HPLC-MS/MS based method for the determination of 2-(3-hydroxy-5-phosphonooxymethyl-2-methyl-4-pyridyl)-1,3-thiazolidine-4-carboxylic acid in human plasma.
2-(3-hydroxy-5-phosphonooxymethyl-2-methyl-4-pyridyl)-1,3-thiazolidine-4-carboxylic acid
Cysteine
Hydrophilic interactions liquid chromatography
Plasma
Pyridoxal 5’-phosphate, tandem mass spectrometry
Journal
Scientific reports
ISSN: 2045-2322
Titre abrégé: Sci Rep
Pays: England
ID NLM: 101563288
Informations de publication
Date de publication:
18 Oct 2024
18 Oct 2024
Historique:
received:
05
07
2024
accepted:
08
10
2024
medline:
19
10
2024
pubmed:
19
10
2024
entrez:
18
10
2024
Statut:
epublish
Résumé
The report presents first high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) based method for the determination of plasma 2-(3-hydroxy-5-phosphonooxymethyl-2-methyl-4-pyridyl)-1,3-thiazolidine-4-carboxylic acid (HPPTCA), an adduct of cysteine and active form of vitamin B6 pyridoxal 5'-phosphate. The assay employs 4-deoxypyridoxine (4-DPD) as an internal standard. Sample preparation procedure primarily involves acetonitrile (ACN) extraction of HPPTCA from plasma proteins, sample deproteinization by ultrafiltration, and dilution of ultrafiltrate with mobile phase prior to chromatographic analysis. The chromatographic separations of HPPTCA and 4-DPD are achieved within 6 min at 20 °C on X-Bridge Glycan BEH Amide (100 × 2.1 mm, 2.5 μm) column using gradient elution. The eluent consists of 0.1% formic acid in a mixture of solvent A (water and ACN (95:5, v: v)) and solvent B (water and ACN (5:95, v: v)) delivered at a flow rate of 0.3 mL/min. The assay linearity was observed within 0.25-10 µmol/L in plasma. The limit of quantification was found to be 0.25 µmol/L. The method was successfully applied to plasma samples delivered by apparently healthy donors showing that the HPLC-MS/MS assay is suitable for human plasma screening. The presence of HPPTCA was confirmed in eleven of fifteen study samples. The HPPTCA concentration ranged from 0.55 to 8.39 µmol/L.
Identifiants
pubmed: 39424903
doi: 10.1038/s41598-024-75760-z
pii: 10.1038/s41598-024-75760-z
doi:
Substances chimiques
Thiazolidines
0
thiazolidine-4-carboxylic acid
E5913T3IBL
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
24425Subventions
Organisme : National Science Centre, Poland
ID : 2017/27/B/ST4/01476
Informations de copyright
© 2024. The Author(s).
Références
Oliveira, P. & Laurindo, F. Implications of plasma thiol redox in disease. Clin. Sci. 132, 1257–1280 (2018).
doi: 10.1042/CS20180157
Moretti, R. & Caruso, P. The controversial role of homocysteine in neurology: From labs to clinical practice. Int. J. Mol. Sci. 20, 231, 1–22 (2019).
doi: 10.3390/ijms20010231
Chrysant, S. G. & Chrysant, G. S. The current status of homocysteine as a risk factor for cardiovascular disease: A mini review. Expert Rev. Cardiovasc. Ther. 16, 559–565 (2018).
doi: 10.1080/14779072.2018.1497974
pubmed: 29979619
Muzurović, E., Kraljević, I., Solak, M., Dragnić, S. & Mikhailidis, D. P. Homocysteine and diabetes: Role in macrovascular and microvascular complications. J. Diabetes Complicat.. 35, 107834, 1–16 (2021).
doi: 10.1016/j.jdiacomp.2020.107834
Hasan, T. et al. Disturbed homocysteine metabolism is associated with cancer. Exp. Mol. Med. 51, 21–34 (2019).
