Identification of Free Radicals Formed in Gamma-Irradiated Chlorpropamide and Procainamide Hydrochloride Pharmaceutical Raw Materials by EPR Spectroscopy

Yıl 2023, Cilt: 13 Sayı: 4, 2616 - 2621, 01.12.2023

Kerem Sütçü , Yunus Emre Osmanoğlu

https://doi.org/10.21597/jist.1302560

Öz

In this study, it was aimed to determine the structural properties of free radicals formed by gamma irradiation in chlorpropamide and procainamide hydrochloride drug raw materials, which are widely used in medicine, by using electron paramagnetic resonance spectroscopy. As a result of gamma irradiation, it was determined that two different radicals were formed in both chlorpropamide and procainamide hydrochloride samples. It was suggested that –NĊH-, -NCH2ĊH2- and –NĊH-, -NĊHCH2- radicals were formed in chlorpropamide and procainamide hydrochloride samples, respectively. The simulated spectra closest to the experimental spectra recorded at room temperature of the samples studied in powder form were obtained using simulation software. The contributions of the proposed radicals to the experimental spectra were calculated. The g values of the obtained radicals and the hyperfine structure constants of the unpaired electrons were calculated.

Anahtar Kelimeler

Electron paramagnetic resonance, Gamma irradiation, Pharmaceutical raw material

Gama ile Işınlanmış Klorpropamid ve Prokainamid Hidroklorür İlaç Hammaddelerinde Oluşan Serbest Radikallerin EPR Spektroskopisi ile Tanımlanması

Öz

Bu çalışmada tıpta yaygın kullanılan klorpropamid ve prokainamid hidroklorür ilaç hammaddelerinde gama ile ışınlanarak oluşan serbest radikallerin yapısal özelliklerinin elektron paramanyetik rezonans spektroskopisi kullanılarak belirlenmesi amaçlanmıştır. Gama ile ışınlama sonucunda hem klorpropamid ve hem de prokainamid hidroklorür numunelerinde iki farklı radikal oluştuğu tespit edilmiştir. Klorpropamid ve prokainamid hidroklorür numunelerinde sırasıyla -NĊH-, -NCH2ĊH2- ve –NĊH-, -NĊHCH- radikallerinin oluştuğu önerilmiştir. Toz formunda çalışılan örneklerin oda sıcaklığında kaydedilmiş deneysel spektrumlarına en yakın simüle spektrumları simülasyon yazılımı kullanılarak elde edilmiştir. Önerilen radikallerin deneysel spektrumlara olan katkıları hesaplanmıştır. Elde edilen radikallerin g değerleri ve eşlenmemiş elektronların aşırı ince yapı sabitleri hesaplanmıştır.

