{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,24]],"date-time":"2026-07-24T03:25:19Z","timestamp":1784863519449,"version":"3.55.0"},"reference-count":24,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2021,8,25]],"date-time":"2021-08-25T00:00:00Z","timestamp":1629849600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"the Hong Kong Branch of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou)","award":["SMSEGL20SC01"],"award-info":[{"award-number":["SMSEGL20SC01"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Butenolide derivatives have the potential to be effective and environmentally friendly antifouling agents. In the present study, a butenolide derivative was structurally modified into Boc-butenolide to increase its melting point and remove its foul smell. The structurally modified Boc-butenolide demonstrated similar antifouling capabilities to butenolide in larval settlement bioassays but with significantly lower toxicity at high concentrations. Release-rate measurements demonstrated that the antifouling compound Boc-butenolide could be released from polycaprolactone-polyurethane (PCL-PU)-based coatings to inhibit the attachment of foulers. The coating matrix was easily degraded in the marine environment. The performance of the Boc-butenolide antifouling coatings was further examined through a marine field test. The coverage of biofouler on the Boc-butenolide coatings was low after 2 months, indicating the antifouling potential of Boc-butenolide.<\/jats:p>","DOI":"10.3390\/md19090481","type":"journal-article","created":{"date-parts":[[2021,8,26]],"date-time":"2021-08-26T00:19:26Z","timestamp":1629937166000},"page":"481","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Synthetic Analogue of Butenolide as an Antifouling Agent"],"prefix":"10.3390","volume":"19","author":[{"given":"Ho Yin","family":"Chiang","sequence":"first","affiliation":[{"name":"Department of Ocean Science, Division of Life Science and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), The Hong Kong University of Science and Technology, Hong Kong, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3585-6645","authenticated-orcid":false,"given":"Jinping","family":"Cheng","sequence":"additional","affiliation":[{"name":"Department of Ocean Science, Division of Life Science and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), The Hong Kong University of Science and Technology, Hong Kong, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xuan","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Ocean Science, Division of Life Science and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), The Hong Kong University of Science and Technology, Hong Kong, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1649-723X","authenticated-orcid":false,"given":"Chunfeng","family":"Ma","sequence":"additional","affiliation":[{"name":"Faculty of Materials Science and Engineering, South China University of Technology, Guangzhou 510000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pei-Yuan","family":"Qian","sequence":"additional","affiliation":[{"name":"Department of Ocean Science, Division of Life Science and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), The Hong Kong University of Science and Technology, Hong Kong, China"},{"name":"Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Nansha 510000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,8,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1016\/j.jenvman.2008.08.013","article-title":"The legal design of the international and European Union ban on tributyltin antifouling paint: Direct and indirect effects","volume":"90","author":"Gipperth","year":"2009","journal-title":"J. Environ. Manag."},{"key":"ref_2","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_3","doi-asserted-by":"crossref","first-page":"400","DOI":"10.1039\/C0NP00034E","article-title":"Antifouling marine natural products","volume":"28","author":"Fusetani","year":"2011","journal-title":"Nat. Prod. Rep."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1080\/08927014.2014.997226","article-title":"Mini-review: Marine natural products and their synthetic analogs as antifouling compounds: 2009\u20132014","volume":"31","author":"Qian","year":"2015","journal-title":"Biofouling"},{"key":"ref_5","first-page":"1210","article-title":"Marine natural products as antifouling molecules\u2014A mini-review (2014\u20132020)","volume":"36","author":"Liu","year":"2020","journal-title":"Biofouling"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1080\/08927010500504784","article-title":"Inhibition of biofouling by marine microorganisms and their metabolites","volume":"22","author":"Dobretsov","year":"2006","journal-title":"Biofouling"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1331","DOI":"10.1016\/j.biortech.2009.09.046","article-title":"Potent antifouling compounds produced by marine Streptomyces","volume":"101","author":"Xu","year":"2010","journal-title":"Bioresour. Technol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1080\/08927010600967261","article-title":"Antifouling potential of cyanobacteria: A mini-review","volume":"22","author":"Dahms","year":"2006","journal-title":"Biofouling"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1007\/s10126-007-9001-9","article-title":"Marine biofilms as mediators of colonization by marine macroorganisms: Implications for antifouling and aquaculture","volume":"9","author":"Qian","year":"2007","journal-title":"Mar. Biotechnol."},{"key":"ref_10","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_11","doi-asserted-by":"crossref","first-page":"857","DOI":"10.1080\/08927014.2012.717071","article-title":"Structural optimization and evaluation of butenolides as potent antifouling agents: Modification of the side chain affects the biological activities of compounds","volume":"28","author":"Li","year":"2012","journal-title":"Biofouling"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1007\/978-1-62703-342-8_6","article-title":"On exploring structure-activity relationships","volume":"993","author":"Guha","year":"2013","journal-title":"Methods Mol. Biol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6304","DOI":"10.1021\/acssuschemeng.7b01385","article-title":"Environmentally friendly antifouling coatings based on biodegradable polymer and natural antifoulant","volume":"5","author":"Ma","year":"2017","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_14","unstructured":"Simone, B., and Rupika, D. (2017). Pharmacokinetics. Pharmacognosy, Academic Press. [1st ed.]."},{"key":"ref_15","unstructured":"Ka, M.N., Rafiqul, G., and Kim, D.-J. (2007). Marine biofouling protection: Design of controlled release antifouling paints. Computer Aided Chemical Engineering, Elsevier."},{"key":"ref_16","unstructured":"Claire, H., and Diego, Y. (2009). 18\u2014Tin-free self-polishing marine antifouling coatings. Advances in Marine Antifouling Coatings and Technologies, Woodhead Publishing."},{"key":"ref_17","unstructured":"ASTM (2013). Standard Practice for the Preparation of Substitute Ocean Water, ASTM International. ASTM D1141-98."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1080\/08927010109378480","article-title":"Effect of cyprid age on the settlement of Balanus amphitrite darwin in response to Natural Biofilms","volume":"17","author":"Harder","year":"2001","journal-title":"Biofouling"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/S0022-0981(97)00267-0","article-title":"Effects of larval starvation and delayed metamorphosis on juvenile survival and growth of the tube-dwelling polychaete Hydroides elegans (Haswell)","volume":"227","author":"Qian","year":"1998","journal-title":"J. Exp Mar. Biol. Ecol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1139\/m62-029","article-title":"Studies of marine planktonic diatoms. I. Cyclotella nana Hustedt, and Detonula confervacea (cleve) Gran","volume":"8","author":"Guillard","year":"1962","journal-title":"Can. J. Microbiol."},{"key":"ref_21","unstructured":"ASTM (2013). Standard Test Method for Determination of Organic Biocide Release Rate from Antifouling Coatings in Substitute Ocean Water, ASTM International. ASTM D6903-07."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1075","DOI":"10.1016\/j.chemosphere.2014.09.056","article-title":"Degradation kinetics of a potent antifouling agent, butenolide, under various environmental conditions","volume":"119","author":"Chen","year":"2015","journal-title":"Chemosphere"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1080\/08927014.2017.1409891","article-title":"Anti-biofilm effect of a butenolide\/polymer coating and metatranscriptomic analyses","volume":"34","author":"Ding","year":"2018","journal-title":"Biofouling"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"671","DOI":"10.1038\/nmeth.2089","article-title":"NIH Image to ImageJ: 25 years of image analysis","volume":"9","author":"Schneider","year":"2012","journal-title":"Nat. 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