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

Yvonne BeckerErik UngerManuela A H FichteDaniel Alexander Gacek Andreas Dreuw Josef WachtveitlPeter J WallaAlexander Heckel

Published in: Chemical science (2018)

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.

Keyphrases

living cells
monte carlo
visible light
energy transfer
single molecule
drug delivery
fluorescent probe
high throughput
molecular dynamics
density functional theory
molecular dynamics simulations
nucleic acid
circulating tumor cells