Calculation of Nuclear Magnetic Resonance and Electron Paramagnetic Resonance Parameters of Captopril Molecule
Öz
In this study, the active ingredient Captopril, which is an ACE inhibitor and used in the treatment of high blood pressure patients, was examined. First of all, optimization and frequency calculation were performed using the B3LYP functional and /6-31+G(d) basis set to reveal the molecular structure of the Captopril molecule. Using the molecular structure, the 1H chemical shift values of the Captopril molecule were calculated using the GIAO method and the B3LYP/6-31+G(d) functional and basis set. Using the molecular structure of the captopril molecule, six possible radicals were modeled with the help of the B3LYP/6-31+G(d) method basis set combination. Electron Paramagnetic Resonance parameters (g and hyperfine coupling constant values) of the modeled possible radicals were calculated using the same calculation method. Thus, parameters that may assist future research on experimental radical studies of the Captopril molecule have been presented to the literature.
Anahtar Kelimeler
Captopril Nuclear magnetic resonance parameters Electron paramagnetic resonance parameters
Kaynakça
- F. N. Aslan, İ. Varlı, Synchronous fluorescence spectroscopy method based on chemometrics: authentication of extra virgin olive oils harvested in Mut (Mersin) region and refined edible oils, Necmettin Erbakan Üniversitesi Fen ve Mühendislik Bilimleri Dergisi. 5(2) (2023), 278–287. doi:10.47112/neufmbd.2023.25
- M. İ. Özgün, A.B. Batıbay, B. Ünal, Y. R. Eker, A. Terlemez, Investigation of the use of TiO2 obtained from endodontic NiTi Files in dye-sensitized solar cells, Necmettin Erbakan Üniversitesi Fen ve Mühendislik Bilimleri Dergisi. 5(1) (2023), 1–8. doi:10.47112/neufmbd.2023.4
- K. Çetin, K. Şarkaya, B. Kavakcıoğlu Yardımcı, Bakır (II) iyonu ve histidin içeren polimerlerin Saccharomyces cerevisiae mayası üzerindeki antifungal etkileri, Necmettin Erbakan Üniversitesi Fen ve Mühendislik Bilimleri Dergisi. 5(2) (2023). doi:10.47112/neufmbd.2023.24
- 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, Radiaiton Physics and Chemistry. 195(2022), 110082. doi:10.1016/j.radphyschem.2022.110082
- H. U. Tasdemir, Efects of intramolecular hydrogen bonding on nuclear magnetic resonance, electron paramagnetic resonance and molecular docking studies: Mexiletine molecule, Journal of Molecular Modeling. 30(41) (2024). doi:10.1007/s00894-024-05838-y
- W.J. Hehre, L. Radom, P.V.R. Schleyer, J. Pople, AB INITIO Molecular Orbital Theory, John Wiley & sons Ltd., New York, United States of America, 1986.
- V.G. Malkin, O.L. Malkina, L.A. Eriksson, D.R. Salahub, The calculation of NMR and ESR spectroscopy parameters using density functional theory, in: Theoretical and computational chemistry, 1995: pp. 273–347. doi:10.1016/s1380-7323(05)80039-1
- H. U. Tasdemir, E. Turkkan, U. Sayin, A. Ozmen, EPR study of gamma-irradiated 2-Bromo-4′- methoxyacetophenone single crystals, Radiation Effect and Defect in Solids. 171 (2016), 214–222. doi:10.1080/10420150.2016.1170017
- M.A. Ondetti, B. Rubin, D.W. Cushman, Design of specific inhibitors of Angiotensin-Converting enzyme: new class of orally active antihypertensive agents, Science. 196 (1977), 441–444. doi:10.1126/science.191908.
- D.W. Cushman, H.S. Cheung, E.F. Sabo, M.A. Ondetti, Design of potent competitive inhibitors of angiotensin-converting enzyme. Carboxyalkanoyl and mercaptoalkanoyl amino acids, Biochemistry. 16 (1977), 5484–5491. doi:10.1021/bi00644a014
- N.S. Akhtar, A.A. Isab, A.R. Al-Arfaj, 13C and 15N NMR studies of the ınteraction of gold(I) captopril with selenocyanate, selenourea and thiourea in aqueous solution, Journal of Inorganic Biochemistry. 3(1997), 197–205. doi:10.1016/S0162-0134(96)00205-X
- M.J. Frisch, G.W. Trucks, H.B. Schlegel, v.d., Gaussian 03, Revision E.01. Gaussian Inc., Pittsburg PA, 2003.
