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Novel probes for selective fluorometric sensing of Fe(II) and Fe(III) based on BODIPY dyes

Year 2019, Volume: 6 Issue: 2, 207 - 216, 15.06.2019
https://doi.org/10.18596/jotcsa.488181

Abstract

Two novel
boron-dipyrromethene (BODIPY) based fluorescence turn-off sensors, which
demonstrate high selectivity and sensitivity toward Fe2+ and Fe3+
ions have been reported. A simple and high yielded synthesis of
fluorescent BODIPY derivatives with malonyl unit for sensitization have been
described. This approach provides quick, high yielded and low-cost preparation
of probes. The two sensors have been comprised of combination of one and two
BODIPY fluorophore and a malonyl unit, substituted on meso position of BODIPYs.
Synthesized BODIPY derivatives have been characterized via elemental analyses,
mass spectrometry, 1H and 13C spectroscopy and their
photophyisical properties were investigated by UV- Vis absorption and
fluorescence emission spectroscopy.  The
synthesized sensors (2, 3) have been
used as a fluorescent probe towards the selective and sensitive detection of
biologically important Fe2+ and Fe3+ ions in
tetrahydrofuran by fluorescence spectroscopy. The limit of detection (LOD) have
been calculated to be for the BODIPY 2,
14.61 (Fe2+), 1.22 (Fe3+) and for BODIPY 3, 1.16 (Fe2+) and 1.06 (Fe3+).

References

  • 1. Hua C-j, Zheng H, Zhang K, Xin M, Gao J-r, Li Y-j. A novel turn off fluorescent sensor for Fe (III) and pH environment based on coumarin derivatives: the fluorescence characteristics and theoretical study. Tetrahedron. 2016;72(51):8365-72.
  • 2. Chen F, Hou F, Huang L, Cheng J, Liu H, Xi P, et al. Development of a novel fluorescent probe for copper ion in near aqueous media. Dyes and Pigments. 2013;98(1):146-52.
  • 3. Wu X, Xu B, Tong H, Wang L. Phosphonate-functionalized polyfluorene film sensors for sensitive detection of iron (III) in both organic and aqueous media. Macromolecules. 2010;43(21):8917-23.
  • 4. Atkinson A, Winge DR. Metal acquisition and availability in the mitochondria. Chemical reviews. 2009;109(10):4708-21.
  • 5. Brugnara C. Iron deficiency and erythropoiesis: new diagnostic approaches. Clinical chemistry. 2003;49(10):1573-8.
  • 6. Zhang X-B, Cheng G, Zhang W-J, Shen G-L, Yu R-Q. A fluorescent chemical sensor for Fe3+ based on blocking of intramolecular proton transfer of a quinazolinone derivative. Talanta. 2007;71(1):171-7.
  • 7. Hirayama T, Nagasawa H. Chemical tools for detecting Fe ions. Journal of clinical biochemistry and nutrition. Journal of clinical biochemistry and nutrition. 2017; 60(1): 39-48.
  • 8. McRae R, Bagchi P, Sumalekshmy S, Fahrni CJ. In situ imaging of metals in cells and tissues. Chemical Reviews. 2009;109(10):4780-827.
  • 9. Chen W-d, Gong W-t, Ye Z-q, Lin Y, Ning G-l. FRET-based ratiometric fluorescent probes for selective Fe 3+ sensing and their applications in mitochondria. Dalton Transactions. 2013;42(28):10093-6.
