Ferrocene encapsulated Zn zeolitic imidazole framework (ZIF-8) for

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Ferrocene encapsulated Zn zeolitic imidazole framework (ZIF-8) for optical and electrochemical sensing of amyloid# oligomer and for the early diagnosis of Alzheimer's Disease Jieling Qin, Misuk S. Cho, and Youngkwan Lee ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.8b21425 • Publication Date (Web): 07 Mar 2019 Downloaded from http://pubs.acs.org on March 8, 2019

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ACS Applied Materials & Interfaces

Ferrocene encapsulated Zn zeolitic imidazole framework (ZIF-8) for optical and electrochemical sensing of amyloid-β oligomer and for the early diagnosis of Alzheimer's Disease

Jieling Qin, Misuk Cho*, and Youngkwan Lee* School of Chemical Engineering, Sungkyunkwan University, 16419 Suwon, Korea Fax: +82-31-290-7272 Tel.: +82-31-290-7248 *Correspondence: [email protected] (Misuk Cho) and [email protected] (Youngkwan Lee) *These authors contributed equally.

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ABSTRACT In this work, the ferrocene encapsulated Zn zeolitic imidazole framework (ZIF-8) was prepared by the self-assembly of Zn ions and 2-methylimidazole and used for the dual detection of amyloid-beta oligomer (AβO), which is the main neuropathological hallmark of Alzheimer’s disease (AD). Ferrocene is an optically and electrochemically active signal which was successfully encapsulated inside of the ZIF-8 and released by the competitive coordination between Zn ions and AβO after treated with AβO. The released ferrocene content was monitored by ultraviolet/visible spectrometer and cyclic voltammetry. The dual determination of AβO played a synergetic role in the quickly qualitative and precisely quantitative analysis in a wide detection range of 10-5~102 μM and good feasibility in artificial cerebrospinal fluid.

KEYWORDS: ZIF-8, ferrocene, amyloid beta, Alzheimer’s disease, dual detection

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1. INTRODUCTION Metal organic frameworks (MOFs) as a kind of hybrid materials containing organic and inorganic ingredients, have been widely studied and have attracted much attention due to their facile synthesis, porous structure, and chemical stability

1-4.

In particular, zinc zeolitic

imidazole frameworks (Zn-ZIFs) self-assembled from zinc ion and imidazole linkers have been concerned in many potential applications including drug delivery, gas storage and separation, nanoscale reactors, electrode materials, and catalysis

5-6.

In addition, the Zn-ZIFs shows

considerable potential in intracellular drug delivery and molecular sensing in biomedical applications 7. Deng et al. reported a common fluorescent sensitive dye, Rhodamine B (RhB), encapsulated ZIF-90 which was self-assembled from Zn ions and 2-Imidazolecarboxaldehyde (ICA) and then used to monitor the level and capture the images of the mitochondrial adenosine triphosphate (ATP). Owning to the competitive coordination between Zn2+ and ATP, ZIF-90 was disassembled and RhB was released for the indirect determination of ATP in a live cell 8. Wang and his coworkers prepared ferrocene trapped ZIF-8 as a precursor for the synthesis of single-atom Fe embedded N-doped carbon (Fe-N-C) through the calcination at 900°C. The FeN-C was used as an electroreduction catalyst and showed high activity for oxygen reduction 9. Han et al. reported the sandwich type amyloid-β Aβ immunosensor prepared using antibody labeled Zn-ZIF 10, in which it was utilized to immobilize the antibody. It has been confirmed that the metal ions including Zn2+ have affinity to several proteins such as thrombin 11, bovine serum album (BSA) 12, immunoglobulin G (IgG) 13 and Aβ 14, etc. The affinity for Aβ can be used as Zn2+ sensor for the electrochemical determination. However, the poor selectivity and detection range made the research limited. Inspired by the decomposition of ZIF-90 after treatment with ATP 8, the Zn-ZIF nanoparticles are designed for the carriers of active molecules and then de-assembled by target materials to release the signal probe for the indirect detection of the target materials. The Zn-ZIFs are sensitive to Aβ1-42 by the coordination between Zn2+ and several amino acids such as the aspartic acid (Asp), glutamic acid (Glu) and histidine (His) in Aβ1-42 14-15. Based on these properties, we design a ferrocene encapsulated into ZIF-8 to form ZIF-8/Fer. Ferrocene is a well-known material having optical and electrochemical activity which exhibits ultraviolet/visible (UV/Vis) absorbance around 3



320 and 440 nm and undergoes a one-electron oxidation at a low potential. This bifunctional active signal allows the quick qualitative analysis using optical method as well as the precise quantitative determination by electrochemical method. Originally, owning to the “selfquenching” effect, the emission of encapsulated ferrocene in the ZIF-8 is largely suppressed 16.

