Establishment of a two-dimensional chiral HPLC system for the simultaneous detection of lactate and 3-hydroxybutyrate enantiomers in human clinical samples

Liu, Shu Ling; Oyama, Tsubasa; Miyoshi, Y.; Sheu, Sheh Yi; Mita, Masashi; Ide, Tomomi; Lindner, Wolfgang; Hamase, Kenji; Lee, Jen Ai

doi:10.1016/j.jpba.2015.05.036

Cited by 20 publications

(33 citation statements)

References 38 publications

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“…Although the reported values obtained using various methods were different, it might mostly be due to the difference in the urinary concentration. Considering the proportion of the d form, the percentage of d‐ LA to total LA, the values were 14.9 and 18.6%, respectively, in previous results , and similar value of 19.5% was obtained in the present study. Concerning the values of 3HB enantiomers in the urine, the levels of the d‐ 3HB and l‐ 3HB have been reported to be almost the same , and the present results are quite similar.…”

Section: Resultssupporting

confidence: 91%

“…Considering the proportion of the d form, the percentage of d‐ LA to total LA, the values were 14.9 and 18.6%, respectively, in previous results , and similar value of 19.5% was obtained in the present study. Concerning the values of 3HB enantiomers in the urine, the levels of the d‐ 3HB and l‐ 3HB have been reported to be almost the same , and the present results are quite similar. These results indicate that the values obtained in the present study are consistent with the values observed by other methods, and the present method is useful for determination of the LA and 3HB enantiomers in human physiological fluids.…”

Section: Resultssupporting

confidence: 91%

“…Several studies have reported the concentrations of the LA and 3HB enantiomers in human physiological fluids. For the plasma/serum, the reported values of d‐ LA and l‐ LA were 8.0–12.8 and 841–1140 μM, respectively . The reported values of d‐ 3HB and l‐ 3HB were 62.8 and 1.9 μM, respectively .…”

Section: Resultsmentioning

confidence: 99%

“…Besides, two injections were needed to simultaneously determine the four enantiomers. Recently, an online narrow‐bore‐2D‐HPLC system was developed with 4‐( N ‐chloroformylmethyl‐ N ‐methylamino)‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐COCl) as a sensitive fluorescent derivatization reagent . Although the simultaneous analysis of the four enantiomers could be performed by one injection, numerous fluorescence interfering compounds were found due to the high reactivity of NBD‐COCl, and the stability of the NBD‐COCl reagent itself was also an issue of concern.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective and simultaneous determination of lactate and 3‐hydroxybutyrate in human plasma and urine using a narrow‐bore online two‐dimensional high‐performance liquid chromatography system

Hsieh

Koga

Furusho

et al. 2018

J of Separation Science

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For the enantioselective and simultaneous analysis of lactate and 3-hydroxybutyrate, a validated online two-dimensional high-performance liquid chromatography system using 4-nitro-7-piperazino-2,1,3-benzoxadiazole as a fluorescent derivatization reagent has been developed. For the reversed-phase separation in the first dimension, a Capcell Pak C18 ACR column (1.5 × 250 mm, particle size 3 μm) was used, and the target fractions were isolated by their hydrophobicity. In the second dimension, a polysaccharide-coated enantioselective column, Chiralpak AD-H (2.0 × 250 mm, 5 μm), was used. The system was validated by the calibration curve, intraday precision, interday precision, and accuracy using standards and real human samples, and satisfactory results were obtained. The present method was applied to human plasma and urine, and in the plasma, trace amounts of d-lactate (8.4 μM) and l-3-hydroxybutyrate (1.0 μM), besides high levels of l-lactate (860.9 μM) and d-3-hydroxybutyrate (59.4 μM), were successfully determined. In urine, trace levels of d-lactate (3.7 μM), d-3-hydroxybutyrate (2.3 μM), and l-3-hydroxybutyrate (3.3 μM) in addition to a relatively large amount of l-lactate (15.4 μM) were observed. The present online two-dimensional high-performance liquid chromatography system is useful for the simultaneous determination of all the lactate and 3-hydroxybutyrate enantiomers in human physiological fluids, and further clinical applications are ongoing.

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Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enantioselective and simultaneous determination of lactate and 3‐hydroxybutyrate in human plasma and urine using a narrow‐bore online two‐dimensional high‐performance liquid chromatography system

Hsieh

Koga

Furusho

et al. 2018

J of Separation Science

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“…Different studies have approached the enantioseparation of 2-hydroxycarboxylic acids. Some of them are ligand exchange CE [19][20][21], ligand exchange LC [22], GC analysis after derivatization [23], LC after derivatization [24], direct LC by using macrocyclic antibiotic chiral stationary phases (CSPs) [25][26][27], and quinine-or quinidine-derived CSPs [28][29][30][31][32][33], amongst others.…”

Section: F I G U R E 1 Structures Of the Studied 2-hydroxycarboxylic mentioning

confidence: 99%

Chiral separation of disease biomarkers with 2‐hydroxycarboxylic acid structure

Calderón

SANTI

Lämmerhofer

2017

J of Separation Science

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Chiral 2-hydroxycarboxylic acids are compounds that have been linked to particular diseases and are putative biomarkers with some diagnostic potential. The importance of identifying whether a particular enantiomer is related to certain diseases has been encouraged recently. However, in many cases it has not yet been elucidated whether there are stereochemical implications with respect to these biomarkers and whether their enantioselective analysis provides new insights and diagnostic potential. In this study 13 disease-related chiral 2-hydrocarboxylic acids were studied for their chiral separation by high-performance liquid chromatography on three cinchona alkaloid-derived chiral stationary phases. From a subgroup of eight 2-hydroxymonocarboxylic acids, baseline resolution could be achieved and inversion of elution order by exchanging tert-butylcarbamoyl quinidine chiral stationary phase (Chiralpak QD-AX) for the corresponding quinine analogue (Chiralpak QN-AX) is shown for seven of them. Furthermore, conditions for chiral separation of the 2-hydroxydicarboxylic acids, citramalic acid, 2-isopropylmalic acid, and 2-hydroxyadipic acid are reported and compared to the previous reported conditions for 2-hydroxyglutaric acid and malic acid.

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Chiral Stationary Phases Derived from Cinchona Alkaloids

Lämmerhofer

Lindner

2023

Chiral Separations and Stereochemical Elucidation

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Establishment of a two-dimensional chiral HPLC system for the simultaneous detection of lactate and 3-hydroxybutyrate enantiomers in human clinical samples

Cited by 20 publications

References 38 publications

Enantioselective and simultaneous determination of lactate and 3‐hydroxybutyrate in human plasma and urine using a narrow‐bore online two‐dimensional high‐performance liquid chromatography system

Enantioselective and simultaneous determination of lactate and 3‐hydroxybutyrate in human plasma and urine using a narrow‐bore online two‐dimensional high‐performance liquid chromatography system

Chiral separation of disease biomarkers with 2‐hydroxycarboxylic acid structure

Chiral Stationary Phases Derived from Cinchona Alkaloids

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