Photorelease of Pyridines Using a Metal-Free Photoremovable Protecting Group.

Angewandte Chemie
Xiao-Jun TangXiaohong Fang

Abstract

The photorelease of bioactive molecules has emerged as a valuable tool in biochemistry. Nevertheless, many important bioactive molecules, such as pyridine derivatives, cannot benefit from currently available organic photoremovable protecting groups (PPGs). We found that the inefficient photorelease of pyridines is attributed to intramolecular photoinduced electron transfer (PET) from PPGs to pyridinium ions. To alleviate PET, we rationally designed a strategy to drive the excited state of PPG from S1 to T1 with a heavy atom, and synthesized a new PPG by substitution of the H atom at the 3-position of 7-dietheylamino-coumarin-4-methyl (DEACM) with Br or I. This resulted in an improved photolytic efficiency of the pyridinium ion by hundreds-fold in aqueous solution. The PPG can be applied to various pyridine derivatives. The successful photorelease of a microtubule inhibitor, indibulin, in living cells was demonstrated for the potential application of this strategy in biochemical research.

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Citations

Sep 26, 2020·Angewandte Chemie·Max WienholdRyan Gilmour
Jan 23, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aitor CarneiroLourdes Santana
Oct 31, 2020·Chemical Reviews·Roy WeinstainPetr Klán
Sep 25, 2021·Photochemistry and Photobiology·Jayme CannonSeok Ki Choi
Oct 12, 2021·Organic & Biomolecular Chemistry·Chenghong ZhuYan Zhang

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