A resorufin-based fluorescent probe for hydrazine detection and its application in environmental analysis and bioimaging

Ruan, Minghao; Zhang, Bo; Wang, Jiamin; Fan, Guanwen; Lu, Xiaoyan; Zhang, Jian; Zhao, Weili

doi:10.1039/d3ay01629c

Cited by 1 publication

(1 citation statement)

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“…The identification and quantification of hydrazine in various environments remains a relevant task. Over the years, several chemical sensors for hydrazine have been developed [9][10][11]. Turnon fluorescent detection of hydrazine is probably the most attractive method and some examples in both environmental and biological systems have been reported [12][13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Turn-on Coumarin Precursor: From Hydrazine Sensor to Covalent Inhibition and Fluorescence Detection of Rabbit Muscle Aldolase

Amer,

Miles,

Firer

et al. 2024

Molecules

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Hydrazine, a highly toxic compound, demands sensitive and selective detection methods. Building upon our previous studies with pre-coumarin OFF–ON sensors for fluoride anions, we extended our strategy to hydrazine sensing by adapting phenol protecting groups (propionate, levulinate, and γ-bromobutanoate) to our pre-coumarin scaffold. These probes reacted with hydrazine, yielding a fluorescent signal with low micromolar limits of detection. Mechanistic studies revealed that hydrazine deprotection may be outperformed by a retro-Knoevenagel reaction, where hydrazine acts as a nucleophile and a base yielding a fluorescent diimide compound (6,6′-((1E,1′E)-hydrazine-1,2diylidenebis(methaneylylidene))bis(3(diethylamino)phenol, 7). Additionally, our pre-coumarins unexpectedly reacted with primary amines, generating a fluorescent signal corresponding to phenol deprotection followed by cyclization and coumarin formation. The potential of compound 3 as a theranostic Turn-On coumarin precursor was also explored. We propose that its reaction with ALDOA produced a γ-lactam, blocking the catalytic nucleophilic amine in the enzyme’s binding site. The cleavage of the ester group in compound 3 induced the formation of fluorescent coumarin 4. This fluorescent signal was proportional to ALDOA concentration, demonstrating the potential of compound 3 for future theranostic studies in vivo.

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Section: Introductionmentioning

confidence: 99%

Turn-on Coumarin Precursor: From Hydrazine Sensor to Covalent Inhibition and Fluorescence Detection of Rabbit Muscle Aldolase

Amer,

Miles,

Firer

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

A resorufin-based fluorescent probe for hydrazine detection and its application in environmental analysis and bioimaging

Abstract: A novel “turn-on” fluorescent probe RFT for selective detection of N2H4 was constructed. RFT could not only detect the exogenous hydrazine in zebrafish and mice, but also image the up-regulation of endogenous N2H4 induced by isoniazid in zebrafish.

Cited by 1 publication

References 55 publications

Turn-on Coumarin Precursor: From Hydrazine Sensor to Covalent Inhibition and Fluorescence Detection of Rabbit Muscle Aldolase

Turn-on Coumarin Precursor: From Hydrazine Sensor to Covalent Inhibition and Fluorescence Detection of Rabbit Muscle Aldolase

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