Dataset Information

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications.

ABSTRACT: The ability to detect hypochlorite (HOCl/ClO^-) in vivo is of great importance to identify and visualize infection. Here, we report the use of imidazoline-2-thione (R ₁ SR ₂ ) probes, which act to both sense ClO^- and kill bacteria. The N₂C=S moieties can recognize ClO^- among various typical reactive oxygen species (ROS) and turn into imidazolium moieties (R ₁ IR ₂ ) via desulfurization. This was observed through UV-vis absorption and fluorescence emission spectroscopy, with a high fluorescence emission quantum yield (Փ_F = 43-99%) and large Stokes shift (∆v∼115 nm). Furthermore, the DIM probe, which was prepared by treating the DSM probe with ClO^-, also displayed antibacterial efficacy toward not only Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) but also methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum ß-lactamase-producing Escherichia coli (ESBL-EC), that is, antibiotic-resistant bacteria. These results suggest that the DSM probe has great potential to carry out the dual roles of a fluorogenic probe and killer of bacteria.

SUBMITTER: Pham TC

PROVIDER: S-EPMC8311462 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications.

Pham Thanh Chung TC Nguyen Van-Nghia VN Choi Yeonghwan Y Kim Dongwon D Jung Ok-Sang OS Lee Dong Joon DJ Kim Hak Jun HJ Lee Myung Won MW Yoon Juyoung J Kim Hwan Myung HM Lee Songyi S

Frontiers in chemistry 20210712

The ability to detect hypochlorite (HOCl/ClO-) in vivo is of great importance to identify and visualize infection. Here, we report the use of imidazoline-2-thione (R 1 SR 2 ) probes, which act to both sense ClO- and kill bacteria. The N2C=S moieties can recognize ClO- among various typical reactive oxygen species (ROS) and turn into imidazolium moieties (R 1 IR <su ...[more]

PMID: 34322477

Similar Datasets

Project description:Fluorescein derivatives with thermally activated delayed fluorescence (TADF) show much stronger competition ability and vaster prospects than traditional fluorescein dyes due to their prominent long lifetime. It will be of great significance to synthesize more fluorescein derivatives with TADF. In this work, compounds DCF-MPYA and FL with TADF properties were obtained by fine tuning the substituents' structure on the basis of fluorescein derivative DCF-MPYM. Their long-lived triplet excited states (21.78 μs, 32.0 μs) were proved by nanosecond time-resolved transient difference absorption spectra. The steady-state and time-resolved fluorescence spectra showed that DCF-MPYA and FL exhibited red fluorescence around 645 nm and 651 nm, respectively. The results of sensitivity to oxygen and heavy atoms further demonstrated that the time-resolved fluorescence spectra originate from the delayed fluorescence. The time correlated single-photon counting (TCSPC) data indicated that DCF-MPYA and FL showed long-lived lifetimes of 13.16 μs and 23.72 μs, respectively. The energy gap (ΔE ST) between the singlet (S1) and triplet (T1) states of DCF-MPYA and FL was calculated to be 3.32 meV and 9.98 meV from the decay rate of DF as a function of temperature. The small energy gap is conducive to the occurrence of efficient TADF at room temperature. Meanwhile, Gaussian calculation was employed to observe the electron density of DCF-MPYA and FL in the ground and excited states. The calculation results indicate that the shapes and energy levels of the highest occupied molecular orbitals (HOMOs), lowest unoccupied molecular orbitals (LUMOs), and LUMOs+1 for the monoanion and dianion forms are similar and thus DCF-MPYA and FL exhibit almost the same luminescence properties. Finally, DCF-MPYA and FL with low toxicity were used in confocal and time-resolved fluorescence imaging. Our construction strategy will be beneficial for developing more fluorescein derivatives with TADF in the future.

Dataset Information

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications.

Publications

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets