3-Iodoacetylaminobenzanthrone as a fluorescent derivatizing reagent for thiols in high-performance liquid chromatography

Wang, Hong; Liang, Shucai; Zhang, Zhimin; Zhang, Hua‐Shan

doi:10.1016/j.aca.2004.03.002

Cited by 45 publications

(24 citation statements)

References 23 publications

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“…According to previously reported data on iodoacetamide probes [36,37], several conditions affect the reaction of DMDSPAB-I and thiols, including concentration of probe, buffer pH, buffer volume, and derivatization time and temperature.…”

Section: Optimization Of Derivatization Conditionsmentioning

confidence: 95%

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

Zhang

Guo

et al. 2014

Anal Bioanal Chem

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A new long-wavelength fluorescent probe, 1,7-dimethyl-3,5-distyryl-8-phenyl-(4'-iodoacetamido)difluoroboradiaza-s-indacene (DMDSPAB-I), was designed and synthesized for thiol labeling in high-performance liquid chromatography (HPLC). The excitation and emission wavelengths of DMDSPAB-I are 620 and 630 nm, respectively, with a high fluorescence quantum yield of 0.557, which is advantageous in preventing interference of intrinsic fluorescence from complex biological matrices and enabling high sensitivity HPLC. Based on DMDSPAB-I, a reversed-phase HPLC method was developed for measuring low-molecular-weight thiols including glutathione, cysteine, homocysteine, N-acetylcysteine, cysteinylglycine, and penicillamine. After the specific reaction of DMDSPAB-I with thiols, baseline separation of all six stable derivatives was achieved through isocratic elution on a C18 column within 25 min, with the limits of detection (signal-to-noise ratio = 3) from 0.24 nmol L(-1) for glutathione to 0.72 nmol L(-1) for penicillamine. The proposed method was validated in part by measuring thiols in blood samples from mice, with recoveries of 95.3-104.3%.

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Section: Optimization Of Derivatization Conditionsmentioning

confidence: 95%

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

Zhang

Guo

et al. 2014

Anal Bioanal Chem

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“…According to the previously reported data of iodoacetamide probes [41][42][43], several conditions affect the reaction of DMDSPAB-I with thiols, including the reagent concentration, the buffer pH and buffer volume, as well as the derivatization temperature and derivatization time. Taking ␥ -GluCys as the representative, the derivatization conditions were optimized in the following.…”

Section: Optimization Of Derivatization Conditionsmentioning

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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“…So far, the derivatization of thiols was performed at room temperature, for example, using OPA at room temperature for 2-3 min at pH 8-10 (Molnar-Perl, 2001), BrB at room temperature for 5 min at pH 8 (Luo et al, 1995), ThioGlo 3 and NPM at room temperature for 5 min at pH above 7 (Ercal et al, 2001) and IAB at 35°C for 15 min at pH 8.3 (Wang et al, 2004). Considering the results obtained here, under these conditions, thiol exchange reaction should occur between the reduced form and the oxidized-form thiols, and this reaction is not negligible, if the co-existing oxidized-form thiols are in high concentration.…”

Section: T Santa Et Al Original Researchmentioning

confidence: 99%

“…The levels of these thiols in physiological liquids asso- Parmentier et al, 1998) Ercal et al, 2001), 3-iodoacetylaminobenzanthrone (IAB; Wang et al, 2004), dansyl chloride (Komatsu and Obata, 2003) and benzofurazan reagents. Among them, benzofurazan reagents including ABD-F (4-aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole) and SBD-F (7-fluoro-2,1,3-benzoxadiazole-4-sulfonate; [ Fig.…”

Section: Introductionmentioning

confidence: 99%

Suppression of thiol exchange reaction in the determination of reduced‐form thiols by high‐performance liquid chromatography with fluorescence detection after derivatization with fluorogenic benzofurazan reagent, 7‐fluoro‐2,1,3‐benzoxadiazole‐4‐sulfonate and 4‐aminosulfonyl‐7‐fluoro‐2,1,3‐benzoxadiazole

Santa

Aoyama

Fukushima

et al. 2006

Biomedical Chromatography

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The derivatization of the reduced-form thiols with SBD-F (7-fluoro-2,1,3-benzoxadiazole-4-sulfonate) and ABD-F (4-aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole) was studied. The yields of the derivatives of the reduced-form thiols (cysteine, homocysteine, reduced-form glutathione) with SBD-F at 60 degrees C for 45 min in the borate buffer (pH 9.3) were significantly decreased in the presence of the oxidized-form thiols (cystine, homocystine, oxidized-form glutathione) because of the thiol exchange reaction between the reduced-form and the oxidized-form thiols. The use of ABD-F at low temperature enabled the suppression of these thiol exchange reactions, and the recommended conditions were below 5 degrees C for 90 min in borate buffer (pH 9.3). These results suggest that ABD-F is a preferred derivatization reagent for the accurate determination of the reduced-form thiols in samples containing the oxidized-form thiols. In addition, it was also suggested that the derivatization of the reduced-form thiols should also be performed at low temperature when derivatization reagents such as o-phthalaldehyde (OPA) and monobromobimane (BrB) are used.

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3-Iodoacetylaminobenzanthrone as a fluorescent derivatizing reagent for thiols in high-performance liquid chromatography

Cited by 45 publications

References 23 publications

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

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

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

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