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Formation of homogeneous epinephrine-melanin solutions to fabricate electrodes for enhanced photoelectrochemical biosensing Hongmin Ma, Qi Fan, Bobo Fan, Yong Zhang, Dawei Fan, Dan Wu, and Qin Wei Langmuir, Just Accepted Manuscript • DOI: 10.1021/acs.langmuir.8b00264 • Publication Date (Web): 08 Jun 2018 Downloaded from http://pubs.acs.org on June 8, 2018

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Formation of homogeneous epinephrine-melanin solutions to fabricate electrodes for enhanced photoelectrochemical biosensing Hongmin Ma, Qi Fan, Bobo Fan, Yong Zhang, Dawei Fan, Dan Wu, Qin Wei* Key Laboratory of Interfacial Reaction and Sensing Analysis in Universities of Shandong, School of Chemistry and Chemical Engineering, University of Jinan, Jinan, 250022, China

ABSTRACT: The development of a simple but effective surface modification method is very important for the construction of biosensing interfaces. In this work, a post-synthetic water-soluble epinephrine-melanin (EPM) prepared from the self-polymerization of epinephrine has been demonstrated as an alternative of the widely used in-situ formed polydopamine (PDA) for the surface coating of TiO2 nanoparticles and the construction of a photoelectrochemical (PEC) biosensing interface. In contrast to the formation of insoluble aggregates in solution for dopamine, a homogenous solution was obtained for epinephrine after the self-polymerization. The use of EPM as a post-synthetic material enables the surface coating of TiO2 with simple drop-casting method. Compared with the widely used dip-coating method for in-situ PDA modification, the developed drop-casting method based on the use of water soluble post-synthetic EPM saves more time, avoid the waste of bulk solution, and undoubtedly decrease the batch-to-batch inconsistencies. The simple coating of commercially available TiO2 nanoparticles with EPM greatly enhances the PEC performance due to the charge transfer property of EPM. The application of EPM in the construction of the PEC biosensing interface was demonstrated by the immobilization of a model biorecognition element (prostate specific antigen (PSA) antibody) onto EPM modified Indium Tin Oxide (ITO) photoanode. Sensitive detection of PSA with high selectivity and stability were obtained based on the biological recognition ability of PSA antibody. This work may renew the use of post-synthetic 1 ACS Paragon Plus Environment

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melanin-like biopolymers in other fields. INTRODUCTION Photoelectrochemical (PEC) biosensing has aroused considerable interest in recent years because this technique possesses some unique merits.1-2 As the evolutionary generation of traditional electrochemical method, the well-established biosensing events and signal amplification strategies can be incorporated into this platform.3-7 PEC process has found wide applications in the field of bioanalysis,8 such as immunoassay and DNA analysis. As one important component of the PEC process, the PEC active materials usually are organic/inorganic semiconductors, act as transducers from light to electrical signal.9-10 The PEC property of transducing materials determines the analytical performance of the constructed sensing platform.11-12 With the rapid development of nanotechnology and material science, various nanomaterials have been applied in the PEC bioanalysis.13-16 Although great eﬀort has been devoted to the development of PEC bioanalysis,17 the complex fabrication process may hamper the real application in many fields. One issue is the binding of inorganic semiconductor nanomaterials with the biological recognition elements, which usually involves the surface functionalization of nanomaterial with amino or other groups and the subsequent covalent conjugation.18-19 A simple fabrication of biosensing interface is highly in demand for PEC bioanalysis. Mussel-inspired formation of polydopamine (PDA) thin films has proven to be a unique material-independent surface functionalization method.20 Due to the universality and chemical activity to form ad-layers, the self-polymerization of dopamine has been widely used in contrast agents,21 energy,22 batteries,23environmental,24 and biomedical fields.25 The charge transfer and optical properties of PDA also enable its application in artificial photosynthesis and dye-sensitized 2 ACS Paragon Plus Environment

