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Int. J. Mol. Sci. 2011, 12(10), 7059-7076; doi:10.3390/ijms12107059
Article

Anti-UVC Irradiation and Metal Chelation Properties of 6-Benzoyl-5,7-dihydroxy-4-phenyl-chromen-2-one: An Implications for Anti-Cataract Agent

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1,*  and 2,*
1 Institute of Biological Chemistry, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115, Taiwan 2 School of Pharmacy, College of Pharmacy, Taipei Medical University, 250 Wuxing Street, Taipei 11031, Taiwan 3 Institute of Biochemical Sciences, National Taiwan University, No. 1, Section 4, Roosevelt Road, Taipei 10617, Taiwan
* Authors to whom correspondence should be addressed.
Received: 29 July 2011 / Revised: 23 September 2011 / Accepted: 11 October 2011 / Published: 21 October 2011
(This article belongs to the Special Issue Antioxidants)
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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 irradiation; anti-cataract; coumarin; γ-crystallin; iron-chelation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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