AIE-Active Pyrene Fluorescence Detector for Selective Detection and Imaging of Hg2+ in Living Cells

Acta Spectrachem Sinica Μέρος Α: Molecular and Biomolecular Spectroscopy 223 (2019) 117315

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An Active AIE Pyrene-Based Fluorescence Detector for Selective Detection and Imaging of Hg2+ in Living Cells Yaqin Wu, Xiaoye Wen, Zhefeng Fan ⁎ School of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004, China

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Article history: Received 3 May 2019 Accepted 22 June 2019 as revised Accepted 23 June 2019 Available online 25 June 2019 Keywords: Pyrene aggregation-induced Hg2+ emission Cell imaging

Sažetak A new pyrenyl derivative of a fluorescent probe with Aggregation Induced Emission (AIE) properties was synthesized by a simple procedure (1). Probe 1 was characterized using UV-Vis, fluorescence, NMR, mass spectrometry and scanning electron microscopy. Compared with other metal ions in H2O/DMF solvent, it showed higher sensitivity and selectivity for Hg2+, the detection limit is 4.2×10 −7 M. After adding Hg2+, compound 1-Hg2+ was formed in a ratio of 2:1 . Most importantly, the probe showed extremely low cytotoxicity and strong fluorescence emission in living cells. This indicates that the probe has potential applications in the detection of Hg2+ in the environment and biological systems. © 2019 Elsevier B.V. All rights reserved.

1. Introduction In recent years, heavy metals are widely present in water, soil and atmospheric environment, seriously threatening the good cycle of the global ecological environment [1]. Heavy metal residues in the environment are difficult to biodegrade. They mainly enter animals and plants through environmental means (soil, water, air, etc.). They persist for a long time and accumulate through the food chain. Among them, mercury ions (Hg2+) are the main toxic pollutants. It is highly toxic and bioaccumulative to living organisms. Long-term accumulation in the body can cause changes in normal tissues and organs. Even at very low concentrations, mercury can disrupt the normal physiological activities of the human body [2-3]. In order to monitor the severity of heavy metal pollution, it is important to develop a new analytical method for the detection of heavy metals in the environment and biological systems. Currently, the main methods for the detection of heavy metals are atomic absorption spectrometry [4], atomic fluorescence spectrometry [5], electrochemical analysis [6-7], inductively coupled plasma [8-9], liquid high performance chromatography [10 ] - 11]. ] and capillary electrophoresis [12-13]. However, these methods usually require expensive and complex instruments, also exhibit low selectivity and are time-consuming. In contrast, fluorescence methods are the most suitable methods for ion identification. Its advantages are easy handling, high sensitivity and selectivity, and short response time. In particular, it has potential for use in live cell imaging, and changes in fluorescent color can be observed with the naked eye [14-17].

Corresponding author. email adress:[email protected](Z. Fan).

Traditional small molecule organic fluorescent chromophores have an aggregation fluorescence quenching (ACQ) effect [18]. The fluorescence intensity is weakened or quenched in highly concentrated solutions or condensed states, which greatly limits its potential applications. Aggregation-induced emission (AIE) defined by Tang Benzhong's research group can effectively avoid this drawback [19-20]. AIE materials exhibit weak fluorescence in dilute solutions, but high fluorescence in highly concentrated solutions or aggregated states. Many fluorescent detectors active in AIE have appeared and show potential applications in various fields such as chemical/biosensing, cell imaging, environmental, optical devices, etc. Recently, many researchers have worked to develop AIE sensors for mercury determination. Among the designed AIEactive molecules, multifunctional fluorophores were synthesized, such as quinoline-activated pylaarene[21], salicylaldehyde Schiff's base[22], tetraphenylethylene derivatives[23,24], pyrrole5]6haptenyl[23,24]benzene[6] derivatives. , ractylene derivatives [23,24]. e[ 27]], α-cyanostilbene derivatives[28], triphenylamine derivatives, etc.[29]. However, reported pyrene-based derivatives for Hg2+ detection are very rare [30]. Pyrene-based derivatives have attracted the interest of scientists because of their good properties as fluorescence detectors. They show rapid response to specific analytes and possess AIE properties [31,32]. Here, we have successfully designed and synthesized a novel AIE detector based on a pyrene derivative (1) using a simple procedure. Probe 1 showed weak green emission with AIE characteristics in H2O/DMF solvent, while the emission color changed to blue and the fluorescence intensity increased when Hg2+ was added. The probe can be used to detect Hg2+ in aqueous solution and perform cellular imaging through the fluorescence enhancement effect, indicating that it has broad prospects for applications in environmental and biological systems.

