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A red-shifted two-photon-only caging group for three-dimensional photorelease.

ABSTRACT: Based on nitrodibenzofuran (NDBF) a new photocage with higher two-photon action cross section and red-shifted absorption was developed. Due to calculations, a dimethylamino functionality (DMA) was added at ring position 7. The uncaging of nucleobases after two-photon excitation (2PE) could be visualized via double-strand displacement in a hydrogel. With this assay we achieved three-dimensional photorelease of DMA-NDBF-protected DNA orthogonal to NDBF-protected strands. While being an excellent 2P-cage, DMA-NDBF is surprisingly stable under visible-light one-photon excitation (1PE). This case of excitation-specific photochemistry enhances the scope of orthogonal photoregulation.

SUBMITTER: Becker Y

PROVIDER: S-EPMC5914290 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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A red-shifted two-photon-only caging group for three-dimensional photorelease.

Becker Yvonne Y Unger Erik E Fichte Manuela A H MAH Gacek Daniel A DA Dreuw Andreas A Wachtveitl Josef J Walla Peter J PJ Heckel Alexander A

Chemical science 20180209 10

Based on nitrodibenzofuran (NDBF) a new photocage with higher two-photon action cross section and red-shifted absorption was developed. Due to calculations, a dimethylamino functionality (DMA) was added at ring position 7. The uncaging of nucleobases after two-photon excitation (2PE) could be visualized <i>via</i> double-strand displacement in a hydrogel. With this assay we achieved three-dimensional photorelease of DMA-NDBF-protected DNA orthogonal to NDBF-protected strands. While being an exce ...[more]

PMID: 29732066

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