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solar cells.26-27 We have reported the construction of a PEC biosensing chip based on PDA coating strategy.28-29 The PDA coating was used for directly immobilizing capture antibodies based on the reactivity with biomolecules. Furthermore, the PEC performance of the semiconductor transducers was obviously enhanced. However, the batch-to-batch reproducibility, which is very important for the bioanalysis, was not very good because it is difficult to control the polymer solution and then the film quality. Besides the formation of PDA coating on immersed substrate, melanin-like precipitate was formed in solution due to the unceasing self-polymerization of dopamine.30 Although the dopamine-melanin has been studied for many years,31 the research interest of dopamine self-polymerization seems to focus on the surface chemistry since the report of the above mentioned intriguing property.20 The insolubility may also make dopamine-melanin a less favorable candidate for surface coating. In this work, the self-polymerization of epinephrine, also a neurotransmitter with similar structure with dopamine, was re-exploited to the surface coating of semiconductor transducer and the construction of a PEC biosensing interface. In contrast to the formation of precipitate for dopamine, homogenous and stable aqueous dispersions were obtained for epinephrine. The terms dopamine-melanin (DAM) rather than PDA, epinephrine-melanin (EPM) rather than polyepinephrine, and norepinephrine-melanin (NEPM) rather than polynorepinephrine were adopted in this work to differentiate the post-synthetic products with the in-situ formed thin films. Due to the charge transfer property, the EPM greatly enhance the PEC response of TiO2 nanoparticles. The biological recognition elements can be easily immobilized on them and the antioxidant property of EPM inhibits the PEC-induced damage to the biomolecules. More importantly, the use of water soluble post-synthetic products enables the surface coating with simple drop-casting method. Compared with 3 ACS Paragon Plus Environment

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the dip-coating method, this strategy saves more time, avoids the waste of polymer solution, and undoubtedly decreases the batch-to-batch inconsistencies. EXPERIMENTAL SECTION Materials and Reagents. Dopamine hydrochloride, epinephrine hydrochloride, norepinephrine hydrochloride, and bovine serum albumin (BSA) were purchased from Sigma-Aldrich. Prostate specific antigen (PSA) antibody and antigen, insulin, carcinoembryonic antigen (CEA), and cardiac troponin I (cTnI) were purchased from Shanghai Linc-Bio Science Co., Ltd., China. Ascorbic acid (AA) was obtained from Shanghai Sinopharm Chemical Reagent Co., Ltd., China. P25 TiO2 nanoparticles with diameters of 20 nm and Tris(hydroxymethyl)aminomethane (Tris) were purchased from Shanghai Macklin Biochemical Co., Ltd., China. All other chemicals were of analytical grade and were used without further purification. The buffer solution was 0.1 mol·L-1 phosphate buffered saline (PBS). Apparatus. Scanning electron microscope (SEM) images and energy dispersive spectrometry (EDS) were obtained using a field emission SEM (Zeiss, Germany). Electrochemical impedance spectroscopy (EIS) and electrochemical measurements were carried out on a CHI 760D electrochemical workstation (Chenhua Instrument Shanghai Co., Ltd, China). Photocurrent was measured on a PEC workstation (Zahner Zennium PP211, Germany) at a bias voltage of 0 V. Both the electrochemical and PEC measurement were performed using a three-electrode system with modified ITO glass (1×2.5 cm2) as the working electrode, a Pt wire electrode as the counter electrode and an Ag/AgCl electrode as the reference electrode. Preparation of DAM, EPM and NEPM. Dopamine hydrochloride, epinephrine hydrochloride and norepinephrine hydrochloride (3 mg·mL-1) were separately dissolved in Tris-HCl buffer 4 ACS Paragon Plus Environment

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solutions (pH 8.5) and kept stirring for 72 h to obtain the DAM, EPM and NEPM. Fabrication of the PEC Biosensing Interface for PSA. ITO glass were sequently sonicated in acetone, ethanol and distilled water for about 30 min. Then ITO slices were dried using nitrogen stream. The construction of the photoelectrochemical biosensing interface were illustrated in Scheme 1. 10 µL of TiO2 nanoparticle aqueous dispersion (5 mg·mL-1) was dropped on a ITO slice keeping an area of 0.3 cm2. After dried in air, it was calcinated at 400 °C for 1 h. 5 µL of EPM solution was dropped on the surface of TiO2 and dried. After cleaned with water, 5 µL of PSA antibody solution (10 µg·mL-1) was dropped on the modified electrode and then 3 µL of BSA solution (1%) was dropped on it to block the nonspecific binding sites. For the detection of PSA, the fabricated electrodes were incubated with different concentrations of PSA antigen and were used for the PEC measurement in 0.1 M PBS solution containing 0.1 mol·L-1 AA.

