Journal
MOLECULES
Volume 16, Issue 2, Pages 1888-1900Publisher
MDPI
DOI: 10.3390/molecules16021888
Keywords
curcumin; prodrug; succinylation; stability; hydrolysis
Funding
- Faculty of Pharmaceutical Sciences, Chulalongkorn University
- Thailand Research Fund [PHD/0217/2548]
Ask authors/readers for more resources
A novel series of succinyl derivatives of three curcuminoids were synthesized as potential prodrugs. Symmetrical (curcumin and bisdesmethoxycurcumin) and unsymmetrical (desmethoxycurcumin) curcuminoids were prepared through aldol condensation of 2,4-pentanedione with different benzaldehydes. Esterification of these compounds with a methyl or ethyl ester of succinyl chloride gave the corresponding succinate prodrugs in excellent yields. Anticolon cancer activity of the compounds was evaluated using Caco-2 cells. The succinate prodrugs had IC50 values in the 1.8-9.6 mu M range, compared to IC50 values of 3.3-4.9 mu M for the parent compounds. Curcumin diethyl disuccinate exhibited the highest potency and was chosen for stability studies. Hydrolysis of this compound in phosphate buffer at pH 7.4 and in human plasma followed pseudo first-order kinetics. In phosphate buffer, the k(obs) and t(1/2) for hydrolysis indicated that the compound was much more stable than curcumin. In human plasma, this compound was
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available