{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,11]],"date-time":"2026-02-11T18:32:13Z","timestamp":1770834733067,"version":"3.50.1"},"reference-count":64,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2020,12,24]],"date-time":"2020-12-24T00:00:00Z","timestamp":1608768000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["PTDC\/BTA-BTA\/31422\/2017"],"award-info":[{"award-number":["PTDC\/BTA-BTA\/31422\/2017"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["PTDC\/SAU-PUB\/28736\/2017"],"award-info":[{"award-number":["PTDC\/SAU-PUB\/28736\/2017"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["PTDC\/AAG-TEC\/0739\/2014"],"award-info":[{"award-number":["PTDC\/AAG-TEC\/0739\/2014"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"North Portugal Regional Operational Programme (Norte 2020)","award":["NORTE-01-0145-FEDER-000040"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000040"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Over the last decades, antifouling coatings containing biocidal compounds as active ingredients were used to prevent biofouling, and eco-friendly alternatives are needed. Previous research from our group showed that polymethoxylated chalcones and glycosylated flavones obtained by synthesis displayed antifouling activity with low toxicity. In this work, ten new polymethoxylated flavones and chalcones were synthesized for the first time, including eight with a triazole moiety. Eight known flavones and chalcones were also synthesized and tested in order to construct a quantitative structure-activity relationship (QSAR) model for these compounds. Three different antifouling profiles were found: three compounds (1b, 11a and 11b) exhibited anti-settlement activity against a macrofouling species (Mytilus galloprovincialis), two compounds (6a and 6b) exhibited inhibitory activity against the biofilm-forming marine bacteria Roseobacter litoralis and one compound (7b) exhibited activity against both mussel larvae and microalgae Navicula sp. Hydrogen bonding acceptor ability of the molecule was the most significant descriptor contributing positively to the mussel larvae anti-settlement activity and, in fact, the triazolyl glycosylated chalcone 7b was the most potent compound against this species. The most promising compounds were not toxic to Artemia salina, highlighting the importance of pursuing the development of new synthetic antifouling agents as an ecofriendly and sustainable alternative for the marine industry.<\/jats:p>","DOI":"10.3390\/md19010005","type":"journal-article","created":{"date-parts":[[2020,12,24]],"date-time":"2020-12-24T09:02:44Z","timestamp":1608800564000},"page":"5","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Flavonoid Glycosides with a Triazole Moiety for Marine Antifouling Applications: Synthesis and Biological Activity Evaluation"],"prefix":"10.3390","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5711-7598","authenticated-orcid":false,"given":"Daniela","family":"Pereira","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\u2014Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"given":"Catarina","family":"Gon\u00e7alves","sequence":"additional","affiliation":[{"name":"CIIMAR\u2014Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"given":"Beatriz T.","family":"Martins","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1391-2143","authenticated-orcid":false,"given":"Andreia","family":"Palmeira","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\u2014Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3585-2417","authenticated-orcid":false,"given":"Vitor","family":"Vasconcelos","sequence":"additional","affiliation":[{"name":"CIIMAR\u2014Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"},{"name":"Departamento de Biologia, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre S\/N, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4676-1409","authenticated-orcid":false,"given":"Madalena","family":"Pinto","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, R. Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"CIIMAR\u2014Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9356-7265","authenticated-orcid":false,"given":"Joana R.","family":"Almeida","sequence":"additional","affiliation":[{"name":"CIIMAR\u2014Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4150-8532","authenticated-orcid":false,"given":"Marta","family":"Correia-da-Silva","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, R. 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Drugs, 15.","DOI":"10.3390\/md15090266"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1080\/10408347.2012.743846","article-title":"Organotin Compounds: Environmental Fate and Analytics","volume":"43","author":"Dubalska","year":"2013","journal-title":"Crit. Rev. Anal. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1140","DOI":"10.1016\/j.chemosphere.2012.09.022","article-title":"Acute and chronic toxicities of Irgarol alone and in combination with copper to the marine copepod Tigriopus japonicus","volume":"90","author":"Bao","year":"2013","journal-title":"Chemosphere"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1007\/s11998-019-00294-3","article-title":"Chemistry and application of emerging ecofriendly antifouling paints: A review","volume":"17","author":"Kyei","year":"2020","journal-title":"J. Coat. Technol. Res."