Fluorogenic bisazide cyanine probe as a highly efficient acrolein detection tool for diagnosing triple negative breast cancer

Choi, Hyun Sun; Yum, Ji Hye; Jeong, Yeonsu; Lim, S. I.; Kumagai, Tomotaka; Joon, Hyung; Park, Soyoung

doi:10.1016/j.snb.2023.133404

“…ACR can be produced in oxidative stress cells by amino acid and polyamine metabolism and lipid peroxidation . The abnormally elevated ACR is a biomarker of a range of disorders involving oxidative stress. , Therefore, we investigated the ability of the probe to monitor endogenous ACR under oxidative stress conditions. As shown in Figure , control group cells (5a) were incubated with only probe HBT-SH , and experimental group cells (5b) was pretreated with 1 μg/mL LPS, 100 ng/mL IFN-γ and 10 nM PMA to stimulate cells to undergo oxidative stress. , The results showed that the green channel fluorescence was significantly enhanced.…”

Section: Resultsmentioning

confidence: 99%

“…This method uses high-performance liquid chromatography to isolate the products, which is not suitable for rapid analysis of a large number of samples, and the reaction conditions are strict, which is not conducive to the detection of biological samples. − Alternatively, the adduct of ACR with protein or DNA can be detected using monoclonal antibodies, but this method is expensive, requires complex procedures, and has a delay of several hours between the production of ACR and the formation of the ACR adduct. , Therefore, in order to overcome the limitations of traditional methods, researchers have developed inexpensive and practical fluorescence probes for the determination of the ACR in biological samples. Few ACR fluorescent probes have been reported, which are further summarized in Table S1 (Supporting Information). − These probes are based on three different reaction types, including the formation of quinoline based on Skraup reaction, the formation of triazoline based on 1,3-dipolar cycloaddition, and Michael addition between the thiol group of the probe and vinyl group of ACR (Figure ). However, the above strategies are more or less faced with the following disadvantages, such as strict reaction conditions, unable to achieve effective fluorescence signal changes after reaction and poor selectivity.…”

Section: Introductionmentioning

confidence: 99%

Visualization of Acrolein Upregulation during Ferroptosis by a Ratiometric Fluorescent Probe

Duan,

Wang,

Zhang

et al. 2024

Anal. Chem.

1

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Ferroptosis is a pattern of cell death caused by irondependent accumulation of lipid peroxides and is closely associated with the occurrence and development of multiple diseases. Acrolein (ACR), one of the final metabolites of lipid peroxidation, is a reactive carbonyl species with strong biotoxicity. Effective detection of ACR is important for understanding its role in the progression of ferroptosis and studying the specific mechanisms of ferroptosis-mediated diseases. However, visualization detection of ACR during ferroptosis has not yet been reported. In this work, the first ratiometric fluorescent probe (HBT-SH) based on 2-(2′-hydroxyphenyl) benzothiazole (HBT) was designed for tracing endogenous ACR with an unprecedented regiospecific ACRinduced intramolecular cyclization strategy, which employs 2-aminoethanethiol as an ACR-selective recognition receptor. The experimental results showed that HBT-SH has excellent selectivity, high sensitivity (LOD = 0.26 μM) and good biocompatibility. More importantly, the upregulation of ACR levels was observed during ferroptosis in HeLa cells and zebrafish, indicating that ACR may be a specific active molecule that plays an essential biological role during ferroptosis or may serve as a potential marker of ferroptosis, which has great significance for studying the pathological process and treatment options of ferroptosis-related diseases.

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Atom‐Efficient Synthesis of Trimethine Cyanines Using Formaldehyde as a Single‐Carbon Source

Lee,

Sarkar

et al. 2024

Angewandte Chemie

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In this work, we present an innovative and atom‐efficient synthesis of trimethine cyanines (Cy3) using formaldehyde (FA) as a single‐carbon reagent. The widespread application of Cy3 dyes in bioimaging and genomics/proteomics is often limited by synthetic routes plagued with low atom economy and substantial side‐product formation. Through systematic investigation, we have developed a practical and efficient synthetic pathway for both symmetric and asymmetric Cy3 derivatives, significantly minimizing resource utilization. Notably, this approach yields water as the byproduct, in alignment with sustainable chemistry principles. Moreover, the efficient one‐pot synthesis facilitates the detection of intracellular FA levels, utilizing the fluorescence signal of Cy3 in live cells. It is also possible to detect the endogenous FA in the intestinal tissues. We observed a significant decrease of FA in the small intestine of the inflammatory bowel disease (IBD) mice compared to the healthy mice. This methodological advancement not only enhances the scope of fluorescent dye synthesis but also contributes to the sustainable practices within chemical manufacturing, offering a significant leap forward in the development of environmentally friendly synthetic strategies.

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Atom‐Efficient Synthesis of Trimethine Cyanines Using Formaldehyde as a Single‐Carbon Source

Lee,

Sarkar

et al. 2024

Angew Chem Int Ed

0

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In this work, we present an innovative and atom‐efficient synthesis of trimethine cyanines (Cy3) using formaldehyde (FA) as a single‐carbon reagent. The widespread application of Cy3 dyes in bioimaging and genomics/proteomics is often limited by synthetic routes plagued with low atom economy and substantial side‐product formation. Through systematic investigation, we have developed a practical and efficient synthetic pathway for both symmetric and asymmetric Cy3 derivatives, significantly minimizing resource utilization. Notably, this approach yields water as the byproduct, in alignment with sustainable chemistry principles. Moreover, the efficient one‐pot synthesis facilitates the detection of intracellular FA levels, utilizing the fluorescence signal of Cy3 in live cells. It is also possible to detect the endogenous FA in the intestinal tissues. We observed a significant decrease of FA in the small intestine of the inflammatory bowel disease (IBD) mice compared to the healthy mice. This methodological advancement not only enhances the scope of fluorescent dye synthesis but also contributes to the sustainable practices within chemical manufacturing, offering a significant leap forward in the development of environmentally friendly synthetic strategies.

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Fluorogenic bisazide cyanine probe as a highly efficient acrolein detection tool for diagnosing triple negative breast cancer

Cited by 5 publications

References 49 publications

Visualization of Acrolein Upregulation during Ferroptosis by a Ratiometric Fluorescent Probe

Visualization of Acrolein Upregulation during Ferroptosis by a Ratiometric Fluorescent Probe

Atom‐Efficient Synthesis of Trimethine Cyanines Using Formaldehyde as a Single‐Carbon Source

Atom‐Efficient Synthesis of Trimethine Cyanines Using Formaldehyde as a Single‐Carbon Source

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