Pyrazole-Triazine Conjugate as Highly Selective and Sensitive Fluorescence Probe for Silver (I) Detection and Its Imaging in Living Cells
LIU Yanhong, YU Bingqiong, ZHU Qingya, YAN Kun†College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei, China
A new fluorescence probe 2,2’-（6-（4-（diethylamino）phenyl）-1,3,5-triazine-2,4-diyl）bis（1H-pyrazole-1,3-diyl）diacetate (EATPA) based on 1, 3, 5-triazine was designed and synthesized. It exhibited distinct fluo-rescence quenching in the presence of silver ions that can be used for highly sensitive and selective detection of Ag+. Fluorescence titration and Job’s plot analysis revealed the formation of [Ag(EATPA)2]+ entity with high binding constant (1.43×104 L/mol) and low detection limit (0.882 µmol/L). Fur-thermore, live-cell imaging experiments demonstrated that EATPA is potentially applicable for the tracking of Ag+ in living cells.
 Fu F, Wang Q. Removal of heavy metal ions from wastewaters: A review [J]. Journal of Environmental Management, 2011, 92(3): 407-418.
 Sud D, Mahajan G, Kaur M P. Agricultural waste material as potential adsorbent for sequestering heavy metal ions from aqueous solutions—A review [J]. Bioresource Technology, 2008, 99(14): 6017-6027.
 Ratte H T. Bioaccumulation and toxicity of silver compounds: A review [J]. Environmental Toxicology and Chemistry, 2010, 18(1): 89-108.
 Wood C M, Playle R C, Hogstrand C. Physiology and modeling of mechanisms of silver uptake and toxicity in fish [J]. Environmental Toxicology and Chemistry, 2010, 18(1): 71-83.
 Kim T N, Kim J O, Wu J, et al. Antimicrobial effects of metal ions (Ag+, Cu2+ Zn2+) in hydroxyapatite [J]. Journal of Materials Science: Materials in Medicine, 1998, 9(3): 129-134.
 Yamanaka M, Hara K, Kudo J. Bactericidal actions of a silver ion solution on Escherichia coli, studied by energy-filtering transmission electron microscopy and proteomic analysis [J]. Applied and Environmental Microbiology, 2005, 71(11): 7589-7593.
 Nandre J P, Patil S R, Sahoo S K, et al. A chemosensor for micro- to nano-molar detection of Ag+ and Hg2+ ions in pure aqueous media and its applications in cell imaging [J]. Dalton Transactions, 2017, 46(41): 14201-14209.
 Wang Y J, Liu J G, Tan H Y, et al. A colorimetric and farred fluorescent probe for the highly sensitive detection of silver (Ⅰ) [J]. RSC Advances, 2017, 7(88): 55567-55570.
 Chen B, Liu J, Yang T, et al. Development of a portable device for Ag+ sensing using CdTe QDs as fluorescence probe via an electron transfer process [J]. Talanta, 2019, 191: 357-363.
 Chamsaz M, Arbab-Zavar M H, Akhondzadeh J. Triple-phase single-drop microextraction of silver and its determination using graphite-furnace atomic-absorption spectrometry [J]. Analytical Sciences, 2008, 24(6): 709-801.
 Mikelova R, Baloun J, Petrlova J, et al. Electrochemical determination of Ag-ions in environment waters and their action on plant embryos [J]. Bioelectrochemistry, 2007, 70 (2): 508-518.
 Tan E, Yin P, Lang X F, et al. Functionalized gold nanoparticles as nanosensor for sensitive and selective detection of silver ions and silver nanoparticles by surface-enhanced Raman scattering [J]. Analyst, 2012, 137 (17): 3925-3928.
 Yang X J, Foley R, Low G K C. A modified digestion procedure for analysing silver in environmental water samples [J]. Analyst, 2002, 127(2): 315-318.
 Ding Y B, Tang Y Y, Zhu W H, et al. Fluorescent and colorimetric ion probes based on conjugated oligopyrroles [J]. Chemical Society Reviews, 2015, 44(5): 1101-1112.
 Wang X, Wang T X, Tian X J, et al. Europium complex doped luminescent solar concentrators with extended absorption range from UV to visible region [J]. Solar Energy, 2011, 85(9): 2179-2184.
 Paul P, Tyagi B, Bilakhiya A K, et al. Synthesis and characterization of rhodium complexes containing 2,4,6-Tris(2-pyridyl)-1,3,5-triazine and its metal-promoted hydrolytic products: Potential uses of the new complexes in electrocatalytic reduction of carbon dioxide [J]. Inorganic Chemistry, 1998, 37(22): 5733-5742.
 Lebreton S, Newcombe N, Bradley M. Antibacterial single-bead screening [J]. Tetrahedron, 2003, 59(51): 10213- 10222.
 Hoog P D, Gamez P, Driessen W L, et al. New polydentate and polynucleating N-donor ligands from amines and 2,4,6-trichloro-1,3,5-triazine [J]. Tetrahedron Letters, 2002, 43(38): 6783-6786.
