Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings

The accumulation of marine biofouling on ship hulls causes material damage, the spread of invasive species, and, indirectly, an increase in full consumption and subsequent pollutant gas emissions. Most efficient antifouling (AF) strategies rely on the conventional release of persistent, bioaccumulat...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Cátia Vilas-Boas, Ana Rita Neves, Francisca Carvalhal, Sandra Pereira, Maria José Calhorda, Vitor Vasconcelos, Madalena Pinto, Emília Sousa, Joana R. Almeida, Elisabete R. Silva, Marta Correia-da-Silva
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	Biofouling Econea Eco-friendly Non-release systems Synthetic Xanthones Environmental pollution TD172-193.5 Environmental sciences GE1-350
Acceso en línea:	https://doaj.org/article/0a5a5cec16c349768a418e40d004bcd2
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:0a5a5cec16c349768a418e40d004bcd2
record_format	dspace
spelling	oai:doaj.org-article:0a5a5cec16c349768a418e40d004bcd22021-11-14T04:28:21ZMultidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings0147-651310.1016/j.ecoenv.2021.112970https://doaj.org/article/0a5a5cec16c349768a418e40d004bcd22021-12-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S0147651321010824https://doaj.org/toc/0147-6513The accumulation of marine biofouling on ship hulls causes material damage, the spread of invasive species, and, indirectly, an increase in full consumption and subsequent pollutant gas emissions. Most efficient antifouling (AF) strategies rely on the conventional release of persistent, bioaccumulative, and toxic biocides incorporated in marine coatings. A simple oxygenated xanthone, 3,4-dihydroxyxanthone (1), was previously reported as a promising AF agent toward the settlement of Mytilus galloprovincialis larvae, with a therapeutic ratio higher than the commercial biocide Econea®. In this work, a structure-AF activity relationship study, an evaluation of environmental fate, and an AF efficiency in marine coatings were performed with compound 1. Hydroxy or methoxy groups at 3 and 4 positions in compound 1 favored AF activity, and groups with higher steric hindrances were detrimental. Compound 1 demonstrated low water-solubility and a short half-life in natural seawater, contrary to Econea®. In silico environmental fate predictions showed that compound 1 does not bioaccumulate in organism tissues, in contrast to other current emerging biocides, has a moderate affinity for sediments and slow migrates to ground water. No toxicity was observed against Vibrio fischeri and Phaeodactylum tricornutum. Polyurethane-based marine coatings containing compound 1 prepared through an innovative non-release-strategy were as efficient as those containing Econea® with low releases to water after 45 days. This proof-of-concept helped to establish compound 1 as a promising eco-friendly AF agent.Cátia Vilas-BoasAna Rita NevesFrancisca CarvalhalSandra PereiraMaria José CalhordaVitor VasconcelosMadalena PintoEmília SousaJoana R. AlmeidaElisabete R. SilvaMarta Correia-da-SilvaElsevierarticleBiofoulingEconeaEco-friendlyNon-release systemsSyntheticXanthonesEnvironmental pollutionTD172-193.5Environmental sciencesGE1-350ENEcotoxicology and Environmental Safety, Vol 228, Iss , Pp 112970- (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Biofouling Econea Eco-friendly Non-release systems Synthetic Xanthones Environmental pollution TD172-193.5 Environmental sciences GE1-350
spellingShingle	Biofouling Econea Eco-friendly Non-release systems Synthetic Xanthones Environmental pollution TD172-193.5 Environmental sciences GE1-350 Cátia Vilas-Boas Ana Rita Neves Francisca Carvalhal Sandra Pereira Maria José Calhorda Vitor Vasconcelos Madalena Pinto Emília Sousa Joana R. Almeida Elisabete R. Silva Marta Correia-da-Silva Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings
description	The accumulation of marine biofouling on ship hulls causes material damage, the spread of invasive species, and, indirectly, an increase in full consumption and subsequent pollutant gas emissions. Most efficient antifouling (AF) strategies rely on the conventional release of persistent, bioaccumulative, and toxic biocides incorporated in marine coatings. A simple oxygenated xanthone, 3,4-dihydroxyxanthone (1), was previously reported as a promising AF agent toward the settlement of Mytilus galloprovincialis larvae, with a therapeutic ratio higher than the commercial biocide Econea®. In this work, a structure-AF activity relationship study, an evaluation of environmental fate, and an AF efficiency in marine coatings were performed with compound 1. Hydroxy or methoxy groups at 3 and 4 positions in compound 1 favored AF activity, and groups with higher steric hindrances were detrimental. Compound 1 demonstrated low water-solubility and a short half-life in natural seawater, contrary to Econea®. In silico environmental fate predictions showed that compound 1 does not bioaccumulate in organism tissues, in contrast to other current emerging biocides, has a moderate affinity for sediments and slow migrates to ground water. No toxicity was observed against Vibrio fischeri and Phaeodactylum tricornutum. Polyurethane-based marine coatings containing compound 1 prepared through an innovative non-release-strategy were as efficient as those containing Econea® with low releases to water after 45 days. This proof-of-concept helped to establish compound 1 as a promising eco-friendly AF agent.
format	article
author	Cátia Vilas-Boas Ana Rita Neves Francisca Carvalhal Sandra Pereira Maria José Calhorda Vitor Vasconcelos Madalena Pinto Emília Sousa Joana R. Almeida Elisabete R. Silva Marta Correia-da-Silva
author_facet	Cátia Vilas-Boas Ana Rita Neves Francisca Carvalhal Sandra Pereira Maria José Calhorda Vitor Vasconcelos Madalena Pinto Emília Sousa Joana R. Almeida Elisabete R. Silva Marta Correia-da-Silva
author_sort	Cátia Vilas-Boas
title	Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings
title_short	Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings
title_full	Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings
title_fullStr	Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings
title_full_unstemmed	Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings
title_sort	multidimensional characterization of a new antifouling xanthone: structure-activity relationship, environmental compatibility, and immobilization in marine coatings
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/0a5a5cec16c349768a418e40d004bcd2
work_keys_str_mv	AT catiavilasboas multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT anaritaneves multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT franciscacarvalhal multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT sandrapereira multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT mariajosecalhorda multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT vitorvasconcelos multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT madalenapinto multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT emiliasousa multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT joanaralmeida multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT elisabetersilva multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings AT martacorreiadasilva multidimensionalcharacterizationofanewantifoulingxanthonestructureactivityrelationshipenvironmentalcompatibilityandimmobilizationinmarinecoatings
_version_	1718429999108718592

Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings

Ejemplares similares