A glassy carbon electrode modified with boron-doped graphene oxide/ polyaspartic acid for electrochemical determination of oxazepam

محورهای موضوعی : Iranian Journal of Catalysis

Maryam Behravan ¹ (Department of Chemistry, Sciences and Research Brench, Islamic Azad University, Tehran, Iran)
Hossein Aghaie ² (Department of Chemistry, Sciences and Research Brench, Islamic Azad University, Tehran, Iran)
Masoud Giahi ³ (Department of Chemistry, South Tehran Branch, Islamic Azad University, Tehran, Iran)
Laleh Maleknia ⁴ (Department of Biomedical Enginiring, South Tehran Branch, Islamic Azad University, Tehran, Iran)

تاریخ دریافت : 1401/02/22 تاریخ پذیرش : 1401/06/05 تاریخ انتشار : 1401/06/10

کلید واژه: Boron, Differential pulse voltammetry, Graphene oxide, aspartic acid, Glassy carbon electrode, Oxazepam,

چکیده مقاله :

In this study, the electrochemical determination of oxazepam in plasma samples was studied. The composite of graphene oxide/boron (B-RGO) was synthesized via the hydrothermal method and it was cast on the glassy carbon electrode (GCE). The polyaspartic acid (poly(ASP)) was deposited on the B-RGO by electropolymerization to prepare the modified electrode named B-RGO/ poly(ASP)|GCE. The B-RGO and B-RGO/poly ASP were characterized using scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR). Electrochemical studies were performed by cyclic voltammetry (CV), linear sweep voltammetry (LSV) and differential pulse voltammetry (DPV) methods. The experimental parameters affecting the reduction of oxazepam such as pH, preconcentration time, scan rate and other analysis conditions, and instrumental parameters were optimized. Under the optimal conditions, the linear range was obtained from 0.001 to 800 μM with a correlation coefficient of 0.998. The repeatability of the method for the electrode to electrode and one electrode were 4.3% and 4.9%, respectively. The limit of detection (LOD) of 0.3 nM and the limit of quantitation (LOQ) of 1 nM were obtained. The high efficiency of the developed electrode in the determination of oxazepam in the plasma sample was proved by using acceptable results and satisfactory relative recovery percentage (>90%). Based on our calculation, the heterogeneous electron transfer rate constant (ks) was 1.92 s-1. The interaction between oxazepam and modifier was single-layer and multi-layer adsorption, respectively in low and high concentrations.

منابع و مأخذ:

[1] J. Janecek, N.D. Vestre, B.C. Schiele, R. Zimmermann, Oxazepam in the treatment of anxiety states: A controlled study, J. Psy. Res. 4 (1966) 199-206.

[2] J. Sarris, A. Scholey, I. Schweitzer, C. Bousman, E. LaPorte, C. Ng, G. Murray, C. Stough, The acute effects of kava and oxazepam on anxiety, mood, neurocognition; and genetic correlates: a randomized, placebo‐controlled, double‐blind study, Hum. Psychopharmacol. 27 (2012) 262-269.

[3] G.L. Mackinnon, W.A. Parker, Benzodiazepine withdrawal syndrome: a literature review and evaluation, Am J Drug Alcohol Abuse. 9 (1982) 19-33.

[4] A. Goldnik, M. Gajewska, M. Jaworska, Determination of oxazepam and diazepam in body fluids by HPLC, Acta Pol. Pharm. 50 (1993) 421-421.

[5] L. Banaszkiewicz, M.K. Woźniak, M. Kata, E. Domagalska, M. Wiergowski, B. Szpiech, A. Kot-Wasik, Rapid and simple multi-analyte LC–MS/MS method for the determination of benzodiazepines and Z-hypnotic drugs in blood samples: development, validation and application based on three years of toxicological analyses, J. Pharm. Biomed. 191 (2020) 113569.

[6] A. Bakhshi, A.P. Daryasari, M. Soleimani, A Molecularly Imprinted Polymer as the Adsorbent for the Selective Determination of Oxazepam in Urine and Plasma Samples by High-Performance Liquid Chromatography with Diode Array Detection, J. Anal. Chem. 76 (2021) 1414-1421.

[7] G. Popović, D. Sladić, V.M. Stefanović, L.B. Pfendt, Study on protolytic equilibria of lorazepam and oxazepam by UV and NMR spectroscopy, J. Pharm. Biomed. Anal. 31 (2003) 693-699.

[8] A.B. Tabrizi, M. Harasi, Applying cloud point extraction technique for the extraction of oxazepam from human urine as a colour or fluorescent derivative prior to spectroscopic analysis methods, Drug Test. Anal. 4 (2012) 145-150.

[9] U. Guth, W. Vonau, J. Zosel, Recent developments in electrochemical sensor application and technology—a review, Meas. Sci. Technol. 20 (2009) 042002.

