Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Mechanistic Studies of the Photoinduced Quinone Trimethyl Lock Decaging Process

“…[2][3][4] Either reducing a quinone or revealing a phenol produces a nucleophile that can exploit the remarkable rate enhancements associated with the trimethyl lock system, releasing HX as a generic alcohol, amine, thiol, or phosphate. Of course, deprotection of the phenol can be accomplished photochemically using established caging groups, 5,6 but this approach does not lead naturally to longer wavelength systems. With a goal of creating a photochemically triggered trimethyl lock system, we considered compound 1 ( Figure 2).…”

Near‐IR‐Triggered, Remote‐Controlled Release of Metal Ions: A Novel Strategy for Caged Ions

“…[3] For nitrobenzyl derivatives and related moieties the lowest-energy limit is approximately l = 360 nm. Although for some other molecules the lowest-energy limit can be pushed back to l = 400-450 nm, there is a penalty in the form of significantly decreased reaction quantum yields and diminished conversion efficiencies.…”

Switchable Materials Containing Polyzwitterion Moieties

“…Despite the advantages of using photolytic transformation, further studies should be directed towards the employment of a photolabile group (i.e., coumarine type ester) with a non-toxic site product of photolysis [63] and satisfy the two photon absorption properties for improved biomedical applications [64]. (18) and irreversible switch to poly(19) (b) schematic application of poly (18) in the complexation with negatively charged BSA to form self-assembly polyionic complex that improve the protection of the protein against denaturation, shields the negative charge of the protein and penetration to the tumor cell due to the enhanced and permeability and retention (EPR) effect and by UV light irradiation accelerated the release of bovine serum albumin (BSA).…”