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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

1
, 2
, 2
, 1
, 2
, 3
, 2
, 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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