Y. Wu et al. / Acta Spectrochemical Sinica Dio A: Molecular and Biomolecular Spectroscopy 223 (2019) 117315

2. Experimental part 2.1. Materials and Instruments Tritylamine, 1-pyrene formaldehyde and other materials were obtained from Aladdin Company. They are analytical grade reagents. UV-Vis absorption spectra were recorded with a TU-1901 spectrophotometer (China). Fluorescence emission measurements were performed on a Cary Eclipse spectrophotometer (USA). FT-IR spectra were measured with a compressed KBr disk and a Nicolet 380 spectrometer. Mass spectrometry was performed on a BrukerImpact II spectrometer (Germany). All NMR spectra were recorded in DMSO on an AVANCE III HD NMR instrument. Scanning electron microscope (SEM) measurements were taken on a JSM-7500F (Japan). Cell images were collected on a Leica TCS SP5 II confocal laser scanning microscope (Germany).

Figure 1. UV-Vis absorption spectra of probe 1 (2 μM) in H2O/DMF solutions with different water contents.

2.2.1 Synthesis A mixture of 1-pyrenecarbaldehyde (0.2303 g, 1 mmol) and tritylamine (0.2593 g, 1 mmol) was refluxed in ethanol for 12 h to give a pale yellow solid. The product was filtered, then washed with ethanol and the yield was 68% (Scheme 1). 1H NMR (DMSO d6, 600 MHz), δ (ppm): 8.86 (s, 1H), 8.71 (d, J = 7.8 Hz, 1H), 8.61 (d, J = 9, 0 Hz, 1H), 8.41 (d, J = 7.8 Hz, 1H), 8.38 (d, J = 7.2 Hz, 1H), 8.35 (d, J = 7.8 Hz , 1H), 8.24-8.31 (m, 2H), 8.26 (d, J = 9.0 Hz, 1H), 8.13 (t, J = 7.8 Hz, 1H), 7 .43 (t, J = 7.8 Hz, 6H), 7.34–7.36 (m, 9H) (Figure S1). 13C NMR (DMSO d6, 150 MHz), δ (ppm): 159.3, 146.1, 133.1, 129.9, 129.7, 129.3, 128.7, 128.6, 127.9 , 127.9, 1126, 1127. 5 .7, 124.6, 124.2, 122.3 , 79.4 (Figure S2). FT-IR (KBr, cm-1): 3051, 2360, 1629, 1441, 1384, 1181, 1018, 848, 758, 701 (Figure S3). MS: m/z determined [1 + H]+ = 472.3248 (Figure S4). 2.3 General analytical procedure Prepare a 1 mM stock solution of probe 1 using pure N,ND dimethylformamide (DMF). Prepare different metal ion stock solutions (10 mM) using deionized water. The final test solution consists of 6 µM 1, 10 mM PBS buffer (pH = 7.0) and an appropriate amount of Hg 2+ . Mix the solution well in H2O/DMF (2:3, v/v) solution. All fluorescence spectra were obtained at an excitation wavelength of 363 nm. 2.4 Cytotoxicity Test and Cytofluorescence Imaging Cytotoxicity of Probe 1 was evaluated using the Cell Counting Kit 8 (CCK-8) experiment. In a 96-well cell culture plate, add 100 µL of cell suspension per well (5×103 cells per well). After incubation for 24 h at 37 °C in Dulbecco's modified Eagle's medium (DMEM) containing 5% CO2, cells were incubated with different concentrations of probes (0 μM, 10 μM, 20 μM, 40 μM, 60 μM, 80 μM) and incubate for another 12 hours. After decanting the supernatant, add fresh CCK-8 to each well and process for 3 h. Measure the absorbance at 450 nm with a microplate reader. Live HeLa cells were treated in Dulbecco's modified Eagle's medium (DMEM) for 24 h at 37 °C in a 5% CO2 atmosphere. Cells were then loaded with probe 1 (6 μM) in PBS buffer containing 1% DMSO for 20 min at 37°C. After removing the free probe 1 by washing

Cells were treated 3 times with PBS buffer (pH 7.0) and imaged under a confocal laser scanning microscope. Then, the cells were incubated with different concentrations of Hg 2+ (4 μM and 12 μM) for 30 min, washed with PBS buffer, and their images were taken.

