Redox Mechanism of Azathioprine and Its Interaction with DNA
The electrochemical behavior and the interaction of the immunosuppressive drug azathioprine (AZA) with deoxyribonucleic acid (DNA) were investigated using voltammetric techniques, mass spectrometry (MS), and scanning electron microscopy (SEM). The redox mechanism of AZA on glassy carbon (GC) was inv...
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| Format: | Article |
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MDPI AG
2021-06-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/13/6805 |
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| author | Mihaela-Cristina Bunea Victor-Constantin Diculescu Monica Enculescu Horia Iovu Teodor Adrian Enache |
| author_facet | Mihaela-Cristina Bunea Victor-Constantin Diculescu Monica Enculescu Horia Iovu Teodor Adrian Enache |
| author_sort | Mihaela-Cristina Bunea |
| collection | DOAJ |
| description | The electrochemical behavior and the interaction of the immunosuppressive drug azathioprine (AZA) with deoxyribonucleic acid (DNA) were investigated using voltammetric techniques, mass spectrometry (MS), and scanning electron microscopy (SEM). The redox mechanism of AZA on glassy carbon (GC) was investigated using cyclic and differential pulse (DP) voltammetry. It was proven that the electroactive center of AZA is the nitro group and its reduction mechanism is a diffusion-controlled process, which occurs in consecutive steps with formation of electroactive products and involves the transfer of electrons and protons. A redox mechanism was proposed and the interaction of AZA with DNA was also investigated. Morphological characterization of the DNA film on the electrode surface before and after interaction with AZA was performed using scanning electron microscopy. An electrochemical DNA biosensor was employed to study the interactions between AZA and DNA with different concentrations, incubation times, and applied potential values. It was shown that the reduction of AZA molecules bound to the DNA layer induces structural changes of the DNA double strands and oxidative damage, which were recognized through the occurrence of the 8-oxo-deoxyguanosine oxidation peak. Mass spectrometry investigation of the DNA film before and after interaction with AZA also demonstrated the formation of AZA adducts with purine bases. |
| first_indexed | 2024-03-09T04:56:37Z |
| format | Article |
| id | doaj.art-d94e861008cb41ecbef64c3ca72e50eb |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T04:56:37Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-d94e861008cb41ecbef64c3ca72e50eb2023-12-03T13:05:47ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-06-012213680510.3390/ijms22136805Redox Mechanism of Azathioprine and Its Interaction with DNAMihaela-Cristina Bunea0Victor-Constantin Diculescu1Monica Enculescu2Horia Iovu3Teodor Adrian Enache4Laboratory of Multifunctional Materials and Structures, National Institute of Materials Physics, Atomistilor 405A, 077125 Magurele, RomaniaLaboratory of Multifunctional Materials and Structures, National Institute of Materials Physics, Atomistilor 405A, 077125 Magurele, RomaniaLaboratory of Multifunctional Materials and Structures, National Institute of Materials Physics, Atomistilor 405A, 077125 Magurele, RomaniaAdvanced Polymer Materials Group, University Politehnica of Bucharest, 1-7 Gh. Polizu, 011061 Bucharest, RomaniaLaboratory of Multifunctional Materials and Structures, National Institute of Materials Physics, Atomistilor 405A, 077125 Magurele, RomaniaThe electrochemical behavior and the interaction of the immunosuppressive drug azathioprine (AZA) with deoxyribonucleic acid (DNA) were investigated using voltammetric techniques, mass spectrometry (MS), and scanning electron microscopy (SEM). The redox mechanism of AZA on glassy carbon (GC) was investigated using cyclic and differential pulse (DP) voltammetry. It was proven that the electroactive center of AZA is the nitro group and its reduction mechanism is a diffusion-controlled process, which occurs in consecutive steps with formation of electroactive products and involves the transfer of electrons and protons. A redox mechanism was proposed and the interaction of AZA with DNA was also investigated. Morphological characterization of the DNA film on the electrode surface before and after interaction with AZA was performed using scanning electron microscopy. An electrochemical DNA biosensor was employed to study the interactions between AZA and DNA with different concentrations, incubation times, and applied potential values. It was shown that the reduction of AZA molecules bound to the DNA layer induces structural changes of the DNA double strands and oxidative damage, which were recognized through the occurrence of the 8-oxo-deoxyguanosine oxidation peak. Mass spectrometry investigation of the DNA film before and after interaction with AZA also demonstrated the formation of AZA adducts with purine bases.https://www.mdpi.com/1422-0067/22/13/6805azathioprineredox mechanismDNA biosensorDNA interactionmass spectrometry |
| spellingShingle | Mihaela-Cristina Bunea Victor-Constantin Diculescu Monica Enculescu Horia Iovu Teodor Adrian Enache Redox Mechanism of Azathioprine and Its Interaction with DNA International Journal of Molecular Sciences azathioprine redox mechanism DNA biosensor DNA interaction mass spectrometry |
| title | Redox Mechanism of Azathioprine and Its Interaction with DNA |
| title_full | Redox Mechanism of Azathioprine and Its Interaction with DNA |
| title_fullStr | Redox Mechanism of Azathioprine and Its Interaction with DNA |
| title_full_unstemmed | Redox Mechanism of Azathioprine and Its Interaction with DNA |
| title_short | Redox Mechanism of Azathioprine and Its Interaction with DNA |
| title_sort | redox mechanism of azathioprine and its interaction with dna |
| topic | azathioprine redox mechanism DNA biosensor DNA interaction mass spectrometry |
| url | https://www.mdpi.com/1422-0067/22/13/6805 |
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