A Fast and Selective Approach for Profiling Vicinal Diols Using Liquid Chromatography-Post Column Derivatization-Double Precursor Ion Scanning Mass Spectrometry
Vicinal diols are important signaling metabolites of various inflammatory diseases, and some of them are potential biomarkers for some diseases. Utilizing the rapid reaction between diol and 6-bromo-3-pyridinylboronic acid (BPBA), a selective and sensitive approach was established to profile these v...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/1/283 |
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| author | Debin Wan Christophe Morisseau Bruce D. Hammock Jun Yang |
| author_facet | Debin Wan Christophe Morisseau Bruce D. Hammock Jun Yang |
| author_sort | Debin Wan |
| collection | DOAJ |
| description | Vicinal diols are important signaling metabolites of various inflammatory diseases, and some of them are potential biomarkers for some diseases. Utilizing the rapid reaction between diol and 6-bromo-3-pyridinylboronic acid (BPBA), a selective and sensitive approach was established to profile these vicinal diols using liquid chromatography-post column derivatization coupled with double precursor ion scan-mass spectrometry (LC-PCD-DPIS-MS). After derivatization, all BPBA-vicinal-diol esters gave a pair of characteristic isotope ions resulting from <sup>79</sup>Br and <sup>81</sup>Br. The unique isotope pattern generated two characteristic fragment ions of <i>m/z</i> 200 and 202. Compared to a traditional offline derivatization technique, the new LC-PCD-DPIS-MS method retained the capacity of LC separation. In addition, it is more sensitive and selective than a full scan MS method. As an application, an in vitro study of the metabolism of epoxy fatty acids by human soluble epoxide hydrolase was tested. These vicinal-diol metabolites of individual regioisomers from different types of polyunsaturated fatty acids were easily identified. The limit of detection (LOD) reached as low as 25 nM. The newly developed LC-PCD-DPIS-MS method shows significant advantages in improving the selectivity and therefore can be employed as a powerful tool for profiling vicinal-diol compounds from biological matrices. |
| first_indexed | 2024-03-10T03:30:24Z |
| format | Article |
| id | doaj.art-f013983d16ae4408b032b54e141c0b7f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:30:24Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f013983d16ae4408b032b54e141c0b7f2023-11-23T11:59:23ZengMDPI AGMolecules1420-30492022-01-0127128310.3390/molecules27010283A Fast and Selective Approach for Profiling Vicinal Diols Using Liquid Chromatography-Post Column Derivatization-Double Precursor Ion Scanning Mass SpectrometryDebin Wan0Christophe Morisseau1Bruce D. Hammock2Jun Yang3Department of Entomology and Nematology and UCD Comprehensive Cancer Center, University of California, One Shields Avenue, Davis, CA 95616, USADepartment of Entomology and Nematology and UCD Comprehensive Cancer Center, University of California, One Shields Avenue, Davis, CA 95616, USADepartment of Entomology and Nematology and UCD Comprehensive Cancer Center, University of California, One Shields Avenue, Davis, CA 95616, USADepartment of Entomology and Nematology and UCD Comprehensive Cancer Center, University of California, One Shields Avenue, Davis, CA 95616, USAVicinal diols are important signaling metabolites of various inflammatory diseases, and some of them are potential biomarkers for some diseases. Utilizing the rapid reaction between diol and 6-bromo-3-pyridinylboronic acid (BPBA), a selective and sensitive approach was established to profile these vicinal diols using liquid chromatography-post column derivatization coupled with double precursor ion scan-mass spectrometry (LC-PCD-DPIS-MS). After derivatization, all BPBA-vicinal-diol esters gave a pair of characteristic isotope ions resulting from <sup>79</sup>Br and <sup>81</sup>Br. The unique isotope pattern generated two characteristic fragment ions of <i>m/z</i> 200 and 202. Compared to a traditional offline derivatization technique, the new LC-PCD-DPIS-MS method retained the capacity of LC separation. In addition, it is more sensitive and selective than a full scan MS method. As an application, an in vitro study of the metabolism of epoxy fatty acids by human soluble epoxide hydrolase was tested. These vicinal-diol metabolites of individual regioisomers from different types of polyunsaturated fatty acids were easily identified. The limit of detection (LOD) reached as low as 25 nM. The newly developed LC-PCD-DPIS-MS method shows significant advantages in improving the selectivity and therefore can be employed as a powerful tool for profiling vicinal-diol compounds from biological matrices.https://www.mdpi.com/1420-3049/27/1/283vicinal diolsepoxide hydrolasedouble precursor ion scanonline post-column derivatization |
| spellingShingle | Debin Wan Christophe Morisseau Bruce D. Hammock Jun Yang A Fast and Selective Approach for Profiling Vicinal Diols Using Liquid Chromatography-Post Column Derivatization-Double Precursor Ion Scanning Mass Spectrometry Molecules vicinal diols epoxide hydrolase double precursor ion scan online post-column derivatization |
| title | A Fast and Selective Approach for Profiling Vicinal Diols Using Liquid Chromatography-Post Column Derivatization-Double Precursor Ion Scanning Mass Spectrometry |
| title_full | A Fast and Selective Approach for Profiling Vicinal Diols Using Liquid Chromatography-Post Column Derivatization-Double Precursor Ion Scanning Mass Spectrometry |
| title_fullStr | A Fast and Selective Approach for Profiling Vicinal Diols Using Liquid Chromatography-Post Column Derivatization-Double Precursor Ion Scanning Mass Spectrometry |
| title_full_unstemmed | A Fast and Selective Approach for Profiling Vicinal Diols Using Liquid Chromatography-Post Column Derivatization-Double Precursor Ion Scanning Mass Spectrometry |
| title_short | A Fast and Selective Approach for Profiling Vicinal Diols Using Liquid Chromatography-Post Column Derivatization-Double Precursor Ion Scanning Mass Spectrometry |
| title_sort | fast and selective approach for profiling vicinal diols using liquid chromatography post column derivatization double precursor ion scanning mass spectrometry |
| topic | vicinal diols epoxide hydrolase double precursor ion scan online post-column derivatization |
| url | https://www.mdpi.com/1420-3049/27/1/283 |
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