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Article

Paper-Based Analytical Device for One-Step Detection of Bisphenol-A Using Functionalized Chitosan

by
Abdelhafid Karrat
* and
Aziz Amine
*
Laboratory of Process Engineering and Environment, Faculty of Sciences and Techniques, Hassan II University of Casablanca, P.A. 146., Mohammedia 28806, Morocco
*
Authors to whom correspondence should be addressed.
Chemosensors 2022, 10(11), 450; https://doi.org/10.3390/chemosensors10110450
Submission received: 5 October 2022 / Revised: 26 October 2022 / Accepted: 26 October 2022 / Published: 31 October 2022
(This article belongs to the Special Issue Selected Papers from Optical Materials: Synthesis and Biological Applications Symposium (XXXVIII Biennial Meeting RSEQ))
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Abstract

:
Bisphenol-A (BPA) is defined as one of the endocrine disrupting compounds. The accurate and inexpensive colorimetric paper-based analytical devices (PADs) are of crucial importance for BPA analysis. In this context, we developed for the first time a new PAD modified with chitosan and sulfamethoxazole (Chitosan-PAD) for the visual detection of BPA in water. The PAD was characterized by Fourier-transform infrared spectroscopy, which confirmed its modification by the functionalized chitosan. A yellow coloration was developed when a small volume of BPA was added to the Chitosan-PAD, allowing for visual and smartphone detection. This new strategy is based on a specific combination of BPA with chitosan and sulfamethoxazole that provides a hight selectivity to the Chitosan-PAD. The proposed PAD was successfully employed in combination with a pre-concentration step for the detection of 0.01 µg mL−1 of PBA with the naked eye using a 10-fold preconcentration factor. The PAD was effectively applied for BPA quantification in water samples with good recoveries. The developed PAD provides a green and cost-effective strategy for the on-site and one-step detection of BPA in water samples.

1. Introduction

Bisphenol A or 2,2-bis(4-hydroxydiphenyl)propane, is a monomer of plastics type polycarbonates and epoxy resins. It results from a condensation reaction catalysed by hydrochloric acid involving two phenols and a ketone [1]. BPA is found in many products used in daily life under different forms, such as polycarbonates and epoxyphenolic resins. Polycarbonates represent 66% of total BPA usage. Thanks to its versatile properties such as durability, transparency, lightness, heat, chemical, and impact resistance, polycarbonate is the preferred material for a wide range of products such as plastic bottles, baby bottles, and plastic boxes for food preservation [2,3]. Although BPA is an important compound in plastic materials, it has adverse health effects. It causes a decrease in body weight, a decrease in the weight of certain adult organs (liver, kidney, spleen, adrenal gland, pituitary gland, brain) [4,5,6,7,8,9], and the development of hepatic pathologies [10]. On the other hand, BPA is defined as one of the endocrine disrupting compounds [11,12,13], which can imitate the hormone estrogen action and disrupt the estrogen-estrogen receptor binding process. As a result, research interest in the detection and monitoring of BPA has increased.
Currently, conventional detection methods are widely used for the detection of BPA, including high-performance liquid chromatography [14,15,16], liquid chromatography-mass spectrometry [16,17], and gas chromatography [18,19,20]. Nevertheless, as it is well known these methods are highly expensive. In addition, the strict requirements of tedious sample processing and the necessary professional staff have considerably limited the application in the field of rapid and on-site BPA detection. For this reason, the development of new devices for rapid and on-site detection is in high demand. The paper-based analytical devices (PAD) are small devices that allow the rapid and on-site detection of the desired analyte. PAD was applied for bioassays by Whitesides’ group in 2007. Since then, it has been used in colorimetric [21,22,23,24,25], fluorescent [26,27,28], and electrochemical methods [29,30,31] due to its outstanding characteristics, including low cost, adequate porosity, biocompatibility, biodegradability, and flexibility. PADs were already used for the determination of BPA, for example, Li et al. [32] developed a paper-based electrochemical sensor based on stacked gold nanoparticles supported carbon nanotubes for the determination of BPA in ABS plastic toys and PC drinking bottles. Additionally, Zeng et al. [33], prepared a paper-based analytical device (PAD) using a metal-organic framework of UiO-66-NH2 coated with molecularly imprinted polymers for the determination of BPA. Paper-based, portable, rapid, and inexpensive methods are preferred over time-consuming laboratory analyses. They are widely used for point-of-care medical diagnostics and environmental analysis [34,35].
Chitosan is a biopolymer obtained from chitin by deacetylation reaction. It is widely used in the analytical field [36,37,38] because of its interesting properties including biodegradability [39], film-forming ability [40,41], and free amines groups. For example, Kim et al. [42] reported a two-dimensional μPAD based on chitosan for the determination of glucose from whole blood. Indeed, the plasma was successfully separated from the whole blood using this µPAD. Moreover, a filter paper functionalized by chitosan for the rapid detection of sulfonamide in milk samples was developed by Yuyang et al. [43]. The proposed paper exhibits a better usability because of the inexpensive and easily available filter paper.
In this work, a new Chitosan-PAD was developed for the selective and sensitive colorimetric detection of BPA. The PAD was characterized by Fourier-transform infrared to confirm its well modification with functionalized chitosan. The color of the PAD changed from white to yellow upon addition of BPA which can be monitored visually or by the smartphone camera.

