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Light-induced antibiotic release from a coumarin-caged compound on the ultrafast timescale

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Abstract

A synthesis route for puromycin caged with the photo-responsive 7-diethylaminocoumarinyl protecting group carbamate was developed. The inactivation and recovery of the cytotoxic effect of puromycin was tested with a XTT cell viability assay. The uncaging mechanism was studied by ultrafast transient absorption spectroscopy and by time-correlated single photon counting. The combination of these results with quantum-chemical calculations provided detailed insights in dynamics upon excitation. Interestingly, a change of the dipole moment due to structural rearrangements of the amino moiety led to an intermolecular charge transfer on the picosecond time-scale. IR measurements marked the successful uncaging via the release of CO2, resulting from the carbamate linker. This decarboxylation constituted the rate-limiting step of the uncaging reaction and occurred on the subsecond timescale. DEACM-puromycin, thus, represents an efficient photo-activatable antibiotic for in-cell applications.

Graphical abstract: Light-induced antibiotic release from a coumarin-caged compound on the ultrafast timescale

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Publication details

The article was received on 29 Mar 2017, accepted on 19 May 2017 and first published on 19 May 2017


Article type: Paper
DOI: 10.1039/C7CP02030A
Citation: Phys. Chem. Chem. Phys., 2017, Advance Article
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    Light-induced antibiotic release from a coumarin-caged compound on the ultrafast timescale

    L.-M. Herzig, I. Elamri, H. Schwalbe and J. Wachtveitl, Phys. Chem. Chem. Phys., 2017, Advance Article , DOI: 10.1039/C7CP02030A

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