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"124475","DOI":"10.1016\/j.chemosphere.2019.124475","article-title":"Biotoxicity and life cycle assessment of two commercial antifouling coatings in marine systems","volume":"237","author":"Rossini","year":"2019","journal-title":"Chemosphere"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3260","DOI":"10.1080\/14786419.2018.1470514","article-title":"Marine natural flavonoids: Chemistry and biological activities","volume":"33","author":"Martins","year":"2019","journal-title":"Nat. Prod. Res."},{"key":"ref_8","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_9","doi-asserted-by":"crossref","first-page":"98","DOI":"10.1016\/j.scitotenv.2018.06.169","article-title":"Potential of synthetic chalcone derivatives to prevent marine biofouling","volume":"643","author":"Almeida","year":"2018","journal-title":"Sci. Total Environ."},{"key":"ref_10","first-page":"23","article-title":"Imidazole and Triazole Coordination Chemistry for Antifouling Coatings","volume":"2013","author":"Trojer","year":"2013","journal-title":"J. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1517\/17460441.2012.682725","article-title":"The impact of click chemistry in medicinal chemistry","volume":"7","author":"Hou","year":"2012","journal-title":"Expert Opin. Drug Discov."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2853","DOI":"10.1016\/j.tetlet.2015.03.136","article-title":"New click-chemistry methods for 1,2,3-triazoles synthesis: Recent advances and applications","volume":"56","author":"Totobenazara","year":"2015","journal-title":"Tetrahedron Lett."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2696","DOI":"10.1002\/asia.201100432","article-title":"Click chemistry: 1,2,3-triazoles as pharmacophores","volume":"6","author":"Agalave","year":"2011","journal-title":"Chem Asian J."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1128","DOI":"10.1016\/S1359-6446(03)02933-7","article-title":"The growing impact of click chemistry on drug discovery","volume":"8","author":"Kolb","year":"2003","journal-title":"Drug Discov. Today"},{"key":"ref_15","first-page":"1585","article-title":"The application of click chemistry in the synthesis of agents with anticancer activity","volume":"9","author":"Ma","year":"2015","journal-title":"Drug Des. Devel Ther."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1002\/med.20107","article-title":"Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides and alkynes","volume":"28","author":"Tron","year":"2008","journal-title":"Med. Res. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"871","DOI":"10.1080\/08927014.2016.1200562","article-title":"Screening of bromotyramine analogues as antifouling compounds against marine bacteria","volume":"32","author":"Andjouh","year":"2016","journal-title":"Biofouling"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3687","DOI":"10.1039\/C4RA12739K","article-title":"The impact of 1,2,3-triazoles in the design of functional coatings","volume":"5","author":"Kantheti","year":"2015","journal-title":"RSC Adv."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2855","DOI":"10.1021\/jo048685z","article-title":"Solvent-free synthesis of functionalized flavones under microwave irradiation","volume":"70","author":"Seijas","year":"2005","journal-title":"J. Org. Chem"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2596","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4","article-title":"A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective \"ligation\" of azides and terminal alkynes","volume":"41","author":"Rostovtsev","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3057","DOI":"10.1021\/jo011148j","article-title":"Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides","volume":"67","author":"Christensen","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2933","DOI":"10.1016\/j.ccr.2011.06.028","article-title":"The copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) \u201cclick\u201d reaction and its applications. An overview","volume":"255","author":"Liang","year":"2011","journal-title":"Coord Chem Rev."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2540","DOI":"10.1016\/j.bmcl.2015.04.051","article-title":"Design, synthesis and anticancer activity of matrine-1H-1,2,3-triazole-chalcone conjugates","volume":"25","author":"Zhao","year":"2015","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Park, J., Khloya, P., Seo, Y., Kumar, S., Lee, H.K., Jeon, D.-K., Jo, S., Sharma, P.K., and Namkung, W. (2016). Potentiation of \u0394F508- and G551D-CFTR-Mediated Cl- Current by Novel Hydroxypyrazolines. PLoS ONE, 11.","DOI":"10.1371\/journal.pone.0149131"},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Zhang, J., Fu, X.L., Yang, N., and Wang, Q.A. (2013). Synthesis and cytotoxicity of chalcones and 5-deoxyflavonoids. Sci. World J., 2013.","DOI":"10.1155\/2013\/649485"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"749","DOI":"10.1002\/cmdc.201900735","article-title":"Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities","volume":"15","author":"Loureiro","year":"2020","journal-title":"ChemMedChem"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1021\/ed200596p","article-title":"Synthesis of a d-Glucopyranosyl Azide: Spectroscopic Evidence for Stereochemical Inversion in the SN2 Reaction","volume":"89","author":"Adesoye","year":"2012","journal-title":"J. Chem. Educ."