3. Results and discussion 3.1. UV-vis properties The UV-vis spectral properties of detector 1 were investigated in H2O/DMF solutions with different water ratios. Probe 1 showed three absorption maxima at 390, 363 and 288 nm, which were attributed to n - π* and π - π* charge transitions (Figure 1) [31]. Absorption decreases with increasing water content. When the water ratio reaches 70%, the maximum absorption peak has an obvious red shift. These phenomena can be attributed to the formation of aggregates.

3.2 AIE 1 detector characteristics Pyrene derivatives often exhibit aggregation-induced luminescence characteristics. As expected, probe 1 showed weak fluorescence emission in pure DMF solution. However, at 500 nm, the fluorescence emission increases with increasing water content in the H2O/DMF solution. The fluorescence intensity of probe 1 increased 45-fold as the moisture content increased from 0% to 80%, after which the fluorescence intensity decreased with increasing moisture content (Figure 2). This finding suggests that detector 1 has AIE properties. Probe 1 showed weak fluorescence, which was attributed to a photoinduced electron transfer (PET) mechanism between the N donor and the pyrene ring [32]. When the proportion of water increases, the rotation of C-N and C-C single bonds is restricted to some extent, resulting in enhanced fluorescence. When the moisture content exceeds 80%, the probe molecules aggregate into larger particles and the fluorescence intensity decreases [33].

Figure 1. Synthetic pathway of Probe 1

Y. Wu et al. / Acta Spectrochemical Sinica Dio A: Molecular and Biomolecular Spectroscopy 223 (2019) 117315

Figure 2. (a) Fluorescence spectra of probe 1 (2 μM) in H2O/DMF solutions with different water content, λex = 363 nm. (b) Detector 1 in different ratios of H2O/DMF solutions under UV light (365 nm).

3.3 Selectivity of 1 towards Hg2+ It is very important to study the selectivity of the analytes. The sensing ability of probe 1 was tested in HO/DMF solution (v:v = 2:3, PBS buffer, pH 7.0). Various metal ions such as Al3+, Cr3+, Fe3+, Zn2+, Cd2+, Ni2+, Co2+, Ca2+, Cu2+, Mn2+, Mg2+, Ag+, Pb2+ and Hg2

When added to the H2O/DMF solution containing probe 1, there was no obvious difference in the UV-Vis spectrum, but in the fluorescence spectrum, except for Hg2+, other metal ions did not produce obvious fluorescence changes (Figure 3). When the moisture content was increased to 60%, there was a noticeable color change from green to blue under UV light upon addition of Hg2+. The fluorescence peak is obvious

Figure 3. (a) UV-Vis absorption and (b) fluorescence spectra, λex = 363 nm. (c) photo 1, equivalent to 10.0. Metal ions in H2O/DMF solution (v:v = 2:3, PBS buffer, pH 7.0) under sunlight and UV lamp (365 nm).

Y. Wu et al. / Acta Spectrochemical Sinica Dio A: Molecular and Biomolecular Spectroscopy 223 (2019) 117315

Scenario 2.1 and possible Hg2+ mechanisms.

Figure 4. Selectivity from 1 to Hg2+ in the presence of other metal ions.

A 50 nm blue shift is accompanied by an increase in fluorescence intensity. In contrast, there was almost no fluorescence when other metal ions were added (Fig. S5). To further investigate the specific selectivity, we investigated the interference in the presence of other co-existing metal ions. The fluorescence spectrum of probe 1 did not change significantly in the presence of 10 equiv of Hg 2+ . Metal ions such as Al3+, Cr3+, Fe3+, Zn2+, Cd2+, Ni2+, Co2+, Ca2+, Cu2+, Mn2+, Mg2+, Ag+ and Pb2+. When other metal ions are present, the probe has little effect on Hg2+ selectivity (Figure 4). A possible mechanism can be considered to interact with Hg2+ once to form a coordination compound. N donor sites interfere with the PET process and increase the fluorescence intensity [34,35]. A scanning electron microscope (SEM) was used to study its mechanism. As shown in Figure 5, probe 1 showed a crystalline mass morphology, but packed into an amorphous mass after the addition of Hg 2+ . Probe 1 showed different morphologies in the presence and absence of Hg2+ in H2O/DMF (2:3, v/v) solution. The dramatic change in morphology reveals that complexes 1 and 1-Hg2+ have different

ENT properties. To further elucidate the mechanism, mass spectra of probe 1 and probe 1-Hg 2+ were obtained. In the absence of Hg2+, the peak at m/z 472.3248 corresponds to [1 + H]+. When Hg2+ was added to the probe, the peak at m/z 1143.0206 corresponds to [1 + Hg2+]+ (Figure S4).

