{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T02:20:32Z","timestamp":1777429232788,"version":"3.51.4"},"reference-count":23,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2022,8,25]],"date-time":"2022-08-25T00:00:00Z","timestamp":1661385600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"FCT (Foundation for Science and Technology)","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}]},{"name":"FCT (Foundation for Science and Technology)","award":["UIDP\/04423\/2020 (CIIMAR)"],"award-info":[{"award-number":["UIDP\/04423\/2020 (CIIMAR)"]}]},{"name":"FCT (Foundation for Science and Technology)","award":["UIDB\/04046\/2020"],"award-info":[{"award-number":["UIDB\/04046\/2020"]}]},{"name":"FCT (Foundation for Science and Technology)","award":["UIDP\/04046\/2020 (BioISI)"],"award-info":[{"award-number":["UIDP\/04046\/2020 (BioISI)"]}]},{"name":"FCT (Foundation for Science and Technology)","award":["PTDC\/CTA-AMB\/0853\/2021"],"award-info":[{"award-number":["PTDC\/CTA-AMB\/0853\/2021"]}]},{"name":"FCT (Foundation for Science and Technology)","award":["NORTE-01-0145-FEDER-000040"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000040"]}]},{"DOI":"10.13039\/501100001871","name":"Norte Portugal Regional Operational Programme (NORTE 2020)","doi-asserted-by":"publisher","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Norte Portugal Regional Operational Programme (NORTE 2020)","doi-asserted-by":"publisher","award":["UIDP\/04423\/2020 (CIIMAR)"],"award-info":[{"award-number":["UIDP\/04423\/2020 (CIIMAR)"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Norte Portugal Regional Operational Programme (NORTE 2020)","doi-asserted-by":"publisher","award":["UIDB\/04046\/2020"],"award-info":[{"award-number":["UIDB\/04046\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Norte Portugal Regional Operational Programme (NORTE 2020)","doi-asserted-by":"publisher","award":["UIDP\/04046\/2020 (BioISI)"],"award-info":[{"award-number":["UIDP\/04046\/2020 (BioISI)"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Norte Portugal Regional Operational Programme (NORTE 2020)","doi-asserted-by":"publisher","award":["PTDC\/CTA-AMB\/0853\/2021"],"award-info":[{"award-number":["PTDC\/CTA-AMB\/0853\/2021"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Norte Portugal Regional Operational Programme (NORTE 2020)","doi-asserted-by":"publisher","award":["NORTE-01-0145-FEDER-000040"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000040"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>The development of marine-inspired compounds as non-toxic antifouling (AF) agents has been pursued in the last years. Sulfur is the third most common element in seawater. Sulfur is present in oxygenated seawater as sulfate anion (SO42\u2212), which is the most stable combination of sulfur in seawater, and several promising AF secondary metabolites with sulfate groups have been described. However, sulfated compounds proved to be an analytical challenge to quantify by HPLC. Taking these facts into consideration, this work presents the development and validation of a method for the quantification of gallic acid persulfate (GAP) in seawater and ultrapure water matrix, based on hydrophilic interaction liquid chromatography (HILIC). This method was used to evaluate GAP stability following several abiotic and biotic degradation assays, and to quantify its release in seawater from room-temperature-vulcanizing polydimethylsiloxane commercial coating. GAP was very stable in several water matrices, even at different pH values and in the presence\/absence of marine microorganisms and presented a leaching value lower than 0.5%. This work discloses HILIC as an analytical method to overcome the difficulties in quantifying sulfated compounds in water matrices and highlights the potential of GAP as a promising long-lasting coating.