Abstract: Coumarin derivative 1, 5,7-dihydroxy-6-(3-methyl-1-butyryl)-4-phenyl-chromen-2-one, has been reported to possess radical scavenging activity and DNA protection. We have synthesized a series of coumarins with structural modifications at positions C4, C5, C6 and C7 and evaluated them for their anti-UVC properties. Coumarin 7, 6-benzoyl-5,6-dihydroxy-4-phenyl-chromen-2-one, was found to have the most potent activity in protecting porcine γ-crystallin against UVC insults. Results of fluorescence assays indicated that compound 7 was capable of decreasing the loss of intensity while lens crystallins and DNA PUC19 were irradiated with UVC. Presence of compound 7 decreased hydroxyl radical levels determined by probe 1b and the free iron concentrations determined by Ferrozine reagent. The chelation assay showed that compound 7 was chelated to metal via 6-CO and 5-OH on the benzopyrone ring. The observed protective effects of compound 7 towards crystallins from insults of UVC and free radicals may be due to its iron-chelating activity and its peak absorption at 254 nm.
Keywords: irradiation; anti-cataract; coumarin; γ-crystallin; iron-chelation
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Liao, J.-H.; Wu, T.-H.; Hsu, F.-L.; Huang, Y.-S.; Chiang, P.-H.; Huang, Z.-Y.; Huang, C.-H.; Wu, S.-H.; Lin, M.-H. Anti-UVC Irradiation and Metal Chelation Properties of 6-Benzoyl-5,7-dihydroxy-4-phenyl-chromen-2-one: An Implications for Anti-Cataract Agent. Int. J. Mol. Sci. 2011, 12, 7059-7076.
Liao J-H, Wu T-H, Hsu F-L, Huang Y-S, Chiang P-H, Huang Z-Y, Huang C-H, Wu S-H, Lin M-H. Anti-UVC Irradiation and Metal Chelation Properties of 6-Benzoyl-5,7-dihydroxy-4-phenyl-chromen-2-one: An Implications for Anti-Cataract Agent. International Journal of Molecular Sciences. 2011; 12(10):7059-7076.
Liao, Jiahn-Haur; Wu, Tzu-Hua; Hsu, Feng-Lin; Huang, Yi-Shiang; Chiang, Po-Hung; Huang, Zih-You; Huang, Chi-Hsien; Wu, Shih-Hsiung; Lin, Mei-Hsiang. 2011. "Anti-UVC Irradiation and Metal Chelation Properties of 6-Benzoyl-5,7-dihydroxy-4-phenyl-chromen-2-one: An Implications for Anti-Cataract Agent." Int. J. Mol. Sci. 12, no. 10: 7059-7076.