- C. Lee, W. Yang, R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical Review. B, Condensed Matter. 37 (1988), 785–789. doi:10.1103/physrevb.37.785
- A.D. Becke, Density-functional thermochemistry. III. The role of exact exchange, The Journal of Chemical Physics. 98 (1993), 5648–5652. doi:10.1063/1.464913
- P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields, The Journal of Physical Chemistry. 98 (1994), 11623–11627. doi:10.1021/j100096a001
- H. Kadin, Captopril, in: Analytical profiles of drug substances, 1982: pp. 79–137. doi:10.1016/s0099-5428(08)60261-0
- W. A. Bernhard, D. M. Close, J. Huttermann, H. Zehner, The alkoxy radical, RCH2O, as a free radical product in x-irradiated single crystals of nucleosides and nucleotides, The Journal of Chemical Physics. 67(3) (1977), 1211-1219. doi:10.1063/1.434931
- H. U. Tasdemir, U. Sayin, E. Turkkan, A. Ozmen, EPR investigation of gamma irradiated single crystal guaifenesin: A combined experimental and computational study, Radiation Physics and Chemistry. 121 (2016), 61–68. doi:10.1016/j.radphyschem.2015.12.016
Kaptopril Molekülünün Nükleer Manyetik Rezonans ve Elektron Paramanyetik Rezonans Parametrelerinin Hesaplanması
Öz
Bu çalışmada ACE inhibitörü olan ve yüksek tansiyon hastalarının tedavisinde kullanılan Kaptopril ilaç etken maddesi incelenmiştir. Öncelikle Kaptopril molekülünün moleküler yapısını açığa çıkarmak için optimizasyon ve frekans hesaplaması B3LYP fonksiyoneli ve /6-31+G(d) baz seti kullanılarak gerçekleştirilmiştir. Moleküler yapı kullanılarak Kaptopril molekülünün 1H kimyasal kayma değerleri GIAO metodu ve B3LYP/6-31+G(d) fonksiyoneli ve baz seti kullanılarak hesaplanmıştır. Kaptopril molekülünün moleküler yapısı kullanılarak altı olası radikal B3LYP/6-31+G(d) metot baz seti kombinasyonu yardımıyla modellenmiştir. Modellenen olası radikallere ait Elektron Paramanyetik Rezonans parametreleri (aşırı ince yapı sabiti ve g değerleri) yine aynı metot ve baz seti kombinasyonu kullanılarak hesaplanmıştır. Böylece Kaptopril molekülünün deneysel radikal çalışmaları için gelecekte yapılacak araştırmalara yardımcı olabilecek parametreler literatüre sunulmuştur.
Anahtar Kelimeler
Kaptopril Nükleer Manyetik Rezonans Parametreleri Elektron Paramanyetik Rezonans Parametreleri
Etik Beyan
Bu çalışma, 7. Uluslararası Moleküler Biyoloji ve Biyoteknoloji Kongresinde poster bildirisi özeti şeklinde sunulmuştur.
Kaynakça
- F. N. Aslan, İ. Varlı, Synchronous fluorescence spectroscopy method based on chemometrics: authentication of extra virgin olive oils harvested in Mut (Mersin) region and refined edible oils, Necmettin Erbakan Üniversitesi Fen ve Mühendislik Bilimleri Dergisi. 5(2) (2023), 278–287. doi:10.47112/neufmbd.2023.25
- M. İ. Özgün, A.B. Batıbay, B. Ünal, Y. R. Eker, A. Terlemez, Investigation of the use of TiO2 obtained from endodontic NiTi Files in dye-sensitized solar cells, Necmettin Erbakan Üniversitesi Fen ve Mühendislik Bilimleri Dergisi. 5(1) (2023), 1–8. doi:10.47112/neufmbd.2023.4
- K. Çetin, K. Şarkaya, B. Kavakcıoğlu Yardımcı, Bakır (II) iyonu ve histidin içeren polimerlerin Saccharomyces cerevisiae mayası üzerindeki antifungal etkileri, Necmettin Erbakan Üniversitesi Fen ve Mühendislik Bilimleri Dergisi. 5(2) (2023). doi:10.47112/neufmbd.2023.24
- 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, Radiaiton Physics and Chemistry. 195(2022), 110082. doi:10.1016/j.radphyschem.2022.110082
- H. U. Tasdemir, Efects of intramolecular hydrogen bonding on nuclear magnetic resonance, electron paramagnetic resonance and molecular docking studies: Mexiletine molecule, Journal of Molecular Modeling. 30(41) (2024). doi:10.1007/s00894-024-05838-y
- W.J. Hehre, L. Radom, P.V.R. Schleyer, J. Pople, AB INITIO Molecular Orbital Theory, John Wiley & sons Ltd., New York, United States of America, 1986.
