A highly selective two-photon fluorescent chemosensor for tracking homocysteine via situ reaction

Xia, Ying; Zhang, Huihui; Zhu, Xiaojiao; Zhang, Gaojian; Yang, Xingyuan; Li, Fēi; Zhang, Xuanjun; Fang, Min; Yu, Jianhua; Zhou, Hongping

doi:10.1016/j.dyepig.2018.03.034

Cited by 15 publications

(7 citation statements)

References 26 publications

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“…Hyperhomocysteinemia has been linked with pulmonary embolism, stroke, deep vein thrombosis, and ischemic heart disease. − This is because Hcy and its cyclic metabolite homocysteine thiolactone modify the behavior of endothelial cells, which can promote vascular injury as their surface becomes a procoagulant, rather than anticoagulant. , They also promote platelet aggregation and oxidative stress due to the reactivity of the sulfhydryl group . Detection of homocysteine tends to be via fluorescence coupled to high-performance liquid chromatography, , electrochemical, or colorimetric methods . There are currently no methods for the detection of Hcy directly from blood samples or using ECL as the detection method.…”

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confidence: 99%

“…16 Detection of homocysteine tends to be via fluorescence coupled to high-performance liquid chromatography, 17,18 electrochemical, 19 or colorimetric methods. 20 There are currently no methods for the detection of Hcy directly from blood samples or using ECL as the detection method. Hcy contains a sulfhydryl group, which is a potent radical quencher, 21,22 and so it was proposed that detection of Hcy could be accomplished through monitoring a decrease in ECL intensity.…”

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Cathodic Quantum Dot Facilitated Electrochemiluminescent Detection in Blood

2018

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The expansion of electrochemical sensors to biomedical applications at point of care requires these sensors to undergo analysis without any pre-treatment of extraction. This poses a major challenge for all electrochemical sensors including electrochemiluminescent (ECL) based sensors. ECL offers many advantages for biomedical applications however; obtaining results from complex matrices has proven to be a large hurdle for the application of ECL sensors within this field. This work demonstrates the potential of cathodic ECL to detect and quantify homocysteine with 0.1 nM limit of detection, which is associated with hyperhomocysteinemia, in blood. This near infrared quantum dot (NIR QD) based ECL sensor displays good linearity allowing for rapid detection and providing a basis for exploitation of ECL based sensors for biomedical diagnostics utilising homocysteine as a model cathodic co-reactant. This work will lay the foundations for future developments in biosensing and imaging fields and stands as an initial proof of concept for the utilization of cathodic ECL technologies for biomedical applications once the limits of detection within clinically relevant levels has been achieved. This work illustrates the potential of cathodic ECL sensors, using Hcy as a model complex, for the detection of biomolecules. EXPERIMENTAL Materials Qdot® 800 ITK™ organic quantum dots, (1 μM in decane) were obtained from Invitrogen. Lumidot™ 560 and 640 nm QDs, (5 mg/mL in toluene), chitosan (medium molecular weight, 75-85 % de-acetylated), and all other chemicals were purchased from Sigma-Aldrich. All solutions were prepared in milli-Q water (18 mΩ cm). Bovine whole blood samples utilised within this study were obtained from Wishaw Abattoir Ltd following University of Strathclyde ethical approval. These were stored in aliquots at-20 ºC. Aliquots were defrosted at room temperature on the day of analysis and used immediately. Instrumentation A CH instrument model 760D electrochemical analyser using a standard 3 electrode setup including a 3 mm diameter GC working electrode, Pt wire counter electrode and Ag/AgCl 3 M KCl reference electrode purchased from IJ Cambria Scientific Ltd (UK) was utilised to record all electrochemical measurements. GC electrodes were cleaned following the pro-ASSOCIATED CONTENT Supporting Information Supporting material includes ECL responses for the interactions with reactive oxygen species (Figure S1), ECL responses for 1 mM K2S2O8 in blood with the Stern-Volmer and modified Stern-Volmer plots for this data (Figure S2). The ECL dependence for the interferents given in Figure 6 (Figure S3). Chromatographic experimental details are also included (Figure S4). This material is available free of charge via the Internet at http://pubs.acs.org.