However, the ZIF-8 is prone to be destroyed after treated with AβO if the coordination

between Zn2+ and AβO is more powerful than methyl imidazole (MIM). The released signal molecules can be readout for the indirect detection of AβO by dual detection method containing quick qualitative and concise quantitative determination simultaneously. In the present study, we try to employ Zn-ZIF as an affinity material for direct sensing of AO. The ferrocene encapsulated ZIF-8 (ZIF-8/Fer), which was prepared by the self-assembly of Zn ions and MIM in the presence of ferrocene molecules, was designed for the quantitative detection of AO. Competitive coordination between AβO and Zn ions disassembled ZIF, and the ferrocene molecules in ZIF were released, as shown in Fig. 1. The concentration of the released ferrocene was linearly proportional to A content and determined by UV/Vis spectrometer and cyclic voltammetry (CV).

Figure 1. Schematic representation of the nanoscale ZIF-8/Fer for AβO sensing using optical and electrochemical methods.

This is a new and robust way for the dual detection of AO. The combination of optical and electrochemical sensing plays a synergetic role in the quick qualitative analysis and precise 4


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quantitative detection of AβO. And the dual detection of the AβO shows high possibility for the early diagnosis of AD in practical approach.

2. EXPERIMENTAL 2.1 Materials Zn(NO3)2·6H2O, MIM, ferrocene and hydrochloric acid were purchased from Sigma-Aldrich (South Korea). The Aβ1-42 monomers were purchased from AnaSpec, Inc. (Fremont, USA). The artificial cerebrospinal fluid (ACSF) containing CSF-A (within HCO3-) and CSF-B (without HCO3-) were received from EcoCyte Bioscience. Phosphate buffered saline (0.01 M PBS, pH=7.4) was produced from Na2HPO4, KH2PO4, NaCl and KCl.

2.2 Preparation of the ferrocene encapsulated ZIF-8 (ZIF-8/Fer) and sensing AO The ZIF-8/Fer was synthesized by referring to the literature method 8 with minor modifications. Typically, 0.2 g Zn(NO3)2·6H2O was dissolved in MeOH (methanol, 0.8 mL). Then the prepared Zn(NO3)2 solution was mixed with 10 mL of ferrocene solution in MeOH under vigorous stirring. After 5 min, MIM (0.2 g) was added dropwise and stirred for a further 30 min to prepare the yellow ZIF-8/Fer nanoparticles. The precipitants were washed three times with MeOH, three times with EtOH (ethanol), and then dried in vacuum overnight. The final ZIF-8/Fer powder was stored at 4 °C and keep in dark place before use. The Aβ monomer (AβM), AβO and fibril (AβF) were prepared in accordance with the literature17. The successful preparation of Aβ samples was checked by Western Blot (Fig. S1). For the AβO sensing performance, in general, 2 mL of AβO solution (0.01 M PBS) was added in the ZIF-8/Fer (4 mg/mL, 0.01 M PBS) solution followed by the 15 min incubation. The suspension was then centrifuged at 10000 rpm for 10 min at RT. The supernatant of the released ferrocene was measured by UV/Vis and CV.

