Abstract
This research delves into the radiation sensitivities of tiopronin when exposed to gamma irradiation within the 2–20 kGy dose range. This particular drug sample is commonly employed in the treatment of severe homozygous cystinuria. The paramagnetic species detected within tiopronin were ascribed to the presence of the -HNĊHCOOH- radical. The g factor and hyperfine constants for H atoms were computed as follows: aα = 1.60 mT, aβ = 1.11 mT, aN = 0.87 mT, and g = 2.0225 ± 0.0005. In the spectra recorded across different microwave power ranges, it was found that all signals exhibited the most favorable correlations with polynomial and logarithmic functions. It was established that the experimental data within the spectra recorded across the 2–20 kGy dose range exhibited a high degree of compatibility with power and polynomial functions. Obtaining EPR signals in the spectra recorded at high temperatures and after approximately 3 months showed that stable radicals were formed in the structure as a result of irradiation.
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References
G. Damian, V. Miclăuş, Study of free radicals in gamma-irradiated metoclopramide using spin trapping ESR spectroscopy. Rom. J. Biophys. 15, 121–126 (2005)
K. Sütçü, Y.E. Osmanoğlu, Identification of free radicals formed in gamma-irradiated acetazolamide using electron paramagnetic resonance spectroscopy. Appl. Magn. Reson. 54, 737–750 (2023)
E. Ece, H.U. Tasdemir, R. Biyik, A. Ozmen, U. Sayin, Paramagnetic characterization and dosimetric properties of Airfix drug and its ingredients (Montelukast sodium, Sorbitol): an EPR and DFT study. Radiat. Phys. Chem. 195, 110082 (2022)
Ş Çolak, A. Maquille, B. Tilquin, Chemical analysis applied to the radiation sterilization of solid ketoprofen. Radiat. Effec. Defec. Solids 161, 75–80 (2006)
S. Kempe, H. Metz, K. Mäder, Application of electron paramagnetic resonance (EPR) spectroscopy and imaging in drug delivery research–chances and challenges. Europ. J. Pharma. Biopharma. 74, 55–66 (2010)
V. Mišík, K. Ondriaš, A. Staško, EPR spectroscopy of free radical intermediates of antiarrhythmic-antihypoxic drug stobadine, a pyridoindole derivative. Life Scien. 65, 1879–1881 (1999)
H.B. Ambroż, E.M. Kornacka, B. Marciniec, M. Ogrodowczyk, G.K. Przybytniak, EPR study of free radicals in some drugs γ-irradiated in the solid state. Radiat. Phys. Chem. 58, 357–366 (2000)
G. Damian, V. Miclăuş, Study of free radicals in gamma-irradiated metoclopramide using spin trapping ESR spectroscopy. Rom. J. Biophys 15, 121–126 (2005)
M. Aydin, The identity and structure of free radicals in γ-irradiated amino acid derivatives. Bulgar. Chem. Commun. 43, 419–422 (2011)
A. Engalytcheff, M. Kolberg, A.L. Barra, K. Kristoffer Andersson, B. Tilquin, The use of multi-frequency EPR techniques to identify the radicals produced in irradiated β-blockers. Free Rad. Resear. 38, 59–66 (2004)
G.P. Jacobs, Stability of cefazolin and other new cephalosporins following gamma irradiation. Int. J. Pharm. 17, 29–38 (1983)
K. Sütçü, Y.E. Osmanoğlu, Electron spin resonance study of free radicals induced in single crystal of oxcarbazepine. Appl. Magn. Reson. 54, 737–750 (2023)
M.H. Başkan, Y.E. Osmanoğlu, K. Sütçü, M. Aydın, Ş Osmanoğlu, Radiation effect studies in single crystal of trifluoroacetyl-α-aminoisobutyric acid. Radiat. Eff. Def. Solids 170, 854–861 (2015)
G. Strzelczak, J. Bergès, C. Houée-Levin, D. Pogocki, K. Bobrowski, EPR spectroscopy and theoretical study of γ-irradiated asparagine and aspartic acid in solid state. Biophys. Chem. 125, 92–103 (2007)
S. Talbi, J. Raffi, S. Aréna, J. Colombani, P. Piccerelle, P. Prinderre, J.M. Dolo, EPR study of gamma induced radicals in amino acid powders. Spectrochim. Acta Part A: Molecul. Biomolec. Spectro. 60, 1335–134 (2004)
D. Santoriello, R. Ramaswamy, S. Kudose, G.S. Markowitz, Segmental NELL-1 membranous nephropathy complicating tiopronin therapy. Kidney Int. Rep. 8, 1683 (2023)
A.M. Dam, L.G. Gazso, S. Kaewpila, I. Maschek, Radiation sterilization dose calculation for heparin and aprotinin based on ISO Method 1. Int. J. Pharma. 121, 245–248 (1995)
NIH 2012. Public Electron Paramagnetic Resonance Software Tools, https:// www. niehs. nih. gov/resea rch/ resou rces/ softw are/ tox- pharm/ tools/ index. Cfm.
R. Köseoǧlu, E. Köseoǧlu, F. Köksal, Electron paramagnetic resonance of some γ-irradiated drugs. Appl. Radiat. Isot. 58, 63–68 (2003)
Y.E. Osmanoğlu, K. Sütçü, Ş Osmanoğlu, Radiation effect studies on some glycine 195 derivatives in solid state. Radiat. Effec. Defec. Solids 172, 621–628 (2017)
K. Sütçü, Y.E. Osmanoğlu, Electron spin resonance identification of gamma irradiated 2, 4′-dichlorodiphenyl dichloroethane and 6-mercaptopurine monohydrate in the solid state. J. Mol. Struct. 1174, 67–73 (2018)
J.P. Basly, I. Basly, M. Bernard, Electron spin resonance identification of irradiated ascorbic acid: dosimetry and influence of powder fineness. Anal. Chim. Acta 372, 373–378 (1998)
G. Damian, EPR investigation of γ-irradiated anti-emetic drugs. Talanta 60, 923–927 (2003)
C. Aydaş, B.I. Engin, M. Polat, T. Aydin, Electron Spin Resonance Study of γ-Irradiated Anatolian Chickpea (Cicer Arietinum L.). Radiat. Effec. Defec. Sol. 163, 7–17 (2008)
Ş Çolak, M. Korkmaz, Spectroscopic features of radiolytic intermediates induced in gamma irradiated sulfatiazole: an ESR study. Int. J. Pharma. 285, 1–11 (2004)
J.P. Basly, I. Longy, M. Bernard, Radiosterilization dosimetry by electron-spin resonance spectroscopy: cefotetan. Anal. Chim. Acta 359, 107–113 (1998)
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Kerem SÜTÇÜ: Conceptualization, Methodology, Software, Validation, Formal analysis, Investigation, Data Curation, Writing—Original Draft, Writing—Review & Editing, Visualization, Supervision. Yunus Emre OSMANOĞLU: Conceptualization, Methodology, Resources, Data Curation, Writing—Original Draft, Writing—Review & Editing, Visualization, Supervision.
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Sütçü, K., Osmanoğlu, Y.E. EPR Investigation of Gamma-Irradiated Tiopronin. Appl Magn Reson (2024). https://doi.org/10.1007/s00723-024-01645-z
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DOI: https://doi.org/10.1007/s00723-024-01645-z