3.4 Optimum Experimental Conditions For the accurate detection of Hg2+, it is very necessary to optimize the analytical conditions. The fluorescence intensities of the 1-Hg2+ complex with different water ratios were investigated (Fig. 6, Fig. S6). When the percentage of water is 60%, the fluorescence emission of the probe is very sensitive. However, the performance of the quantitative experiment under this condition is not good. Therefore, in the following experiments, the proportion of water was fixed at 40%. We investigated the sensitivity of detector 1 to Hg2+ at different pH conditions in H2O/DMF (v:v = 2:3). The fluorescence intensity was maximal at a pH of about 7 (Fig. S7). Under acidic conditions, the protonated imine group can prevent coordination with Hg2+. When the pH is alkaline, mercury precipitates may form. this phenomenon

Figure 5. SEM images of (a) probe 1 (6 μM) and (b) complex 1 - Hg2+ in H2O/DMF solution (2:3, v/v, PBS buffer, pH 7.0).

Figure 6. Photographs of 1 − Hg2+ in different ratios of H2O/DMF solutions under UV light (365 nm).

Y. Wu et al. / Acta Spectrochemical Sinica Dio A: Molecular and Biomolecular Spectroscopy 223 (2019) 117315

Figure 7. (a) Fluorescence spectra of probe 1 (6 μM) and different concentrations of Hg 2+ , (b) linear fit graph of fluorescence intensity of probe 1 and Hg 2+ at 450 nm.

Detector 1 proved suitable for Hg2+ monitoring under physiological conditions. 3.5.1 Hg2+ Binding Model Job's plot experiments were used to estimate the binding stoichiometry of 1 − Hg2+. The total concentration of probe 1 and Hg 2+ was fixed (20 µM). Projects are planned at 450 nm. As shown in Figure S8, the inflection point occurs at a mole fraction of 0.7, indicating a 2:1 formation ratio of 1 and Hg 2+ . Based on the 2:1 complex, we calculated the dissociation constant Ka of the 1-Hg2+ complex using the Benesi-Hildebrand method [31,34], and the binding constant of Ka 1 to Hg2+ was determined to be 3.62 × 104 M− 1 ( Figure S9). This indicates that the probe has a strong binding ability to Hg2+. The proposed reading process is shown in figure 2. 3.6. Fluorescence titration of probe 1 against Hg2+ In order to evaluate the utility of the probe, we investigated its application to real samples. In the concentration range of 0–20 µM, the fluorescence intensity increased with the addition of Hg 2+ . The fluorescence intensity of 1 is linearly related to the concentration of Hg2+. The limit of detection (LOD) for Hg2+ was 4.2 × 10-7 M based on 3σ/S (Figure 7). We use probes to test real water samples. Different amounts of Hg2+ were added to tap water and river water (Linfen). Triplicates were obtained for each sample. The obtained Hg2+ concentrations were consistent with the spiked samples. The recoveries were in the range of 89.0–94.5%, which is satisfactory (Table 1). The results showed that detector 1 can be applied to detect Hg2+ in the environment.

Probe 1 was used to monitor intracellular Hg2+ changes in living HeLa cells. HeLa cells were incubated with probe 1 for 20 min and we could observe a faint green fluorescent signal. When HeLa cells were exposed to 4 µM Hg2+, we could observe blue fluorescence. However, when HeLa cells were exposed to 12 μM Hg2+, we could observe enhanced blue fluorescence. Blue fluorescence increased with increasing Hg2+ concentration (Figure 8). These results indicate that probe 1 has good membrane penetration and can be used to image Hg2+ in living cells. 3.8 Comparison of other probes Although some probes for measuring Hg2+ have AIE properties, there are not many probes for cell detection. Determination of Hg2+ based on pyrene derivatives is very rare. Compared with other probes (Table 2), probe 1 has the advantages of simple synthesis, high selectivity, low toxicity, good membrane permeability, and can be used for cell imaging. 4. Conclusions A new fluorescence detector with AIE effect based on pyrene derivatives was synthesized by a simple method. Probe 1 characterizes

3.7. Cell Imaging The Cell Count Assay Kit 8 (CCK-8) was used to evaluate the cytotoxicity of probe 1. After 12 h of incubation with different concentrations of the probe (0 μM, 10 μM, 20 μM, 40 μM, 60 μM, 80 μM), recorded cell viability is in the range of 81–95%, indicating that the probe has good biocompatibility (Figure S10).

