Advertisement

Journal of Fluorescence

, Volume 24, Issue 4, pp 995–1001 | Cite as

The Smart 2-(2-Fluorobenzoyl)-N-(2-Methoxyphenyl)Hydrazinecarbothioamide Functionalized as Ni(II) Sensor in Micromolar Concentration Level and its Application in Live Cell Imaging

  • Muhammad Saleem
  • Anser Ali
  • Chang-Shik Choi
  • Bong Joo Park
  • Eun Ha Choi
  • Ki Hwan Lee
RAPID COMMUNICATION

Abstract

In recent years, fluorescent probes for the detection of environmentally and biologically important metal cations have received extensive attention for designing and development of fluorescent chemosensors. Herein, we report the photophysical results of 2-(2-fluorobenzoyl)-N-(2-methoxyphenyl) hydrazinecarbothioamide (4) functionalized as Ni (II) sensor in micromolar concentration level. Through fluorescence titration at 488 nm, we were confirmed that ligand 4 showed the remarkable emission by complexation between 4 and Ni (II) while it appeared no emission in case of the competitive ions (Cr3+, Fe2+, Co2+, Ba2+, Cu2+, Ca2+, Na+, K+, Cu+, Cs+). Furthermore, ligand 4 exhibited no toxicity with precise cell permeability toward normal living cells using L929 cell lines in bio imaging experiment investigated through confocal fluorescence microscope. The non-toxic behavior of ligand 4 (assessed by MTT assay) and its ability to track the Ni2+ in living cells suggest its possibility to use in biological system as nickel sensor.

Keywords

Fluorescent probe Substituted thiosemicarbazide Cytotoxicity Cell permeability Bioimaging 

Notes

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, (No. 2011–0015056) and the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (NRF-2010-0027963).