Anahtar Kelimeler

Elektron paramanyetik rezonans, Gama ışınlaması, İlaç hammaddesi

Kaynakça

• Al-Tamrah, S., & Al-Abbad, S. (2015). Spectrophotometric determination of procainamide hydrochloride using sodium periodate. Arabian Journal of Chemistry, 8(5), 609-613.
• Ambroż, H. B., Kornacka, E. M., Marciniec, B., Ogrodowczyk, M., & Przybytniak, G. K. (2000). EPR study of free radicals in some drugs γ-irradiated in the solid state. Radiation Physics and Chemistry, 58(4), 357-366.
• Ambroż, H., Kornacka, E., Marciniec, B., & Przybytniak, G. (2002). Radical decay in irradiated drugs: Flutamide, ifosfamide. Journal of radioanalytical and nuclear chemistry, 254(2), 293-298.
• Aydin, M., Baskan, M. H., & Emre Osmanoglu, M. Y. (2009). EPR study of gamma induced radicals in amino and iminodiacetic acid derivatives. Brazilian Journal of Physics, 39, 583-586.
• Aydin, M., Osmanoglu, Y. E., & Başkan, M. H. (2008). Electron paramagnetic resonance of rγ-irradiated glycyl-L-glutamine monohydrate, iminodiacetic acid and methyliminodiacetic acid. Radiation Effects & Defects in Solids, 163(1), 47-53.
• Bakare-Odunola, M. T., Mustapha, A., & Abdu Aguye, I. (2008). Effect of Nigerian meals on the pharmacokinetics of chlorpropamide in type II diabetic patients. European journal of drug metabolism and pharmacokinetics, 33, 31-35.
• Başkan, M. H., Aydın, M., & Osmanoğlu, Ş. (2010). Investigation of 60Co γ-irradiated l-(−) malic acid, N-methyl-dl-valine and l-glutamic acid γ-ethyl ester by electron paramagnetic resonance technique. Journal of Molecular Structure, 983(1-3), 200-202.
• Başkan, M. H., Osmanoğlu, Y. E., Sütçü, K., Aydın, M., & Osmanoğlu, Ş. (2015). Radiation effect studies in single crystal of Trifluoroacetyl-α-Aminoisobutyric acid. Radiation Effects & Defects in Solids, 170(10), 854-861.
• Çolak, Ş., & Korkmaz, M. (2004). Kinetics of the radicals induced in gamma irradiated sulfafurazole: an EPR study. Zeitschrift für Naturforschung A, 59(7-8), 481-487.
• Çolak, Ş., Maquille, A., & Tilquin, B. (2006). Chemical analysis applied to the radiation sterilization of solid ketoprofen. Radiation Effects & Defects in Solids, 161(1), 75-80.
• Damian, G. (2003). EPR investigation of γ-irradiated anti-emetic drugs. Talanta, 60(5), 923-927.
• Desrosiers, M. F. (1996). Current status of the EPR method to detect irradiated food. Applied Radiation and isotopes, 47(11-12), 1621-1628.
• Ece, E., Tasdemir, H. U., Biyik, R., Ozmen, A., & Sayin, U. (2022). Paramagnetic characterization and dosimetric properties of Airfix drug and its ingredients (Montelukast sodium, Sorbitol): An EPR and DFT study. Radiation Physics and Chemistry, 195, 110082.
• Iweala, E. E., & Okeke, C. U. (2005). Comparative study of the hypoglycemic and biochemical effects of Catharanthus roseus (Linn) g. apocynaceae (Madagascar periwinkle) and chlorpropamide (diabenese) on alloxan-induced diabetic rats. Biokemistri, 149-156.
• Karakaş Sarıkaya, E., Ateş, L., Sayin, U., Ozmen, A., & Dereli, Ö. (2018). Experimental and theoretical research on γ-irradiated 7-methoxy-4-methylcoumarin powder through EPR and DFT methods. Radiation Effects and Defects in Solids, 173(5-6), 377-387.
• Kasumov, V. T., Taş, E., Kartal, I., Ucun, F., Köksal, F., Çukurovali, A. (2001). Complexation of metal ions with 3, 5-di-tert-butyl-1, 2-benzoquinone-1-monooxime, ESR studies of radical intermediates. Journal of Coordination Chemistry, 52(3), 207-227.
• Köseoǧlu, R., Köseoǧlu, E., & Köksal, F. (2003). Electron paramagnetic resonance of some γ-irradiated drugs. Applied radiation and isotopes, 58(1), 63-68.
• Murrieta, H. S., Munoz, E. P., Adem, E., Burillo, G., Vazquez, M., & Cabrera, E. B. (1996). Effect of irradiation dose, storage time and temperature on the ESR signal in irradiated oat, and corn and wheat. Applied Radiation and Isotopes, 47(11-12), 1657-1661.
• NIH. 2012. Public Electron Paramagnetic Resonance Software Tools, https://www.niehs.nih.gov/research/resources/software/tox-pharm/tools/index.cfm.
• Osmanoğlu, Ş., Aydın, M., & Başkan, M. H. (2005). EPR of gamma-irradiated L-glutamine hydrochloride and N-carbamoyl-L-glutamic acid. Zeitschrift für naturforschung A, 60(7), 549-553.
• Osmanoğlu, Y. E., Sütçü, K., & Osmanoğlu, Ş. (2017). Radiation effect studies on some glycine derivatives in solid state. Radiation Effects & Defects in Solids, 172(7-8), 621-628.
• Sayın, Ü. (2013). EPR analysis of gamma irradiated single crystal cimetidine. Journal of Molecular Structure, 1031, 132-137.
• Sezer, M. Ö., Kaplan, N., & Sayin, U. (2017). ESR analysis of natural and gamma irradiated coriander (Coriandrum sativum L.) seeds. Radiation Effects & Defects in Solids, 172(11-12), 815-823.
• Sütçü, K. (2018). EPR investigation of damage centers formed in some drug powders irradiated with gamma rays. Journal of Molecular Structure, 1163, 1-3.
• Sütçü, K. (2019). Gama ile Işınlanmış Etosüksimid Numunesinin Radyasyon Duyarlılığının Elektron Paramanyetik Rezonans Spektroskopisi Yöntemiyle İncelenmesi. Journal of the Institute of Science and Technology, 9(2), 800-810.
• Şimşek, R., Gündüz, M. G., Şafak, C., Kökpınar, Ö., & Aydın, M. (2017). Free radicals properties of some gamma-irradiated organic compounds. Bulgarian Chemical Communications, 49(1), 82-86.
• Tokatli, A., Ucun, F., Sütçü, K., Osmanoğlu, Y. E., Osmanoğlu, Ş. (2018). Spectral analysis and quantum chemical studies of chair and twist-boat conformers of cycloheximide in gas and solution phases. Journal of Molecular Structure, 1154, 428-436.
• Varshney, L., & Dodke, P. B. (2004). Radiation effect studies on anticancer drugs, cyclophosphamide and doxorubicin for radiation sterilization. Radiation Physics and Chemistry, 71(6), 1103-1111.
• Zhang, H. M. (2015). Investigation on the EPR parameters and local structure for the Cu2+ center in ZnAl2O4 spinel. Journal of Magnetism and Magnetic Materials, 389, 176-179.
• Zincircioğlu, S. B., Canoruç, N., Osmanoğlu, Ş., Başkan, M. H., Dicle, I. Y., & Aydın, M. (2006). Electron paramagnetic resonance of some γ-irradiated amino acid derivatives. Zeitschrift für Naturforschung A, 61(10-11), 577-582.