  • 10. Yang Z, She M, Yin B, Cui J, Zhang Y, Sun W, et al. Three Rhodamine-based “off–on” Chemosensors with high selectivity and sensitivity for Fe3+ imaging in living cells. The Journal of organic chemistry. 2011;77(2):1143-7.
  • 11. Liu M, Hu M, Jiang Q, Lu Z, Huang Y, Tan Y, et al. A novel coumarin derivative as a sensitive probe for tracing intracellular pH changes. RSC Advances. 2015;5(21):15778-83.
  • 12. Zhu X, Zhang Z, Xue Z, Huang C, Shan Y, Liu C, Wang T, et al. Understanding the selective detection of Fe3+ based on graphene quantum dots as fluorescent probes: the K sp of a metal hydroxide-assisted mechanism. Analytical chemistry. 2017; 89(22): 12054-12058.
  • 13. Qin W, Dou W, Leen V, Dehaen W, Van der Auweraer M, Boens N. A ratiometric, fluorescent BODIPY-based probe for transition and heavy metal ions. RSC Advances. 2016;6(10):7806-16.
  • 14. Boens N, Leen V, Dehaen W. Fluorescent indicators based on BODIPY. Chemical Society Reviews. 2012;41(3):1130-72.
  • 15. Loudet A, Burgess K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chemical reviews. 2007;107(11):4891-932.
  • 16. Ulrich G, Ziessel R, Harriman A. The chemistry of fluorescent bodipy dyes: versatility unsurpassed. Angewandte Chemie International Edition. 2008;47(7):1184-201.
  • 17. Okutan E, Tümay SO, Yeşilot S. Colorimetric fluorescent sensors for hemoglobin based on BODIPY dyes. Journal of fluorescence. 2016;26(6):2333-43.
  • 18. Gabe Y, Urano Y, Kikuchi K, Kojima H, Nagano T. Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore rational design of potentially useful bioimaging fluorescence probe. Journal of the American Chemical Society. 2004;126(10):3357-67.
  • 19. Aron AT, Ramos-Torres KM, Cotruvo Jr JA, Chang CJ. Recognition-and reactivity-based fluorescent probes for studying transition metal signaling in living systems. Accounts of chemical research. 2015;48(8):2434-42.
  • 20. Murale DP, Manjare ST, Lee Y-S, Churchill DG. Fluorescence probing of the ferric Fenton reaction via novel chelation. Chemical Communications. 2014;50(3):359-61.
  • 21. Carter KP, Young AM, Palmer AE. Fluorescent sensors for measuring metal ions in living systems. Chemical reviews. 2014;114(8):4564-601.
  • 22. Likussar W, Boltz D. Theory of continuous variations plots and a new method for spectrophotometric determination of extraction and formation constants. Analytical Chemistry. 1971;43(10):1265-72.
  • 23. Bano S, Mohd A, Khan AAP, and Siddiq KS. Complexation and Mechanism of Fluorescence Quenching of Telmisartan with Y(III) and Nd(III). Journal of Chemical Engineering Data. 2010;55:5759–5765.
  • 24. De Costa MDP, Jayasinghe WAPA. Detailed studies on complexation behaviour and mechanism of fluorescence quenching of naphthalene linked hydroxamic acid with transition metal ions by UV-visible and fluorescence spectra. Journal of Photochemistry and Photobiology A: Chemistry. 2004;162(2-3):591-598.
Year 2019, Volume: 6 Issue: 2, 207 - 216, 15.06.2019
https://doi.org/10.18596/jotcsa.488181

