Synthesis and biological evaluation of novel curcuminoid derivatives

• Published in: Molecules (Basel, Switzerland) Vol. 19; no. 10; pp. 16349 - 16372
• Main Authors: Cao, Ya-Kun, Li, Hui-Jing, Song, Zhi-Fang, Li, Yang, Huai, Qi-Yong
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 13.10.2014; MDPI
• Subjects: Acids; Alzheimer's disease; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; antibacterial; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; antioxidant; Antioxidants; Antioxidants - chemical synthesis; Antioxidants - pharmacology; antiproliferative; Cancer; Cell Line, Tumor; Cell Proliferation - drug effects; Curcumin - analogs & derivatives; curcuminoids; Escherichia - classification; Escherichia - drug effects; Hep G2 Cells; Humans; Natural products; Staphylococcus - classification; Staphylococcus - drug effects; China
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules191016349

Curcuminoids have been reported to possess multiple bioactivities, such as antioxidant, anticancer and anti-inflammatory properties. Three novel series of curcuminoid derivatives (11a-h, 15a-h and 19a-d) with enhanced bioactivity have been synthesized. Among the synthesized compounds, 11b exhibited the most significant activity with an MIC of 0.5 µM /mL against selected medically important Gram-positive cocci (S. aureus and S. viridans) and Gram-negative bacilli (E. coli and E. cloacae). The derivatives exhibited remarkable results in an antioxidant test with an IC50 2.4- to 9.3-folder smaller than curcuminoids. With respect to antiproliferative activity against Hep-G2, LX-2, SMMC7221 and MDA-MB-231, the derivatives exhibited an effect stronger than curcuminoids with an IC50 ranging from 0.18 to 4.25 µM.