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Chemiluminescence of Lucigenin/Riboflavin and Its Application for Selective and Sensitive Dopamine Detection lan yixiang, Fan Yuan, Tadesse Haile Fereja, Chao Wang, Baohua Lou, Jianping Li, and Guobao Xu Anal. Chem., Just Accepted Manuscript • DOI: 10.1021/acs.analchem.8b04670 • Publication Date (Web): 24 Dec 2018 Downloaded from http://pubs.acs.org on December 25, 2018

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Analytical Chemistry

Chemiluminescence of Lucigenin/Riboflavin and Its Application for Selective and Sensitive Dopamine Detection Yixiang Lana,b, Fan Yuanb,c, Tadesse Haile Ferejab,d, Chao Wanga,b, Baohua Loub,c*, Jianping Lia,*, and Guobao Xua,b,c* College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, PR China c University of Science and Technology of China, Hefei, China d University of the Chinese Academy of Sciences, Chinese Academy of Sciences, No. 19A Yuquanlu, Beijing 100049, China a

b

ABSTRACT: Lucigenin-riboflavin chemiluminescence is reported for the first time. Moreover, most dopamine chemiluminescence (CL) detection methods are based on the quenching of CL by dopamine. In contrast, we find that dopamine can significantly enhance lucigenin/riboflavin CL and establish a highly sensitive turn-on method for dopamine detection based on the enhancement of lucigenin/riboflavin CL. Under the optimal conditions, the CL intensity of lucigenin/riboflavin system increased linearly with the concentration of dopamine in the range of 0.0056 -55.56 μM and the limit of detection is 1.87 nM.

Chemiluminescence (CL) is a well-known and popular analytical method with many outstanding characteristics, such as low cost and high sensitivity, low detection limit, wide linear range, rapid and simple operation, as well as safety1-7. It has been widely employed in various fields, including clinical diagnosis, biotechnology, food analysis, environmental monitoring and metal ion detections8-14. Lucigenin (N,Ndimethylbiacridinium dinitrate) is used as one of the most efficient CL luminophores in conventional luminescent materials. Most lucigenin systems reported use hydrogen peroxide as the co-reactant15-19. Riboflavin (RF), also known as vitamin B2, is found in a wide variety of food substances and plays a very important role to maintain human health. The deficiency of RF in the body results in many diseases, such as various kinds of skin disorders, cardiovascular disease, eye lesions and cellular growth retardation. It also has a significant influence in protecting the body against malignant cancer20-23. Besides, RF is commonly used as a photochemical agent and the source of active oxygen species due to its susceptibility to oxidation in the presence of oxygen and light conditions. In excited form, RF can act as an electron donor for many redox systems24-25. However, RF CL systems have been rarely reported24,26,27. Dopamine (DA) is a vital neurotransmitter that plays an active role in a wide array of physiological processes, such as feeling, hormone secretion, memory, cognition and activities of central nervous system, cardiovascular disease, etc28-29. The abnormal quantities of dopamine in human serum usually have devastating impacts on human health and are associated with many diseases. On the one hand, the deficiency of DA may cause muscle cramp, attention deficit hyperactivity disorder, Parkinson’s disease, and schizophrenia; on the other hand,

excessive secretion of DA leads to the failure in energy metabolism and causes untimely death30-33. Therefore, it is critical to regulate the concentration of DA to the required amount necessary for proper functioning of the body, and there is a great need for effective, selective and sensitive approaches to detect dopamine. Various methods have been successfully applied to detect DA, including CL, electrochemiluminescence (ECL), voltammetry, fluorescence, colorimetry, UV − vis spectroscopy, Surface-enhanced Raman Scattering (SERS), high performance liquid chromatography (HPLC), etc28,34-39. DA is usually considered as a quenching agent of CL40-41, the enhancing effect of DA on CL has seldom been reported. In the present work, lucigenin-RF CL is reported for the first time. Surprisingly, DA was found to be able to remarkably enhance lucigenin-RF CL, which is utilized to develop a new DA CL detection method. The mechanism was discussed. The new DA CL detection method has high sensitivity, and nice selectivity against common interfering biological compounds, including amino acids, ascorbic acid, uric acid and glucose.