2.3 Instrumentation/Characterization The basic information including the surface morphology, size and qualitative component analysis of the ZIF-8/Fer were examined by scanning electron microscopy and energy 5



dispersive X-Ray spectroscopy (SEM and EDS, JEOL JSM-700F) and transmission electron microscopy (TEM, JEM ARM 200F). The UV/Vis spectra were obtained using the spectrophotometer HP 8453. Powder X-ray diffraction (PXRD) patterns were recorded on a Bruker D8 Advance diffractometer with a Cu sealed tube (λ = 1.54056 Å) at RT. Attenuated total reflection infrared spectroscopy (ATR-IR) (Bruker, Tensor 27) was used to determine the function group of crystal with 100 scans and 4 cm-1, an ATR platform was used by pressing the solid electrodes onto a diamond crystal. The electrochemical experiments were tested via VSP Potentiostat (Princeton Applied Research, USA) and the results were readout by the affiliated VSP EC-Lab software. CV was performed with a conventional three-electrode cell in which a gold plate, an Ag/AgCl and a platinum plate were applied as the working, reference, and counter electrode, respectively. To evaluate the real sample analysis, ACSF was prepared by using CSF-A and CSF-B mixed in equal proportions (v:v) and keep in dark place at 4℃ before use.

3. RESULTS AND DISCUSSION 3.1 Preparation and characterization of the ZIF-8/Fer The successful preparation of ZIF-8/Fer and its encapsulation of ferrocene was already confirmed by others

7-8, 10.

The encapsulated ferrocene was single molecule due to the

molecular size of ferrocene (6.4 Å) and the cavity diameter of ZIF-8 (11 Å) 9. The morphology of the proposed ZIF-8/Fer was monitored by FESEM and TEM images showing the welldefined ZIF-8/Fer nanoparticles with an average size about 100 nm and rhombic dodecahedron crystal in Fig. 2A. The identity of the ZIF-8/Fer can be confirmed by PXRD in Fig.2B and ATR-IR spectrum in Fig. 2C, respectively3. As shown in Fig.2B, the peaks of ZIF-8 were similar with the simulated pure ZIF-8 crystals indicating the successful preparation of ZIF-8. Ferrocene encapsulated ZIF8 had similar peaks to the ZIF-8, suggesting that the ferrocene encapsulation made minor effect on the lattice distortion of ZIF-8. There was no undesirable PXRD peak originated from ferrocene in the pattern of ZIF-8/Fer, further confirming that ferrocene was located inside the pore of ZIF-8 instead of adsorbed on its appearance physically. 6


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In the ATR spectrum (Fig. 2C), the characteristic peaks from 690 to 1600 cm-1 were assigned to the ZIF-8. Moreover, minor blue shift of the peaks was observed after the encapsulation of ferrocene because of the ZIF-8 retention. In addition, any trace of ferrocene was not found at 1408, 1105, 1000 and 816 cm-1 in ZIF-8/Fer, indicating that ferrocene was located inside the pore of ZIF-8 and shielded by the ZIF-8 framework, which was consistent with the PXRD results before 2, 7-8. Furthermore, in order to confirm the encapsulation of ferrocene, ZIF-8/Fer (4 mg/mL in 0.01M PBS) was also treated with 12M HCl solution and then, centrifuged. The supernatant (as expected ferrocene) and precipitates (as expected ZIF-8) were exposed to UV/Vis (in Fig. 2D). No specific peaks were presented in the ZIF-8/Fer and the precipitates. In the case of supernatant, characteristic peaks at 325 and 440 nm were appeared which were well matched with pure ferrocene (2 mM) confirming the presence of ferrocene. In addition, the EDS mapping of Fe in the ZIF-8/Fer (Fig. S2) also proved the presence of ferrocene inside of the ZIF-8. Considering to the aforementioned results, we can deduce that the ferrocene located inside of the ZIF-8 instead of adsorbed outside on the surface simply.

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Figure 2. FESEM and TEM (inset) images of ZIF-8/Fer (A). PXRD patterns of simulated ZIF-8, ferrocene, ZIF-8 and ZIF-8/Fer (B). ATR spectra of Fer, ZIF-8/Fer and pure ZIF-8 (C). UV/Vis spectra of the centrifuged supernatants of ZIF-8/Fer reacted with HCl (D). 3.2 AβO sensing performance based on ZIF-8/Fer It was previously reported that the Zn2+ can be coordinated with Asp, Glu and His of AβO 1415.

So, the competitive coordination between AβO and Zn ions possibly disassembled ZIF in

Fig.3A. After treatment with 5 mM AβO for 15 min, the ZIF-8 particles were deformed in FESEM image as well as the trace of Fe element was disappeared in EDS data as shown in Fig. 3B and 3C. These results proved AβO can de-assemble the ZIF-8 crystals and the inside ferrocene was released successfully.

