Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase
Curcumin is a natural product with enormous biological potential. In this study, curcumin synthesis was revisited using different reaction solvents, a catalyst (n-butylamine) and a water scavenger [(n-BuO)3B], to develop the optimal procedure for its rapid acquisition. During synthesis, solvent choi...
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| Format: | Article |
| Language: | English |
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Sciendo
2017-09-01
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| Series: | Acta Pharmaceutica |
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| Online Access: | https://doi.org/10.1515/acph-2017-0023 |
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| _version_ | 1832572163805151232 |
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| author | Ahmed Mahmood Abdul Qadir Muhammad Imtiaz Shafiq Muhammad Muddassar Muhammad Hameed Abdul Nadeem Arshad Muhammad Asiri Abdullah M. |
| author_facet | Ahmed Mahmood Abdul Qadir Muhammad Imtiaz Shafiq Muhammad Muddassar Muhammad Hameed Abdul Nadeem Arshad Muhammad Asiri Abdullah M. |
| author_sort | Ahmed Mahmood |
| collection | DOAJ |
| description | Curcumin is a natural product with enormous biological potential. In this study, curcumin synthesis was revisited using different reaction solvents, a catalyst (n-butylamine) and a water scavenger [(n-BuO)3B], to develop the optimal procedure for its rapid acquisition. During synthesis, solvent choice was found to be an important parameter for better curcumin yield and high purity. In a typical reaction, acetyl acetone was treated with boron trioxide, followed by condensation with vanillin in the presence of tri-n-butyl borate as water scavenger and n-butylamine as catalyst at 80 °C in ethyl acetate to afford curcumin. Moreover, curcumin was also extracted from turmeric powder and spectroscopic properties such as IR, MS, 1H NMR and 13C NMR with synthetic curcumin were established to identify any impurity. The purity of synthetic and extracted curcumin was also checked by TLC and HPLC-DAD. To computationally assess its therapeutic potential against cyclin dependent kinases (CDKs), curcumin was docked in different isoforms of CDKs. It was observed that it did not dock at the active sites of CDK2 and CDK6. However, it could enter into weak interactions with CDK4 protein. |
| format | Article |
| id | doaj-art-ddf63695560442969f0817782b7f9838 |
| institution | Kabale University |
| issn | 1846-9558 |
| language | English |
| publishDate | 2017-09-01 |
| publisher | Sciendo |
| record_format | Article |
| series | Acta Pharmaceutica |
| spelling | doaj-art-ddf63695560442969f0817782b7f98382025-02-02T11:50:20ZengSciendoActa Pharmaceutica1846-95582017-09-0167338539510.1515/acph-2017-0023acph-2017-0023Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinaseAhmed Mahmood0Abdul Qadir Muhammad1Imtiaz Shafiq Muhammad2Muddassar Muhammad3Hameed Abdul4Nadeem Arshad Muhammad5Asiri Abdullah M.6Institute of Chemistry, University of the Punjab, Lahore, Pakistan54590Institute of Chemistry, University of the Punjab, Lahore, Pakistan54590Institute of Biochemistry and Biotechnology, University of the Punjab, Lahore, Pakistan54590Department of Biosciences, COMSATS Institute of Information Technology, Islamabad-PakistanH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270PakistanChemistry Department, Faculty of Science, King Abdulaziz University, Jeddah21589, Saudi ArabiaChemistry Department, Faculty of Science, King Abdulaziz University, Jeddah21589, Saudi ArabiaCurcumin is a natural product with enormous biological potential. In this study, curcumin synthesis was revisited using different reaction solvents, a catalyst (n-butylamine) and a water scavenger [(n-BuO)3B], to develop the optimal procedure for its rapid acquisition. During synthesis, solvent choice was found to be an important parameter for better curcumin yield and high purity. In a typical reaction, acetyl acetone was treated with boron trioxide, followed by condensation with vanillin in the presence of tri-n-butyl borate as water scavenger and n-butylamine as catalyst at 80 °C in ethyl acetate to afford curcumin. Moreover, curcumin was also extracted from turmeric powder and spectroscopic properties such as IR, MS, 1H NMR and 13C NMR with synthetic curcumin were established to identify any impurity. The purity of synthetic and extracted curcumin was also checked by TLC and HPLC-DAD. To computationally assess its therapeutic potential against cyclin dependent kinases (CDKs), curcumin was docked in different isoforms of CDKs. It was observed that it did not dock at the active sites of CDK2 and CDK6. However, it could enter into weak interactions with CDK4 protein.https://doi.org/10.1515/acph-2017-0023curcumin synthesiscdksmolecular docking |
| spellingShingle | Ahmed Mahmood Abdul Qadir Muhammad Imtiaz Shafiq Muhammad Muddassar Muhammad Hameed Abdul Nadeem Arshad Muhammad Asiri Abdullah M. Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase Acta Pharmaceutica curcumin synthesis cdks molecular docking |
| title | Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase |
| title_full | Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase |
| title_fullStr | Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase |
| title_full_unstemmed | Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase |
| title_short | Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase |
| title_sort | curcumin synthesis optimization and in silico interaction with cyclin dependent kinase |
| topic | curcumin synthesis cdks molecular docking |
| url | https://doi.org/10.1515/acph-2017-0023 |
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