<abstract xmlns="http://www.w3.org/1999/xhtml">Curcumin is a natural product with enormous biological potential. In this study, curcumin synthesis was revisited using different reaction solvents, a catalyst (<italic>n</italic>-butylamine) and a water scavenger [(<italic>n</italic>-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-<italic>n</italic>-butyl borate as water scavenger and <italic>n</italic>-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.</abstract>

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.

Curcumin: Synthesis optimization and <italic>in silico</italic> interaction with cyclin dependent kinase

Institute of Biochemistry and Biotechnology

Department of Biosciences, COMSATS Institute of Information Technology

H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences

Center of Excellence for Advanced Materials Research (CEAMR), Faculty of Science

Acta Pharmaceutica

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Curcumin: Synthesis optimization and  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...

Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase

Publicado en línea: 30 ago 2017

Páginas: 385 - 395

Aceptado: 04 abr 2017

DOI: https://doi.org/10.1515/acph-2017-0023

Palabras clave
curcumin synthesis, CDKs, molecular docking

© 2017 Mahmood Ahmed et al., published by De Gruyter Open

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Curcumin: Synthesis optimization and in silico interaction with cyclin dependent kinase

Publicado en línea: 30 ago 2017

Páginas: 385 - 395

Aceptado: 04 abr 2017

DOI: https://doi.org/10.1515/acph-2017-0023

Palabras clavecurcumin synthesis, CDKs, molecular docking

© 2017 Mahmood Ahmed et al., published by De Gruyter Open

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Palabras clave
curcumin synthesis, CDKs, molecular docking