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Figure 3. Image (A), SEM image (B) and EDS data (C) of ZIF-8/Fer after reacted with AβO. The 4 mg/mL of ZIF-8/Fer was first incubated with 5 mM AβO for 15 min in PBS, and then centrifugated for SEM measurements. In order to measure the concentration of released ferrocene, the calibration curves of pure ferrocene were constructed by employing UV/Vis and CV as shown in Fig. S3, demonstrating the ferrocene can be used as a standard signal for the optical and electrochemical detection of AβO. When the ferrocene was released from the ZIF, the UV/Vis spectra were recorded in a wavelength range 300-600 nm. The two absorption maxima around 320 nm and 440 nm (Fig. 4A) corresponded to the ferrocene as shown in the literature 18. And the intensity of absorption band at 440 nm was increased with increasing concentration of AβO. Moreover, the linear relationships were shown between UV/Vis absorption of ferrocene released from the ZIF-8 and reacted AβO in the range of 0.5~100 μM (Fig. 4C), indicating the potential of ZIF-8/Fer optical sensors for the determination of intracellular AβO. The colorimetric signal can also be recorded and read out by a Smartphone with a linear detection range from 200~1000 μM in Fig. S4. The portable assay with the concise signal capture, rapid on-site readout and qualifiable detection 9



made the sensor applicable in the near future. For the investigation of more sensitive detection technique for AβO, we also applied electrochemical analysis technique, utilizing electrochemical activity of ferrocene. The peaks of CV at 0.155 V and 0.33 V represented to the reduction/oxidation of the ferrocene respectively 19-20. And the CVs of supernatant of ZIF-8, ZIF-8/Fer in 0.01 M PBS, 1 mM AβO and PBS were examined for control experiments in Fig. S5. All the CVs were operated at applied potential from -0.1~0.5 V and a scan rate of 20 mVs-1. As displayed in Fig. 4B, the CV curves of supernatant of ZIF-8/Fer increased after reacted with increased concentrations of AβO. The redox peaks referred to the redox reaction of ferrocene in the electrolyte. According to the Randles-Sevcik equation 21: Ip = 0.446 nFAC0[(nFνD0)/RT](1/2) In which n indicates the number of transferred electrons within the redox reaction. While A (cm2) represents the surface area of electrode, and C0 (mol cm−3) demonstrates the analyte bulk concentration. Then ν (mV/s) is the scan rate of the electrode, and D0 (cm2 s−1) is the oxidized analyte’s diffusion coefficient. During the CV test, all the factors in the equation are quasiconstants except the C0, hence, with the increase of the released ferrocene, the Ip can increase afterwards. As shown in Fig. 4C, the current was proportional to the logarithmic concentration of AβO (log CAβO) from 10-5~10 μM with the linear regression equation I = 0.45 log C AβO + 3.78, R2 = 0.985 as well as the relative standard deviation (RSD) of 5.61 %. As expected, the detection by electrochemical analysis exhibited much higher sensitivity in a wider detection range than that by optical sensing technique. And the combination curves demonstrating the potential of ZIF-8/Fer sensor for the quickly qualifiable and precisely quantifiable determination of AβO in the range of 10-5~102 μM.

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Figure 4. UV/Vis absorption spectra of ZIF-8 (black curve), ZIF-8/Fer (red curve, reacted with 0 μM AβO) and the ZIF-8/Fer (4 mg/mL) in various concentrations of AβO (from bottom to top, 0.5, 1, 10, 20, 50, 100, 200 μM) (A); CVs of the supernatant of ZIF8/Fer (black curve, reacted with 0 μM AβO) and ZIF-8/Fer in the various concentrations of AβO (from bottom to top, 10-5, 10-4, 10-3, 10-2, 10-1, 10, 50 μM) (B); The combination curves of linear relationship between UV/Vis absorbance (440 nm), CV current (oxidation peak) and log CAβO (C). The performance of our sensor was compared with other Aβ sensors and summarized in Table 1. In comparison, our proposed ZIF-8/Fer sensor provided dual detection of AβO in which quick qualitative analysis and concise quantitative determination was possible by UV/Vis and CV, respectively.

