Curcumin analogs

Zambre AP, Kulkarni YM, Padhye S, Sandur SK, Aggarwal BB. 2006. Novel curcumin analogs targeting TNF-induced NF-kappaB activation and proliferation in human leukemic KBM-5 cells. Bioorg Med Chem 14 7196-7204. 

Dinkova-Kostova AT, Talalay P. 1999. Relation of structure of curcumin analogs to their potencies as inducers of Phase 2 detoxification enzymes. Carcinogenesis 20 911-914. 

Tonnesen HH. Studies on curcumin and curcuminoids. XIII. Catalytic effect of curcumin on the peroxidation of linoleic acid by 15-Upoxygenase. Int J Pharm 1989 50 67. Tonnesen HH. Studies on curcumin and curcuminoids. XVI. Effect of curcumin analogs on hyaluronic acid degradation in vitro. Int J Pharm 1989 51 259. 

Fig. (4). Curcumin and semi-synthetic curcumin analogs tested for anti-inflammatory activity [11, 12]...

Venkantesan et al. [22] used three models to investigate the importance of the phenolic hydroxy groups, as well as other substituents in the phenyl rings of curcumin and curcumin analogs, to antioxidant... 

Recently, Youssef et al. [24] reported the synthesis of curcumin analogs as potential antioxidant and cancer chemopreventive agents. The general structures of the synthesized analogs are shown in Fig. (8). These compounds were tested for scavenging ability of DPPH free radicals and in an ATP chemiluminescence assay. The SAR conclusions from the results were mainly consistent with the prior conclusions drawn by other researchers. In addition, they found that di-substitution of the central methylene group resulted in decreased antioxidative activity. 

Fig. (8). General structures of curcumin analogs synthesized by Youssef et al. [24]...

However, a curcumin analog without phenolic and methoxy groups was reported to be as active as curcumin in terms of scavenging hydroxy radicals and other redox properties [34]. 

Mazumder et al. [39] synthesized curcumin analogs (Table 5) as probes for an anti-HIV-1 integrase mechanism study. Evidence suggested that curcumin does not bind to the DNA-binding domain of HIV-1 integrase [40] or the same binding site of another HIV-1 integrase... 

Table 5. Structures of curcumin analogs and anti-HIV-1 integrase ability [39]...

In order to search for new chemopreventive enzyme inducers and to elucidate the structural features responsible for the ability of curcumin to induce Phase 2 detoxification enzymes, Dinkova-Kostova et al.[48, 49] examined some natural as well as synthetic curcumin analogs for ability to induce NAD(P)H quinone reductase (a prototype for phase 2 detoxification enzymes) in murine hepatoma cells. Compounds... 

Fig. (11). Structures of curcumin analogs and their inducer potencies (CD/pM) in the QR assay in Hepa lc lc7 murine hepatoma cells [48] (CD value is the concentration required to double the quinone reductase specific activity.)...

Table 8. Percent inhibition of in vitro endothelial cell proliferation by curcumin analogs [66]...

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