yu T, Sun M, Sun J, Zhang S, Wang S, Jiang H (2014) A symmetric pseudo salen based turn-on fluorescent probe for sensitive detection and visual analysis of zinc ion. Talanta 125:301–305

    Article  CAS  PubMed  Google Scholar 

  35. Lin HY, Cheng PY, Wan CF, Wu AT (2012) A turn-on and reversible fluorescence sensor for zinc ion. Analyst 137:4415–4417

    Article  CAS  PubMed  Google Scholar 

  36. Dong ZP, Guo YP, Tian X, Ma JT (2013) Quinoline group based fluorescent sensor for detecting zinc ions in aqueous media and its logic gate behaviour. J Lumin 134:635–639

    Article  CAS  Google Scholar 

  37. Lee J, Kim H, Kim S, Noh JY, Song EJ, Kim C, Kim J (2013) Fluorescent dye containing phenol-pyridyl for selective detection of aluminum ions. Dyes Pigments 96:590–594

    Article  CAS  Google Scholar 

  38. Goswami S, Maity S, Das AK, Maity AC (2013) Single chemosensor for highly selective colorimetric and fluorometric dual sensing of Cu (II) as well as ‘NIRF’ to acetate ion. Tetrahedron Lett 54:6631–6634

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (21176125), the Science Research Project of the Ministry of Education of Heilongjiang Province of China (12521594, 2012TD012, JX201205), the Natural Science Foundation of Heilongjiang province of China (B201114, B201313), and the Key Program of Science and Technology of Qiqihar, Heilongjiang Province (GYGG–201108).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Key Laboratory of Fine Chemicals of College of Heilongjiang Province, Qiqihar University, Qiqihar, 161006, China

    Xuhua Tian, Xiangfeng Guo, Lihua Jia & Yu Zhang

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  1. Xuhua Tian
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  2. Xiangfeng Guo
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  3. Lihua Jia
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  4. Yu Zhang
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Correspondence to Xiangfeng Guo or Lihua Jia.

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Tian, X., Guo, X., Jia, L. et al. Bi-8-carboxamidoquinoline Derivatives for the Fluorescent Recognition of Zn2+ . J Fluoresc 25, 441–449 (2015). https://doi.org/10.1007/s10895-015-1531-3

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  • DOI: https://doi.org/10.1007/s10895-015-1531-3

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