2,2'-Fluorine mono-carbonyl curcumin induce reactive oxygen species-Mediated apoptosis in Human lung cancer NCI-H460 cells.
In this paper, we synthesized three fluorine-substituted mono-carbonyl curcumin analogs and evaluated their cytotoxicity against several cancer cells by the MTT assay. The results exhibited that all the three compounds were more active than the leading curcumin. Especially, 2,2'-F mono-carbonyl curcumin, 1a, surfaced as an important lead compound displaying almost 4-fold cytotoxicity relative to curcumin. More importantly, 1a was more stable in (RPMI)-1640 medium and more massive uptake than curcumin, which may be relationship to their cytotoxicity, apoptotic acitivity and reactive oxygen species generation. And then, the generation of reactive oxygen species can disrupt the intracellular redox balance, induce lipid peroxidation, cause the collapse of the mitochondrial membrane potential and ultimately lead to apoptosis. The results not only suggest that 2,2'-F mono-carbonyl curcumin (1a) may cause cancer cells apoptosis through reactive oxygen species-Mediated pathway, but also gives us an important information for design of mono-carbonyl curcumin analog.
School of Pharmacy, Liaocheng University, 1 Hunan Street, Liaocheng, Shandong 252000, China.
Guo-Yun
GY
Liu
School of Pharmacy, Liaocheng University, 1 Hunan Street, Liaocheng, Shandong 252000, China.
Qiang
Q
Zhai
School of Pharmacy, Liaocheng University, 1 Hunan Street, Liaocheng, Shandong 252000, China.
Jia-Zhuang
JZ
Chen
School of Pharmacy, Liaocheng University, 1 Hunan Street, Liaocheng, Shandong 252000, China.
Zhuo-Qing
ZQ
Zhang
School of Pharmacy, Liaocheng University, 1 Hunan Street, Liaocheng, Shandong 252000, China. Electronic address: yangjie1110@163.com.
Jie
J
Yang
D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects*; D001692:Biological Transport; D045744:Cell Line, Tumor; D003474:Curcumin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D036381:Diarylheptanoids; D006801:Humans; D042541:Intracellular Space / Q000187:drug effects / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D008175:Lung Neoplasms / Q000473:pathology*; D053078:Membrane Potential, Mitochondrial / Q000187:drug effects; D010084:Oxidation-Reduction / Q000187:drug effects; D017382:Reactive Oxygen Species / Q000378:metabolism*; D013329:Structure-Activity Relationship
C000614921:1,5-bis(2-fluorophenyl)penta-1,4-dien-3-one; D000970:Antineoplastic Agents; D036381:Diarylheptanoids; D017382:Reactive Oxygen Species; D003474:Curcumin
Apoptosis; Curcumin analogs; Fluorine; Reactive oxygen species