RESUMO
Phosgene and its substitutes (diphosgene and triphosgene) are widely utilized as chemical industrial materials and chemical warfare agents and pose a threat to public health and environmental safety due to their extreme toxicity. Research efforts have been directed to develop selective and sensitive detection methods for phosgene and its substitutes. In this paper, we have prepared two BODIPY-based fluorescent probes, o-Pah and o-Pha, which are two isomers with different active sites, ortho-aminohydroxy (3',4' or 4',3') phenyls at meso position of BODIPY, and compared their sensing performance toward triphosgene. The probe with o-(4'-amino-3'-hydroxyl), o-Pha, exhibits better sensing performance over the o-(3'-amino-4'-hydroxyl), o-Pah, for instance, a lower limit of detection (LOD) (0.34â nm vs. 1.2â nm), and more rapid response (10â s vs. 200â s). Furthermore, based on the above comparative studies, a red-fluorescence probe o-Phae has been constructed through extending 3,5-conjugation of o-Pha. The probe o-Phae displays rapid response (60â s), high sensitivity to triphosgene (LOD=0.88â nm), and high selectivity for triphosgene over relevant analytes including nitric oxide. Finally, a facile test strip for phosgene was fabricated by immobilizing o-Phae in a polyethylene oxide membrane for sensitive (<2â ppm) and selective detection of phosgene in the gas phase.
RESUMO
Nitric oxide (NO) is an important signaling molecule involved in many physiological and pathological processes. To understand these NO-mediated processes, it is a key to develop rapid and specific detection methods for NO. In the past 2 decades, numerous excellent fluorescent probes for NO have been designed; however, it still remains limitations such as slow response, low selectivity, and short excitation wavelength (<600 nm). In this Article, a two-photon fluorescent probe, NO-QA5, has been developed with 3-dimethylaminophenyl linking at the 6-position of 5-aminoquinoline as both the active site and prefluorophore for detection of NO. The nonfluorescent NO-QA5 can fast react with NO via a diazonium intermediate to generate two azoic regioisomers, one of which exhibits intramolecular charge transfer (ICT) emission, and two-photon absorption behavior (Î´Φ = 57 GM), giving a turn-on fluorescence rapid response. The sensing reaction is pH-insensitive in the range of 6-11 and highly selective and well sensitive (LOD = 15 nM), possible undergoing the same intermediate diazonium with the reaction under diazotization condition (NaNO2/HCl). Also, as a nitrite fluorescent probe NO-QA5 exhibits highly sensitive (LOD = 7 nM). Therefore, NO-QA5 can serve as a dual functional fluorescent probe for NO and NO2-. Furthermore, NO-QA5 as a specific imaging agent has been demonstrated by achieving both exogenous and endogenous detections of NO in living cells under both one- and two-photon excitation and high resolution in tissue slices under two-photon excitation.
Assuntos
Corantes Fluorescentes/química , Fígado/metabolismo , Microscopia de Fluorescência por Excitação Multifotônica , Óxido Nítrico/análise , Animais , Sobrevivência Celular/efeitos dos fármacos , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/toxicidade , Concentração de Íons de Hidrogênio , Limite de Detecção , Camundongos , Óxido Nítrico/metabolismo , Nitroprussiato/química , Células RAW 264.7 , Ratos , Espectrometria de Fluorescência , Imagem com Lapso de TempoRESUMO
Mercury ion (Hg2+), a heavy metal cation with greater toxicity, is widely present in the ecological environment and has become a serious threat to human health and environmental safety. Currently, developing a solution to simultaneously visualize and monitor Hg2+ in environmental samples, including water, soil, and plants, remains a great challenge. In this work, we created and synthesized a near-infrared fluorescent probe, BBN-Hg, and utilized Hg2+ to trigger the partial cleavage of the carbon sulfate ester in BBN-Hg as a sensing mechanism, and the fluorescence intensity of BBN-Hg was significantly enhanced at 650 nm, thus realizing the visualization of Hg2+ with good selectivity (detection limit, 53 nM). In live cells and zebrafish, the probe BBN-Hg enhances the red fluorescence signal in the presence of Hg2+, and successfully performs 3D imaging on zebrafish, making it a powerful tool for detecting Hg2+ in living systems. More importantly, with BBN-Hg, we are able to detect Hg2+ in actual water samples, soil and plant seedling roots. Furthermore, the probe was prepared as a test strip for on-site determination of Hg2+ with the assistance of a smartphone. Therefore, this study offers an easy-to-use and useful method for tracking Hg2+ levels in living organisms and their surroundings.
RESUMO
Heavy metals, including Hg2+, Cr6+ and Cd2+, have always been a major issue in environmental pollution, leading to abnormal changes in the levels of biologically active molecules including Cys in plants, seriously affecting all aspects of the growth and development of plants. This makes it essential to develop a simple and practical method to study the potential impact of heavy metals on plants. In this paper, our research group has developed near-infrared fluorescent probe WRM-S, which has the advantages of fast response, sensitivity to Cys, and successfully applying it to cells and zebrafish. Moreover, it combined the close relationship between heavy metal stress on plants and Cys, using Cys as the detection target, monitoring the internal environment changes of two plants under Hg2+, Cr6+, and Cd2+ stress in the environment, and then conducting 3D imaging. The results indicated that the probe has strong penetration ability in plant tissues, and revealed abnormal changes in plant Cys levels caused by heavy metal stress-induced cellular oxidative stress or cytotoxicity. Thus, the in-situ imaging detection of this probe provides a direction for the physiological dynamics research of plant environmental stress.
Assuntos
Cisteína , Corantes Fluorescentes , Metais Pesados , Raízes de Plantas , Peixe-Zebra , Corantes Fluorescentes/química , Cisteína/metabolismo , Cisteína/química , Animais , Raízes de Plantas/metabolismo , Raízes de Plantas/química , Raízes de Plantas/efeitos dos fármacos , Arabidopsis/efeitos dos fármacos , Arabidopsis/metabolismoRESUMO
Hydrogen sulfide (H2S) is a hazardous gas found in living organisms and is directly tied to our daily lives. Recent studies show that it plays a significant role in plant growth, development, and response to environmental stresses. However, few of the reported near-infrared (NIR) fluorescent probes have been applied to rice and deeply investigated the influence of the external environment on the biological molecules in its internal environment. Therefore, our team created BSZ-H2S, which has the advantage of an emission wavelength of up to 720 nm with fast response, successfully applying it to cell and zebrafish imaging. More importantly, the probe detected H2S in rice roots by in situ imaging in a facile manner and verified the existence of an upregulation process of H2S in response to salt and drought stress. This work provides a concept for the intervention of external stresses in rice culture.
Assuntos
Sulfeto de Hidrogênio , Oryza , Animais , Humanos , Corantes Fluorescentes , Secas , Peixe-Zebra , Cloreto de Sódio , Cloreto de Sódio na Dieta , Imagem Óptica , Células HeLaRESUMO
The reaction of hydrazides with triphosgene in the presence of triethylamine is a facile method to construct various oxadiazolones. Utilizing this reaction, a new class of colorimetric and fluorogenic phosgene chemosensors were developed with the BODIPY as fluorophore, five BODIPY-based hydrazides, which exhibited highly effective reactions with phosgene. The mechanism was updated. Finally, the test paper with a hydrazide was fabricated for facile, selective, and visual detection of phosgene gas.