ABSTRACT
Nitric oxide (NO), as a vital cellular signalling molecule in physiological processes, has been found to play an important role in various biological functions. In this study, we rationally designed three NO donors by tethering nitrobenzene derivatives to three fluorescent chromophores. NX-NO was found to release NO and exhibit a high fluorescence turn-on signal ratio upon exposure to LED yellow light. Additionally, it had excellent photo-stability and good inhibitory activity against cancer cell proliferation, and was successfully applied to cell imaging. Moreover, we detected the release of NO and fluorescence response in the blood of a mouse, suggesting its potential therapeutic application in living organisms.
Subject(s)
Fluorescent Dyes , Nitric Oxide Donors , Mice , Animals , Nitric Oxide Donors/pharmacology , Nitric Oxide , Fluorescence , Cell ProliferationABSTRACT
Hydrazine is a substance harmful to humans and the environment, necessitating the development of a sensitive and specific detection method. Herein, a novel chemiluminescent probe based on Schaap's adamantylidene-dioxetane (CL-HZ) for detecting hydrazine was synthesized and evaluated. The probe was activated by the removal of a protecting group to form free phenoxy-dioxetane, when treated with hydrazine. It then showed a noticeable and sustainable fluorescent response without excitation, with intensity increasing 51-fold in the presence of hydrazine. CL-HZ can be used in 96-well high-throughput assays for analysis of hydrazine in polluted water samples and was successfully applied for the detection of hydrazine in living cells.
Subject(s)
Adamantane/chemistry , Fluorescent Dyes/chemistry , Heterocyclic Compounds, 1-Ring/chemistry , Hydrazines/analysis , Water Pollutants, Chemical/chemistry , HeLa Cells , Humans , Luminescent Measurements , Molecular Structure , Optical ImagingABSTRACT
o-Alkenylation of unprotected phenols has been developed by direct C-H functionalization catalyzed by PdII . This work features phenol group as a directing group and realizes highly site-selective C-H bond functionalization of phenols to achieve the corresponding products in moderate to excellent yields at 60 °C. The advantages of this reaction include unprecedented C-H functionalization using phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C-H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under this catalytic system in good yields. Furthermore, this novel method enables a late-stage modification of complex phenol-containing bioactive molecules toward a diversity-oriented drug discovery.