Scheme 1. The fabrication process of the photoelectrochemical biosensing interface.

RESULTS AND DISCUSSION Preparation of EPM from the Self-polymerization of Epinephrine. As mentioned in the Introduction, it is very difficult to control the polymerization process of dopamine, because it is fast and depends on many factors, such as concentration, pH, temperature, oxidant, and even the type of buffer solution. Another issue for synthetic melamine is the structural uncertainty of the product.

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Although the term polydopamine, polyepinephrine, and polynorepinephrine have been widely used in the field of material science and many advanced technologies have been used to characterize the product, the exact chemical structure is still under debate.32 For DAM, the formation of dark brown aggregates seems like the generation of melanin, a natural pigment that exists in human skin, hair, and eyes. As a neurotransmitter with similar structure with dopamine, norepinephrine shows similar interface polymerization behavior but unique property.33 Both dopamine and norepinephrine form insoluble aggregates in basic aqueous solutions. Also as a neurotransmitter with similar structure, epinephrine forms a stable homogenous dispersion at the same reaction conditions (Fig. 1). The middle images in Panel A, B, and C show the vortexed solutions under irradiation with red laser light. An obvious Tyndall effect was observed for the homogenous solution of epinephrine-melanin. The bottom images in Panel A, B, and C show the centrifuged solution with a speed of 5000 r/min for 5 minutes (bottom). Precipitates were formed for the solutions of dopamine-melanin and norepinephrine-melanin while no precipitate was formed for the solution of epinephrine-melanin. This is a good case where the chemical structure determines the behaviors. All the DAM, EPM and NEPM coatings can increase the signals, the photocurrent signals of the EPM coating is highest (Fig. S1).


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Fig. 1. Panel A: The molecular structure of dopamine (top) and the prepared dopamine-melanin solution. Panel B: The molecular structure of norepinephrine (top) and the prepared norepinephrine-melanin solution. Panel C: The molecular structure of epinephrine (top) and the prepared epinephrine-melanin solution.

The formation of polymers from self-polymerization of epinephrine has been reported for a long time.34-36 Before the formation of melanin-like polymers, epinephrine undergoes complex oxidation process including the produce of aminochromes which has unique chromic band in visible region..37 The disappearance of the distinct chromophoric band and the appearance of a broad-band monotonic absorption ranging from the ultraviolet to the visible region confirmed the formation of melanin-like polymers (Fig. S2).25 However, it is still difficult to determine the exact chemical components of EPM due to the complex oxidation process. Compared with the molecular structure of dopamine, the presence of another hydroxyl group and methyl group should both contribute to the formation of homogenous dispersion,35 which improves the hydrophilicity and inhibits the further polymerization, respectively. The obtained EPM solution is stable for more than 3 months without any precipitates.


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This enables the utilization of EPM as a reproducible post-synthetic material for surface functionalization. Electrochemical and PEC Property of EPM. Take consider of the unique binding interactions between

catechol

derivatives

and

TiO2

and

the

most

widely

application,

commercially available TiO2 nanoparticles were used as semiconductor transducers to investigate the PEC performance of EPM. The crystalline state of TiO2 before and after the calcination can be confirmed by the well-designated XRD patterns (Fig. S3). The coating of EPM on calcinated TiO2 does not apparently change the morphology of the porous surface (Fig. 2A and B). The existence of the elements of Ti and O could be observed from the EDS spectrum (Fig 2C), and the existence of the elements of Ti, O and C could be observed from the EDS spectrum (Fig 2D), reveal that the EPM was successfully modified on TiO2.

Fig. 2. SEM images of TiO2 modified photoanodes before (A) and after (B) the coating of EPM. EDS images of TiO2 modified photoanodes before (C) and after (D) the coating of EPM.

The PEC signal mainly depends on the photon-to-electricity conversion efficiency of the 8 ACS Paragon Plus Environment

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photoexcited transducer material, which is usually decreased by the high rate of electron-hole recombinant. For photo-anode (TiO2 was in this case), electron donors should be incorporated into the PEC system to scavenge the photoexcited holes, thus suppress the recombination of the electron-hole pairs. Although EPM possesses good antioxidant property and dopamine has been exploited as an electron donor for PEC application,38 the EPM coating cannot perform well without the additional electron donors. However, in the presence of AA, the PEC signal was greatly enhanced at the same conditions (Fig. 3A).