2. Experimental

2.1. Reagents and Materials

BPA, Chitosan, Sulfamethoxazole (SMX), Sodium nitrite, Disodium phosphate (Na2HPO4), Hydroquinone, 17-estradiol, Dicofol, Caffeine, Acetic acid, and Hydrochloric acid were purchased from Sigma Aldrich (St. Louis, MO, USA). Glass microfiber paper (pore diameter of 47 mm) was acquired from filtra TECH France.
A JENWAY Model 6850 UV–Visible Double beam Spectrophotometer (Bibby Scientific Brand-UK) was used for spectrophotometric measurements.

2.2. Fabrication of Chitosan-PAD

For the preparation of Chitosan-PAD (Scheme 1), 0.5 g of chitosan was solubilized in 100 mL of hydrochloride acid (0.25%). Then, 3 mL of chitosan solution was mixed with 600 µL of SMX (1 mg mL−1) and 600 µL of NaNO2 (2 mg mL−1). A filter paper with 47 mm diameter was immersed in the prepared chitosan-SMX diazotized solution. Then, another paper was soaked in a buffer solution (Na2HPO4 (0.5 M) pH = 12) for 10 min. The two papers were dried at 45 °C for 15 min. Thereafter, they were superposed on each other, and then a disc of 1 cm diameter was sliced. The obtained Chitosan-PAD was stored and sealed with parafilm until use.

2.3. Characterization

In order to confirm the modification of the paper with the diazotized chitosan, Fourier-transform infrared (FT-IR) spectra were collected using an IR Affinity-1S SHIMADZU spectrophotometer, in the Attenuated Total Reflectance (ATR) mode and in the range of 4000–500 cm−1.

2.4. Detection of BPA Using Chitosan-PAD

For the detection of BPA using the developed chitosan-PAD, 100 µL of BPA solution was added to the chitosan-PAD and a yellow coloration was developed immediately. Indeed, the Chitosan-PAD is composed of two papers, one containing the diazotized chitosan-SMX and the other one containing the buffer (pH = 12); 100 µL of sample is enough to soak the paper and the reaction is carried out between BPA and the diazotized chitosan-SMX in a basic medium. The images were captured by an Android-type smartphone (Resolution: 13 MP, 4:3), the camera was located in the circular pointer, and was matched to the detection zone on the Chitosan-PAD. The images were processed by the imageJ software (National Institutes of Health (NIH), Bethesda, MD, USA) to measure the color intensity channels RGB (red, green and blue). After comparing the color intensities, the most sensitive channel to the analyte concentration will be used for the BPA analysis.

2.5. Selectivity Study

In order to test the selectivity of the developed Chitosan-PAD, hydroquinone, 17-estradiol, dicofol, and caffeine at a concentration of 3 µg mL−1 were examined by the similar procedure mentioned above. Moreover, the corresponding photos were taken using a dark box in order to evaluate the interference of external light.

2.6. Pre-Concentration Study

For the determination of low BPA concentrations, the developed chitosan-PAD was used as sorbent in solid-phase extraction by placing the chitosan-PAD on an Eppendorf cap (Scheme 2). As mentioned above, the sample volume used for plotting the calibration curve without pre-concentration is 100 µL. Thus, the optimal pre-concentration factor was chosen by using the following sample volumes: 200 μL of 0.1 µg mL−1, 500 µL of 0.04 µg mL−1, 1 mL of 0.02 µg mL−1, and 2 mL of 0.01 µg mL−1 which correspond to the pre-concentration factors of 2, 5, 10, and 20, respectively. Then, the solutions were shaken for 5 min to develop the yellow coloration. The recovery was calculated by the ratio of the final concentration obtained under pre-concentration and the initial conditions (100 µL of 0.2 µg mL−1) without pre-concentration.