Abstract

References

  • 1. Hua C-j, Zheng H, Zhang K, Xin M, Gao J-r, Li Y-j. A novel turn off fluorescent sensor for Fe (III) and pH environment based on coumarin derivatives: the fluorescence characteristics and theoretical study. Tetrahedron. 2016;72(51):8365-72.
  • 2. Chen F, Hou F, Huang L, Cheng J, Liu H, Xi P, et al. Development of a novel fluorescent probe for copper ion in near aqueous media. Dyes and Pigments. 2013;98(1):146-52.
  • 3. Wu X, Xu B, Tong H, Wang L. Phosphonate-functionalized polyfluorene film sensors for sensitive detection of iron (III) in both organic and aqueous media. Macromolecules. 2010;43(21):8917-23.
  • 4. Atkinson A, Winge DR. Metal acquisition and availability in the mitochondria. Chemical reviews. 2009;109(10):4708-21.
  • 5. Brugnara C. Iron deficiency and erythropoiesis: new diagnostic approaches. Clinical chemistry. 2003;49(10):1573-8.
  • 6. Zhang X-B, Cheng G, Zhang W-J, Shen G-L, Yu R-Q. A fluorescent chemical sensor for Fe3+ based on blocking of intramolecular proton transfer of a quinazolinone derivative. Talanta. 2007;71(1):171-7.
  • 7. Hirayama T, Nagasawa H. Chemical tools for detecting Fe ions. Journal of clinical biochemistry and nutrition. Journal of clinical biochemistry and nutrition. 2017; 60(1): 39-48.
  • 8. McRae R, Bagchi P, Sumalekshmy S, Fahrni CJ. In situ imaging of metals in cells and tissues. Chemical Reviews. 2009;109(10):4780-827.
  • 9. Chen W-d, Gong W-t, Ye Z-q, Lin Y, Ning G-l. FRET-based ratiometric fluorescent probes for selective Fe 3+ sensing and their applications in mitochondria. Dalton Transactions. 2013;42(28):10093-6.
  • 10. Yang Z, She M, Yin B, Cui J, Zhang Y, Sun W, et al. Three Rhodamine-based “off–on” Chemosensors with high selectivity and sensitivity for Fe3+ imaging in living cells. The Journal of organic chemistry. 2011;77(2):1143-7.
  • 11. Liu M, Hu M, Jiang Q, Lu Z, Huang Y, Tan Y, et al. A novel coumarin derivative as a sensitive probe for tracing intracellular pH changes. RSC Advances. 2015;5(21):15778-83.
  • 12. Zhu X, Zhang Z, Xue Z, Huang C, Shan Y, Liu C, Wang T, et al. Understanding the selective detection of Fe3+ based on graphene quantum dots as fluorescent probes: the K sp of a metal hydroxide-assisted mechanism. Analytical chemistry. 2017; 89(22): 12054-12058.
  • 13. Qin W, Dou W, Leen V, Dehaen W, Van der Auweraer M, Boens N. A ratiometric, fluorescent BODIPY-based probe for transition and heavy metal ions. RSC Advances. 2016;6(10):7806-16.
  • 14. Boens N, Leen V, Dehaen W. Fluorescent indicators based on BODIPY. Chemical Society Reviews. 2012;41(3):1130-72.
  • 15. Loudet A, Burgess K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chemical reviews. 2007;107(11):4891-932.
  • 16. Ulrich G, Ziessel R, Harriman A. The chemistry of fluorescent bodipy dyes: versatility unsurpassed. Angewandte Chemie International Edition. 2008;47(7):1184-201.
  • 17. Okutan E, Tümay SO, Yeşilot S. Colorimetric fluorescent sensors for hemoglobin based on BODIPY dyes. Journal of fluorescence. 2016;26(6):2333-43.
  • 18. Gabe Y, Urano Y, Kikuchi K, Kojima H, Nagano T. Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore rational design of potentially useful bioimaging fluorescence probe. Journal of the American Chemical Society. 2004;126(10):3357-67.
  • 19. Aron AT, Ramos-Torres KM, Cotruvo Jr JA, Chang CJ. Recognition-and reactivity-based fluorescent probes for studying transition metal signaling in living systems. Accounts of chemical research. 2015;48(8):2434-42.
  • 20. Murale DP, Manjare ST, Lee Y-S, Churchill DG. Fluorescence probing of the ferric Fenton reaction via novel chelation. Chemical Communications. 2014;50(3):359-61.
  • 21. Carter KP, Young AM, Palmer AE. Fluorescent sensors for measuring metal ions in living systems. Chemical reviews. 2014;114(8):4564-601.
  • 22. Likussar W, Boltz D. Theory of continuous variations plots and a new method for spectrophotometric determination of extraction and formation constants. Analytical Chemistry. 1971;43(10):1265-72.
  • 23. Bano S, Mohd A, Khan AAP, and Siddiq KS. Complexation and Mechanism of Fluorescence Quenching of Telmisartan with Y(III) and Nd(III). Journal of Chemical Engineering Data. 2010;55:5759–5765.
  • 24. De Costa MDP, Jayasinghe WAPA. Detailed studies on complexation behaviour and mechanism of fluorescence quenching of naphthalene linked hydroxamic acid with transition metal ions by UV-visible and fluorescence spectra. Journal of Photochemistry and Photobiology A: Chemistry. 2004;162(2-3):591-598.
There are 24 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Elif Şenkuytu 0000-0002-3579-8062

Elif Okutan 0000-0002-6576-4453

Publication Date June 15, 2019
Submission Date November 27, 2018
Acceptance Date May 6, 2019
Published in Issue Year 2019 Volume: 6 Issue: 2

Cite

Vancouver Şenkuytu E, Okutan E. Novel probes for selective fluorometric sensing of Fe(II) and Fe(III) based on BODIPY dyes. JOTCSA. 2019;6(2):207-16.