This review focuses on utilization of the excited state meta effect (ESME) in the development of photolabile protecting groups (PPGs). Structurally simple ESME-based PPGs for release of various functional groups (such as carbonyl, hydroxyl, carboxyl, amino and thiol groups) are discussed. Examples that demonstrate the appealing advantages of these new PPGs are provided, including their efficient release of "poor" leaving groups such as hydroxyl or amino group directly instead of in their respective carbonate or carbamate form. Applications of these PPGs in synthesis, release of biologically important molecules, materials science and biomedical engineering are also described.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1111/php.13690 | DOI Listing |
Photochem Photobiol Sci
December 2024
Novosibirsk State University, Novosibirsk, Russia.
Control of biological activity with light is a fascinating idea. "Caged" compounds, molecules modified with photolabile protecting group, are one of the instruments for this purpose. Adrenergic receptors are essential regulators of neuronal, endocrine, cardiovascular, vegetative, and metabolic functions.
View Article and Find Full Text PDFChem Sci
December 2024
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University Xi'an 710119 China
Photoacid generators (PAGs) and photohydride generators (PHGs) are specific photolabile protecting groups that release acid and hydride, respectively. Over the past decade, great efforts have been devoted to developing novel PAGs and PHGs with advanced efficiency, among which, two of the promising candidates are diarylethene (DAE)-based PAGs and PHGs, which release acids/hydrides during photochromic electrocyclization. The release quantum yield for PAGs is acceptable, while that of PHGs is only 4.
View Article and Find Full Text PDFAdv Healthc Mater
October 2024
Department Tianjin Key Laboratory of Biosensing and Molecular Recognition, Research Center for Analytical Sciences, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, Tianjin, 300071, P. R. China.
Highly spatiotemporal-resolved photomodulation demonstrates promise for investigating key biological events in vivo and in vitro, such as cell signaling pathways, neuromodulation, and tumor treatment without side effects. However, enhancing the performance of photomodulation tools remains challenging due to the limitations of the physicochemical properties of the photoactive molecules. Here, a compact, stable intramolecular π-π stacking conformation forming between the target molecule (naproxen) and the perylene-based photoremovable protecting group is discovered to confine the motion of the photolabile bond and then enhance the photocleavage quantum yield.
View Article and Find Full Text PDFACS Appl Mater Interfaces
October 2024
BrainVisionCenter, 43-45 Liliom Str., H-1094 Budapest, Hungary.
The advancements in targeted drug release and experimental neuroscience have amplified the scientific interest in photolabile protecting groups (PPGs) and photouncaging. The growing need for the detection of uncaging events has led to the development of reporters with fluorescence turn-on upon uncaging. In contrast, fluorescent tags with turn-off properties have been drastically underexplored, although there are applications where they would be sought after.
View Article and Find Full Text PDFChembiochem
November 2024
Signalling Research Centres BIOSS and CIBSS, Faculty of Biology, University of Freiburg, Schänzlestrasse 18, Freiburg, 79104, Germany.
Protein phosphatase-1 (PP1) is a ubiquitous enzyme that counteracts hundreds of kinases in cells. PP1 interacts with regulatory proteins via an RVxF peptide motif that binds to a hydrophobic groove on the enzyme. PP1-disrupting peptides (PDPs) compete with these regulatory proteins, leading to the release of the active PP1 subunit and promoting substrate dephosphorylation.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!