{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T17:12:03Z","timestamp":1787505123848,"version":"build-2736575974"},"reference-count":60,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2022,6,9]],"date-time":"2022-06-09T00:00:00Z","timestamp":1654732800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000001","name":"The National Science Foundation Partnerships in International Research and Education program","doi-asserted-by":"publisher","award":["1743802"],"award-info":[{"award-number":["1743802"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"The National Science Foundation Partnerships in International Research and Education program","doi-asserted-by":"publisher","award":["279247"],"award-info":[{"award-number":["279247"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005416","name":"The Research Council of Norway","doi-asserted-by":"publisher","award":["1743802"],"award-info":[{"award-number":["1743802"]}],"id":[{"id":"10.13039\/501100005416","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005416","name":"The Research Council of Norway","doi-asserted-by":"publisher","award":["279247"],"award-info":[{"award-number":["279247"]}],"id":[{"id":"10.13039\/501100005416","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Toxins"],"abstract":"<jats:p>Ciguatera poisoning is a global health concern caused by the consumption of seafood containing ciguatoxins (CTXs). Detection of CTXs poses significant analytical challenges due to their low abundance even in highly toxic fish, the diverse and in-part unclarified structures of many CTX congeners, and the lack of reference standards. Selective detection of CTXs requires methods such as liquid chromatography coupled to tandem mass spectrometry (LC\u2013MS\/MS) or high-resolution MS (LC\u2013HRMS). While HRMS data can provide greatly improved resolution, it is typically less sensitive than targeted LC\u2013MS\/MS and does not reliably comply with the FDA guidance level of 0.1 \u00b5g\/kg CTXs in fish tissue that was established for Caribbean CTX-1 (C-CTX-1). In this study, we provide a new chemical derivatization approach employing a fast and simple one-pot derivatization with Girard\u2019s reagent T (GRT) that tags the C-56-ketone intermediate of the two equilibrating C-56 epimers of C-CTX-1 with a quaternary ammonium moiety. This derivatization improved the LC\u2013MS\/MS and LC\u2013HRMS responses to C-CTX-1 by approximately 40- and 17-fold on average, respectively. These improvements in sensitivity to the GRT-derivative of C-CTX-1 are attributable to: the improved ionization efficiency caused by insertion of a quaternary ammonium ion; the absence of adduct-ions and water-loss peaks for the GRT derivative in the mass spectrometer, and; the prevention of on-column epimerization (at C-56 of C-CTX-1) by GRT derivatization, leading to much better chromatographic peak shapes. This C-CTX-1\u2013GRT derivatization strategy mitigates many of the shortcomings of current LC\u2013MS analyses for C-CTX-1 by improving instrument sensitivity, while at the same time adding selectivity due to the reactivity of GRT with ketones and aldehydes.<\/jats:p>","DOI":"10.3390\/toxins14060399","type":"journal-article","created":{"date-parts":[[2022,6,13]],"date-time":"2022-06-13T06:31:59Z","timestamp":1655101919000},"page":"399","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Reductive Amination for LC\u2013MS Signal Enhancement and Confirmation of the Presence of Caribbean Ciguatoxin-1 in Fish"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8611-9330","authenticated-orcid":false,"given":"Fedor","family":"Kryuchkov","sequence":"first","affiliation":[{"name":"Toxinology Research Group, Norwegian Veterinary Institute, P.O. Box 64, 1431 \u00c5s, Norway"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2537-0943","authenticated-orcid":false,"given":"Alison","family":"Robertson","sequence":"additional","affiliation":[{"name":"School of Marine and Environmental Sciences, 600 Clinic Drive, Mobile, AL 36688, USA"},{"name":"Marine Ecotoxicology, Dauphin Island Sea Laboratory, 101 Bienville Blvd., Dauphin Island, AL 36528, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elizabeth M.","family":"Mudge","sequence":"additional","affiliation":[{"name":"Biotoxin Metrology, National Research Council, 1411 Oxford Street, Halifax, NS B3H 3Z1, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8537-4439","authenticated-orcid":false,"given":"Christopher O.","family":"Miles","sequence":"additional","affiliation":[{"name":"Biotoxin Metrology, National Research Council, 1411 Oxford Street, Halifax, NS B3H 3Z1, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Soetkien","family":"Van Gothem","sequence":"additional","affiliation":[{"name":"Department of Bioanalysis, Faculty of Pharmaceutical Sciences, Ghent University, Ottergemsesteenweg 460, 9000 Gent, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6419-9563","authenticated-orcid":false,"given":"Silvio","family":"Uhlig","sequence":"additional","affiliation":[{"name":"Toxinology Research Group, Norwegian Veterinary Institute, P.O. Box 64, 1431 \u00c5s, Norway"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,6,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1016\/S0041-0101(00)00161-6","article-title":"The changing face of ciguatera","volume":"39","author":"Lewis","year":"2001","journal-title":"Toxicon"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1016\/0041-0101(80)90074-4","article-title":"Origins of ciguatera fish poisoning: A new dinoflagellate, Gambierdiscus toxicus Adachi and Fukuyo, definitively involved as a causal agent","volume":"18","author":"Bagnis","year":"1980","journal-title":"Toxicon"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1111\/jeu.12292","article-title":"Characterization of a strain of Fukuyoa paulensis (Dinophyceae) from the Western Mediterranean Sea","volume":"63","author":"David","year":"2016","journal-title":"J. Eukaryot. 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