3. Results

3.1. Chitosan-PAD Preparation

The amine groups of chitosan (powder) and SMX were protonated by hydrochloride acid then the obtained ammonium groups were diazotized by nitrite. Afterward, the paper was emerged in this solution to incorporate the resulting BPA prob then dried at T = 40 °C. The obtained paper was superposed with another paper containing buffer (pH = 12). For the BPA detection, a sample containing BPA was added in one-step onto the Chitosan-PAD and the coloration developed immediately. Indeed, the hydroxide groups of BPA are deprotonated by the buffer (pH = 12) which allows the coupling of BPA in its ortho positions with SMX and chitosan as mentioned in the mechanism (Figure 1). The resulting product changes the PAD coloration to yellow.

3.2. FTIR Characterization

FT-IR spectra of the paper, chitosan, and Chitosan-PAD are characterized and compared in Figure 2. For the paper, two absorbance bands were observed at 790 cm− 1 and 1110 cm− 1 corresponding to Si-OH (symmetric stretching vibration of Si-OH) and Si-O-Si (asymmetric stretching vibration), respectively. The spectrum of chitosan showed a wide absorption band 3291–3361 cm−1, which was assigned to the asymmetric stretching of N-H and -OH groups. The bands at around 1645 cm−1 (C=O stretching of amide I) and 1325 cm−1 (C-N stretching of amide III) confirmed the presence of the residual N-acetyl groups. The bands at 1066 and 1028 cm−1 correspond to C-O stretching. Moreover, the spectrum of the Chitosan-PAD included the characteristic absorption peaks of both paper and chitosan, confirming that the chitosan was successfully integrated into the paper. It should be noted that sulfamethoxazole peaks were not detected by FTIR because of the low concentration used for the preparation of Chitosan-PAD.

3.3. Method Optimization

The colorimetric assay is based on the diazotization reaction for the combination of chitosan platform with BPA. Therefore, to obtain the optimal conditions for the colorimetric detection of BPA, the reagents concentration and the final pH were optimized by measuring the absorbance of developed azo dye at a wavelength of 450 nm. All the experiments were performed in triplicate.
The effect of the SMX concentration on the colorimetric reaction was optimized in the range of 0.1–1.8 mg mL−1. As shown in Figure 3a, the absorbance increased with an increase in BPA concentration. When the concentration of BPA was greater than 1 mg mL−1, the absorbance remained constant. Thus, 1 mg mL−1 was selected as the optimal concentration for BPA detection.
The color intensity of the formed azo-dye highly depends on the NaNO2 concentration. Thus, the NaNO2 concentration was optimized in the range of 0.2–4 mg mL−1. The obtained results are shown in Figure 3b. The absorbance increased with the BPA concentration and reached a maximum at 2 mg mL−1.
The pH study was investigated by adding the NaOH (0.1 M) to the mixture. As shown in Figure 3c, when the pH is lower than 10, the yellow coloration declines which could be explained by the absence of hydroxide groups deprotonation in BPA which facilitates its combination with chitosan and SMX. However, when the pH is between 10 and 11, the BPA reacts with chitosan and sulfamethoxazole, resulting in a maximum absorbance. Therefore, 10 is the optimal pH for the BPA detection. To improve the method’s reproducibility, a phosphate buffer (Na2HPO4, pH = 12) was used for the further studies instead of NaOH, that stabilized the pH of the final solution (pH = 10–11) better than the strong base of NaOH.

3.4. Detection by Smartphone

After the optimisation of all procedure parameters using a spectrophotometer, a PAD based on chitosan allowed a rapid, on-site, sensitive and specific detection of BPA was developed. Moreover, the detection is very easy since it occurs just in a single step. Indeed, after the addition of the sample the color of the PAD turns into yellow and the intensity of the color depends on the BPA concentration. The images were captured by smartphone and then the RGB color intensities were measured by ImageJ software. Figure 4a indicates that as the BPA concentration increased the color intensities decreased. However, the blue color curve decreases more significantly with the increase of BPA concentration than the green and red channels. Thus, we selected the blue color as the optimal parameter for the detection of BPA.