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Table 1. Comparison table of sensing performance from several Aβ sensors Sensor

Method

Detection range

LOD

(μM) Aβ1-16

Reference

(μM)

/Zn2+/Ligand

UV-Vis

50-500

50

22

Aβ1-40/Cu2+/AuNPs

UV-Vis

1.05×10-3-0.3135

6×10-4

23

AβO/Antibody-aptamer a

DPV

5 x10-4-0.03

10-4

24

Aβ/An-Aβ Ab/Au b

EIS

10-5-0.1

10-5

25

AβO/PrPC/CdTe /AuNPs

Fluorescence

2×10-4-0.1

2×10-4

26

UV-Vis

5×10-4-0.5

5×10-4

UV-Vis

0.5-100

0.5

CV

10-5-

10-5

AβO/ZIF-8-ferrocne

a Antibody-aptamer/graphene/Au; b An-Aβ

10

This work

Ab: specific anti-beta-amyloid antibodies

3.3 Real sample analysis The determination of AβO in the ACSF was performed using the ZIF-8/Fer sensor for the real sample test, and the results were summarized in Table 2. As shown in the table, the addition and the recovery for spiked samples were analyzed from the calibration curve (from CV in Fig. 4C) and utilized to test the accuracy of the analysis 27-28.The acceptable data was obtained in the AβO recovery test suggesting the suitability of the proposed sensor to monitor AβO in biological samples. Table 2. The detection of AβO using ZIF-8/Fer to in ACSF Analyzed sample

Added (μM)

Found (μM)

RSDa (%)

Recovery b (%)

1

0.005

0.0051

2.02

102

2

0.05

0.049

1.85

98

3

0.5

0.489

1.47

97.8

ACSF is a constant at 2 mL; RSD a: the calculated relative standard deviation from 3 individual experiments; Recovery b = [found value (μM) /added value (μM)] ×100

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3.4 Selectivity, reproducibility and stability of ZIF-8/Fer based sensor The response of the AβM, AβO and AβF from ZIF-8/Fer based sensor was tested for the selectivity test in which high selectivity to AβO was revealed. The possible explanation was suggested in Fig. S6, specifically, compared with the suitable configuration of the oligomer, the dispersed monomer has weaker strength to de-assemble the ZIF-8, while the aggregated Aβ fibril will hide the effective amino acids to quench the coordination effect. Hence, in comparison of the response toward AβM and AβF, the determination of AβO showed high sensitivity. The reproducibility of the ZIF-8/Fer sensor was evaluated from the CV for various types of ZIF-8/Fer prepared three times with an RSD of 7.8%. Moreover, in order to receive the stability results, the ZIF-8/Fer was stored at 4 °C and away from light, and the electrochemical data was readout each 7 days for a month. Insignificant change was observed indicating the sufficient stability of the sensor. In general, the ZIF-8/Fer sensor can be suitable for the determination of AβO in practical.

4. CONCLUSIONS This is the first study on the ZIF/Fer applied for an AβO sensor research. Optical sensing was used to qualitatively monitor the AβO. While the electrochemical analysis was applied to detect AβO quantitatively. The dual detection with the combined two sensing methods played a synergetic role in the qualifiable and quantifiable determination of AβO. The ferrocene encapsulated ZIF-8/Fer enabled to determined AβO at a wide range and low limit of detection. The ZIF/Fer is a promising analytical platform for AβO monitoring under in vivo conditions.

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ASSOCIATED CONTENT Supporting information. This material is available free of charge via the Internet at http://pubs.acs.org. Additional characterization data and electrochemical performances (PDF).

AUTHOR INFORMATION Corresponding Author *Give contact information for the author(s) to whom correspondence should be addressed. [*] Prof. Youngkwan Lee Email: [email protected]; Tel: +82 31 290 7248 [*] Dr. Misuk Cho Email: [email protected]: +82 31 290 7326

ACKNOWLEDGMENTS This work was sponsored by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by Ministry of Science and ICT (NRF2016R1A2B40008389, NRF-2019R1A2C1003551) and by the Ministry of Education (NRF2016R1D1A1B03930806).

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Ferrocene encapsulated Zn zeolitic imidazole framework (ZIF-8) for

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