EXPERIMENTAL SECTION Materials and apparatus. Ascorbic acid (AA) was purchased from Beijing Chemical Reagent Company (Beijing, China). Uric acid (UA), glucose and amino acids (arginine, lysine, tyrosine, alanine, and cysteine) were purchased from Sinopharm Chemical Reagent Co. Ltd. (Beijing, China). Lucigenin and Riboflavin were purchased from TCI (Shanghai, China). Dopamine hydrochloride (DA) was obtained from Aladdin Chemistry Co., Ltd. (Shanghai, China). Lucigenin stock solution (5.0 mM) was prepared by dissolving

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0.1021 g lucigenin in 40 mL water. RF stock solution (20.0 mM) was prepared by dissolving 0.3011 g RF in 40 mL NaOH (0.1 M) solution, and then stored at 4 °C shielded from light. The pH of 0.1 M phosphate buffer solution was adjusted with 0.1 M NaOH solution. All the chemicals were analyticalreagent grade and were used as received without further purification. BPCL ultra-weak luminescence analyzer (the Institute of Biophysics, Chinese Academic of Sciences) was used to measure the CL intensities. For studying the effect of oxygen on lucigenin-RF CL by flow injection analysis, a IFIS-C mode intelligent flow injection sampler (ReMax Inc., Xi’an, China) was coupled with BPCL ultra-weak luminescence analyzer. Procedure of CL spectrum measurement. Optical filters that selectively transmit light of different wavelengths ranging from 420 to 650 nm were put on the detector. Then the CL reaction cell was put on the optical filter, and 200 μL of 5.0 mM lucigenin solution, 100 μL of 20 mM RF solution, and 600 μL of pH 10.0 phosphate buffer solution were added to the CL reaction cell. Finally, the CL signals were detected and recorded. The photomultiplier tube voltage was set at 1000 V. Determination of DA. 200 μ L of lucigenin (5.0 mM) and 100 μ L of RF (20 mM) were added to a 550 μ L phosphate buffer solution (pH=10.0). After mixing, 50 μL of DA in water with different concentrations were added to achieve a total volume was 900 μ L. Then CL intensity was recorded immediately after the addition of DA. The photomultiplier tube voltage was set at 800 V. The final concentrations of lucigenin and RF were 1.11 mM and 2.22 mM, respectively.

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singlet oxygen (1O2), hydroxyl radical (OH • ) and superoxide radical (O2 • −), on CL intensities were investigated.43 Sodium azide, thiourea and SOD all have little effect on CL intensity. It indicates that singlet oxygen (1O2), hydroxyl radical (OH • ) and superoxide radical (O2 • −) play little role in the generation of CL.43-47 It has been reported that riboflavin can oxidize alcohols, such as methanol, and thus be converted to oneelectron reduced radical semiquinone (also call riboflavin radical). Riboflavin radical, fully reduced riboflavin, and riboflavin can rapidly set up an equilibrium (Eq. 3 in Scheme S2).48-50 Therefore, the mechanism of lucigenin-RF CL is proposed as follows (Scheme S2). Lucigenin is converted to intermediate radicals by reaction with hydroxide ion in alkaline solution (Eq. 1), and then the radicals react with RF to produce the emitter (excited N-methylacridone) and riboflavin radical (Eq. 2). Finally, the excited N-methylacridone returns to its ground state, leading to CL.26,43-50