3.5. Calibration Curve

Under the optimal conditions, the color intensity of the Chitosan-PAD for the detection of BPA amplified with increasing concentrations of the BPA. Figure 4b displays the calibration plots of the color intensity obtained from varying the BPA concentration. The linearity of the calibration curve was good with correlation coefficient (r2) of 0.990. The lowest concentration measurable by the naked eye is 0.1 µg mL−1. The limit of detection obtained by using the smartphone was estimated to be 0.02 µg mL−1 using the following equation: 3 SD/Slope, where SD is the standard deviation of the blank.

3.6. Pre-Concentration Study

Pre-concentration is a powerful technique allowing the detection of lower analyte concentrations using a sorbent. Indeed, the developed PAD was applied as sorbent for the pre-concentration and determination of BPA. Different pre-concentration factors including 2, 5, 10, and 20 were tested. As shown in Figure 5a, the recovery is still near 100% until 10-fold time and it decreased at the pre-concentration factor of 20, because of the buffer leakage in high volumes. Thus, we selected the pre-concentration factor of 10 for the determination of BPA. Indeed, we successfully detected 0.01, and 0.04 µg mL−1 by the naked eye (Figure 5b). These results confirmed that the PAD-Chitosan could be used as a specific sorbent for the pre-concentration and determination of BPA traces.

3.7. Selectivity Study

Membrane modifications are widely used to improve their selectivity for the removal of molecules, heavy metals, gas, etc. [44,45,46]. In the present study, we modified the quartz membrane with functionalized chitosan and sulfamethoxazole to improve the selectivity of the developed Chitosan-PAD. As shown in Figure 6a, only BPA could induce a significant decrease of the blue intensity value whereas no obvious color development was observed for the interferents. This result is likely due to the specific reaction between chitosan, BPA, and SMX that leads to the formation of the yellow azo-dye as mentioned above in the mechanism which corresponds to blue color intensity measured with a smartphone (Figure 1). This specific combination of BPA with chitosan and SMX contributed to the specific detection of BPA and the absence of reaction with the other molecules that are not able to be coupled with chitosan and SMX.
The effect of some potential interferences on the color intensity of BPA was investigated. The environmental interferences studied were ions including Cu2+, Ca2+, K+, and Na+. The concentration of the interferent ions was 20-fold higher than that of BPA (1.5 µg mL−1). Figure 6b showed no significant interference which confirms that the Chitosan-PAD exhibits a high selectivity for monitoring BPA in water.

3.8. Stability Study

Another key requirement of the chitosan-PAD is long-term stability. Thus, the stability of the developed chitosan-PAD was determined by keeping the chitosan-PAD at 48 °C, and measurements were made every three days. As shown in Figure 7, the intensity response of BPA showed no significant changes after 15 days. Since the material showed good stability at high temperatures, it could be stable for a long time at room temperature.

3.9. Advantages and Versatility of the Proposed Strategy

The PAD proposed here offers a low-cost method to selectively identify the BPA. Unlike conventional sensors that need time, reagents, materials, lab equipment, solvents, etc. [47,48,49], this on-site method detects BPA immediately and in only one-step. With this technique, the sample can be used directly without being diluted by chemical reagents, enabling the visual and smartphone detection of low BPA quantities without the need for laboratory apparatus.
This device can be easily modified to allow the detection of other compounds, such as molecules, heavy metals, viruses, etc. Indeed, the existence of the colorimetric assays for a wide variety of metals and molecules will permit the functionalization of Chitosan-PADs with the specific agents for the desired analytes. Moreover, due to the free amino groups present in the surface of the chitosan-based PADs, the biomolecules including enzymes, antibodies, and DNA could be attached to the PAD by covalent and electrostatic bonds for the development of new specific colorimetric PADs. This research work paves the way for the development of green and inexpensive PADs for on-site, one-step, and selective detection.

3.10. Real Sample

The proposed Chitosan-PAD was applied for the analysis of BPA in tap and river water. The samples were collected and spiked with the following concentrations: 1, 0.5, and 0.04 µg mL−1. Then, 100 µL of the sample solution was added onto the Chitosan-PAD. The BPA concentration was quantified using smartphone. Table 1 shows that the recoveries of BPA in water samples are ranged from 90% to 105% with a relative standard deviation less than 5.1%. The result shows that the developed Chitosan-PAD has good accuracy for the determination of BPA in water.

