A novel colorimetric and ratiometric fluorescent probe for cysteine based on conjugate addition-cyclization-elimination strategy with a large Stokes shift and bioimaging in living cells

Zhu, Dandan; Yan, Xiao‐Wei; Ren, Aishan; Xie, Wei; Duan, Zhenhua

doi:10.1016/j.aca.2019.01.013

Cited by 29 publications

(5 citation statements)

References 52 publications

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“…When Cys was added, the Michael addition occurred between Cys and probe 2, and then generated seven-membered cyclolactam and uorophore compound 4 (Scheme 2a) through the intramolecular cyclization. 28,[37][38][39][40][41] Moreover, due to the inuence of ring tension and spatial steric hindrance, 26 probe 2 had a poor ability to identify Hcy and GSH. Furthermore, the reaction between probe 2 and Cys was further supported by in situ 1 H NMR study (Scheme 2b).…”

Section: Reaction Mechanism and Density Functional Theory Studiesmentioning

confidence: 99%

A novel fluorescent probe with a large Stokes shift for colorimetric and selective detection of cysteine in water, milk, cucumber, pear and tomato

Luo,

Guo,

Wang

et al. 2024

Anal. Methods

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Section: Reaction Mechanism and Density Functional Theory Studiesmentioning

confidence: 99%

A novel fluorescent probe with a large Stokes shift for colorimetric and selective detection of cysteine in water, milk, cucumber, pear and tomato

Luo,

Guo,

Wang

et al. 2024

Anal. Methods

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“…In addition to the Michael addition reaction, RTCs can easily undergo nucleophilic substitution reactions with appropriate compounds [33] . Many studies have designed probes with significant…”

Section: Principle Of the Reaction Between Rtcs And Biosensor Probementioning

confidence: 99%

“…With the absorption wavelength red shift, strong NIR fluorescence emission can be observed at 760 nm, thus guiding the detection of Cys (Figure 5). This kind of fluorescent probe with Michael addition as the basic reaction generally has a large Stokes shift, can detect the corresponding substances with high sensitivity, and has great potential in the detection of RTCs content in living cells [33‐34] …”

Section: Principle Of the Reaction Between Rtcs And Biosensor Probementioning

confidence: 99%

Reduced Thiol Compounds – Induced Biosensing, Bioimaging Analysis and Targeted Delivery

et al. 2020

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Reduced thiol compounds (RTCs), such as glutathione (GSH), cysteine (Cys), and homocysteine (Hcy), are important components of many amino acids and proteins. They are also basic building blocks that make up organisms and play an important role in physiology and pathology. Therefore, based on the fundamental characteristics of RTCs in vivo, researchers have reported their use in biosensing and imaging analysis and as carriers in life sciences and health sciences. In this review, we will introduce the principles of RTCs and highlight their applications in biosensing and imaging analysis and as carriers reported from 2015 to 2020. Yingshu Guo (top left) obtained her Ph.D. degree from Qingdao University of Science and Technology in 2012. She is currently a professor at Linyi University, China, with research interests in bioanalytical chemistry and chemical biology. Xiaofei Zheng (top middle) obtained his B.S. degree from Linyi University in 2019. Then he pursued his M.S. degree under the supervision of Prof. Yingshu Guo at Linyi University. His current research is focused on bioanalytical chemistry. Xiuping Cao (top right) obtained her B.S. degree from Shandong University of Traditional Chinese Medicine in 2019. Then she pursued her M.S. degree under the supervision of Prof. Yingshu Guo at Linyi University. Her current research is focused on bioanalytical chemistry and chemical biology. Wenxin Li (bottom left) obtained her B.S. degree from Qilu Institute of Technology in 2020. Then she pursued her M.S. degree under the supervision of Prof. Yingshu Guo at Linyi University. Her current research is focused on bioanalytical chemistry and chemical biology. Di Wu (bottom middle) obtained her B.S. degree from Linyi University in 2020. Then she pursued her M.S. degree under the supervision of Prof. Yingshu Guo at Linyi University. Her current research is focused on bioanalytical chemistry. Shusheng Zhang (bottom right) obtained his Ph.D. degree from Nanjing University in 1999. He is a leading researcher at Linyi University with research interests in bioanalytical chemistry.

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“…[ 4–6 ] If an aromatic group is connected with a second substituted phenyl ring through the vinylene linkage, the molecule with long chain‐conjugated system (such as stilbene and 1‐furyl/thienyl‐2‐arylethylene derivatives) will be formed, which plays an important role in photochemistry. [ 15–17 ]…”

Section: Introductionmentioning

confidence: 99%

Determination and application of the excited‐state substituent constants of pyridyl and substituted phenyl groups

Cao¹,

Yan²

2021

J of Physical Organic Chem

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Thirty six 1‐pyridyl‐2‐arylethenes XCH=CHArY (abbreviated XAEY) were synthesized, in which, X is 2‐pyridyl, 3‐pyridyl and 4‐pyridyl and Y is OMe, Me, H, Br, Cl, F, CF3, and CN. Their ultraviolet absorption spectra were measured in anhydrous ethanol, and their wavelengths of absorption maximum λmax were recorded. Also, the 234 λmax values of 1‐substituted phenyl‐2‐arylethylene compounds (XAEY, where X is substituted phenyl) were collected. The excited‐state substituent constants σCC()pex()X of three pyridyl groups and 23 substituted phenyl groups (total of 26) were obtained by means of curve‐fitting method. Taking the λmax values of 358 samples of bi‐arylethene derivatives as a data set and 126 samples of bi‐aryl Schiff bases (including nine compounds synthesized by this work) as another data set, quantitative correlation analyses were performed by employing the obtained σCC()pex()X as a parameter, and good results were obtained for the two data sets. The reliability of the obtained σCC()pex()X values was verified. The results of this paper can provide excited‐state substituent constants for the study and application of optical properties of conjugated organic compounds containing aryl groups.

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A novel colorimetric and ratiometric fluorescent probe for cysteine based on conjugate addition-cyclization-elimination strategy with a large Stokes shift and bioimaging in living cells

Cited by 29 publications

References 52 publications

A novel fluorescent probe with a large Stokes shift for colorimetric and selective detection of cysteine in water, milk, cucumber, pear and tomato

A novel fluorescent probe with a large Stokes shift for colorimetric and selective detection of cysteine in water, milk, cucumber, pear and tomato

Reduced Thiol Compounds – Induced Biosensing, Bioimaging Analysis and Targeted Delivery

Determination and application of the excited‐state substituent constants of pyridyl and substituted phenyl groups

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