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1080\/08927010902745316","article-title":"Marine antifouling laboratory bioassays: An overview of their diversity","volume":"25","author":"Briand","year":"2009","journal-title":"Biofouling"},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Kojima, R., Kobayashi, S., Satuito, C.G.P., Katsuyama, I., Ando, H., Seki, Y., and Senda, T. (2016). A Method for Evaluating the Efficacy of Antifouling Paints Using Mytilus galloprovincialis in the Laboratory in a Flow-Through System. PLoS ONE, 11.","DOI":"10.1371\/journal.pone.0168172"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1098\/rsif.2005.0074","article-title":"Mussel (Mytilus edulis) byssus deposition in response to variations in surface wettability","volume":"3","author":"Aldred","year":"2006","journal-title":"J. R Soc. Interface"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1080\/08927010903470815","article-title":"Natural products as antifouling compounds: Recent progress and future perspectives","volume":"26","author":"Qian","year":"2010","journal-title":"Biofouling"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"213","DOI":"10.2174\/138620706776055539","article-title":"Computational methods in developing quantitative structure-activity relationships (QSAR): A review","volume":"9","author":"Dudek","year":"2006","journal-title":"Comb. Chem. High. Throughput Screen."},{"key":"ref_33","unstructured":"Dunn, W.J., and Hopfinger, A.J. (2002). 3D QSAR of Flexible Molecules Using Tensor Representation, Kluwer Academic Publishers."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Kubinyi, H. (1993). QSAR: Hansch Analysis and Related Approaches, Wiley-VCH.","DOI":"10.1002\/9783527616824"},{"key":"ref_35","first-page":"511","article-title":"Validation of QSAR Models-Strategies and Importance","volume":"2","author":"Veerasamy","year":"2011","journal-title":"Int. J. Drug Design Discov."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1316","DOI":"10.1021\/acs.jcim.5b00206","article-title":"Beware of R(2): Simple, Unambiguous Assessment of the Prediction Accuracy of QSAR and QSPR Models","volume":"55","author":"Alexander","year":"2015","journal-title":"J. Chem. Inf. Model."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1978","DOI":"10.3390\/ijms10051978","article-title":"Current Mathematical Methods Used in QSAR\/QSPR Studies","volume":"10","author":"Liu","year":"2009","journal-title":"Int. J. Mol. Sci."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Reisfeld, B., and Mayeno, A.N. (2013). On the Development and Validation of QSAR Models. Computational Toxicology: Volume II, Humana Press.","DOI":"10.1007\/978-1-62703-059-5"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1023\/A:1025386326946","article-title":"Rational selection of training and test sets for the development of validated QSAR models","volume":"17","author":"Golbraikh","year":"2003","journal-title":"J. Comput.-Aided Mol. Des."},{"key":"ref_40","unstructured":"OECD (2007). Guidance Document on the Validation of (Quantitative) Structure-Activity Relationships [(Q)SAR] Models, OECD."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Todeschini, R., and Consonni, V. (2009). Molecular Descriptors for Chemoinformatics, Wiley-VCH.","DOI":"10.1002\/9783527628766"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"7198","DOI":"10.1021\/ja015204+","article-title":"Handbook of Molecular Descriptors. Methods and Principles in Medicinal Chemistry Series. Volume 11 By Roberto Todeschini and Viviana Consonni (Universita degli Studi di Milano-Bicocca). Edited by R. Mannold, H. Kubinyi, and H. Timmerman. Wiley-VCH:\u2009 Weinheim and New York. 2000. xxi + 668 pp. 498 DM. ISBN 3-527-29913-O","volume":"123","author":"Dunn","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_43","unstructured":"Roy, K., Kar, S., and Das, R.N. (2015). Understanding the Basics of QSAR for Applications in Pharmaceutical Sciences and Risk Assessment, Academic Press."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1016\/j.biotechadv.2015.01.013","article-title":"Natural antifouling compounds: Effectiveness in preventing invertebrate settlement and adhesion","volume":"33","author":"Almeida","year":"2015","journal-title":"Biotechnol. Adv."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1080\/08927014.2013.776546","article-title":"Mini-review: Molecular mechanisms of antifouling compounds","volume":"29","author":"Qian","year":"2013","journal-title":"Biofouling"},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Chen, L., and Qian, P.Y. (2017). Review on Molecular Mechanisms of Antifouling Compounds: An Update since 2012. Mar. Drugs, 15.","DOI":"10.3390\/md15090264"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1840","DOI":"10.1021\/acs.est.6b05523","article-title":"Identification of Molecular Targets for 4,5-Dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) in Teleosts: New Insight into Mechanism of Toxicity","volume":"51","author":"Chen","year":"2017","journal-title":"Environ. Sci. Technol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/j.aquatox.2014.09.010","article-title":"Proteomic changes in brain tissues of marine medaka (Oryzias melastigma) after chronic exposure to two antifouling compounds: Butenolide and 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT)","volume":"157","author":"Chen","year":"2014","journal-title":"Aquat. Toxicol. (Amst. Neth.)"