Table 1. Results of detection of Hg2+ in real water (mean ± ts, n = 3). sample

Supplement (µM)

Found (µM)

recovery (%)

Relative standard deviation (%)

tap water

4 8 4 8

3,56 ± 0,28 7,40 ± 0,42 3,78 ± 0,37 7,25 ± 0,49

89,0 92,5 94,5 90,6

2,56 3,12 2,93 3,45

river water

Figure 8. Confocal fluorescence images of HeLa cells treated with probe 1 (6 μM) for 20 min (a, b, c). Cells were treated with probe 1 for 20 min and then treated with 4 μM Hg 2+ (d, e, f). cells treated with 1 and 12 μM Hg 2+ probe (g, h, i). Fluorescent images (a, d, g). bright field images (b, e, h). overlay images (c, f, i).

Y. Wu et al. / Acta Spectrochemical Sinica Dio A: Molecular and Biomolecular Spectroscopy 223 (2019) 117315

Table 2. Comparison of Hg2+ and pyrene chemical sensors with AIE properties. detection

Ion detection

Detection limit (µM)

biological research

report

Pyrrole molecule S1 Anthracene molecule DTPES

Hg2+ Hg2+ Hg2+ Hg2+

−A549 − −

[25] [36] [26] [23]

p-crezola hexafenilbenzene deriv

Mercury 2+ Mercury 2+

HepG2 MCF-7

[37] [27]

Tetraarylethene Phenazines TPE-QN Cyanostilbene Amphiphiles Thiosemicarbazones

Hg2+ Hg2+ Hg2+ Hg2+ Hg2+

− − − − −

[38] [39] [40] [41] [42]

Benzyl imin

Hg2+

Hello

[43]

Cyanostilbene

Hg2+

69,4 nm 19,4 nm 8,21 nm 1 × 10-5 M 0,27 μm 100 × 10-9 M 48 nm 4,8 nm 71,8 nm 0,11 μm 9,07 × 10-7 M 2,4 × 10-7 M 1,5 × 10-6 M 2,4 × 1 0− 5 m 3,4 × 10−7 m

Hello

[28]

−

[44]

−

[45]

Hello

[31] [46]

−

[32]

- - - RAW264.7

[47] [48] [49] [34]

complex thyme

Hg2+

Pyrene derivatives 1 Pyr-1

Cu2+ Ni2+

Aminoantipyrine derivatives

Baccarat 2+ 3+

[Butyryl]Ornithine Derivative Hexamine Derivative Py-BTZ 2-((pyren-1-ylmethylene)amino)ethanol PHP Biginelli Pyrene Based

Fe, Pb Cu2+, Fe3+ Fe3+, Fe2+ Fe3+, Cr3+, Al3+ Cu2+ Zn2+, Fe3+

Pyrenyl derivatives 1

Mercury 2+ Mercury 2+

35 nM 2,5 × 10–7 M 2,5 × 10–6 M 0,1 μM 4,9 μM 2,61 μM 10–7 M 0,04 μM 7,94, 6,31 μM 3,4 pM 4,2 × 10–7 M

RAW264.7 [35] − [50] Hella Hella

[51] This work

NMR, MS, SEM, etc. show good selectivity towards Hg2+, accompanied by an enhanced fluorescence signal. The detection limit1 of Hg2+ is 4.2×10-7 M. Detector 1 was used to detect Hg2+ in aqueous solution and living cells, which indicates its promising application in the environment and biological systems.

Acknowledgments This work was supported by the Doctoral Fund of Shanxi Normal University (0505/02070465) and Project 1331 of Shanxi Province. Appendix A. Supplementary data Supplementary data for this article are available online at https://doi. org/10.1016/j.saa.2019.117315.

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