(1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies
In this study, (1E)-1-(2-Pyrazinyl)ethanone thiosemicarbazone (PT) was synthesized and characterized using Fourier-transform infrared (FTIR), ultraviolet-visible (UV–Vis), proton nuclear magnetic resonance (1HNMR ) and carbon-13 nuclear magnetic resonance (13CNMR ) spectroscopy. The vibrational freq...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English English |
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Elsevier Ltd
2023
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| Online Access: | http://umpir.ump.edu.my/id/eprint/42333/1/1-s2.0-S0022286023011328-main.pdf http://umpir.ump.edu.my/id/eprint/42333/2/1E-1-2-pyrazinyl-ethanone%20thiosemicarbazone.pdf |
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| author | Syamimi Sulfiza, Shamsuri Erna Normaya, . Hakimah, Ismail Anwar, Iqbal Mohd Bijarimi, Mat Piah Yang Farina, . Ahmad Sazali, Hamzah Mohamad Norazmi, Ahmad |
| author_facet | Syamimi Sulfiza, Shamsuri Erna Normaya, . Hakimah, Ismail Anwar, Iqbal Mohd Bijarimi, Mat Piah Yang Farina, . Ahmad Sazali, Hamzah Mohamad Norazmi, Ahmad |
| author_sort | Syamimi Sulfiza, Shamsuri |
| collection | UMP |
| description | In this study, (1E)-1-(2-Pyrazinyl)ethanone thiosemicarbazone (PT) was synthesized and characterized using Fourier-transform infrared (FTIR), ultraviolet-visible (UV–Vis), proton nuclear magnetic resonance (1HNMR ) and carbon-13 nuclear magnetic resonance (13CNMR ) spectroscopy. The vibrational frequencies were analysed using the Vibrational Energy Distribution Analysis (VEDA) program. The chemical properties of PT, including electron density distribution and intramolecular interactions, were characterized using in-silico methods based on Mulliken atomic charges, molecular electrostatic potential (MEP), quantum theory of atoms in molecules and reduced density gradient noncovalent interaction approaches. PT exhibits a significant inhibitory effect on enzymatic browning (6 and 24 h) and tyrosinase enzymes (IC50 = 7.75 μM). Kinetic analysis shows that PT is a mixed-type inhibitor, with respective Km and Vmax values of 0.632 mM and 0.0044 μM/s, and that it forms a reversible enzyme-inhibitor interaction. The PT-tyrosinase interaction was experimentally evaluated based on 1D, second derivatives of 1D, 2D and 3D IR spectroscopy. Furthermore, analysis of absorption, distribution, metabolism, excretions and toxicity properties revealed good physicochemical properties of PT according to the drug scores and Lipinski's Rule of Five. Lastly, the mechanisms of PT against tyrosinase were visualized and supported by means of a molecular docking approach. |
| first_indexed | 2024-09-25T03:52:31Z |
| format | Article |
| id | UMPir42333 |
| institution | Universiti Malaysia Pahang |
| language | English English |
| last_indexed | 2024-09-25T03:52:31Z |
| publishDate | 2023 |
| publisher | Elsevier Ltd |
| record_format | dspace |
| spelling | UMPir423332024-08-13T06:49:23Z http://umpir.ump.edu.my/id/eprint/42333/ (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies Syamimi Sulfiza, Shamsuri Erna Normaya, . Hakimah, Ismail Anwar, Iqbal Mohd Bijarimi, Mat Piah Yang Farina, . Ahmad Sazali, Hamzah Mohamad Norazmi, Ahmad TP Chemical technology In this study, (1E)-1-(2-Pyrazinyl)ethanone thiosemicarbazone (PT) was synthesized and characterized using Fourier-transform infrared (FTIR), ultraviolet-visible (UV–Vis), proton nuclear magnetic resonance (1HNMR ) and carbon-13 nuclear magnetic resonance (13CNMR ) spectroscopy. The vibrational frequencies were analysed using the Vibrational Energy Distribution Analysis (VEDA) program. The chemical properties of PT, including electron density distribution and intramolecular interactions, were characterized using in-silico methods based on Mulliken atomic charges, molecular electrostatic potential (MEP), quantum theory of atoms in molecules and reduced density gradient noncovalent interaction approaches. PT exhibits a significant inhibitory effect on enzymatic browning (6 and 24 h) and tyrosinase enzymes (IC50 = 7.75 μM). Kinetic analysis shows that PT is a mixed-type inhibitor, with respective Km and Vmax values of 0.632 mM and 0.0044 μM/s, and that it forms a reversible enzyme-inhibitor interaction. The PT-tyrosinase interaction was experimentally evaluated based on 1D, second derivatives of 1D, 2D and 3D IR spectroscopy. Furthermore, analysis of absorption, distribution, metabolism, excretions and toxicity properties revealed good physicochemical properties of PT according to the drug scores and Lipinski's Rule of Five. Lastly, the mechanisms of PT against tyrosinase were visualized and supported by means of a molecular docking approach. Elsevier Ltd 2023-11-05 Article PeerReviewed pdf en http://umpir.ump.edu.my/id/eprint/42333/1/1-s2.0-S0022286023011328-main.pdf pdf en http://umpir.ump.edu.my/id/eprint/42333/2/1E-1-2-pyrazinyl-ethanone%20thiosemicarbazone.pdf Syamimi Sulfiza, Shamsuri and Erna Normaya, . and Hakimah, Ismail and Anwar, Iqbal and Mohd Bijarimi, Mat Piah and Yang Farina, . and Ahmad Sazali, Hamzah and Mohamad Norazmi, Ahmad (2023) (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies. Journal of Molecular Structure, 1291 (136039). pp. 1-14. ISSN 0022-2860. (Published) https://doi.org/10.1016/j.molstruc.2023.136039 https://doi.org/10.1016/j.molstruc.2023.136039 |
| spellingShingle | TP Chemical technology Syamimi Sulfiza, Shamsuri Erna Normaya, . Hakimah, Ismail Anwar, Iqbal Mohd Bijarimi, Mat Piah Yang Farina, . Ahmad Sazali, Hamzah Mohamad Norazmi, Ahmad (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies |
| title | (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies |
| title_full | (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies |
| title_fullStr | (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies |
| title_full_unstemmed | (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies |
| title_short | (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies |
| title_sort | 1e 1 2 pyrazinyl ethanone thiosemicarbazone pt as a tyrosinase inhibitor with anti browning activity spectroscopy dft and molecular docking studies |
| topic | TP Chemical technology |
| url | http://umpir.ump.edu.my/id/eprint/42333/1/1-s2.0-S0022286023011328-main.pdf http://umpir.ump.edu.my/id/eprint/42333/2/1E-1-2-pyrazinyl-ethanone%20thiosemicarbazone.pdf |
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