doi: 10.1038/s12276-019-0216-4
pubmed: 30804341
pmcid: 6389897
Azarpazhooh, M. R., Bogiatzi, C. & Spence, J. D. Stroke prevention: Little-known and neglected aspects. Cerebrovasc. Dis. 50, 622–635 (2021).
doi: 10.1159/000515829
pubmed: 34044404
Sohouli, M. H. et al. A comprehensive review and meta-regression analysis of randomized controlled trials examining the impact of vitamin B12 supplementation on homocysteine levels. Nutr. Rev. 82, 726–737 (2024).
doi: 10.1093/nutrit/nuad091
pubmed: 37495210
Zhang, D. M., Ye, J. X., Mu, J. S. & Cui, X. P. Efficacy of vitamin B supplementation on cognition in elderly patients with cognitive-related diseases: A systematic review and meta-analysis. J. Geriatr. Psychiatry Neurol. 30, 50–59 (2017).
doi: 10.1177/0891988716673466
pubmed: 28248558
Mandaviya, P. R., Stolk, L. & Heil, S. G. Homocysteine and DNA methylation: A review of animal and human literature. Mol. Genet. Metab. 113, 243–252 (2014).
doi: 10.1016/j.ymgme.2014.10.006
pubmed: 25456744
Martí-Carvajal, A., Solà, I., Lathyris, D. & Dayer, M. Homocysteine-lowering interventions for preventing cardiovascular events. Cochrane Database Syst. Rev. 8, 1–126 (2017).
Smith, A. D., Refsum, H. & Homocysteine B vitamins, and cognitive impairment. Annu. Rev. Nutr. 36, 211–239 (2016).
doi: 10.1146/annurev-nutr-071715-050947
pubmed: 27431367
Matsuo, Y. Formation of Schiff bases of pyridoxal phosphate. Reaction with metal ions. J. Am. Chem. Soc. 79, 2011–2015 (1957).
doi: 10.1021/ja01565a068
Buell, M. V. & Hansen, R. E. Reaction of pyridoxal-5-phosphate with aminothiols. J. Am. Chem. Soc. 82, 6042–6049 (1960).
doi: 10.1021/ja01508a018
Bergel, F. & Harrap, K. Interaction between carbonyl groups and biologically essential substituents. Part 111 the formation of a thiazolidine derivative in aqueous solution from pyridoxal phosphate and L-cysteine. J. Chem. Soc. 789, 4051–4056 (1961).
doi: 10.1039/jr9610004051
Mackay, D. The mechanism of the reaction of cysteine with pyridoxal 5’-phosphate. Arch. Biochem. Biophys. 99, 93–100 (1962).
doi: 10.1016/0003-9861(62)90248-5
Mackay, D. & Shepherd, D. M. Inhibition of histidine decarboxylases and interaction of the inhibitors with pyridoxal 5′-phosphate. Biochim. Biophys. Acta. 59, 553–561 (1962).
doi: 10.1016/0006-3002(62)90633-9
pubmed: 14467926
Terzuoli, L. et al. Some chemical properties and biological role of thiazolidine compounds. Life Sci. 63, 1251–1267 (1998).
doi: 10.1016/S0024-3205(98)00387-7
pubmed: 9771914
Głowacki, R., Stachniuk, J., Borowczyk, K. & Jakubowski, H. Quantification of homocysteine and cysteine by derivatization with pyridoxal 5’-phosphate and hydrophilic interaction liquid chromatography. Anal. Bioanal Chem. 408, 1935–1941 (2016).
doi: 10.1007/s00216-016-9308-3
pubmed: 26794212
Pestaña, A., Sandoval, I. & Sols, A. Inhibition by homocysteine of serine dehydratase and other pyridoxal 5’-phosphate enzymes of the rat through cofactor blockage. Arch. Biochem. Biophys. 146, 373–379 (1971).
doi: 10.1016/0003-9861(71)90139-1
pubmed: 4398884
Tunnicliff, G. & Ngo, T. T. The mode of action of homocysteine on mouse brain glutamic decarboxylase and γ-aminobutyrate aminotransferase. Can. J. Biochem. 55, 1013–1018 (1977).