Fig. 3. (A) Photocurrent signals obtained for TiO2 modified photoanodes (a and b) TiO2/EPM modified photoanodes (c and d) in PBS solution (a and c) and in the presence of 0.1 mol·L-1 ascorbic acid (AA) (b and d). (B) Photocurrent for TiO2 modified photoanodes before (a) and after (b) the coating of EPM with different excitation light wavelength. (C) Electrochemical response for glassy carbon electrode (GCE) (a), GCE/TiO2 (b) and GCE/TiO2/EPM (c) in 5 mmol·L-1 K3Fe(CN)6 solution.

Synthetic melamines and natural pigments have been used as photosensitizers for the development of dye-sensitized solar cells.27,

39

Compared with epinephrine, epinephrine–melanin shows high

UV-absorbing ability (Fig. S2), increased the peak width and enhanced the light absorption range. The PEC enhancement seems independent of the excitation wavelength of the light source (Fig. 3B). The enhancement effect is not induced by the light-harvesting property but is attributed to the electron transfer property of EPM, which was confirmed by the electrochemical characterization (Fig. 3C) and the subsequently discussed EIS decrease (Fig. 4B). Using K3Fe(CN)6 as an electronic media, slightly increased electrochemical response was obtained after the coating of non-conductive EPM in


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comparison with the current response for TiO2 modified electrode. The presence of semiquinones and quinones should in charge of the efficient proton-coupled electron transfer.26 The use of post-synthetic EPM as coating material also eliminate the reported impulsion effect on anions in the case of in-situ formed PDA thin films,40 which promotes the electron acceptance from the donor AA. Besides the enhancement effect, an increased batch-to-batch consistency was achieved for the drop-casting method over the dip-coating method (Table S1). Moreover, the electrode prepared by the EPM coating shows high storage stability (Table S2). Construction of PEC Biosensor for the Detection of PSA. The facile immobilization of biomolecules onto catecholamine modified surfaces based on the reactivity of quinone functional groups toward amine and thiol groups have been well demonstrated.41-42 In view of the PEC enhancement effect of EPM and the latent reactivity toward biomolecules, PSA antibodies were used as bio-recognition elements for the construction of a PEC biosensing interface (Scheme 1). While the coating of EPM greatly enhances the photocurrent signal, the immobilization of PSA antibodies and the further blocking of nonspecific binding sites using BSA decrease the photocurrent due to the formation of protein layer (Fig. 4A). Also due to this steric hindrance effect, the specific binding of PSA molecules onto the surface further decreases the photocurrent signal. The successful immobilization of PSA antibody and the fabrication process of the biosensor can be confirmed by the EIS measurement. It is worthy to note that, due to the above mentioned electron transfer property, great decreased EIS was obtained after the EPM coating (line c in Fig. 4B). The gradual increase of EIS for the formation of protein layer and the specific binding of PSA is responsible for the decreases of the photocurrent signal (Fig. 4B).


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Fig. 4. PEC (A) and the EIS (B) characterizations of the fabrication process of the biosensor:(a)ITO, (b)ITO/TiO2, (c)ITO/TiO2/PEP, (d)ITO/TiO2/PEP/anti-PSA, (e)ITO/TiO2/PEP/anti-PSA/BSA, (f)ITO/PEP/anti-PSA/BSA/PSA.

The effects of the substrates (Fig. S4), the concentration of EPM (Fig. S5), the volume of EPM coating (Fig. S6), the concentration of AA (Fig. S7) and the pH of buffer solution (Fig. S8) on the electrode response were investigated to obtain the optimal detection conditions. The simple coating of TiO2 nanoparticles with EPM greatly enhances the PEC performance, so TiO2 was selected as the substrates for the PEC measurements. 3 mg·mL-1 EPM, 5 µL of EPM, 0.1 mol·L-1 of AA and pH 7.4 were selected as the optimal conditions for the PEC measurements. A good linear relationship between the gradually decreased photocurrent signal and the logarithmic concentration of PSA was obtained from 0.1 ng·mL-1 to 20 ng·mL-1, which enables the sensitive detection of PSA (Fig. 5). The limit of detection was calculated as 35 pg·mL-1. The developed biosensing interface shows high signal stability (Fig. 6A), possibly due to the antioxidant character of EPM,43 which inhibits the PEC induced damage to the attached biomolecules. On account of the specific recognition interactions between antibody and antigen, the fabricated biosensor also shows high selectivity toward target biomarker in the presence of some interference proteins (Fig. 6B), such as insulin, CEA, and cTnI.


