Design of mitochondria-targeted colorimetric and ratiometric fluorescent probes for rapid detection of SO 2 derivatives in living cells

Yang, Yutao; Zhou, Tingting; Bai, Bozan; Yin, Caixia; Xu, Wenjun; Li, Wei

doi:10.1016/j.saa.2018.01.066

Cited by 28 publications

(2 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Considering that the main difficulty to specifically synthesize unsymmetrical Cy7 was the lack of disparity in reactivity upon condensation in the two imine groups, we decided to take full advantage of structural characteristics of furfural and exploit a new stepwise condensation strategy to regioselectively synthesize unsymmetrical Cy7. We anticipated that the first condensation could be facilely realized by the Knowengel reaction between furfural and 1 equiv of the heterocycle to afford half-cyanine 4a, 18 and then after the ring opening of the furan ring and affording the half-Stenhouse salt, the second condensation could be accomplished by reacting with another equivalent of the heterocycle. In such a manner, the regioselectivity of both steps of condensation are controllable, and desired unsymmetrical Cy7 could be accessed without the formation of the undesired Cy7 isomer.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of Heptamethine Cyanines from Furfural Derivatives

Hao

Wang

et al. 2023

Org. Lett.

View full text Add to dashboard Cite

Despite the widespread theranostic utilization of cyanine dyes (Cy7), their synthetic method is still limited with pyridine or cyclohexanone derivatives as starting materials. Herein, we report the synthesis of Cy7 from furfural derivatives. First, a one-pot reaction strategy is developed to solve the unstable problem of the Stenhouse salts. Second, a stepwise condensation strategy is exploited to regioselectively synthesize asymmetrical Cy7. The methodology possesses advantages, such as easy handling, high yield, wide substrate scopes, and good functional group tolerance.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of Heptamethine Cyanines from Furfural Derivatives

Hao

Wang

et al. 2023

Org. Lett.

View full text Add to dashboard Cite

show abstract

“…As shown by Scheme 8, probe 33 [66] was a symmetrical semicarbazide structure that allows the probe to undergo two nucleophilic addition reactions with HSO 3 − , thus enabling the detection of large concentrations of HSO 3 − /SO 3 2− and is the probe with the fastest response time (<30 s). In 2017, Yang [67] et al developed two ratiometric probes 34a and 34b based on the electron-poor double bond structure. They studied the spectral properties of both probes and found that 34a has an emission at 568 nm, while 34b has an emission at 644 nm.…”

Section: Ict Mechanismsmentioning

confidence: 99%

Small-Molecule Fluorescent Probe for Detection of Sulfite

Chen

Wang

et al. 2022

Pharmaceuticals

View full text Add to dashboard Cite

Sulfite is widely used as an antioxidant additive and preservative in food and beverages. Abnormal levels of sulfite in the body is related to a variety of diseases. There are strict rules for sulfite intake. Therefore, to monitor the sulfite level in physiological and pathological events, there is in urgent need to develop a rapid, accurate, sensitive, and non−invasive approach, which can also be of great significance for the improvement of the corresponding clinical diagnosis. With the development of fluorescent probes, many advantages of fluorescent probes for sulfite detection, such as real time imaging, simple operation, economy, fast response, non−invasive, and so on, have been gradually highlighted. In this review, we enumerated almost all the sulfite fluorescent probes over nearly a decade and summarized their respective characteristics, in order to provide a unified platform for their standardized evaluation. Meanwhile, we tried to systematically review the research progress of sulfite small−molecule fluorescent probes. Logically, we focused on the structures, reaction mechanisms, and applications of sulfite fluorescent probes. We hope that this review will be helpful for the investigators who are interested in sulfite−associated biological procedures.

show abstract

A Ratio Fluorescent Probe for the Detection of Bisulfite and Its Application in Living Cells

et al. 2021

View full text Add to dashboard Cite

Sulfur dioxide derivatives play excellently vital roles in numerous essential physiology and pathology processes of living systems. The abnormal levels of bisulfite/sulfite (HSO 3 À /SO 3 2À ) may cause the occurrence of a series of diseases, including acute symptoms of respiratory disease, brain damage, neurological disorders, cardiovascular disease, and even cancer. Therefore, it is necessary to develop simple and effective methods to monitor the fluctuation of HSO 3is devised to trace HSO 3 À /SO 3 2À in living cells. In the presence of HSO 3 À /SO 3 2À , the large conjugated system is destroyed by triggering the Michael addition reaction, which further induce the probe to emit a ratio of fluorescence signal. Furthermore, the probe can quickly respond to HSO 3 À /SO 3 2À within 120 s and exhibits low detection limit, which provides the possibility of sensitive and real-time detection of HSO 3 À / SO 3 2À in living cells. Based on the unique advantages of high selectivity, negligible cytotoxicity and great biocompatibility, Cy-DBPS can effectively detect exogenous and endogenous HSO 3 À /SO 3 2À in HepG2 and HeLa cells. The outstanding properties of the probe Cy-DBPS provided a great potential for the further valuable application in living cells and even deeper biological applications for HSO 3 À /SO 3 2À detection.

show abstract

Design of mitochondria-targeted colorimetric and ratiometric fluorescent probes for rapid detection of SO 2 derivatives in living cells

Cited by 28 publications

References 33 publications

Synthesis of Heptamethine Cyanines from Furfural Derivatives

Synthesis of Heptamethine Cyanines from Furfural Derivatives

Small-Molecule Fluorescent Probe for Detection of Sulfite

A Ratio Fluorescent Probe for the Detection of Bisulfite and Its Application in Living Cells

Contact Info

Product

Resources

About