Fluorometric detection of volatile amines using an indanonalkene platform

Zhang, Peng; Wu, Tianhong; Cao, Hui; Zhang, Jie; James, Tony D.; Sun, Xiaolong

doi:10.1039/d2qo02023h

Cited by 7 publications

(3 citation statements)

References 41 publications

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“…Our group recently reported a benzene-based indanonalkene photoluminescent platform suitable for the regulation of macromolecular properties and drug delivery. − However, the luminophores suffered from short emission wavelengths, and low quantum yields (<5%), and as such were not suitable for biological sensing and imaging in situ . To improve the optical properties, we designed and synthesized a new conjugate acceptor named TPA-CA , by introducing triphenylamine to the fundamental conjugate acceptor through Suzuki coupling, to extend electron conjugation and form an electron push–pull resonance structure (Scheme B). , The new molecule containing bis-vinylogous thioesters was nonfluorescent and underwent coupling with thiols and amines to form cyclic molecules, with subsequent fluorescence turn-on under mild conditions (see below).…”

Section: Resultsmentioning

confidence: 99%

A Rationally Designed Prodrug for the Fluorogenic Labeling of Albumin and Theranostic Effects on Drug-Induced Liver Injury

Wu,

Zhang,

Zhang

et al. 2024

Anal. Chem.

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The development of small-molecular fluorogenic tools for the chemo-selective labeling of proteins in live cells is important for the evaluation of intracellular redox homeostasis. Dynamic imaging of human serum albumin (HSA), an antioxidant protein under oxidative stress with concomitant release of antioxidant drugs to maintain redox homeostasis, affords potential opportunities for disease diagnosis and treatment. In this work, we developed a nonfluorogenic prodrug named TPA-NAC, by introducing N-acetyl-L-cysteine (NAC) into a conjugated acceptor skeleton. Through combined thiol and amino addition, coupling with HSA results in fluorescence turn-on and drug release. It was reasoned that the restricted intramolecular motion of the probe under an HSA microenvironment after covalent bonding inhibited the nonradiative transitions. Furthermore, the biocompatibility and photochemical properties of TPA-NAC enabled it to image exogenous and endogenous HSA in living cells in a wash-free manner. Additionally, the released drug evoked upregulation of superoxide dismutase (SOD), which synergistically eliminated reactive oxygen species in a drug-induced liver injury model. This study provides insights into the design of new theranostic fluorescent prodrugs for chemo-selective protein labeling and disease treatments.

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Section: Resultsmentioning

confidence: 99%

A Rationally Designed Prodrug for the Fluorogenic Labeling of Albumin and Theranostic Effects on Drug-Induced Liver Injury

Wu,

Zhang,

Zhang

et al. 2024

Anal. Chem.

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“…Most chemical reaction-based sensing systems share the same modulation strategies related to the above mechanisms (e.g., ICT, PET). 129,[158][159][160] A few examples explored the possibilities of utilizing the in situ formation of emissive products to realize the detection of some analytes. Dou et al designed a sensing system for the high-sensitive and selective detection of ethylenediamine by optimizing an efficient reaction between o-phthalaldehyde, thiols, and ethylenediamine (Fig.…”

Section: Energy Transfermentioning

confidence: 99%

Molecular design and architectonics towards film-based fluorescent sensing

Huang,

Liu,

Peng

et al. 2024

Chem. Soc. Rev.

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“…The sensing mechanisms of MA, DMA, and TMA have been studied both experimentally and theoretically. , Chang et al developed an ultrasensitive porous-electrode-capped organic gas sensor to determine freshness of fish . The results showed electrical sensing in 1 min compared to 4 h with the traditional titration method.…”

Section: Introductionmentioning

confidence: 99%

Density Functional Theory Studies of MXene-Based Nanosensors for Detecting Volatile Organic Compounds in Meat Spoilage Assessment

Vovusha,

Bae,

Lee

et al. 2023

ACS Appl. Nano Mater.

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Emission of selected volatile organic compounds (VOCs), such as methylamine (MA), dimethylamine (DMA), and trimethylamine (TMA), is associated with certain microbial reactions, causing intrinsic decomposition and spoilage of meat and fish. Efficient detection of MA, DMA, and TMA is vital for meat and fish spoilage assessment. Here, density functional theory (DFT) calculations are used to study the sensing properties of selected MXene monolayers (M 2 CT x ; M = Ti, Nb, V; T x = O, OH, F) toward MA, DMA, and TMA. We found that the binding energies of MA (−0.29 to −1.08 eV), DMA (−0.39 to −1.15 eV), and TMA (−0.28 to −1.19 eV) on M 2 CT x are ideal for reversible sensing. Appropriate binding of these VOCs is associated with measurable changes in the electronic properties of M 2 CT x , which is essential for a highly efficient sensing mechanism. Further, we used the Langmuir adsorption model to explore the sensing characteristics of M 2 CT x monolayers in varied temperature and pressure environments. Among the studied systems, Nb 2 C(OH) 2 exhibits excellent sensing capabilities toward DMA and TMA at concentrations below parts per million (ppm), whereas Nb 2 CF 2 exhibits selective adsorption of MA at concentrations below ppm. We strongly believe that our findings will pave the way for the development of highly sensitive nanosensors for monitoring the spoilage of meat and fish products.

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Fluorometric detection of volatile amines using an indanonalkene platform

Abstract: Excessive volatile amines are considered to cause environmental pollution and human health threatening, especially ammonia has been reported to be associated with a variety of human diseases. In this Article,...

Cited by 7 publications

References 41 publications

A Rationally Designed Prodrug for the Fluorogenic Labeling of Albumin and Theranostic Effects on Drug-Induced Liver Injury

A Rationally Designed Prodrug for the Fluorogenic Labeling of Albumin and Theranostic Effects on Drug-Induced Liver Injury

Molecular design and architectonics towards film-based fluorescent sensing

Density Functional Theory Studies of MXene-Based Nanosensors for Detecting Volatile Organic Compounds in Meat Spoilage Assessment

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