Abstract
The activity of two cyclooxygenase-2 enzyme inhibitors, Celecoxib and Lumiracoxib, could be suppressed by coupling to photo-labile protecting groups, so-called photocages. These groups could be further functionalized with a peptide targeting vector for specific cellular delivery. The enzyme inhibition potential of the cyclooxygenase-2 inhibitors could be regained upon two-photon excitation with tissue-transparent near-IR light at 800 nm.
Highlights
It would be highly desirable to have biochemical tools, which allow for spatio-temporally controlled release of enzyme inhibitors in living cells or organisms
The attachment of the targeting moiety to the caged compounds is by design the last step in the synthesis and conveniently adjustable
A peptide, which was shown to bind to annexin[1] and to function as a targeting moiety towards certain cancer cells in mice,[21] was attached to caged Celecoxib 4, producing targeted caged Celecoxib 5
Summary
The single photon uncaging quantum yields were determined upon irradiation with a frequency-tripled Nd-YAG laser at 355 nm with azobenzene as reference, as discussed in recent articles on the accurate determination of uncaging quantum yields.[23,24,25] The caged glutamate by Goeldner et al (Scheme 1) was shown to have a quantum yield of 0.1 at 313 nm.[15] For 3, which links the bio-active compound via an ester to the same cage chromophore, a similar uncaging quantum yield of 0.094 was determined.
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