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Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species.

ABSTRACT: We report self-assembled novel triphenylphosphonium-conjugated dicyanostilbene-based as selective fluorescence turn-on probes for ¹O? and ClO-. Mono- or di-triphenylphosphonium-conjugated dicyanostilbene derivatives 1 and 2 formed spherical structures with diameters of ca. 27 and 56.5 nm, respectively, through ?-? interaction between dicyanostilbene groups. Self-assembled 1 showed strong fluorescent emission upon the addition of ¹O? and ClO- compared to other ROS (O?-, •OH, NO, TBHP, H?O?, GSH), metal ions (K?, Na?), and amino acids (cysteine and histidine). Upon addition of ¹O? and ClO-, the spherical structure of 1 changed to a fiber structure (8-nm wide; 300-nm long). Upon addition of ¹O? and ClO-, the chemical structural conversion of 1 was determined by FAB-Mass, NMR, IR and Zeta potential analysis, and the strong emission of the self-assembled 1 was due to an aggregation-induced emission enhancement. This self-assembled material was the first for selective ROS as a fluorescence turn-on probe. Thus, a nanostructure change-derived turn-on sensing strategy for ¹O? or ClO- may offer a new approach to developing methods for specific guest molecules in biological and environmental subjects.

SUBMITTER: Choi W

PROVIDER: S-EPMC6316551 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species.

Choi Wonjin W Lim Na Young NY Choi Heekyoung H Seo Moo Lyong ML Ahn Junho J Jung Jong Hwa JH

Nanomaterials (Basel, Switzerland) 20181212 12

We report self-assembled novel triphenylphosphonium-conjugated dicyanostilbene-based as selective fluorescence turn-on probes for ¹O₂ and ClO-. Mono- or di-triphenylphosphonium-conjugated dicyanostilbene derivatives 1 and 2 formed spherical structures with diameters of ca. 27 and 56.5 nm, respectively, through π-π interaction between dicyanostilbene groups. Self-assembled 1 showed strong fluorescent emission upon the addition of ¹O₂ and ClO- compared to ...[more]

PMID: 30545092

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Project description:Reactive oxygen species (ROS) function as critical mediators in a broad range of cellular signaling processes. The mitochondrial electron transport chain is one of the major contributors to ROS formation in most cells. Increasing evidence indicates that the respiratory Complex II (CII) can be the predominant ROS generator under certain conditions. A computational, mechanistic model of electron transfer and ROS formation in CII was developed in the present study to facilitate quantitative analysis of mitochondrial ROS production. The model was calibrated by fitting the computer simulated results to experimental data obtained on submitochondrial particles (SMP) prepared from bovine and rat heart mitochondria upon inhibition of the ubiquinone (Q)-binding site by atpenin A5 (AA5) and Complex III by myxothiazol, respectively. The model predicts that only reduced flavin adenine dinucleotide (FADH2) in the unoccupied dicarboxylate state and flavin semiquinone radical (FADH•) feature the experimentally observed bell-shaped dependence of the rate of ROS production on the succinate concentration upon inhibition of respiratory Complex III (CIII) or Q-binding site of CII, i.e., suppression of succinate-Q reductase (SQR) activity. The other redox centers of CII such as Fe-S clusters and Q-binding site have a hyperbolic dependence of ROS formation on the succinate concentration with very small maximal rate under any condition and cannot be considered as substantial ROS generators in CII. Computer simulation results show that CII disintegration (which results in dissociation of the hydrophilic SDHA/SDHB subunits from the inner membrane to the mitochondrial matrix) causes crucial changes in the kinetics of ROS production by CII that are qualitatively and quantitatively close to changes in the kinetics of ROS production by assembled CII upon inhibition of CIII or Q-binding site of CII. Thus, the main conclusions from the present computational modeling study are the following: (i) the impairment of the SQR activity of CII resulting from inhibition of CIII or Q-binding site of CII and (ii) CII disintegration causes a transition in the succinate-dependence of ROS production from a small-amplitude sigmoid (hyperbolic) shape, determined by Q-binding site or [3Fe-4S] cluster to a high-amplitude bell-shaped kinetics with a shift to small subsaturated concentrations of succinate, determined by the flavin site.

Dataset Information

Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species.

Publications

Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species.

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