doi: 10.1139/o77-151
pubmed: 907901
Griffiths, R. et al. Synergistic inhibition of [3H]muscimol binding to calf-brain synaptic membranes in the presence of l-homocysteine and pyridoxal 5′-phosphate. Eur. J. Biochem. 137, 467–478 (1983).
doi: 10.1111/j.1432-1033.1983.tb07850.x
pubmed: 6319125
Piechocka, J., Wrońska, M., Głowacka, I. E. & Głowacki, R. 2-(3-hydroxy-5-phosphonooxymethyl-2-methyl-4-pyridyl)-1,3-thiazolidine-4-carboxylic acid, novel metabolite of pyridoxal 5`-phosphate and cysteine is present in human plasma - chromatographic investigations. Int. J. Mol. Sci. 21, 3548, 1–16 (2020).
doi: 10.3390/ijms21103548
Piechocka, J., Wyszczelska-Rokiel, M. & Głowacki, R. Simultaneous determination of 2-(3-hydroxy-5-phosphonooxymethyl-2-methyl-4-pyridyl)-1,3-thiazolidine-4-carboxylic acid and main plasma aminothiols by HPLC–UV based method. Sci. Rep. 13, 9294, 1–12 (2023).
doi: 10.1038/s41598-023-36548-9
Esteve, M. J., Farré, R., Frígola, A. & García-Cantabella, J. M. Determination of vitamin B6 (pyridoxamine, pyridoxal and pyridoxine) in pork meat and pork meat products by liquid chromatography. J. Chromatogr. A. 795, 383–387 (1998).
doi: 10.1016/S0021-9673(97)00990-4
pubmed: 9528106
Zhang, X., Tang, X. & Daly, T.M. A one-step NIST traceable HPLC method for quantitation of vitamin B6 and 4-pyridoxic acid in human plasma. Pract. Lab. Med. 21(e00160), 1–8 (2020).
Oureshi, S. A. & Huang, H. Determination of B6 vitamers in serum by simple isocratic high performance liquid chromatography. J. Liq Chromatogr. 13, 191–201 (1990).
doi: 10.1080/01483919008051795
Sharma, S. K. & Dakshinamurti, K. Determination of vitamin B6 vitamers and pyridoxic acid in biological samples. J. Chromatogr. B Biomed. Sci. Appl. 578, 45–51 (1992).
doi: 10.1016/0378-4347(92)80223-D
Shephard, G. S., Louw, M. E. J. & Labadarios, D. Analysis of vitamin B6 vitamers in plasma by cation-exchange high-performance liquid chromatography. J. Chromatogr. B Biomed. Sci. Appl. 416, 138–143 (1987).
doi: 10.1016/0378-4347(87)80494-2
van Schoonhoven, J., Schrijver, J., VandenBerg, H. & Haenen, G. R. M. M. Reliable and sensitive HPLC method with fluorometric detection for the analysis of vitamin B6 in foods and feeds. J. Agric. Food Chem. 42, 1475–1480 (1994).
doi: 10.1021/jf00043a016
Gregory, J. F. & Feldstein, D. Determination of vitamin B-6 in foods and other biological materials by paired-ion high-performance liquid chromatography. J. Agric. Food Chem. 33, 359–363 (1985).
doi: 10.1021/jf00063a010
Taylor, P. J. Matrix effects: The Achilles heel of quantitative high-performance liquid chromatography-electrospray-tandem mass spectrometry. Clin. Biochem. 38, 328–334 (2005).
doi: 10.1016/j.clinbiochem.2004.11.007
pubmed: 15766734
Pena-Pereira, F., Wojnowski, W. & Tobiszewski, M. AGREE - Analytical GREEnness metric approach and software. Anal. Chem.92, 10076–10082 (2020).
doi: 10.1021/acs.analchem.0c01887
pubmed: 32538619
pmcid: 7588019
M10 Bioanalytical Method Validation and Study Sample Analysis. Guidance for Industry. (2022).