Abstract
A new ratiometric fluorescent sensor (DQO) based on N,N′-Di(quinolin-8-yl) oxalamide has been designed and synthesized for selective detection of Zn2+. The fluorescence ratio (I 536 nm/I 450 nm) of DQO was enhanced 10-fold when Zn2+ was present in a buffer aqueous solution at pH 8.66. The sensor showed linear response toward Zn2+ in the concentration range 0–15 μM, and the detection limit was calculated to be 2.4 μM. A Job’s plot implied the formation of a DQO/Zn2+ complex with 1:1 stoichiometry, and the apparent association constant of DQO/Zn2+ complex was computed to be 1.5 × 104 M−1.
Similar content being viewed by others
References
Berg JM, Shi Y (1996) The galvanization of biology: a growing appreciation for the roles of zinc. Science 271(5252):1081–1085
Fraker PJ, King LE (2004) Reprogramming of the immune system during zinc deficiency. Annu Rev Nutr 24:277–298
Frederickson CJ, Koh JY, Bush AI (2005) The neurobiology of zinc in health and disease. Nature. Rev Neurosci 6:449–462
Urbanova N, Kadar M, Toth K (2008) Fluorescent iminodiacetamide derivatives as potential ionophores for optical zinc ion-selective sensors. Anal Sci 24:727–733
Tewari PK, Singh AK (2000) Thiosalicylic acid-immobilized amberlite XAD-2: metal sorption behaviour and applications in estimation of metal ions by flame atomic absorption spectrometry. Analyst 125:2350–2355
Lear J, Hare DJ, Fryer F, Adlard PA, Finkelstein DI, Doble PA (2012) High-resolution elemental bioimaging of Ca, Mn, Fe, Co, Cu, and Zn employing LA-ICP-MS and hydrogen reaction gas. Anal Chem 84:6707–6714
Carter KP, Young AM, Palmer AE (2014) Fluorescent sensors for measuring metal ions in living systems. Chem Rev 114:4564–4601
Quang DT, Kim JS (2010) Fluoro-and chromogenic chemodosimeters for heavy metal ion detection in solution and biospecimens. Chem Rev 110:6280–6301
Li H, Zhang SJ, Gong CL, Wang JZ, Wang F (2016) A turn-on and reversible fluorescence sensor for zinc ion based on 4,5-diazafluorene schiff base. J Fluoresc 26:1555–1561
Chen Y, Bai Y, Han Z, He W, Guo Z (2015) Photoluminescence imaging of Zn2+ in living systems. Chem Soc Rev 44:4475–4974
Yuan L, Lin WY, Zheng KB, Zhu SS (2013) FRET-based small-molecule fluorescent sensors: rational design and bioimaging applications. Acc Chem Res 46:1462–1473
Ying Z, Jie D, Liang T, Abdel-Halim ES, Liping J, Jun-Jie Z (2016) FITC doped rattle-type silica colloidal particle-based ratiometric fluorescent sensor for biosensing and imaging of superoxide anion. ACS Appl Mat Interfaces 8:6423–6430
Nolan EM, Ryu JW, Jaworski J, Feazell RP, Sheng M, Lippard SJ (2006) Zinspy sensors with enhanced dynamic range for imaging neuronal cell zinc uptake and mobilization. J Am Chem Soc 128:15517–15528
Ma Y, Wang F, Kambam S, Chen X (2013) A quinoline-based fluorescent chemosensor for distinguishing cadmium from zinc ions using cysteine as an auxiliary reagent. Sens Actuators B Chem 188:1116–1122
Meng X, Wang SX, Zhu M (2012) Quinoline-based fluorescence sensors. In: Saha S (ed) Molecular photochemistry-various aspects. InTech, Rijeka
Chen X, Pradhan T, Wang F, Kim JS, Yoon J (2011) Fluorescent chemosensors based on spiroring- opening of xanthenes and related derivatives. Chem Rev 112:1910–1956
Zhu B, Guo B, Zhao Y, Zhang B, Du B (2013) A highly sensitive ratiometric fluorescent probe with a large emission shift for imaging endogenous cysteine in living cells. Biosens Bioelectron 55C:72–75
Boens N, Leen V, Dehaen W (2012) Fluorescent indicators based on BODIPY. Chem Soc Rev 41:1130–1172
Shi D, Zhou X, Zheng T, Zou Y, Guo S, Lv J, Yan F (2015) Recognition and fluorescent sensing of zinc ions using organic fluorophores-based sensor molecules. J Iran Chem Soc 12:293–308
Stasiuk GJ, Minuzzi F, Sae-Heng M, Rivas C, Juretschke HP, Piemonti L, Allegrini PR, Laurent D, Duckworth AR, Beeby A, Rutter GA, Long NJ (2015) Dual-modal magnetic resonance/fluorescent zinc sensors for pancreatic β-cell mass imaging. Chem Eur J 21:5023–5033