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Fig. 5. (A) Photocurrent responses of the constructed biosensing interface towards different concentrations of PSA and (B) the calibrated curve. The error bars in (B) indicate the standard deviation of the measurement (n = 3).

Fig. 6. (A) Photocurrent signals obtained for 1 ng·mL-1 of PSA under 10 on-off cycles with an interval of 20 s. (B) Photocurrent signals obtained for 1 ng·mL-1 of PSA without interference (a) and in the presence of 100 ng·mL-1 Insulin (b), 100 ng·mL-1 CEA (c), 100 ng·mL-1 cTnI (d). The error bars in (B) indicate the standard deviation of the measurement (n = 3).

Real sample analysis. To further investigate the potential application of the immunosensor for practical analysis, the sensor was used to test the recovery of different concentrations of PSA in serum samples. Different concentrations (3.5, 10.0 and 20.0 ng mL-1) of PSA serum samples were prepared by standard addition method. As shown in Table 1, the PSA concentration of real human blood serum is 1.53 ng mL-1. The recovery of PSA was in the range of 99.79–100.12% and the RSD was in the range of 0.12–0.33%. The proposed PEC imuunosensor displayed satisfactory results and potential application in blood sample determination. Table 1. Analysis results for determination of PSA in spiked human serum sample.


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Content of PSA

The addition

The detection

RSD

in the serum

content

concentration

(%)

(%)

(ng·mL-1)

(ng·mL-1)

(ng·mL-1) 0.33

100.12

0.29

99.79

0.12

99.90

3.50

5.05, 5.03, 5.04,

Recovery

5.01, 5.05 1.53

10.00

11.50, 11.48, 11.53, 11.47, 11.55

20.00

21.50, 21.54, 21.48, 21.53, 21.49

CONCLUSION In this work, we demonstrated that EPM could be used as surface coating for the enhancement of PEC performance and the development of an immunosensor. The exact component of EPM is still open for investigation. Due to the versatile reactivity of quinone functional groups toward amine and thiol groups, various biorecognition elements could be incorporated into this platform for the development of different biosensors. From the perspective of surface chemistry and nanomaterials, it may renew the use of post-synthetic melanin-like biopolymers in other fields. AUTHOR INFORMATION Corresponding Author *Q. Wei. Phone/Fax: +86-531-82767872. E-mail: [email protected]. Notes The authors declare no competing financial interest. ACKNOWLEDGMENTS 13 ACS Paragon Plus Environment

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This work was supported by the National Natural Science Foundation of China (21675063, 21575050), the National Key Scientific Instrument and Equipment Development Project of China (No. 21627809), the Science and Technology Planning Project of Higher Education of Shandong Province (J16LC23), and Q. Wei thanks the Special Foundation for Taishan Scholar Professorship of Shandong Province (No. ts20130937) and UJN. REFERENCES (1). Ma, W.; Wang, L.; Zhang, N.; Han, D.; Dong, X.; Niu, L. Biomolecule-Free, Selective Detection of o-Diphenol and Its Derivatives with WS2/TiO2-Based Photoelectrochemical Platform. Anal. Chem. 2015, 87, 4844-4850. (2). Zheng, Y.-N.; Liang, W.-B.; Xiong, C.-Y.; Yuan, Y.-L.; Chai, Y.-Q.; Yuan, R. Self-Enhanced Ultrasensitive Photoelectrochemical Biosensor Based on Nanocapsule Packaging Both Donor– Acceptor-Type Photoactive Material and Its Sensitizer. Anal. Chem. 2016, 88, 8698-8705. (3). Zhuang, J.; Lai, W.; Xu, M.; Zhou, Q.; Tang, D. Plasmonic AuNP/g-C3N4 Nanohybrid-Based Photoelectrochemical Sensing Platform for Ultrasensitive Monitoring of Polynucleotide Kinase Activity Accompanying Dnazyme-Catalyzed Precipitation Amplification. ACS Appl. Mater.

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