Gas chromatographic—mass spectrometric determination of tiopronin in human blood using acrylic acid esters as a derivatization reagent for the thiol group

Matsuura, Kenji; Takashina, Hideo

doi:10.1016/0378-4347(93)80390-p

Cited by 34 publications

(17 citation statements)

References 11 publications

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“…Because of this extensive use, different methods have been developed and described for detecting this compound in biological samples, including the electrochemical detection system [12], and gas chromatography-mass spectrometry [13]. HPLC, coupled with electrospray tandem mass spectrometry, has been used lately to quantitate MPG levels and other sulfhydryl-containing compounds in biological samples [18][19][20][21].…”

Section: Discussionmentioning

confidence: 99%

“…MPG becomes oxidized to disulfide dimers and forms conjugates with other endogenous thiols [11]. Previous methods used for determining the quantitation of MPG include an electrochemical detection system [12], gas chromatography-mass spectrometry [13], and the HPLC method [14]. However, the time-consuming procedures, extensive manipulation of samples and complicated derivatization steps are common limitations of these detection methods.…”

Section: Introductionmentioning

confidence: 99%

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Liquid chromatography analysis of N-(2-mercaptopropionyl)-glycine in biological samples by ThioGlo™ 3 derivatization

Penugonda

Mare

et al. 2004

Journal of Chromatography B

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N-(2-Mercaptopropionyl)-glycine (MPG) is a synthetic aminothiol antioxidant that is used in the treatment of cystinuria, rheumatoid arthritis, liver and skin disorders. Recent studies have shown that MPG can function as a chelating, cardioprotecting and a radioprotecting agent. Several other studies have shown that it may also act as a free radical scavenger because of its thiol group. Thiol-containing compounds have been detected in biological samples by various analytical methods such as spectrophotometric and colorimetric methods. However, these methods require several milliliters of a sample, time-consuming procedures and complicated derivatization steps, as well as having high detection limits. The present study describes a rapid, sensitive and relatively simple method for detecting MPG in biological tissues by using reverse-phase HPLC. With ThioGlo 3 [3H-Naphto[2,1-b] pyran, 9-acetoxy-2-(4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl) phenyl-3-oxo-)] as the reagent, highly fluorescent derivatives of thiols can be obtained that are suitable for HPLC. MPG is derivatized with ThioGlo 3 and is then detected flourimetrically by reverse phase HPLC using a C18 column as the stationary phase. Acetonitrile: Water (75:25) with acetic acid and phosphoric acid (1 mL/L) is used as the mobile phase (excitation wavelength, 365 nm; emission wavelength, 445 nm). The calibration curve for MPG is linear over a range of 10-2500 nM (r=0.999) and the coefficients of the variation of within-run and between-run precision were found to be 0.3 and 2.1%, respectively. The detection limit was 5.07 nM per 20 microL injection volume. Quantitative relative recovery of MPG in the biological samples (plasma, lung, liver, kidney and brain) ranged from 90+/-5.3 to 106.7+/-9.3 %. Based on these results, we have concluded that this method is suitable for determining MPG in biological samples.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Liquid chromatography analysis of N-(2-mercaptopropionyl)-glycine in biological samples by ThioGlo™ 3 derivatization

Penugonda

Mare

et al. 2004

Journal of Chromatography B

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“…Mass spectrometry is a sensitive and generally applicable detection method for most compounds including those containing no chromophores. Kenji Matsuura developed a GC/MS [9] and a LC/MS/MS [10] methods for the determination of TP using acrylic acid ester as the derivatization reagent without generating asymmetric carbon. Recently, Ma et al reported another LC-MS method for the determination of deoxidized TP using Vitamin C and 2-mercaptoethanol (2-ME) as the reducer and stabilizer.…”

Section: Introductionmentioning

confidence: 99%

Determination of total tiopronin in human plasma by LC–ESI–MS using tris (2-carboxy-ethyl) phosphine as reducing reagent and methyl acrylate as derivatization reagent for the thiol group

Liu

Yan-ning

2006

Journal of Chromatography B

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“…Although numerous reports have shown N-ethylma-leimide or its analog to be a very effective agent in stabilizing thiol compounds (Jemal et al, , 1987(Jemal et al, , 1988Pereira et al, 1988;Matsura and Takashima, 1993), the use of this class of derivatization reagent may pose some logistical problems if the thiol compound requiring stabilization contains a chiral center. Typically, the Michael addition of the thiol compound on to the carbon-carbon double bond of Nethylmaleimide forms a new chiral center on the Nethylmaleimide side of the thiol adduct.…”

Section: Introductionmentioning

confidence: 99%

Bioanalytical considerations for compounds containing free sulfhydryl groups

Srinivas

Mamidi

2003

Biomedical Chromatography

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Thiol-containing compounds pose bioanalytical challenge in several dimensions due to extreme reactivity of the sulfhydryl group. The development of robust bioanalytical methodology for thiol groups should address the aspects of adequate stabilization in the biological matrix and selectivity considerations. In this context, availability of plethora of thiol reagents provides ample opportunity to achieve the above goals. However, several considerations need to be factored into the decision-making of a suitable scheme for the thiol drugs under investigation. This review provides some critical insights to many such considerations that may be vital for development and validation of methods for thiol-containing drugs.

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Gas chromatographic—mass spectrometric determination of tiopronin in human blood using acrylic acid esters as a derivatization reagent for the thiol group

Cited by 34 publications

References 11 publications

Liquid chromatography analysis of N-(2-mercaptopropionyl)-glycine in biological samples by ThioGlo™ 3 derivatization

Liquid chromatography analysis of N-(2-mercaptopropionyl)-glycine in biological samples by ThioGlo™ 3 derivatization

Determination of total tiopronin in human plasma by LC–ESI–MS using tris (2-carboxy-ethyl) phosphine as reducing reagent and methyl acrylate as derivatization reagent for the thiol group

Bioanalytical considerations for compounds containing free sulfhydryl groups

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