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Unambiguous Characterization of p-Cresyl Sulfate, a Protein-Bound Uremic Toxin, as Biomarker of Heart and Kidney Disease

p-Cresyl sulfate is one of the bound uremic toxins whose level increases in the sera of patients with the severity of chronic kidney disease and is therefore used as a standard for clinical investigations. Our first attempts to obtain p-cresyl sulfate led exclusively to the product of sulfonation of...

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Autores principales: Paroni, Rita, Casati, Silvana, Dei Cas, Michele, Bignotto, Monica, Rubino, Federico Maria, Ciuffreda, Pierangela
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6832250/
https://www.ncbi.nlm.nih.gov/pubmed/31618977
http://dx.doi.org/10.3390/molecules24203704
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author Paroni, Rita
Casati, Silvana
Dei Cas, Michele
Bignotto, Monica
Rubino, Federico Maria
Ciuffreda, Pierangela
author_facet Paroni, Rita
Casati, Silvana
Dei Cas, Michele
Bignotto, Monica
Rubino, Federico Maria
Ciuffreda, Pierangela
author_sort Paroni, Rita
collection PubMed
description p-Cresyl sulfate is one of the bound uremic toxins whose level increases in the sera of patients with the severity of chronic kidney disease and is therefore used as a standard for clinical investigations. Our first attempts to obtain p-cresyl sulfate led exclusively to the product of sulfonation of the aromatic ring instead of sulfation on the OH moiety. Nevertheless, this initial discouraging result allowed us to handle both p-cresyl sulfate and 2-hydroxy-5-methylbenzenesulfonic acid obtained by different synthetic pathways. Interestingly, the comparison between the two isomers pointed out that the two molecules show the same fragmentation pattern and are indistinguishable by mass spectrometry. They cannot be separated on several commercially available columns. The only difference between the two compounds is a 10-fold higher ionization yield under negative ion electrospray ionization. NMR spectral studies definitely confirmed the different molecular structures. We present here an unambiguous biomimetic synthetic route for p-cresyl sulfate and the spectroscopic characterization of both the compounds by nuclear magnetic resonance and mass spectrometry.
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spelling pubmed-68322502019-11-21 Unambiguous Characterization of p-Cresyl Sulfate, a Protein-Bound Uremic Toxin, as Biomarker of Heart and Kidney Disease Paroni, Rita Casati, Silvana Dei Cas, Michele Bignotto, Monica Rubino, Federico Maria Ciuffreda, Pierangela Molecules Article p-Cresyl sulfate is one of the bound uremic toxins whose level increases in the sera of patients with the severity of chronic kidney disease and is therefore used as a standard for clinical investigations. Our first attempts to obtain p-cresyl sulfate led exclusively to the product of sulfonation of the aromatic ring instead of sulfation on the OH moiety. Nevertheless, this initial discouraging result allowed us to handle both p-cresyl sulfate and 2-hydroxy-5-methylbenzenesulfonic acid obtained by different synthetic pathways. Interestingly, the comparison between the two isomers pointed out that the two molecules show the same fragmentation pattern and are indistinguishable by mass spectrometry. They cannot be separated on several commercially available columns. The only difference between the two compounds is a 10-fold higher ionization yield under negative ion electrospray ionization. NMR spectral studies definitely confirmed the different molecular structures. We present here an unambiguous biomimetic synthetic route for p-cresyl sulfate and the spectroscopic characterization of both the compounds by nuclear magnetic resonance and mass spectrometry. MDPI 2019-10-15 /pmc/articles/PMC6832250/ /pubmed/31618977 http://dx.doi.org/10.3390/molecules24203704 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Paroni, Rita
Casati, Silvana
Dei Cas, Michele
Bignotto, Monica
Rubino, Federico Maria
Ciuffreda, Pierangela
Unambiguous Characterization of p-Cresyl Sulfate, a Protein-Bound Uremic Toxin, as Biomarker of Heart and Kidney Disease
title Unambiguous Characterization of p-Cresyl Sulfate, a Protein-Bound Uremic Toxin, as Biomarker of Heart and Kidney Disease
title_full Unambiguous Characterization of p-Cresyl Sulfate, a Protein-Bound Uremic Toxin, as Biomarker of Heart and Kidney Disease
title_fullStr Unambiguous Characterization of p-Cresyl Sulfate, a Protein-Bound Uremic Toxin, as Biomarker of Heart and Kidney Disease
title_full_unstemmed Unambiguous Characterization of p-Cresyl Sulfate, a Protein-Bound Uremic Toxin, as Biomarker of Heart and Kidney Disease
title_short Unambiguous Characterization of p-Cresyl Sulfate, a Protein-Bound Uremic Toxin, as Biomarker of Heart and Kidney Disease
title_sort unambiguous characterization of p-cresyl sulfate, a protein-bound uremic toxin, as biomarker of heart and kidney disease
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6832250/
https://www.ncbi.nlm.nih.gov/pubmed/31618977
http://dx.doi.org/10.3390/molecules24203704
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