Synthesis and Cytotoxic Activities of a Curcumin Analogue and Its bis- Mannich Derivatives

Author(s): Kadir Ozden Yerdelen, Halise Inci Gul, Hiroshi Sakagami, Naoki Umemura, Murat Sukuroglu

Journal Name: Letters in Drug Design & Discovery

Volume 12 , Issue 8 , 2015

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Graphical Abstract:


Mannich bases (2-6) of curcumin analogue 1, [1,5-bis(4-hydroxy-phenyl)penta-1,4-dien-3- one], were synthesized.Their cytotoxicity against human HL-60 promyelocytic leukemia and HSC-2, HSC-3, and HSC-4 oral squamous carcinoma cell lines, as well as against normal oral cells was evaluated. Mannich bases 2-5 displayed more potent cytotoxicity than curcumin and curcumin analogue 1 towards malignant cells with high PSE values (93.7-136.6). PARP1 cleavage assay demonstrated the induction of apoptosis of HSC-2 cells by the most potent and tumor selective compound 4, which is a bis Mannich base having N-methyl piperazine moieties. The results obtained suggest that preparation of Mannich bases of a curcumin analogue 1 was a useful chemical modification for cytotoxicity and tumour-selectivity for the compounds synthesized, and apoptosis can be one of the possible mechanisms of action for the cytotoxicity.

Keywords: Anticancer, cytotoxicity, mannich bases, PARP1, PSE, SI.

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Article Details

Year: 2015
Published on: 30 July, 2015
Page: [643 - 649]
Pages: 7
DOI: 10.2174/1570180812666150213225134
Price: $65

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