RESULTS AND DISCUSSION CL of lucigenin-RF system. As shown in Figure 1A, both the lucigenin solution and RF solution have almost no CL emission. An obvious and stable CL is observed upon the addition of RF to lucigenin solution, indicating that RF can effectively enhance the CL of lucigenin. Interestingly, the CL of lucigenin-RF system is so stable that the CL process could last for more than 1 hour (Figure 1B). To study the mechanism of lucigenin-RF CL system, the CL spectrum was measured using optical filters selectively transmitting light of different wavelengths ranging from 420 to 650 nm (Figure 2). It is obvious that the maximum emission wavelength was observed at about 500 nm. This wavelength is consistent with the previous reports in the literature and further confirms that the main CL emitter in the proposed system is lucigenin42. Oxygen frequently participates lucigenin CL reaction. Therefore, the effect of oxygen on lucigenin-RF CL was investigated. To ensure the removal of oxygen, we have done experiments using flow injection system. Both lucigenin solution and RF solution were deoxygenated by bubbling nitrogen for 30 mintues, and then were pumped through channels 1 and 2 into the flow cell (Scheme S1). As shown in the inset of Figure 1B, the CL intensity changes negligibly after the dissolved oxygen was removed from the reactant solutions. This result reveals that the reaction of lucigenin and RF in alkaline solution generate CL in the absence of oxygen. To further reveal the mechanism of the CL system, the effect of sodium azide (1.6 mM), thiourea (1.6 mM) and SOD (0.056 mg/mL), which are the effective radical scavengers of

Figure 1. (A) Comparison diagram of different chemiluminescence; (B) The time-dependent curve of lucigeninRF CL (Inset: the CL kinetic profiles of lucigenin-RF system in the presence (red line) and absence (black line) of oxygen). Clucigenin=1.05 mM, CRF=4.21 mM, Photomultiplier tube voltage (PMT) voltage=1000 V, pH=10.0

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Analytical Chemistry be due to easier deprotonation and decomposition as pH increases from 7.0 to 10.0. The higher pH may cause more side reactions and thus inhibit CL46.

Figure 2. CL spectrum of lucigenin-RF system Clucigenin=1.11 mM; CRF=2.22 mM. PMT=1000 V, pH=10.0.

Enhancement of lucigenin-RF CL by DA. Figure 3 shows the effect of DA on lucigenin-RF CL. DA can remarkably increase the CL intensity of lucigenin-RF system. While both the mixing of lucigenin with DA and the mixing of RF with DA generate very weak CL. These results demonstrate that the increase in lucigenin-RF CL in the presence of DA is not from the CL of lucigenin-DA and the CL of RF-DA. Probably, DA serves as nucleophile and reacts with lucigenin to produce more intermediate radicals, and thus leads to the increase in CL intensities51-52. The lucigenin-RF-DA CL was leveling off after about 300 seconds. Therefore, the CL intensities at t=300 s were used for subsequent comparison.

Figure 4. The effect of pH value of phosphate buffer solution on CL intensities. Clucigenin=1.05 mM, CRF=4.21 mM, PMT=800 V.

The effects of lucigenin and RF concentrations on the chemiluminescence of the system were also studied. As shown in Figure 5, the CL intensity increase with the increase of either lucigenin concentrations or RF concentrations. The lucigenin concentrations of 1.11 mM and the RF concentrations of 2.22 mM were chosen by taking CL intensity, background signal and consumption of the reagents into consideration.

Figure 3. Comparison diagram of different chemiluminescence with DA. c(lucigenin)=1.05 mM, C(RF)=4.21 mM, C(DA)=1.05 mM, pH=10.0, PMT=1000 V.

The optimization of CL conditions. According to the previous literature, the CL of lucigenin system usually generated under alkaline conditions. Therefore, the pH of solution was optimized from 7.0 to 12.0. As shown in Figure 4, the CL intensities of lucigenin-RF system rise with pH increasing from neutral to 10.0 and yields the strongest emission at pH 10.0, and the intensity of CL decreases when the pH is higher than 10.0. The increase in CL intensities may

Figure 5. The interrelation of CL intensity with the concentration of lucigenin (A) and RF (B).

