1-(Hydroxyacetyl)pyrene a new fluorescent phototrigger for cell imaging and caging of alcohols, phenol and adenosine

Abstract

1-(Hydroxyacetyl)pyrene has been introduced as a new fluorescent phototrigger for alcohols and phenols. Alcohols and phenols were protected as their corresponding carbonate esters by coupling with fluorescent phototrigger, 1-(hydroxyacetyl)pyrene. Photophysical studies of caged carbonates showed that they all exhibited strong fluorescence properties. Irradiation of the caged carbonates by visible light (≥410 nm) in aqueous acetonitrile released the corresponding alcohols or phenols in high chemical (95-97%) and quantum (0.17-0.21) yields. The mechanism for the photorelease was proposed based on Stern-Volmer quenching experiments and solvent effect studies. Importantly, 1-(hydroxyacetyl)pyrene showed as a phototrigger for rapid photorelease of the biologically active molecule adenosine. In vitro biological studies revealed that 1-(hydroxyacetyl)pyrene has good biocompatibility, cellular uptake property and cell imaging ability.

Biological activities of pyrenyl-derived thiosemicarbazone half-sandwich complexes

“…A similar fluorescence was recently reported on the fibroblast L929 cancer cells with a pyrenyl-functionalized compound [21]. From these images, it was clear that complex [4]Cl was better taken up by the MCF-7 cells than complex…”

Synthesis of Light‐Responsive Pyrene‐Based Polymer Nanoparticles via Polymerization‐Induced Self‐Assembly

“…This trend suggests the gradual cleavage of the pyrene groups from the nanoparticles. It should be noted that upon light irradiation, the presence of water or a protonic solvent (such as ethanol or methanol) is required for the photolysis reaction and cleavage of the pyrene units . The UV–vis spectra obtained directly before and after UV light irradiation of the nanoparticles also showed the absorbance peaks blue‐shifted as the UV irradiation proceeded (Figure S12a–c, Supporting Information), which is due to the gradual cleavage of 1‐pyrene group yielding pyrene methanol (Py‐CH 2 OH) .…”

“…It should be noted that upon light irradiation, the presence of water or a protonic solvent (such as ethanol or methanol) is required for the photolysis reaction and cleavage of the pyrene units. [4,[78][79][80] The UV-vis The M n, GPC and M w /M n determined by GPC calibrated with PS standards. The polymerizations were performed at 70 °C for 24 h and at a total solids content of ≈5 wt%.…”

Decomposition and Transformation of Pyrene-Derivative Micelles at Intracellular Milieu and Their Influence on Cytoviability

“…In the same acidic cell compartments, however, the hydrolysable micelles are transferred to the Py‐CHO nanorods, which cause higher cytotoxicity (Scheme S1b). Because the pyrene derivatives have been widely utilized for cell imaging and have very little toxicity to cells at such a low concentration, the higher cytotoxicity is mostly attributed to the rod shape and larger size of the nanorods . The possibility of easy exposure of the Py‐CHO molecules after hydrolysis cannot be excluded.…”