DETERMINATION OF ANTIVIRAL-DRUG FAVIPIRAVIR FROM BIOLOGICAL SAMPLES BY USING MOLECULAR IMPRINTED POLYMER-BASED ELECTROCHEMICAL SENSOR

Abstract

Objective: The molecularly imprinted polymer (MIP) technique was applied in this study for selective, fast, and sensitive electrochemical determination of antiviral drug favipiravir (FAVI). Material and Method: By electropolymerizing the functional monomer o-phenylenediamine (o-PD) on a glassy carbon electrode (GCE) in the presence of a template molecule FAVI, the new MIP-based sensor (MIP@o-PD/GCE) was constructed using cyclic voltammetry (CV). For the removal and rebinding procedures, as well as the optimization of conditions and performance measurement of MIP@o-PD/GCE, differential pulse voltammetry (DPV) was used. The ferrocyanide/ferricyanide redox marker was used to monitor each step of the experimental procedure using DPV. Result and Discussion: MIP@o-PD/GCE has a linear response to FAVI in the range from 10 pM to 90 pM under optimal experimental conditions for human serum samples. The detection limit of MIP@o-PD/GCE was obtained to be 1.80 pM, whereas the quantification limit was found to be 6.23 pM. The designed sensor was successfully applied to a synthetic human serum sample to verify its applicability and validity. Electrochemical sensor selectivity was evaluated by comparing the binding of paracetamol and tenofovir, which are similar to favipiravir, and also oseltamivir and famciclovir, which are other drugs used in the treatment of COVID-19.

Keywords

• Antiviral drug
• electroanalysis
• electrochemical sensor
• favipiravir
• molecularly imprinted polymer

BİYOLOJİK ÖRNEKLERDEN MOLEKÜLER BASKILI POLİMER TABANLI ELEKTROKİMYASAL SENSÖR KULLANILARAK ANTİVİRAL-İLAÇ FAVİPİRAVİRİN TAYİNİ

Abstract

Amaç: Bu çalışmada moleküler baskılanmış polimer (MIP) tekniği, antiviral ilaç favipiravirin (FAVI) seçici, hızlı ve hassas elektrokimyasal tayini için uygulanmıştır. Gereç ve Yöntem: Döngüsel voltammetri (CV) kullanılarak, fonksiyonel monomer o-fenilendiaminin (o-PD) bir şablon molekül FAVI varlığında camsı karbon elektrot (GCE) üzerinde elektropolimerize edilmesiyle, yeni MIP tabanlı sensör (MIP@o-PD/GCE) oluşturulmuştur. MIP@o-PD/GCE'nin uzaklaştırma ve yeniden bağlama prosedürlerinin yanı sıra etki edebilecek koşulların optimizasyonu ve performans ölçümü için diferansiyel puls voltametrisi (DPV) kullanılmıştır. Ferrosiyanid/ferrisiyanid redoks işaretleyicisi, DPV kullanılarak deneysel prosedürün her adımını izlemek için kullanılmıştır. Sonuç ve Tartışma: İnsan serum numune örnekleri için MIP@o-PD/GCE, optimum deneysel koşullar altında 10 pM ila 90 pM aralığında FAVI’e doğrusal bir yanıt vermektedir. MIP@o-PD/GCE'nin tespit limiti 1.80 pM olarak elde edilirken, miktar belirleme limiti 6.23 pM olarak bulunmuştur. Tasarlanan sensör, uygulanabilirliğini ve geçerliliğini doğrulamak için sentetik bir insan serumu örneğine başarıyla uygulanmıştır. Elektrokimyasal sensör seçiciliği, FAVI ile benzerlik gösteren parasetamol ve tenofovir ile Covid-19 tedavisinde kullanılan diğer ilaçlar olan oseltamivir ve famsiklovirin bağlanması karşılaştırılarak değerlendirilmiştir.

Keywords

• Antiviral ilaç
• elektroanaliz
• elektrokimyasal sensör
• favipiravir
• moleküler baskılanmış polimer

