Sensitive hydrazine detection and quantification with a fluorescent benzothiadiazole sensor: selective lipid droplets and<i>in vivo</i>imaging

Santos, Camila O. dos; Passos, Saulo T. A.; Sorto, Jenny E. P.; Machado, Daniel F. S.; Corrêa, José R.; Júnior, Eufrânio N. da Silva; Rodrigues, Marcelo O.; Neto, Brenno A. D.

doi:10.1039/d3ob00007a

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00007a

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Sensitive hydrazine detection and quantification with a fluorescent benzothiadiazole sensor: selective lipid droplets andin vivoimaging

Camila O. dos Santos

Saulo T. A. Passos

Jenny E. P. Sorto

et al.

Abstract: A selective hydrazine sensor in solution based on the 2,1,3-benzothiadiazole heterocycle is efficient for in vitro and in vivo analyses. This sensor generates water as the only byproduct, avoiding generation of toxic compounds and interference during in vivo applications.

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Cited by 6 publications

References 150 publications

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5‐N,N‐Diarylaminothiazoles with Electron‐Accepting Groups: Synthesis, Photophysical Properties, and Their Application for the Detection of Hydrazine Hydrate

Murai,

Tanaka,

Takekoshi

et al. 2023

Eur J Org Chem

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Abstract5‐N,N‐diarylaminothiazoles containing cyano and nitro groups were synthesized using the Pd‐catalyzed Buchwald‐Hartwig amination reaction with good yields. The cyano group in the resultant thiazole was reduced to a formyl group. This was then subjected to the Knoevenagel condensation reaction, leading to the formation of thiazoles with a dicyanovinyl group. The nitro group in the thiazole was reduced to an amino group, which was subsequently reacted with triphosgene, yielding a thiazole with an isocyanate group. These thiazoles, with their electron‐accepting properties, demonstrated absorption and emission spectra at longer wavelengths. Notably, the thiazole containing the dicyanovinyl group displayed a red emission. Tests for the detection of hydrazine, a hazardous volatile organic compound, were conducted using the synthesized thiazoles. The results showed that the dicyanovinyl group effectively responded to hydrazine hydrate, evidenced by changes in the absorption and emission spectra. This change in color was also visibly detectable to the naked eye.

show abstract

5‐N,N‐Diarylaminothiazoles with Electron‐Accepting Groups: Synthesis, Photophysical Properties, and Their Application for the Detection of Hydrazine Hydrate

Murai,

Tanaka,

Takekoshi

et al. 2023

Eur J Org Chem

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show abstract

Carbazole-pyrimidine-based novel ratiometric fluorescent probe with large Stokes shift for detection of hydrazine in real environments and organisms

Shen,

Yang,

et al. 2025

Journal of Hazardous Materials

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Phenothiazine-based fluorescent probes for the detection of hydrazine in environment and living cells

Xia,

Wang,

Han

et al. 2024

Talanta

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Sensitive hydrazine detection and quantification with a fluorescent benzothiadiazole sensor: selective lipid droplets andin vivoimaging

Abstract: A selective hydrazine sensor in solution based on the 2,1,3-benzothiadiazole heterocycle is efficient for in vitro and in vivo analyses. This sensor generates water as the only byproduct, avoiding generation of toxic compounds and interference during in vivo applications.

Cited by 6 publications

References 150 publications

5‐N,N‐Diarylaminothiazoles with Electron‐Accepting Groups: Synthesis, Photophysical Properties, and Their Application for the Detection of Hydrazine Hydrate

5‐N,N‐Diarylaminothiazoles with Electron‐Accepting Groups: Synthesis, Photophysical Properties, and Their Application for the Detection of Hydrazine Hydrate

Carbazole-pyrimidine-based novel ratiometric fluorescent probe with large Stokes shift for detection of hydrazine in real environments and organisms

Phenothiazine-based fluorescent probes for the detection of hydrazine in environment and living cells

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