References

  1. 1.
    Wang H, Wang D, Wang Q, Li X, Schalley CA (2010) Nickel (II) and iron (III) selective off-on-type fluorescence probes based on perylene tetracarboxylic diimide. Org Biomol Chem 8:1017–1026PubMedCrossRefGoogle Scholar
  2. 2.
    Moro AV, Ferreira PC, Migowski P, Rodembusch FS, Dupont J, Ludtke DS (2013) Synthesis and photophysical properties of fluorescent 2,1,3-benzothiadiazole-triazole-linked glycoconjugates: selective chemosensors for Ni (II). Tetrahedron 69:201–206CrossRefGoogle Scholar
  3. 3.
    Abebe FA, Eribal CS, Ramakrishna G, Sinn E (2011) A ‘turn-on’ fluorescent sensor for the selective detection of cobalt and nickel ions in aqueous media. Tetrahedron Lett 52:5554–5558CrossRefGoogle Scholar
  4. 4.
    Goswami S, Chakraborty S, Paul S, Halder S, Maity AC (2013) A simple quinoxaline-based highly sensitive colorimetric and ratiometric sensor, selective for nickel and effective in very high dilution. Tetrahedron Lett 54:5075–5077CrossRefGoogle Scholar
  5. 5.
    Qu M, Li W, Zhang C (2013) Assessing the risk costs in delineating soil nickel contamination using sequential Gaussian simulation and transfer functions. Ecol Inform 13:99–105CrossRefGoogle Scholar
  6. 6.
    Quantin C, Ettler V, Garnier J, Sebek O (2008) Sources and extractibility of chromium and nickel in soil profiles developed on Czech serpentinites. Geoscience 340:872–882CrossRefGoogle Scholar
  7. 7.
    Radziemska M, Mazur Z, Jeznach J (2013) Influence of applying halloysite and zeolite to soil contaminated with nickel on the content of selected elements in maize (Zea mays L.). Chem Eng Trans 32:301–306Google Scholar
  8. 8.
    Ruan YB, Yu Y, Li C, Bogliotti N, Tang J, Xie J (2013) Triazolyl benzothiadiazole fluorescent chemosensors: a systematic investigation of 1,4- or 1,5-disubstituted mono- and bis-triazole derivatives. Tetrahedron 69:4603–4608CrossRefGoogle Scholar
  9. 9.
    Vandenbrouck T, Dom N, Novais S, Soetaert A, Ferreira ALG, Loureiro S, Soares AMVM, Coen WD (2011) Nickel response in function of temperature differences: Effects at different levels of biological organization in Daphnia magna. Comp Biochem Physiol 6:271–281Google Scholar
  10. 10.
    Patel E, Lynch C, Ruff V, Reynolds M (2012) Co-exposure to nickel and cobalt chloride enhances cytotoxicity and oxidative stress in human lung epithelial cells. Toxicol Appl Pharmacol 258:367–375PubMedCrossRefGoogle Scholar
  11. 11.
    Yeganeh M, Afyuni M, Khoshgoftarmanesh AH, Khodakarami L, Amini M, Soffyanian AR, Schulin R (2013) Mapping of human health risks arising from soil nickel and mercury contamination. J Hazard Mater 244–245:225–239PubMedCrossRefGoogle Scholar
  12. 12.
    Xiel J, Funakoshi T, Shimada H, Kojima S (1995) Effects of chelating agents on testicular toxicity exposure to nickel. Toxicology 103:147–l 55CrossRefGoogle Scholar
  13. 13.
    Novelli ELB, Hernandes RT, Filho JLVBN, Barbosa LL (1998) Differential/combined effect of water contamination with cadmium and nickel on tissues of rats. Environ Pollut 103:295–300CrossRefGoogle Scholar
  14. 14.
    Rathor G, Adhikari T, Chopra N (2013) Management of nickel contaminated soil and water through the use of carbon nano particles. J Chem Bio Phy Sci Sec A 3:901–905Google Scholar
  15. 15.
    Sharma V, Sachdeva MV, Sakhuja N, Arora D (2011) Impact of heavy metals (Chromium and Nickel) on the health of residents of Jagadhri city due to intake of contaminated underground water. Arch Appl Sci Res 3:207–212Google Scholar
  16. 16.
    Denkhaus E, Salnikow K (2002) Nickel essentiality, toxicity, and carcinogenicity. Crit Rev Oncol Hematol 42:35–56PubMedCrossRefGoogle Scholar
  17. 17.
    Kasprzak KS, Sunderman FW, Salnikow K (2003) Nickel carcinogenesis. Mutat Res 533:67–97PubMedCrossRefGoogle Scholar
  18. 18.
    Dodani SC, He Q, Chang CJ (2009) A turn-on fluorescent sensor for detecting nickel in living cells. J Am Chem Soc 131:18020–18021PubMedCentralPubMedCrossRefGoogle Scholar
  19. 19.
    Kumar P (2012) All solid state nickel (II)-selective potentiometric sensor based on an upper Rim substituted calixarene. Electroanalysis 24:2005–2012CrossRefGoogle Scholar
  20. 20.
    Forzani E, Zhang H, Chen W, Tao N (2005) Detection of heavy metal ions in drinking water using a high-resolution differential surface plasmon resonance sensor. Environ Sci Technol 39:1257–1262PubMedCrossRefGoogle Scholar
  21. 21.
    Lv XL, Luo SZ (2012) A fluorescence chemosensor based on peptidase for detecting nickel (II) with high selectivity and high sensitivity. Anal Bioanal Chem 402:2999–3002PubMedCrossRefGoogle Scholar
  22. 22.
    Huang J, Xu Y, Qian X (2009) A Rhodamine-based Hg2+ sensor with high selectivity and sensitivity in aqueous solution: a NS2-containing receptor. J Org Chem 74:2167–2170PubMedCrossRefGoogle Scholar
  23. 23.
    Yang YK, Yook KJ, Tae J (2005) A rhodamine-based fluorescent and colorimetric chemodosimeter for the rapid detection of Hg2+ ions in aqueous media. J Am Chem Soc 127:16760–16761PubMedCrossRefGoogle Scholar
  24. 24.
    Dolman SJ, Gosselin F, Shea PDO, Davies IW (2006) Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles. J Org Chem 71:9548–9551PubMedCrossRefGoogle Scholar
  25. 25.
    Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63PubMedCrossRefGoogle Scholar
  26. 26.
    Edelhoch H (1967) Spectroscopic determination of tryptophan and tyrosine in proteins. Biochemistry 6:1948–1954PubMedCrossRefGoogle Scholar
  27. 27.
    Gill SC, Hippel PH (1989) Calculation of protein extinction coefficients from amino acid sequence data. Anal Biochem 182:319–326PubMedCrossRefGoogle Scholar
  28. 28.
    Georgiev NI, Sakr AR, Bojinov VB (2011) Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer. Dyes Pigm 91:332–339CrossRefGoogle Scholar
  29. 29.
    Lang K, Chin JW (2013) Fluorescent imaging: shining a light into live cells. Nat Chem 5:81–82PubMedCrossRefGoogle Scholar
  30. 30.
    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 135:13512–13520PubMedCrossRefGoogle Scholar
  31. 31.
    Guo T, Cui L, Shen J, Wang R, Zhu W, Xu Y, Qian X (2013) A dual-emission and large stokes shift fluorescence probe for real-time discrimination of ROS/RNS and imaging in live cells. Chem Commun 49:1862–1864CrossRefGoogle Scholar
  32. 32.
    Xue L, Liu C, Jiang H (2009) A ratiometric fluorescent sensor with a large Stokes shift for imaging zinc ions in living cells. Chem. Commun. 1061–1063.Google Scholar
  33. 33.
    Demas JN, Crosby GA (1971) The measurement of photoluminescence quantum yields. A Review J Phys Chem 75:991–1024Google Scholar
  34. 34.
    Wurth C, Grabolle M, Pauli J, Spieles M, Genger UR (2013) Relative and absolute determination of fluorescence quantum yields of transparent samples. Nat Protoc 8:1535–1550PubMedCrossRefGoogle Scholar
  35. 35.
    Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer science + business media, LLC, New York, pp 54–55CrossRefGoogle Scholar
  36. 36.
    Brouwer AM (2011) Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report). Pure Appl Chem 83:2213–2228CrossRefGoogle Scholar
  37. 37.
    Fanyong Y, Donglei C, Ning Y, Meng W, Linfeng D, Chuying L, Li C (2013) A rhodamine based fluorescent probe for Hg2+ and its application to cellular imaging. Spectrochim. Acta, Part A 106:19–24CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Muhammad Saleem
    • 1
  • Anser Ali
    • 2
  • Chang-Shik Choi
    • 3
  • Bong Joo Park
    • 2
  • Eun Ha Choi
    • 2
  • Ki Hwan Lee
    • 1
  1. 1.Department of ChemistryKongju National UniversityGongjuRepublic of Korea
  2. 2.Department of Plasma Bioscience and displayKwangwoon UniversityNowon-guRepublic of Korea
  3. 3.Department of Oriental Medicine FermentationFar East UniversityChungbukRepublic of Korea

Personalised recommendations