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Detection of DA. Figure 6 shows that the CL intensity increases rapidly with increasing DA concentrations from 0 to 111.11 μM and then increases slowly at higher DA concentrations. The relative standard deviations (RSD) in three consecutive experiments are between 0.06% and 5.1%. Compared with other detection methods, our proposed method also has strong advantages, both in the linear range and detection limit, as shown in Table 1. Figure S1 shows that the CL intensities have a good linear relationship with DA concentrations from 0.0056 to 55.56 μM. The linear equation is ICL=1055.2+125.7*CDA (R2=0.998). The limit of detection (LOD) is 1.87 nM (S/N=3).

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indicated that the method proposed based on the lucigenin-RF CL system for DA detection has good selectivity.

Figure 7. Interference study of DA detection. The concentration of DA, AA and UA is 11.11 μM, and the concentration of amino acids is 22.22 μM.

Figure 6. CL emission-time curves in different concentrations of DA. CDA= 0.0056, 0.056, 0.28, 0.56, 1.11, 2.78, 4.44, 5.56, 11.11, 16.67, 22.22, 27.78, 33.33, 44.44, 55.56 and 111.11 μM. PMT=800 V.

Table 1. Comparison of different methods Used for DA detection.

Determination of DA in real samples. To check the feasibility of the present method, a standard addition method was applied to detect DA in human urine samples. Briefly, human urine samples were diluted by 50 folds with redistilled water, and then different amounts of DA were added to the diluted human urine samples to obtain samples of different concentrations. Table S1 shows that the calculated recoveries of the proposed method were in the range of 89.6%–104.4%, indicating that this method is suitable for the real sample applications.

CONCLUSION In summary, we have reported for the first time that DA can directly enhance the CL of lucigenin-RF system. This fascinating CL phenomenon is contrary to the previous reports in the literature that dopamine generally inhibits CL. This study shows a new detection strategy for DA based on its enhancing effect on lucigenin-RF CL. The dynamic range and detection limits of the proposed method for the determination of DA are better than most of the previously reported CL methods. Furthermore, this study broadens the applications of lucigenin CL.

Analytical method

Linear range

LOD

Ref.

Fluorescence

0 - 3.5 μM

0.01 μM

53

Fluorescence

1 - 200 μM

0.07 μM

54

Colorimetry

33 nM - 3.33 mM

33 nM

55

Electrochemistry

0.1- 10 μM

25±5 nM

56

Electrochemilumine scence

0.1 - 4 μM

32 nM

57

ASSOCIATED CONTENT

Chemiluminescence

0.3 - 9.0 nM

0.1 nM

58

Supporting Information

Chemiluminescence

0.0056 - 55.56 μM

1.87 nM

This work

Procedure of flow injection analysis; Diagram of flow injection analysis system; CL mechanism; Linear calibration curve; Real sample determination (PDF).

Selectivity of dopamine detection. By measuring the relative CL intensity, the proposed method was applied to evaluate the selectivity of DA with other common interfering biological compounds, including amino acids, ascorbic acid, uric acid and glucose. As shown in Figure 7, DA increases the CL intensity dramatically while amino acids, ascorbic acid, uric acid and glucose have little effect on CL intensities, which

AUTHOR INFORMATION Corresponding Author * Phone (+86) 431-85262747. Fax: (+86) 431-85262747. E-Mails: [email protected] (G. Xu), [email protected] (J. Li), (B. Lou).

Notes The authors declare no computing financial interest.

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Analytical Chemistry

ACKNOWLEDGMENT We thank the support from National Natural Science Foundation of China (Nos. 21675148, 21505128, and 21475123), the National Key Research and Development Program of China (No. 2016YFA0201300), the Chinese Academy of Sciences (CAS)the Academy of Sciences for the Developing World (TWAS) President’s Fellowship Program.

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nanoclusters for highly sensitive determination of dopamine released by cells. Microchim. Acta 2016, 184, 735-743. (58) Li, Y.; Peng, W.; You, X. Determination of dopamine by exploiting the catalytic effect of hemoglobin–stabilized gold nanoclusters on the luminol–NaIO4 chemiluminescence system. Microchim. Acta 2017, 184, 3539-3545.

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Analytical Chemistry The picture below for TOC only.

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Riboflavin and Its Application for

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