 Shellaiah M, Rajan Y C, Lin H C. Synthesis of novel triarylamine-based dendrimers with N4, N6-dibutyl-1,3,5- triazine-4,6-diamine probe for electron/energy transfers in H-bonded donor-acceptor-donor triads and as efficient Cu2+ sensors [J]. Journal of Materials Chemistry, 2012, 22(18): 8976-8987.
 Zhang Y, Zeng X, Mu L, et al. Rhodamine-triazine based probes for Cu2+ in aqueous media and living cells [J]. Sensors and Actuators B: Chemical, 2014, 204: 24-30.
 Zhu Y Z, Qiao M, Peng W C, et al. Rapid exfoliation of layered covalent triazine-based frameworks into N-doped quantum dots for the selective detection of Hg2+ ions [J]. Journal of Materials Chemistry A, 2017, 5: 9272-9278.
 Sang Q G, Yang J K. An efficient way for the recognition of zinc ion via the fluorescence enhancement [J]. Chinese Journal of Chemistry, 2012, 30(7): 1410-1414.
 Ge F Y, Yang C, Cai Z S. Fluorescence sensor performance of a new fluorescein derivate: [2-Morpholine-4-(6-chlorine- 1,3,5-s-triazine)-amino]fluorescein [J]. Bulletin of the Korean Chemical Society, 2015, 36(11): 2703-2709.
 Nie L H, Ma H M, Li X H, et al. Recognition of thymine by triazine fluorescent probe through intermolecular multiple hydrogen bonding [J]. Biopolymers, 2010, 72(4): 274-281.
 Ma H M, Nie L N, Xiong S X. Recognition of guanine by a designed triazine based fluorescent probe through intermolecular multiple hydrogen bonding [J]. Supramo- lecular Chemistry, 2004, 16(5): 311-317.
 Ye Z Q, Chen J X, Wang G L, et al. Development of a terbium complex-based luminescent probe for imaging endogenous hydrogen peroxide generation in plant tissues [J]. Analytical Chemistry, 2011, 83(11): 4163-4169.
 Tan M Q, Song B, Wang G L, et al. A new terbium (Ⅲ) chelate as an efficient singlet oxygen fluorescence probe [J]. Free Radical Biology and Medicine, 2006, 40(9): 1644- 1653.
 Kumar K S, Schafer B, Lebedkin S, et al. Highly luminescent charge-neutral europium (Ⅲ) and terbium (Ⅲ) complexes with tridentate nitrogen ligands [J]. Dalton Transactions, 2015, 44(35): 15611-15619.
 Xu L, Xu Y, Zhu W, et al. A highly selective and sensitive fluorescence “turn-on” probe for Ag+ in aqueous solution and live cells [J]. Dalton Transactions, 2012, 41(24): 7212- 7217.
 Su P, Zhu Z, Wang J, et al. A biomolecule-based fluorescence chemosensor for sequential detection of Ag+ and H2S in 100% aqueous solution and living cells [J]. Sensors and Actuators B: Chemical, 2018, 273: 93-100.
 Zhang Y, Wang D, Sun C, et al. A simple 2,6- diphenylpyridine-based fluorescence “turn-on” chemo- sensor for Ag+ with a high luminescence quantum yield [J]. Dyes and Pigments, 2017, 141: 202-208.
 Cui W, Wang L, Xiang G, et al. A colorimetric and fluorescence “turn-off” chemosensor for the detection of silver ion based on a conjugated polymer containing 2,3-di(pyridin-2-yl)quinoxaline [J]. Sensors and Actuators B: Chemical, 2015, 207: 281-290.
 Li W T, Wu G Y, Qu W J, et al. A colorimetric and reversible fluorescent chemosensor for Ag+ in aqueous solution and its application in Implication logic gate [J]. Sensors and Actuators B: Chemical, 2017, 239: 671-678.
 Velmurugan K, Thamilselvan A, Antony R, et al. Imidazoloquinoline bearing thiol probe as fluorescent electrochemical sensing of Ag and relay recognition of proline [J]. Journal of Photochemistry and Photobiology A: Chemistry, 2017, 333: 130-141.
 Saitoh T, Ichikawa J. Bis(triarylmethylium)-mediated diaryl ether synthesis: Oxidative arylation of phenols with N, N-dialkyl-4-phenylthioanilines [J]. Journal of the American Chemical Society, 2005, 127(27): 9696-9697.
 Lo W S, Zhang J, Wong W T, et al. Highly luminescent Sm (Ⅲ) complexes with intraligand charge-transfer sensitization and the effect of solvent polarity on their luminescent properties [J]. Inorganic Chemistry, 2015, 54(8): 3725-3727.
 Smolyar N N, Yutilov Y M. Cyclizations of monocyclic 5-nitropyridin-2(1H)-ones [J]. Russian Journal of Organic Chemistry, 2008, 44(8): 1205-1210.
 Brouwer A M. Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report) [J]. Pure and Applied Chemistry, 2011, 83(12): 2213-2228.
 Zhang Q, Luo L, Xu H, et al. Design, synthesis, linear and nonlinear photophysical properties of novel pyrimidine- based imidazole derivatives [J]. New Journal of Chemistry, 2016, 40(4): 3456-3463.