[10] E. Sohouli, E.M. Khosrowshahi, P. Radi, E. Naghian, M. Rahimi-Nasrabadi, F. Ahmadi, Electrochemical sensor based on modified methylcellulose by graphene oxide and Fe3O4 nanoparticles: Application in the analysis of uric acid content in urine, J. Electroanal. Chem. 877 (2020) 114503.

[11] F. Gandomi, E.M. Khosrowshahi, E. Sohouli, M. Aghaei, M.S. Mohammadnia, E. Naghian, M. Rahimi-Nasrabadi, Linagliptin electrochemical sensor based on carbon nitride-β-cyclodextrin nanocomposite as a modifier, J. Electroanal. Chem. (2020) 114697.

[12] T.H. Sanatkar, A. Khorshidi, R. Yaghoubi, E. Sohouli, J. Shakeri, Stöber synthesis of salen-formaldehyde resin polymer-and carbon spheres with high nitrogen content and application of the corresponding Mn-containing carbon spheres as efficient electrocatalysts for the oxygen reduction reaction, RSC Adv. 10 (2020) 27575-27584.

[13] M. Giahi, O. Marvi, F. Safari, B. Chahkandi, Determination of betamethasone sodium phosphate in pharmaceuticals by potentiometric membrane sensor based on its lidocaine ion pair, J. Anal. Chem. 68 (2013) 900-905.

[14] J. Wang, Modified electrodes for electrochemical sensors, Electroanalysis, 3 (1991) 255-259.

[15] F. Ghaemi-Amiri, H. Aghaie, M. Giahi, M. Mozaffari, Electrocatalytic Oxidation Study of Theophylline on a Copper Nanoparticles-Modified, Carbon Paste Electrode Based on Cyclic Voltammetry, IJCCE. 39 (2020) 99-112.

[16] M. Firouzi, M. Giahi, M. Najafi, S.S. Homami, S.H.H. Mousavi, Electrochemical determination of amlodipine using a CuO-NiO nanocomposite/ionic liquid modified carbon paste electrode as an electrochemical sensor, J Nanopart. Res. 23 (2021) 1-12.

[17] J. Bruinink, C. Kregting, J. Ponjee, Modified viologens with improved electrochemical properties for display applications, J. Electrochem. Soc. 124 (1977) 1854.

[18] E. Naghian, F. Shahdost-fard, E. Sohouli, V. Safarifard, M. Najafi, M. Rahimi-Nasrabadi, A. Sobhani-Nasab, Electrochemical determination of levodopa on a reduced graphene oxide paste electrode modified with a metal-organic framework, Microchem. J. (2020) 104888.

[19] M. Behravan, H. Aghaie, M. Giahi, L. Maleknia, Determination of doxorubicin by reduced graphene oxide/gold/polypyrrole modified glassy carbon electrode: A new preparation strategy, Diam. Relat. Mater.117 (2021) 108478.

[20] M. Rostami, Photodecomposition and adsorption of hazardous organic pollutants by Ce-doped ZnO@ Ce-doped TiO2-N/S-dual doped RGO ternary nano-composites photocatalyst for water remediation, J. Mol. Struct.185 (2019) 191-199.

[21] P. Rani, V. Jindal, Designing band gap of graphene by B and N dopant atoms. RSC Adv. 3 (3): 802–812, in, 2013.

[22] H. Mousavi, R. Moradian, Nitrogen and boron doping effects on the electrical conductivity of graphene and nanotube, Solid State Sci. 13 (2011) 1459-1464.

[23] L. Sun, C. Tian, Y. Fu, Y. Yang, J. Yin, L. Wang, H. Fu, Nitrogen-doped porous graphitic carbon as an excellent electrode material for advanced supercapacitors, Chem. Eur. J. 20 (2014) 564-574.

[24] N.M. Kumar, K. Varaprasad, K.M. Rao, A.S. Babu, M. Srinivasulu, S.V. Naidu, A novel biodegradable green poly (l-aspartic acid-citric acid) copolymer for antimicrobial applications, J Polym Environ. 20 (2012) 17-22.

[25] N. Shadjou, S. Alizadeh, M. Hasanzadeh, Sensitive monitoring of taurine biomarker in unprocessed human plasma samples using a novel nanocomposite based on poly (aspartic acid) functionalized by graphene quantum dots, J. Mol. Recognit. 31 (2018) e2737.

[26] B. Mekassa, M. Tessema, B.S. Chandravanshi, M. Tefera, Square wave voltammetric determination of ibuprofen at poly (l-aspartic acid) modified glassy carbon electrode, IEEE Sens. J. 18 (2017) 37-44.

[27] Y.-P. Chang, C.-L. Ren, J.-C. Qu, X.-G. Chen, Preparation and characterization of Fe3O4/graphene nanocomposite and investigation of its adsorption performance for aniline and p-chloroaniline, Appl. Sur. Sci. 261 (2012) 504-509.

