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. 2011 Feb 23;133(7):2148-50.
doi: 10.1021/ja111585c. Epub 2011 Jan 28.

A new trick (hydroxyl radical generation) for an old vitamin (B12)

Thomas A Shell  1 , David S Lawrence
Affiliations

A new trick (hydroxyl radical generation) for an old vitamin (B12)

Thomas A Shell et al. J Am Chem Soc. .

Abstract

Photolysis of hydroxocobalamin in the presence of plasmid DNA (pBR322) results in DNA cleavage. Temporal control of hydroxyl radical production and DNA strand scission by hydroxocobalamin was demonstrated using a 2-deoxyribose assay and a plasmid relaxation assay, respectively. The light-driven hydroxocobalamin-mediated catalytic formation of hydroxyl radicals was demonstrated using radical scavenging studies of DNA cleavage and via recycling of a hydroxocobalamin-resin conjugate several times without loss of efficacy.

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Figures

Scheme 1
Scheme 1
(A) Photolysis of MeCbl to furnish CH3· and (B) proposed light-dependent generation of ·OH by B12a.
Figure 1
Figure 1
Light-driven ·OH production via photolysis of the B12a-resin conjugate 2. The conjugate 2 was suspended in a deoxyribose solution (50 mM in pH 7.4 PBS). The suspension was sequentially photolyzed (60 min total), stored in the dark (100 min total), and photolyzed (60 min total), with aliquots removed and analyzed at various time points.
Figure 2
Figure 2
Light-mediated DNA (30 μM/bp in pH 7.4 PBS) by hydroxocobalamin (300 pM). Samples were irradiated with Pyrex-filtered light from a mercury arc lamp.
See this image and copyright information in PMC

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