Determination of 2-iminothiazolidine-4-carboxylic acid

doi:10.1016/0003-2697(65)90010-2

Analytical Biochemistry

Volume 11, Issue 2, May 1965, Pages 230-237

https://doi.org/10.1016/0003-2697(65)90010-2 Get rights and content

Abstract

Procedures are described for determination of 2-iminothiazolidine-4-carboxylic acid, using diazotized sulfanilic acid or the mereury-diphenyl-thiocarbazone reaction. The compound should first be separated from interfering substances such as are found in urine. Paper electrophoresis, ion displacement, or chromatography suffice for this purpose.

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Cited by (14)

Development of magnetic carbon nanotubes for dispersive micro solid phase extraction of the cyanide metabolite, 2-aminothiazoline-4-carboxylic acid, in biological samples
2019, Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Citation Excerpt :
Based on the pKa information and the nature of the amine and carboxylic groups, at least one of the moieties, or both, is charged in all pH values in aqueous solutions. Earlier studies in ATCA showed that its ring structure will be opened under heat and strongly basic condition [31,44]; as a result, the Mag-CNT/d-μSPE method was designed to be at an acidic range to avoid the potential degradation of ATCA. The addition of concentrated sulfuric acid during purification of CNT has been demonstrated to provide stronger oxidizing power [45], in which more carbon atom on the surface of the CNT can be oxidized into hydroxyl and/or carboxyl groups.
2-aminothiazoline-4-carboxylic acid (ATCA) is a minor metabolite of cyanide and is suggested to be a promising biomarker for cyanide exposure due to its specificity to cyanide metabolism and its excellent short- and long-term stability during storage. In this study, magnetic carbon nanotubes, including magnetic multi-walled carbon nanotubes (Mag-MWCNT) and magnetic single-walled carbon nanotubes (Mag-SWCNT) were synthesized as a novel sorbent for dispersive micro solid phase extraction (d-μSPE) to extract ATCA from biological matrices. ATCA spiked deionized water samples with the addition of the isotopic internal standard (ATCA – ¹³C, ¹⁵N) were subjected to Mag-CNT/d-μSPE to confirm extraction efficiency of this new technique. The extracted ATCA was derivatized and quantitated using gas chromatography/mass spectrometry (GC/MS) analysis. The extraction parameters were optimized and a detection limits of 15 and 25 ng/mL were obtained for synthetic urine and bovine blood respectively with a linear dynamic range of 30–1000 ng/mL. The optimized Mag-CNT/d-μSPE method facilitated efficient extraction of ATCA using 2 mg of Mag-MWCNT with a 10-minute extraction time. The current assay was also found to be effective for the extraction of ATCA with average recoveries of 97.7 ± 4.0% (n = 9) and 96.5 ± 12.1% (n = 9) from synthetic urine and bovine blood respectively. The approach of using Mag-CNT to facilitate d-μSPE offered a novel alternative to extract ATCA from complex biological matrices.
Plasma persistence of 2-aminothiazoline-4-carboxylic acid in rat system determined by liquid chromatography tandem mass spectrometry
2012, Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Citation Excerpt :
For the purpose of determining ATCA persistence in the circulation, we thought that sampling for two days should be enough. Cation exchange solid-phase extraction (SPE) columns and individual pre-treatment steps for the extraction and analysis of ATCA from biological samples have been reported [18,19]. In our work, the MCX SPE cartridges were activated by adding 1 mL of methanol followed by 1 mL DI water.
2-Aminothiazoline-4-carboxylic acid (ATCA) was intravenously injected to rats in order to investigate its plasma distribution. ATCA was extracted from plasma samples by solid phase extraction (SPE) and molecularly imprinted polymer stir bar sorption extraction (MIP-SBSE). Detection and quantification of ATCA were achieved by using liquid chromatography–tandem mass spectrometry (LC–MS/MS). It was found that the intravenously injected ATCA concentration quickly decreased to half within 2.5 h in the rat system. However, after 2.5 h, the concentration of ATCA in plasma stayed constant at least 5 folds above the endogenous ATCA level for more then 48 h. This finding can be used for evaluating ATCA's diagnostic and forensic value as a biomarker for cyanide exposure.
Analysis of the cyanide metabolite 2-aminothiazoline-4-carboxylic acid in urine by high-performance liquid chromatography
1995, Analytical Biochemistry
The cyanide metabolite 2-aminothiazoline-4-carboxylic acid (ATC) was converted to N-carbamylcysteine and analyzed by high-performance liquid chromatography (HPLC) and fluorometric detection. ATC was first separated from interfering substances by passing through the cation exchanger AG 50W-X8. Interfering disulfides were converted to thiols by reduction of the eluate with thiopropyl-Sepharose 6B. The thiols were then adsorbed to the organomercurial adsorbent p-acetoxymercurianiline-Sepharose 4B while ATC was obtained in the effluent. ATC was then converted to N-carbamylcysteine by ring opening at high temperature in an alkaline environment. Derivatization of N-carbamylcysteine was with N-(7-dimethylamino-4-methyl-3 coumarinyl)maleimide. The imprecision (CV) of the method was 3.6% and the analytical recovery was quantitative. The detection limit was 0.3 μM. ATC in urine was stable for at least 3 months when stored at −196 to +20°C. The ATC concentration in urine was below the limit of detection in healthy nonsmokers. The utility of the method was demonstrated by the finding of up to 10.5 μM ATC concentrations in urine samples from human subjects in Mozambique living on a high dietary intake of cyanide from the cassava root. In a metabolic study rats were exposed to acetonitrile in the drinking water. After 4 weeks very high ATC levels were found in the urine, representative values from two rats being 195 and 525 μM, respectively.
Performance comparison between solid phase extraction and magnetic carbon nanotubes facilitated dispersive-micro solid phase extractions (Mag-CNTs/d-µSPE) of a cyanide metabolite in biological samples using GC–MS
2021, Journal of Analytical Science and Technology
The potential use of 2-aminothiazoline-4-carboxylic acid (Atca) as a forensic marker for cyanide exposure in medicolegal death investigation: A review
2019, Forensic Science Review
The Analysis of Cyanide in Biological Samples
2016, Toxicology of Cyanides and Cyanogens: Experimental, Applied and Clinical Aspects

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^☆: This work was performed under Contract (AT-40-1)-1637 with the Atomic Energy Commission.

²: Present address: Veterans Administration, Little Rock Hospital Division, 300 E. Roosevelt Road, Little Rock, Arkansas.

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Determination of 2-iminothiazolidine-4-carboxylic acid☆

Abstract

J. Biol. Chem

Ber

Ber

Biochem. J