<\/jats:p>","DOI":"10.3390\/md20090548","type":"journal-article","created":{"date-parts":[[2022,8,26]],"date-time":"2022-08-26T02:04:32Z","timestamp":1661479472000},"page":"548","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Quantification of a Sulfated Marine-Inspired Antifouling Compound in Several Aqueous Matrices: Biodegradation Studies and Leaching Assays from Polydimethylsiloxane Coatings"],"prefix":"10.3390","volume":"20","author":[{"given":"C\u00e1tia","family":"Vilas-Boas","sequence":"first","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\/CIMAR\u2014Interdisciplinary Center for Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9151-516X","authenticated-orcid":false,"given":"Virg\u00ednia","family":"Gon\u00e7alves","sequence":"additional","affiliation":[{"name":"UNIPRO\u2014Oral Pathology and Rehabilitation Research Unit, University Institute of Health Sciences (IUCS), CESPU, 4585-116 Gandra, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal"}]},{"given":"Paolo De","family":"Marco","sequence":"additional","affiliation":[{"name":"UNIPRO\u2014Oral Pathology and Rehabilitation Research Unit, University Institute of Health Sciences (IUCS), CESPU, 4585-116 Gandra, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5397-4672","authenticated-orcid":false,"given":"Em\u00edlia","family":"Sousa","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\/CIMAR\u2014Interdisciplinary Center for Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4676-1409","authenticated-orcid":false,"given":"Madalena","family":"Pinto","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\/CIMAR\u2014Interdisciplinary Center for Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6679-4374","authenticated-orcid":false,"given":"Elisabete R.","family":"Silva","sequence":"additional","affiliation":[{"name":"BioISI-Biosystems & Integrative Sciences Institute, Faculdade de Ci\u00eancias, Universidade de Lisboa, 1749-016 Lisboa, Portugal"},{"name":"CERENA-Centro de Recursos Naturais e Ambiente, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3320-730X","authenticated-orcid":false,"given":"Maria Elizabeth","family":"Tiritan","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\/CIMAR\u2014Interdisciplinary Center for Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, Portugal"},{"name":"UNIPRO\u2014Oral Pathology and Rehabilitation Research Unit, University Institute of Health Sciences (IUCS), CESPU, 4585-116 Gandra, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4150-8532","authenticated-orcid":false,"given":"Marta","family":"Correia-da-Silva","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\/CIMAR\u2014Interdisciplinary Center for Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,8,25]]},"reference":[{"key":"ref_1","first-page":"1","article-title":"Sulfated compounds from marine organisms","volume":"119","author":"Kornprobst","year":"1998","journal-title":"Comp. Biochem. Physiol. B Biochem. Mol. Biol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"T211","DOI":"10.1530\/JME-17-0252","article-title":"SULFATION PATHWAYS: Sources and biological activities of marine sulfated steroids","volume":"61","author":"Carvalhal","year":"2018","journal-title":"J. Mol. Endocrinol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"927","DOI":"10.1080\/08927014.2017.1391951","article-title":"An antifouling model from the sea: A review of 25 years of zosteric acid studies","volume":"33","author":"Sousa","year":"2017","journal-title":"Biofouling"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"42424","DOI":"10.1038\/srep42424","article-title":"Antifouling potential of nature-inspired sulfated compounds","volume":"7","author":"Almeida","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"109812","DOI":"10.1016\/j.ecoenv.2019.109812","article-title":"Overcoming environmental problems of biocides: Synthetic bile acid derivatives as a sustainable alternative","volume":"187","author":"Neves","year":"2020","journal-title":"Ecotoxicol. Environ. Saf."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Vilas-Boas, C., Carvalhal, F., Pereira, B., Carvalho, S., Sousa, E., Pinto, M.M.M., Calhorda, M.J., Vasconcelos, V., Almeida, J.R., and Silva, E.R. (2020). One Step Forward towards the Development of Eco-Friendly Antifouling Coatings: Immobilization of a Sulfated Marine-Inspired Compound. Mar. Drugs, 18.","DOI":"10.3390\/md18100489"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Ferreira, O., Rijo, P., Gomes, J., Santos, R., Monteiro, S., Guedes, R., Serralheiro, M.L., Gomes, M., Gomes, L.C., and Mergulh\u00e3o, F.J. (2021). Antimicrobial Ceramic Filters for Water Bio-Decontamination. Coatings, 11.","DOI":"10.3390\/coatings11030323"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.chroma.2005.03.058","article-title":"Retention behavior of small polar compounds on polar stationary phases in hydrophilic interaction chromatography","volume":"1074","author":"Guo","year":"2005","journal-title":"J. Chromatogr. A"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1016\/j.chroma.2004.02.085","article-title":"Separation