Mummidivarapu VVS, 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
Mummidivarapu VVS, Bandaru S, Yarramala DS, Samanta K, Mhatre DS, Rao CP (2015) Binding and ratiometric dual ion recognition of Zn2+ and Cu2+ by 1,3,5-tris- amidoquinoline conjugate of calix[6]arene by spectroscopy and its supramolecular features by microscopy. Anal Chem 87:4988–4995
Zhang Y, Guo X, Si W, Jia L, Qian X (2008) Ratiometric and water-soluble fluorescent zinc sensor of carboxamidoquinoline with an alkoxyethylamino chain as receptor. Org Lett 10:473–476
Zhang Y, Guo X, Zheng L, Jia L, Qian X (2013) A new strategy for the ratiometric fluorescence detection of Zn (II) in the surfactant solution. J Photochem Photobiol B 257:20–25
Zhang Y, Guo X, Jia L, Xu S, Xu Z, Zheng L, Qian X (2012) Substituent-dependent fluorescent sensors for zinc ions based on carboxamidoquinoline. Dalton Trans 4:11776–11782
Tian X, Guo X, Jia L, Yang R, Cao G, Liu C (2015) A fluorescent sensor based on bicarboxamidoquinoline for highly selective relay recognition of Zn2+ and citrate with ratiometric response. Sens Actuators B Chem 22:923–929
He C, Qian X, Xu Y, Yang C, Yin L, Zhu W (2011) A ratiometric fluorescent sensor for oxalate based on alkyne-conjugated carboxamidoquinolines in aqueous solution and imaging in living cells. Dalton Trans 40:1034–1037
Jiang J, Jiang H, Tang X, Yang L, Dong W, Liu W, Fang R, Liu W (2011) An efficient sensor for Zn2+ and Cu2+ based on different binding modes. Dalton Trans 40:6367–6370
Tian X, Guo X, Jia L, Zhang Y (2015) Bi-8-carboxamidoquinoline derivatives for the fluorescent recognition of Zn2+. J Fluoresc 25:441–449
Tian X, Guo X, Yu F, Jia L (2016) An oxalamidoquinoline-based fluorescent sensor for selective detection of Zn2+ in solution and living cells and its logic gate behavior. Sensors Actuators B Chem 232:181–187
Aragoni MC, Arca M, Bencini A, Caltagirone C, Garau A, Isaia F, Light ME, Lippolis V, Lodeiro C, Mameli M, Montis R, Mostallino MC, Pintus A, Puccioni S (2013) Zn2+/Cd2+ optical discrimination by fluorescent chemosensors based on 8-hydroxyquinoline derivatives and sulfur-containing macrocyclic units. Dalton Trans 42:14516–14530
Li Y, Yang Z, Liu Z, Wang B, Li S (2011) Highly selective and sensitive fluorescent nanosensor for zinc ions. Sens Actuators B Chem 160:1504–1507
Joshi BP, Park J, Lee WI, Lee K-H (2009) Ratiometric and turn-on monitoring for heavy and transition metal ions in aqueous solution with a fluorescent peptide sensor. Talanta 78:903–909
Zhang Y, Guo X, Tian X, Liu A, Jia L (2015) Carboxamidoquinoline–coumarin derivative: a ratiometric fluorescent sensor for Cu (II) in a dual fluorophore hybrid. Sens Actuators B Chem 218:37–41
Hessels AM, Merkx M (2016) A simple method for proper analysis of FRET sensor titration data and intracellular imaging experiments based on isosbestic points. ACS Sens 1:498–502
Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707
Yuan M, Zhou W, Liu X, Zhu M, Li J, Yin X, Zheng H, Zou Z, Ouyang C, Liu H, Li Y, Zhu D (2008) A multianalyte chemosensor on a single molecule: promising structure for an integrated logic gate. J Org Chem 73:5008–5014
Song Z-K, Dong B, Lei G-J, Peng X-J, Guo Y (2013) Novel selective fluorescent sensors for sensing Zn2+ ions based on a coumarin Schiff-base. Tetrahedron Lett 54:4945–4949
Acknowledgements
This work was supported by the National Natural Science Foundation of China (21176125).
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
ESM 1
(DOCX 701 kb)
Rights and permissions
About this article
Cite this article
Yu, F., Guo, X., Tian, X. et al. A Ratiomeric Fluorescent Sensor for Zn2+ Based on N,N′-Di(quinolin-8-yl)oxalamide. J Fluoresc 27, 723–728 (2017). https://doi.org/10.1007/s10895-016-2003-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-016-2003-0