[28] M. Rostami, P. Sharafi, S. Mozaffari, K. Adib, A. Sobhani-Nasab, M. Rahimi-Nasrabadi, M. Fasihi-Ramandi, M.R. Ganjali, A. Badiei, A facile preparation of ZnFe 2 O 4–CuO-N/B/RGO and ZnFe 2 O 4–CuO–C 3 N 4 ternary heterojunction nanophotocatalyst: characterization, biocompatibility, photo-Fenton-like degradation of MO and magnetic properties, J. Mat. Sci. 32 (2021) 5457-5472.

[29] S. Bonyadi, K. Ghanbari, Electrochemical synthesis of Poly (melamine)-Poly (aspartic acid) copolymer for highly sensitive and selective determination of dopamine, Mat. Chem. Phy. 267 (2021) 124683.

[30] M.G. Rodríguez, O.V. Kharissova, U. Ortiz-Mendez, Formation of boron carbide nanofibers and nanobelts from heated by microwave, Rev. Adv. Mater. Sci. 7 (2004) 55-60.

[31] K. Shirai, S. Emura, S.i. Gonda, Y. Kumashiro, Infrared study of amorphous B1− x C x films, J. App. Phys. 78 (1995) 3392-3400.

[32] C. Hontoria-Lucas, A. López-Peinado, J.d.D. López-González, M. Rojas-Cervantes, R. Martín-Aranda, Study of oxygen-containing groups in a series of graphite oxides: physical and chemical characterization, Carbon, 33 (1995) 1585-1592.

[33] M. Acik, G. Lee, C. Mattevi, A. Pirkle, R.M. Wallace, M. Chhowalla, K. Cho, Y. Chabal, The role of oxygen during thermal reduction of graphene oxide studied by infrared absorption spectroscopy, J. Phys. Chem. C, 115 (2011) 19761-19781.

[34] A.J. Page, C.-P. Chou, B.Q. Pham, H.A. Witek, S. Irle, K. Morokuma, Quantum chemical investigation of epoxide and ether groups in graphene oxide and their vibrational spectra, Phys. Chem. Chem. Phys. 15 (2013) 3725-3735.

[35] A.K. Das, M. Srivastav, R.K. Layek, M.E. Uddin, D. Jung, N.H. Kim, J.H. Lee, Iodide-mediated room temperature reduction of graphene oxide: a rapid chemical route for the synthesis of a bifunctional electrocatalyst, J. Mat. Chem. A, 2 (2014) 1332-1340.

[36] Y. Xu, H. Bai, G. Lu, C. Li, G. Shi, Flexible graphene films via the filtration of water-soluble noncovalent functionalized graphene sheets, JACS. 130 (2008) 5856-5857.

[37] T. Van Khai, H.G. Na, D.S. Kwak, Y.J. Kwon, H. Ham, K.B. Shim, H.W. Kim, Comparison study of structural and optical properties of boron-doped and undoped graphene oxide films, Chem. Eng. J. 211 (2012) 369-377.

[38] M. Vahidifar, Z. Es’haghi, Magnetic Nanoparticle-Reinforced Dual-Template Molecularly Imprinted Polymer for the Simultaneous Determination of Oxazepam and Diazepam Using an Electrochemical Approach, J. Anal. Chem. 77 (2022) 625-639.

[39] M.E. Lozano-Chaves, J. Palacios-Santander, L. Cubillana-Aguilera, I. Naranjo-Rodríguez, J. Hidalgo-Hidalgo-de-Cisneros, Modified carbon-paste electrodes as sensors for the determination of 1, 4-benzodiazepines: application to the determination of diazepam and oxazepam in biological fluids, Sens. Actuators B Chem. 115 (2006) 575-583.

[40] A. Khoshroo, L. Hosseinzadeh, A. Sobhani-Nasab, M. Rahimi-Nasrabadi, H. Ehrlich, Development of electrochemical sensor for sensitive determination of oxazepam based on silver-platinum core–shell nanoparticles supported on graphene, J. Electroanal. Chem. 823 (2018) 61-66.

[41] H. Ashrafi, S. Hassanpour, A. Saadati, M. Hasanzadeh, K. Ansarin, S.A. Ozkan, N. Shadjou, A. Jouyban, Sensitive detection and determination of benzodiazepines using silver nanoparticles-N-GQDs ink modified electrode: A new platform for modern pharmaceutical analysis, Microchem. J. 145 (2019) 1050-1057.

[42] H. Ashrafi, A. Mobed, M. Hasanzadeh, P. Babaie, K. Ansarin, A. Jouyban, Monitoring of five benzodiazepines using a novel polymeric interface prepared by layer by layer strategy, Microchem. J. 146 (2019) 121-125.