Synthesis and biological activities of 1H-indole-1-carboxylic acid aryl esters as a marine antifouling coating

Wang, Xuemei; Wang, Xuan; Dong, Miao; Li, Zhiming; Liu, Zhongxin; Lu, Juyou; Lin, Qiang; Yang, Jianxin

doi:10.1007/s11998-019-00305-3

Cited by 6 publications

(3 citation statements)

References 35 publications

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“…Inspired by the promising AF activity of natural indoles, a series of indole derivatives (compounds 7-15, Figure 1) were prepared by introducing a carboxylic acid aryl ester at the N-position of the indole ring. All indole-1-carboxylic acid aryl esters displayed AF activity and were submitted to a field test in a resin-based paint [38]. Paints were prepared by adding 90 wt% of acrylic ester resin with 10 wt% of compounds 7-15, and then were coated onto the surface of the steel panels (300 × 150 × 3mm).…”

Section: Acrylic Resin-based Coatingsmentioning

confidence: 99%

“…Moreover, it was found that the presence of electron-withdrawing groups was more beneficial for AF activity than electron-donating groups. The evaluation of the release rates of compounds from the AF coatings showed a downward trend as time prolonged, at first having a higher release rate due to the massive release from the surface layer, which stabilized after 14 days, resulting in the long-lasting and effective inhibition of the growth and attachment of marine fouling organisms [38].…”

Section: Acrylic Resin-based Coatingsmentioning

confidence: 99%

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Proof of Concept of Natural and Synthetic Antifouling Agents in Coatings

Pereira,

Almeida,

Cidade

et al. 2024

Marine Drugs

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Marine biofouling, caused by the deposition and accumulation of marine organisms on submerged surfaces, represents a huge concern for the maritime industries and also contributes to environmental pollution and health concerns. The most effective way to prevent this phenomenon is the use of biocide-based coatings which have proven to cause serious damage to marine ecosystems. Several research groups have focused on the search for new environmentally friendly antifoulants, including marine and terrestrial natural products and synthetic analogues. Some of these compounds have been incorporated into marine coatings and display interesting antifouling activities caused by the interference with the biofilm-forming species as well as by the inhibition of the settlement of macroorganisms. This review highlights the proof-of-concept studies of emerging natural or synthetic antifouling compounds in coatings, from lab-made to commercial ones, performed between 2019 and 2023 and their results in the field or in in vivo laboratorial tests.

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Section: Acrylic Resin-based Coatingsmentioning

confidence: 99%

Section: Acrylic Resin-based Coatingsmentioning

confidence: 99%

Proof of Concept of Natural and Synthetic Antifouling Agents in Coatings

Pereira,

Almeida,

Cidade

et al. 2024

Marine Drugs

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“…However, their high cost and complicated extraction process hinder their widespread application. As a consequence, synthetic antifoulants, which can also be degraded in seawater, are alternative approaches used for antifouling [27][28][29]. Among these synthetic antifoulants, heterocyclic compounds with a considerable inhibition on bacteria, algae, and fungus have been widely investigated [30,31].…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and Synergistic Effect of Heterocyclic Groups Grafted on Acrylic Polymers by Ester Groups for Marine Antifouling

Wang,

Liu,

Liu

et al. 2023

Coatings

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Using a synthetic antifoulant is an alternative technique to using a natural antifoulant for its economical and large-scale production characteristics. In this study, we synthesized allyl 3-oxzo[d]isothiazole-2(3H)-carboxylate (BIT-C) and a series of other heterocyclic compounds, including triazole, pyridine, and thiazole derivatives. These heterocyclic monomers were used to prepare a new series of acrylic polymers by grafting them onto the side chains. The weight change on the 42nd day was less than −0.091 mg/cm−2, indicating that antifoulants can be released into seawater consistently and enduringly. The antibacterial and anti-algae tests revealed that all the polymers had exceptional inhibition rates on E. coli, S. aureus, Chlorella, and Chaetoceros curvisetus, with the highest inhibition rates of 99.81%, 99.22%, 92.70%, and 95.42%, respectively. Furthermore, the oyster and barnacle density and algae coverage rate were only about 200 per square meter and 10%, compared to 1800 per square meter and 100% of a blank plate after 90 days hanging in a real marine environment, showing a promising antifouling performance. This work verifies the possibility of a method for grafting different heterocycles on a single polymer to make a series of polymers that can be useful as an environmentally friendly antifouling coating.

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