- V.G. Malkin, O.L. Malkina, L.A. Eriksson, D.R. Salahub, The calculation of NMR and ESR spectroscopy parameters using density functional theory, in: Theoretical and computational chemistry, 1995: pp. 273–347. doi:10.1016/s1380-7323(05)80039-1
- H. U. Tasdemir, E. Turkkan, U. Sayin, A. Ozmen, EPR study of gamma-irradiated 2-Bromo-4′- methoxyacetophenone single crystals, Radiation Effect and Defect in Solids. 171 (2016), 214–222. doi:10.1080/10420150.2016.1170017
- M.A. Ondetti, B. Rubin, D.W. Cushman, Design of specific inhibitors of Angiotensin-Converting enzyme: new class of orally active antihypertensive agents, Science. 196 (1977), 441–444. doi:10.1126/science.191908.
- D.W. Cushman, H.S. Cheung, E.F. Sabo, M.A. Ondetti, Design of potent competitive inhibitors of angiotensin-converting enzyme. Carboxyalkanoyl and mercaptoalkanoyl amino acids, Biochemistry. 16 (1977), 5484–5491. doi:10.1021/bi00644a014
- N.S. Akhtar, A.A. Isab, A.R. Al-Arfaj, 13C and 15N NMR studies of the ınteraction of gold(I) captopril with selenocyanate, selenourea and thiourea in aqueous solution, Journal of Inorganic Biochemistry. 3(1997), 197–205. doi:10.1016/S0162-0134(96)00205-X
- M.J. Frisch, G.W. Trucks, H.B. Schlegel, v.d., Gaussian 03, Revision E.01. Gaussian Inc., Pittsburg PA, 2003.
- C. Lee, W. Yang, R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical Review. B, Condensed Matter. 37 (1988), 785–789. doi:10.1103/physrevb.37.785
- A.D. Becke, Density-functional thermochemistry. III. The role of exact exchange, The Journal of Chemical Physics. 98 (1993), 5648–5652. doi:10.1063/1.464913
- P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields, The Journal of Physical Chemistry. 98 (1994), 11623–11627. doi:10.1021/j100096a001
- H. Kadin, Captopril, in: Analytical profiles of drug substances, 1982: pp. 79–137. doi:10.1016/s0099-5428(08)60261-0
- W. A. Bernhard, D. M. Close, J. Huttermann, H. Zehner, The alkoxy radical, RCH2O, as a free radical product in x-irradiated single crystals of nucleosides and nucleotides, The Journal of Chemical Physics. 67(3) (1977), 1211-1219. doi:10.1063/1.434931
- H. U. Tasdemir, U. Sayin, E. Turkkan, A. Ozmen, EPR investigation of gamma irradiated single crystal guaifenesin: A combined experimental and computational study, Radiation Physics and Chemistry. 121 (2016), 61–68. doi:10.1016/j.radphyschem.2015.12.016
Ayrıntılar
| Birincil Dil | Türkçe |
|---|---|
| Konular | Kuantum Mekaniğinin Temelleri, Hesaplamalı Kimya |
| Bölüm | Araştırma Makalesi |
| Yazarlar | |
| Gönderilme Tarihi | 5 Nisan 2024 |
| Kabul Tarihi | 20 Ekim 2024 |
| Erken Görünüm Tarihi | 28 Nisan 2025 |
| Yayımlanma Tarihi | 30 Nisan 2025 |
| IZ | https://izlik.org/JA46SH92WD |
| Yayımlandığı Sayı | Yıl 2025 Cilt: 7 Sayı: 1 |