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Cathodic Quantum Dot Facilitated Electrochemiluminescent Detection in Blood

2018

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“… 17 In addition, O 2– produced by complexation of Hcy with Cu 2+ can clear NO and inhibit NO-related cerebrovascular diseases. 18 Therefore, the specific and simultaneous detection of Cu 2+ and Hcy especially at the cellular level is of importance to understand their physiological functions and clinically diagnose the related diseases.…”

Section: Introductionmentioning

confidence: 99%

“… 19 , 20 In recent decades, a mass of fluorescence sensors has been developed to identify Hcy from other amino acids, especially structurally similar mercaptoamino acids such as Cys and GSH 21 − 27 by taking advantage of distinctive redox property of Hcy 21 − 23 or nucleophilic reactions based on −SH and/or −NH 2 of Hcy. 24 − 27 To date, however, only a few sensors can sequentially sense Cu 2+ and Hcy 18 , 28 − 38 that usually operated in a mixed medium of organic solvent and water 18 , 28 , 29 , 31 , 32 , 34 , 35 and suffer from the interference from other analytes ( Table S1 ). 28 − 32 , 34 , 36 , 37 Besides, there are rare sensors available for continuous imaging of Cu 2+ and Hcy in living cells.…”

Section: Introductionmentioning

confidence: 99%

“…Fluorescence sensors are regarded as the most charming method to real-time monitor and track biological species through combining with the laser confocal imaging technology due to its simplicity, sensitivity, and high temporal and spatial resolution. , In recent decades, a mass of fluorescence sensors has been developed to identify Hcy from other amino acids, especially structurally similar mercaptoamino acids such as Cys and GSH − by taking advantage of distinctive redox property of Hcy − or nucleophilic reactions based on −SH and/or −NH 2 of Hcy. − To date, however, only a few sensors can sequentially sense Cu 2+ and Hcy ,− that usually operated in a mixed medium of organic solvent and water ,,,,,, and suffer from the interference from other analytes (Table S1). − ,,, Besides, there are rare sensors available for continuous imaging of Cu 2+ and Hcy in living cells . Thus, it is still urgently needed to develop bifunctional fluorescence sensors for the simultaneous detection of Cu 2+ and Hcy with high sensitivity and selectivity in a prefect aqueous solution and living cells.…”

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Lysosome-Targeting Fluorescence Sensor for Sequential Detection and Imaging of Cu²⁺ and Homocysteine in Living Cells

et al. 2022

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A conjugated polymer-based fluorescence sensor, namely, PTNPy, was constructed on the basis of a polythiophene scaffold coupled with dimethylpyridylamine (DPA) groups in side chains for the consecutive detection and quantification of Cu 2+ and Hcy in a perfect aqueous medium. A dramatic fluorescence quenching of PTNPy by the addition of Cu 2+ was observed in Tris–HCl buffer solution (2 mM, pH 7.4), demonstrating a quick (<1 min) and highly selective response to Cu 2+ with a low limit of detection of 6.79 nM. Subsequently, the Cu 2+ -quenched fluorescence of PTNPy can be completely recovered by homocysteine (Hcy), showing excellent selectivity to Hcy over other competitive species such as cysteine and glutathione. Thanks to the low cytotoxicity and lysosomal targeting ability of PTNPy, it was further applied as an optical sensor for the sequential imaging of Cu 2+ and Hcy in HeLa cells. More importantly, Hcy concentration was linearly related to the fluorescence intensity of PTNPy in living cells, demonstrating huge potential for real-time monitoring the fluctuation of Hcy levels in living cells.

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Pyrene Functionalized Luminescent Phenylalanine for Selective Detection of Copper (II) Ions in Aqueous Media

et al. 2023

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A novel pyrene-based uorescent chemosensor 1 (pyren-1ylmethyl)-L-phenylalanine was designed and synthesized by combining 1-pyrenecarboxyaldehyde and L-phenylalanine. 1 was characterized by several analytical methods and used as a uorescent chemosensor for the selective and sensitive detection of Cu 2+ ions through "turn-off" mechanism with a detection limit of 2 x 10 − 8 M. 1 can also be used to detect Cu 2+ ions in a natural water sample and exhibits gelation properties with high thermal stability.

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A highly selective two-photon fluorescent chemosensor for tracking homocysteine via situ reaction

Cited by 15 publications

References 26 publications

Cathodic Quantum Dot Facilitated Electrochemiluminescent Detection in Blood

Cathodic Quantum Dot Facilitated Electrochemiluminescent Detection in Blood

Lysosome-Targeting Fluorescence Sensor for Sequential Detection and Imaging of Cu²⁺ and Homocysteine in Living Cells

Pyrene Functionalized Luminescent Phenylalanine for Selective Detection of Copper (II) Ions in Aqueous Media

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A highly selective two-photon fluorescent chemosensor for tracking homocysteine via situ reaction

Cited by 15 publications

References 26 publications

Cathodic Quantum Dot Facilitated Electrochemiluminescent Detection in Blood

Cathodic Quantum Dot Facilitated Electrochemiluminescent Detection in Blood

Lysosome-Targeting Fluorescence Sensor for Sequential Detection and Imaging of Cu2+ and Homocysteine in Living Cells

Pyrene Functionalized Luminescent Phenylalanine for Selective Detection of Copper (II) Ions in Aqueous Media

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Lysosome-Targeting Fluorescence Sensor for Sequential Detection and Imaging of Cu²⁺ and Homocysteine in Living Cells