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"6113","DOI":"10.3390\/md12126113","article-title":"Territrem and butyrolactone derivatives from a marine-derived fungus Aspergillus terreus","volume":"12","author":"Nong","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"364","DOI":"10.1021\/np401002s","article-title":"Isolation and synthesis of pulmonarins A and B, acetylcholinesterase inhibitors from the colonial ascidian Synoicum pulmonaria","volume":"77","author":"Tadesse","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1039\/c2tx20009k","article-title":"Induction of plasma acetylcholinesterase activity and apoptosis in mice treated with the organophosphorus toxicant, tri-o-cresyl phosphate","volume":"1","author":"Jiang","year":"2012","journal-title":"Toxicol. Res."},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Martin-Rodriguez, A.J., Babarro, J.M., Lahoz, F., Sanson, M., Martin, V.S., Norte, M., and Fernandez, J.J. (2015). From broad-spectrum biocides to quorum sensing disruptors and mussel repellents: Antifouling profile of alkyl triphenylphosphonium salts. PLoS ONE, 10.","DOI":"10.1371\/journal.pone.0123652"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1016\/S0025-326X(03)00253-4","article-title":"The effects of a copper-based antifouling paint on mortality and enzymatic activity of a non-target marine organism","volume":"46","author":"Katranitsas","year":"2003","journal-title":"Mar. Pollut. Bull."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1016\/j.scitotenv.2007.07.023","article-title":"Toxicity of four antifouling biocides and their mixtures on the brine shrimp Artemia salina","volume":"387","author":"Koutsaftis","year":"2007","journal-title":"Sci. Total Environ."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"5346","DOI":"10.1016\/j.tet.2011.04.104","article-title":"Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei","volume":"67","author":"Sugamoto","year":"2011","journal-title":"Tetrahedron"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"653","DOI":"10.1211\/0022357011775983","article-title":"Synthesis of flavonoids and their effects on aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues","volume":"53","author":"Lim","year":"2001","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/j.bmc.2011.11.042","article-title":"Solid-phase synthesis of 2\u2032-hydroxychalcones. Effects on cell growth inhibition, cell cycle and apoptosis of human tumor cell lines","volume":"20","author":"Neves","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2739","DOI":"10.3390\/toxins7082739","article-title":"Acetylcholinesterase in Biofouling Species: Characterization and Mode of Action of Cyanobacteria-Derived Antifouling Agents","volume":"7","author":"Almeida","year":"2015","journal-title":"Toxins"},{"key":"ref_59","unstructured":"Katritsky, A., Karelson, M., Lobanov, V.S., Dennington, R., and Keith, T. (2004). CODESSA 2.7.10, Semichem, Inc."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"\u0106wik, J., and Koronacki, J. (1998, January 22\u201326). A Heuristic Method of Model Choice for Nonlinear Regression. Proceedings of the Rough Sets and Current Trends in Computing, Berlin, Heidelberg.","DOI":"10.1007\/3-540-69115-4_10"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/0006-2952(61)90145-9","article-title":"A new and rapid colorimetric determination of acetylcholinesterase activity","volume":"7","author":"Ellman","year":"1961","journal-title":"Biochem. Pharmacol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"288","DOI":"10.1039\/B414773A","article-title":"Sea-urchin (Paracentrotus lividus) glutathione S-transferases and cholinesterase activities as biomarkers of environmental contamination","volume":"7","author":"Cunha","year":"2005","journal-title":"J. Environ. Monit"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"353","DOI":"10.1111\/j.1468-2494.2008.00463.x","article-title":"Screening of Nepalese crude drugs traditionally used to treat hyperpigmentation: In vitro tyrosinase inhibition","volume":"30","author":"Adhikari","year":"2008","journal-title":"Int. J. Cosmet. Sci."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1055\/s-2007-971236","article-title":"Brine shrimp: A convenient general bioassay for active plant constituents","volume":"45","author":"Meyer","year":"1982","journal-title":"Planta Med."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/19\/1\/5\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:45:29Z","timestamp":1760179529000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/19\/1\/5"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,12,24]]},"references-count":64,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2021,1]]}},"alternative-id":["md19010005"],"URL":"https:\/\/doi.org\/10.3390\/md19010005","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,12,24]]}}}