4. Conclusions

A cost-effective and simple PAD for on-site and rapid detection of BPA in water samples was developed in this research. The chitosan-PAD was prepared by using quartz membrane and the diazotized chitosan-sulfamethoxazole as a support material and recognition probe for BPA, respectively. The coupling reaction between chitosan, SMX and BPA provides a high selectivity. Under the optimized conditions, the developed Chitosan-PAD was successfully used for rapid detection of BPA by naked-eye and smartphone in water samples. The developed Chitosan-PAD coupled to smartphone offered a highly sensitive, selective, and one-step detection of BPA for in-field analysis.

Author Contributions

A.K.: conceptualization, investigation, visualization, methodology, software, formal analysis, writing–original draft, validation. A.A.: supervision, project administration, writing–reviewing and editing. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.

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Chemosensors 10 00450 sch001 550
Scheme 1. Preparation of chitosan-PAD.
Scheme 1. Preparation of chitosan-PAD.
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Scheme 2. Pre-concentration procedure for BPA trace determination using Chitosan-PAD as sorbent.
Scheme 2. Pre-concentration procedure for BPA trace determination using Chitosan-PAD as sorbent.
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Figure 1. Detailed mechanism for the different steps involved in the reaction of BPA with chitosan and sulfamethoxazole.
Figure 1. Detailed mechanism for the different steps involved in the reaction of BPA with chitosan and sulfamethoxazole.
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Figure 2. FT-IR spectra of the paper, chitosan, and the developed Chitosan-PAD.
Figure 2. FT-IR spectra of the paper, chitosan, and the developed Chitosan-PAD.
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Figure 3. Optimization of reaction conditions: (a) effect of sulfamethoxazole concentration, (b) effect of NaNO2 concentration, (c) effect of pH on the absorbance.
Figure 3. Optimization of reaction conditions: (a) effect of sulfamethoxazole concentration, (b) effect of NaNO2 concentration, (c) effect of pH on the absorbance.
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Figure 4. (a) Plot of the red, green, and blue color channels versus the BPA concentration; (b) the calibration curve of BPA by exploiting the blue color channel, n = 3.
Figure 4. (a) Plot of the red, green, and blue color channels versus the BPA concentration; (b) the calibration curve of BPA by exploiting the blue color channel, n = 3.
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Figure 5. (a) Optimization of the pre-concentration factor using Chitosan-PAD as a sorbent; (b) determination of BPA by naked eye using a pre-concentration factor of 10.
Figure 5. (a) Optimization of the pre-concentration factor using Chitosan-PAD as a sorbent; (b) determination of BPA by naked eye using a pre-concentration factor of 10.
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Figure 6. (a) Selectivity test of the Chitosan-PAD to other phenols [BPA] = 3 µg mL−1; (b) selectivity study of Chitosan-PAD towards BPA (1.5 μg mL−1) in the presence of different ionic compounds (30 μg mL−1), n = 3.
Figure 6. (a) Selectivity test of the Chitosan-PAD to other phenols [BPA] = 3 µg mL−1; (b) selectivity study of Chitosan-PAD towards BPA (1.5 μg mL−1) in the presence of different ionic compounds (30 μg mL−1), n = 3.
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Figure 7. Stability study of the developed Chitosan-PAD, [BPA] = 2.5 µg mL−1.
Figure 7. Stability study of the developed Chitosan-PAD, [BPA] = 2.5 µg mL−1.
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Table
Table 1. Determination of BPA in tap and river water using Chitosan-PAD.
Table 1. Determination of BPA in tap and river water using Chitosan-PAD.
Added (µg mL−1)Found (µg mL−1)Pre-Concentration FactorRecovery (%)RSD (%)
Tap water1.001.05--1051.27
0.500.49--982.45
0.040.03610905.13
River water10.97--973.00
0.500.50--1001.78
0.040.03810954.38
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Karrat, A.; Amine, A. Paper-Based Analytical Device for One-Step Detection of Bisphenol-A Using Functionalized Chitosan. Chemosensors 2022, 10, 450. https://doi.org/10.3390/chemosensors10110450

AMA Style

Karrat A, Amine A. Paper-Based Analytical Device for One-Step Detection of Bisphenol-A Using Functionalized Chitosan. Chemosensors. 2022; 10(11):450. https://doi.org/10.3390/chemosensors10110450

Chicago/Turabian Style

Karrat, Abdelhafid, and Aziz Amine. 2022. "Paper-Based Analytical Device for One-Step Detection of Bisphenol-A Using Functionalized Chitosan" Chemosensors 10, no. 11: 450. https://doi.org/10.3390/chemosensors10110450

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