A simple fluorescent probe for sensing cysteine over homocysteine and glutathione based on PET

Fan, Wenlong; Huang, Ximing; Shi, Xiaomin; Wang, Zhuo; Lü, Zhengliang; Fan, Chunhua; Bo, Qi‐Bing

doi:10.1016/j.saa.2016.10.060

Cited by 40 publications

(15 citation statements)

References 50 publications

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“…Therefore, it is important for the early diagnosis and treatment of vascular disease. Early Hcy-selective detection methods involved high-performance liquid chromatography (HPLC), electrochemical detection, capillary electrophoresis (CE), UV-Vis spectroscopy, and fluorescence spectroscopy [12][13][14][15][16][17][18]. Hcy detection using fluorescence spectroscopy is generally used because of its high sensitivity, facile operation, visual signal transduction, and suitability for in vivo analysis.…”

Section: Introductionmentioning

confidence: 99%

Simple and Novel Assay of the Host-Guest Complexation of Homocysteine with Cucurbit[7]uril

Park¹,

Lee²,

Cho³

et al. 2019

Journal of Microbiology and Biotechnology

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This paper introduces three ways to determine host-guest complexation of cucurbit[7]uril (CB[7]) with homocysteine (Hcy). After preincubating Hcy and cysteine (Cys) with CB[7], Ellman's reagent (DTNB) was used to detect Hcy and Cys. Only Cys reacted with DTNB and Hcy gave a retarded color change. This suggests that the-SH group of Hcy is buried inside CB[7]. Human cystathionine γ-lyase (hCGL) decreased the level of Hcy degradation after preincubating Hcy and CB[7]. These results suggest that the amount of free Hcy available was decreased by the formation of a Hcy-CB[7] complex. The immunological signal of anti-Hcy monoclonal antibody was decreased significantly by preincubating CB[7] with Hcy. The ELISA results also show that ethanethiol group (-CH 2 CH 2 SH) of Hcy, which is an epitope of anti-Hcy monoclonal antibody, was blocked by the cavity in CB[7]. Overall, CB[7] can act as a host by binding selectively with Hcy, but not Cys. The calculated half-complexation formation concentration of CB[7] was 58.2 nmol using Ellman's protocol, 97.9 nmol using hCGL assay and 87.7 nmol using monoclonal antibody. The differing binding abilities of Hcy and Cys towards the CB[7] host may offer a simple and useful method for determining the Hcy concentration in plasma or serum.

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Section: Introductionmentioning

confidence: 99%

Simple and Novel Assay of the Host-Guest Complexation of Homocysteine with Cucurbit[7]uril

Park¹,

Lee²,

Cho³

et al. 2019

Journal of Microbiology and Biotechnology

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“…On the basis of tandem conjugate addition and intramolecular cyclization, Yang et al [33] developed a fluorescent probe for detection of Cys and the probe shows selectivity for Cys over other biothiols. Up to now, some fluorescent probes can selectively monitor Cys [34][35][36]. However, most of these probes have complicated structures and large molecular weight, which may not enter the cells or organisms easily in the real applications.…”

Section: Introductionmentioning

confidence: 99%

A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish

Zhu

Wang

et al. 2019

Analytica Chimica Acta

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Cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) play many crucial physiological roles in organisms. Their abnormal levels can cause and indicate various diseases. In the present study, a small-molecule fluorescent probe 2-(imidazo[1,2-a]pyridin-2-yl)phenyl acrylate (IPPA) was designed, synthesized and characterized by NMR, FT-IR and HRMS. IPPA can selectively detect Cys over other analytes because of an approximately 76 times enhancement in fluorescence intensity. The limit of detection of IPPA for Cys was 0.33 μM. The pseudo-first-order rate constant of the reaction between IPPA and Cys was approximately 10 times that of the reaction between IPPA and Hcy (K Cys 3.18 × 10 −3 S −1 vs K Hcy 4.92 × 10 −4 S −1), indicating that Cys can be distinguished from Hcy. In addition, IPPA exhibits strong anti-interference ability, small molecular weight, high efficiency, low toxicity and good cell permeability. It was successfully used in imaging HepG2 cells and zebrafish. The fluorescence response of IPPA for calf serum are powerful proofs for practical application. Therefore, IPPA has high potential for bioassay applications.

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“…For the synthesis of Cy 1395 , the intermediate Cy 641 was synthesized by replacing the chlorine atom of IR-813 with 1,2-ethanedithiol. The fluorescence of Cy 641 was quenched due to the photoinduced electron transfer (PET) effect of the tail sulfhydryl group 75 (Fig. S10 †).…”

Section: Design Synthesis Characterization and Optical Propertiesmentioning

confidence: 99%

A novel active mitochondrion-selective fluorescent probe for the NIR fluorescence imaging and targeted photodynamic therapy of gastric cancer

et al. 2022

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A simple fluorescent probe for sensing cysteine over homocysteine and glutathione based on PET

Cited by 40 publications

References 50 publications

Simple and Novel Assay of the Host-Guest Complexation of Homocysteine with Cucurbit[7]uril

Simple and Novel Assay of the Host-Guest Complexation of Homocysteine with Cucurbit[7]uril

A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish

A novel active mitochondrion-selective fluorescent probe for the NIR fluorescence imaging and targeted photodynamic therapy of gastric cancer

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