of rutin nona(H-) and deca(H-) sulfonate sodium by ion-pairing reversed-phase liquid chromatography","volume":"1036","author":"Wang","year":"2004","journal-title":"J. Chromatogr. A"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2215","DOI":"10.1002\/elps.201500208","article-title":"Development and validation of a HILIC- MS\/MS multi-targeted method for metabolomics applications","volume":"36","author":"Virgiliou","year":"2015","journal-title":"Electrophoresis"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3603","DOI":"10.1002\/jssc.200900344","article-title":"Utilization of dual retention mechanism on columns with bonded PEG and diol stationary phases for adjusting the separation selectivity of phenolic and flavone natural antioxidants","volume":"32","author":"Jandera","year":"2009","journal-title":"J. Sep. Sci"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/j.aca.2007.07.039","article-title":"Retention prediction of adrenoreceptor agonists and antagonists on a diol column in hydrophilic interaction chromatography","volume":"598","author":"Quiming","year":"2007","journal-title":"Anal. Chim. Acta"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1007\/s00216-011-5308-5","article-title":"Hydrophilic interaction liquid chromatography (HILIC)\u2014A powerful separation technique","volume":"402","author":"Buszewski","year":"2011","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Rodriguez-Gonzalo, E., and Garc\u00eda-G\u00f3mez, D. (2018). Hydrophilic Interaction Chromatography: Current Trends and Applications. Encyclopedia of Analytical Science, Elsevier.","DOI":"10.1016\/B978-0-12-409547-2.12681-2"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"101370","DOI":"10.1016\/j.mex.2021.101370","article-title":"Analysis of highly polar marine biotoxins in seawater by hydrophilic interaction liquid chromatography coupled to high resolution mass spectrometry","volume":"8","year":"2021","journal-title":"MethodsX"},{"key":"ref_16","first-page":"219","article-title":"Chapter 9\u2014Chromatography Coupled to Various Detectors as a Tool for Separation and Determination of Bioactive Compounds","volume":"Volume 65","author":"Duarte","year":"2014","journal-title":"Comprehensive Analytical Chemistry"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"462498","DOI":"10.1016\/j.chroma.2021.462498","article-title":"A systematic investigation of the effect of sample solvent on peak shape in nano- and microflow hydrophilic interaction liquid chromatography columns","volume":"1655","author":"Li","year":"2021","journal-title":"J. Chromatogr. A"},{"key":"ref_18","unstructured":"ICH (2005, January 2\u20135). Validation of Analytical Procedures: Text and Methodology Q2(R1). Proceedings of the International Conference on Harmonization, Geneva, Switzerland. 17p."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.chroma.2004.10.110","article-title":"Liquid chromatography\u2013tandem mass spectrometry for the analysis of pharmaceutical residues in environmental samples: A review","volume":"1067","author":"Hernando","year":"2005","journal-title":"J. Chromatogr. A"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1080\/08927014.2014.889688","article-title":"Nontoxic piperamides and their synthetic analogues as novel antifouling reagents","volume":"30","author":"Huang","year":"2014","journal-title":"Biofouling"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"224","DOI":"10.1021\/bk-1996-0640.ch011","article-title":"Designing an Environmentally Safe Marine Antifoulant","volume":"Volume 640","author":"Willingham","year":"1996","journal-title":"Designing Safer Chemicals"},{"key":"ref_22","unstructured":"ECHA (2017). Guidance on Information Requirements and Chemical Safety Assessment, ECHA."},{"key":"ref_23","unstructured":"(2008). Standard Practice for Determination of Hydrolysis Rate Constants of Organic Chemicals in Aqueous Solutions (Withdrawn 2013) (Standard No. E895\u201489(2008))."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/20\/9\/548\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:15:12Z","timestamp":1760141712000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/20\/9\/548"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,8,25]]},"references-count":23,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2022,9]]}},"alternative-id":["md20090548"],"URL":"https:\/\/doi.org\/10.3390\/md20090548","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,8,25]]}}}