References

1. 1. Assis, L.C., de Castro, A.A., de Jesus, J.P.A., da Cunha, E.F.F., Nepoviomava, E., Krejcar, O., Kuca, K., Ramalho, T.C., La Porta, F.A. (2021). Theoretical Insights into the Effect of Halogenated Substituent on the Electronic Structure and Spectroscopic Properties of the Favipiravir Tautomeric Forms and Its Implications for the Treatment of COVID-19. RSC Advances 11(56), 35228-35244. [CrossRef]
2. 2. Cai, Q., Yang, M., Liu, D., Chen, J., Shu, D., Xia, J., Liao, X., Gu, Y., Cai, Q., Yang, Y., Shen, C., Li, X., Peng, L., Huang, D., Zhang, J., Zhang, S., Wang, F., Liu, J., Chen, L., Chen, S., Wang, Z., Zhang, Z., Cao, R., Zhong, W., Liu, Y., Liu, L. (2020). Experimental treatment with favipiravir for COVID-19: An open-label control study. Engineering, 6(10), 1192–1198. [CrossRef]
3. 3. Joshi, S., Parkar, J., Ansari, A., Vora, A., Talwar, D., Tiwaskar, M., Patil, S., Barkate, H. (2021). Role of favipiravir in the treatment of COVID-19. In International Journal of Infectious Diseases, 102, 501–508.
4. 4. Furuta, Y., Gowen, B.B., Takahashi, K., Shiraki, K., Smee, D.F., Barnard, D.L. (2013). Favipiravir (T-705), a novel viral RNA polymerase inhibitor. In Antiviral Research, 100, Issue 2, 446–454. [CrossRef]
5. 5. Safari, E., Seyfinejad, B., Farajzadeh, M.A., Afshar Mogaddam, M.R., Nemati, M. (2024). Acid-base reaction-based dispersive solid phase extraction of favipiravir using biotin from biological samples prior to capillary electrophoresis analysis. RSC Advances, 14(27), 19612–19618. [CrossRef]
6. 6. Megahed, S.M., Habib, A.A., Hammad, S.F., Kamal, A.H. (2021). Experimental design approach for development of spectrofluorimetric method for determination of favipiravir; a potential therapeutic agent against COVID-19 virus: Application to spiked human plasma. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 249, 119241. [CrossRef]
7. 7. Bulduk, İ. Gungor, S. Aydın, B.S. Sagkan, R.I (2021). Comparison of HPLC and UV spectrophotometric methods for quantification of favipiravir in pharmaceutical formulations. Iranian Journal of Pharmaceutical Research, 20(3), 57–65. [CrossRef]
8. 8. Challenger, E., Penchala, S.D., Hale, C., Fitzgerald, R., Walker, L., Reynolds, H., Chiong, J., Fletcher, T., Khoo, S., Else, L. (2023). Development and validation of an LC-MS/MS method for quantification of favipiravir in human plasma. Journal of Pharmaceutical and Biomedical Analysis, 233, 115436. [CrossRef]

9. 9. Eryavuz Onmaz, D., Abusoglu, S., Onmaz, M., Yerlikaya, F.H., Unlu, A. (2021). Development and validation of a sensitive, fast and simple LC-MS / MS method for the quantitation of favipiravir in human serum. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 1176, 122768. [CrossRef]
10. 10. El-Wekil, M.M., Hayallah, A.M., Abdelgawad, M.A., Abourehab, M.A.S., Shahin, R.Y. (2022). Nanocomposite of gold nanoparticles@nickel disulfide-plant derived carbon for molecularly imprinted electrochemical determination of favipiravir. Journal of Electroanalytical Chemistry, 922, 116745. [CrossRef]
11. 11. Kanbeş Dindar, Ç., Bozal-Palabiyik, B., Uslu, B. (2022). Development of a diamond nanoparticles-based nanosensor for detection and determination of antiviral drug favipiravir. Electroanalysis, 34(7), 1174–1186. [CrossRef]
12. 12. Ozcelikay, G., Karadas-Bakirhan, N., Taskin-Tok, T., Ozkan, S.A. (2020). A selective and molecular imaging approach for anticancer drug: Pemetrexed by nanoparticle accelerated molecularly imprinting polymer. Electrochimica Acta, 354, 136665. [CrossRef]
13. 13. Ozcelikay, G., Kurbanoglu, S., Bozal-Palabiyik, B., Uslu, B., Ozkan, S.A. (2018). MWCNT/CdSe quantum dot modified glassy carbon electrode for the determination of clopidogrel bisulfate in tablet dosage form and serum samples. Journal of Electroanalytical Chemistry, 827, 51–57. [CrossRef]
14. 14. Majidian, M., Ozcelikay, G., Cetinkaya, A., Unal, M.A., Nazır, H., Atici, E.B., Ozkan, S.A. (2023). Nanomaterial-based electrochemical sensing platform for the determination of Olaparib. Electrochimica Acta, 449, 142198. [CrossRef]
15. 15. Bozal-Palabiyik, B., Erkmen, C., Uslu, B. (2019). Molecularly ımprinted electrochemical sensors: analytical and pharmaceutical applications based on ortho-phenylenediamine polymerization. Current Pharmaceutical Analysis, 16(4), 350–366. [CrossRef]
16. 16. Allahverdiyeva, S., Yunusoğlu, O., Yardım, Y., Şentürk, Z. (2021). First electrochemical evaluation of favipiravir used as an antiviral option in the treatment of COVID-19: A study of its enhanced voltammetric determination in cationic surfactant media using a boron-doped diamond electrode. Analytica Chimica Acta, 1159, 338418. [CrossRef]
17. 17. Mohamed, M.A., Eldin, G.M.G., Ismail, S.M., Zine, N., Elaissari, A., Jaffrezic-Renault, N., Errachid, A. (2021). Innovative electrochemical sensor for the precise determination of the new antiviral COVID-19 treatment Favipiravir in the presence of coadministered drugs. Journal of Electroanalytical Chemistry, 895, 115422. [CrossRef]