A new BODIPY-based long-wavelength fluorescent probe for chromatographic analysis of low-molecular-weight thiols

Zhang, Liyun; Tu, Fengqin; Guo, Xiao‐Feng; Wang, Hong; Wang, Peng; Zhang, Hua‐Shan

doi:10.1007/s00216-014-8013-3

Cited by 14 publications

(9 citation statements)

References 42 publications

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“…The high detection sensitivity should enable application of this method in the determination of the reduced-form thiols in biological samples, in addition to total thiols determination. CysGly, and GSH, respectively) [36]. The developed method is advantageousin terms of understanding endogenous sulfur metabolism, becausethere are few analytical methods that can quantify γGluCys in biological fluids [24,37,38].…”

Section: Optimization Of Separation Conditions For Sbd-thiols In Mousmentioning

confidence: 99%

Determination and characterization of total thiols in mouse serum samples using hydrophilic interaction liquid chromatography with fluorescence detection and mass spectrometry

Isokawa

Shimosawa

Funatsu

et al. 2016

Journal of Chromatography B

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Biothiols such as homocysteine, cysteine, and glutathione play many biologically important roles, especially in reduction-oxidation homeostasis and resistance to oxidative stress, and the measurement of their concentrations in model animal fluids is important in clarifying the pathology of thiol-related diseases. In this study, an analytical method for total biothiols in mouse serum using hydrophilic interaction liquid chromatography (HILIC) with fluorescence detection was developed. Mouse serum samples were derivatized with ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate (SBD-F), after reduction by tris(2-carboxyethyl)phosphine. Five biothiols (homocysteine, cysteine, cysteinylglycine, glutathione, and γ-glutamylcysteine) in the mouse sera were separated within 16 min on an amide-type HILIC column. The method possessed good linearity, good reproducibility with an intra-day variance of less than 3%, and low detection limits of 0.2-4 nM. Concentrations of homocysteine, cysteine, cysteinylglycine, glutathione, and γ-glutamylcysteine in the mouse serum samples were calculated as 6.7 ± 0.3, 227.7 ± 16.9, 1.2 ± 0.4, 77.5 ± 29.2, and 8.2 ± 0.9 μM, respectively (mean ± S.D., n = 4). Furthermore, HILIC-negative electrospray ionization-mass spectrometry (MS) analysis using a high-resolution mass spectrometer was conducted to determine the exact masses of two unknown peaks, which were found in the mouse serum samples with high signal intensity and were not detected in human plasma samples. The exact masses of the unknown compounds were determined as 1184.519 and 800.281 (as SBD-derivatized negative ions), which possessed a product ion common to SBD-thiols (m/z 230.954, as [SBD-SH](-)) upon tandem MS spectrometric analysis.

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Section: Optimization Of Separation Conditions For Sbd-thiols In Mousmentioning

confidence: 99%

Determination and characterization of total thiols in mouse serum samples using hydrophilic interaction liquid chromatography with fluorescence detection and mass spectrometry

Isokawa

Shimosawa

Funatsu

et al. 2016

Journal of Chromatography B

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“…Hcy was purchased from Sigma (Shanghai, China). DMDSPAB-I was synthesized in our lab [40], and the synthesis procedure is listed in the Supporting Information. All aqueous solutions were prepared with DI water purified by a Millipore-Q system (Millipore, Bedford, MA, USA).…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

Rapid and sensitive determination of free thiols by capillary zone electrophoresis with near‐infrared laser‐induced fluorescence detection using a new BODIPY‐based probe as labeling reagent

Zhang

Guo

et al. 2014

Electrophoresis

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A CZE with near-infrared (NIR) LIF detection method has been developed for the analysis of six low molecular weight thiols including glutathione, homocysteine, cysteine, γ-glutamylcysteine, cysteinylglycine, and N-acetylcysteine. For this purpose, a new NIR fluorescent probe, 1,7-dimethyl-3,5-distyryl-8-phenyl-(4'-iodoacetamido)difluoroboradiaza-s-indacene was utilized as the labeling reagent, whose excitation wavelength matches the commercially available NIR laser line of 635 nm. The optimum procedure included a derivatization step of the free thiols at 45°C for 25 min and CZE analysis conducted within 14 min in the running buffer containing 16 mmol/L pH 7.0 sodium citrate and 60% v/v ACN. The LODs (S/N = 3) ranged from 0.11 nmol/L for N-acetylcysteine to 0.31 nmol/L for γ-glutamylcysteine, which are better than or comparable to those reported with other derivatization-based CE-LIF methods. As the first trial of NIR CE-LIF method for thiol determination, the practical application of the proposed method has been validated by detecting thiols in cucumber and tomato samples with recoveries of 96.5-104.3%.

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“…The LODs ranged from 0.2 to 0.8 nmol/L by monitoring FL using 505 and 525 nm for λ ex and λ em . Furthermore, 1,3,5,7-tetramethyl-8-phenyl-(4-iodoacetamido)difluoroboradiaza-sindacene (TMPAB-I) was developed for quantifying Hcy, Cys, NAC, GSH, coenzyme A [62], and 6-mercaptopurine, and 1,7-dimethyl-3,5-distyryl-8-phenyl-(4′-iodoacetamido) difluoroboradiaza-s-indacene (DMDSPAB-I) was developed for quantifying Hcy, Cys, NAC, GSH, CysGly, and penicillamine [63]. The excitation and emission wavelengths of DMDSPAB-I are very long (620 and 630 nm, respectively), which is useful for FL detection, allowing a high quantum yield of 0.557 and LODs ranging from 0.24 to 0.72 nmol/L for the substrates.…”

Section: Fluorescence Detectionmentioning

confidence: 99%

HPLC Analysis of Homocysteine and Related Compounds

Wada¹,

Nakamura²,

Nakashima³

2018

Non-Proteinogenic Amino Acids

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Homocysteine (Hcy), a sulfur-containing amino acid, is a representative intermediate metabolite of methionine (Met) to cysteine (Cys) via several intermediates. An elevated level of Hcy in plasma plays an important role in diseases such as neural tube defects and Down syndrome. Homocystinuria is the most common inborn error of sulfur metabolism and is caused by mutations in the metabolic enzymes of Hcy. These errors can be caused by abnormal levels of Met metabolites and classified on the basis of plasma Met levels. Additionally, Hcy and related compounds such as glutathione play an important role in maintaining homeostasis. Therefore, the simultaneous determination of Hcy and/or related compounds is required for appropriate clinical management of several diseases. The sulfur-containing amino acids and their derivatives in biological samples are quantified sensitively using high-performance liquid chromatography methods coupled with various detection methods such as UV/Vis, fluorescence, chemiluminescence, electrochemical, mass spectrometry, and tandem mass spectrometry. In this chapter, we review recent advances in these analytical methods and their applications.

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A new BODIPY-based long-wavelength fluorescent probe for chromatographic analysis of low-molecular-weight thiols

Cited by 14 publications

References 42 publications

Determination and characterization of total thiols in mouse serum samples using hydrophilic interaction liquid chromatography with fluorescence detection and mass spectrometry

Determination and characterization of total thiols in mouse serum samples using hydrophilic interaction liquid chromatography with fluorescence detection and mass spectrometry

Rapid and sensitive determination of free thiols by capillary zone electrophoresis with near‐infrared laser‐induced fluorescence detection using a new BODIPY‐based probe as labeling reagent

HPLC Analysis of Homocysteine and Related Compounds

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