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

Vilas-Boas, Cátia; Neves, Ana Rita; Carvalhal, Francisca; Pereira, Sandra; Calhorda, Maria José; Vasconcelos, Vítor; Pinto, Madalena; Sousa, Emília; Almeida, Joana R.; Silva, Elisabete R.; Correia-da-Silva, Marta

doi:10.1016/j.ecoenv.2021.112970

Cited by 17 publications

(12 citation statements)

References 34 publications

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“…In this direction in this work, we proceeded with efforts to explore the structure-antifouling activity relationship (SAR) of xanthones and achieve optimized xanthone-derived antifoulants. Our findings revealed that the presence of hydroxyl groups at positions 3 and 4 was not crucial for activity since derivatives with methoxy groups at these positions were also active [14]. In this work, a library of 24 synthetic xanthones with three substitution patterns-1,3,4-trisubstituted xanthones (1, 6, 8-10, 12-24), 1,3,4,6tetrasubstituted xanthones (2, 4, 5, 7, and 11) and 1,2,3,4,6-pentasubstituted xanthone (3)was studied.…”

Section: Introductionmentioning

confidence: 68%

“…xanthone 21 (vs. 15), and xanthone 19 (vs. 12). Overall, xanthones containing a hydroxy group at position 4 and a methoxy group at position 3 (9,(12)(13)(14)(15) were not significantly active (p > 0.05) against the settlement of M. galloprovincialis larvae. Neither CHBr 2 (7) or CHO (11) moiety at C-1 produced an enhancement of the anti-settlement activity (65-45% settlement at 50 µM) when compared to the parent xanthone 2.…”

Section: Structure-anti-settlement Activity Relationship Of Xanthone Derivativesmentioning

confidence: 90%

“…In this direction in this work, we proceeded with efforts to explore the structure-antifouling activity relationship (SAR) of xanthones and achieve optimized xanthone-derived antifoulants. Our findings revealed that the presence of hydroxyl groups at positions 3 and 4 was not crucial for activity since derivatives with methoxy groups at these positions were also active [14]. In this work, a library of 24 In an attempt to further explore the potential of xanthone derivatives for antifouling purposes, we explored for the first time the antifouling activity of a series of nineteen synthetic analogs [13].…”

Section: Introductionmentioning

confidence: 91%

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From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents

et al. 2021

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Biofouling, which occurs when certain marine species attach and accumulate in artificial submerged structures, represents a serious economic and environmental issue worldwide. The discovery of new non-toxic and eco-friendly antifouling systems to control or prevent biofouling is, therefore, a practical and urgent need. In this work, the antifouling activity of a series of 24 xanthones, with chemical similarities to natural products, was exploited. Nine (1, 2, 4, 6, 8, 16, 19, 21, and 23) of the tested xanthones presented highly significant anti-settlement responses at 50 μM against the settlement of mussel Mytilus galloprovincialis larvae and low toxicity to this macrofouling species. Xanthones 21 and 23 emerged as the most effective larval settlement inhibitors (EC50 = 7.28 and 3.57 µM, respectively). Additionally, xanthone 23 exhibited a therapeutic ratio (LC50/EC50) > 15, as required by the US Navy program attesting its suitability as natural antifouling agents. From the nine tested xanthones, none of the compounds were found to significantly inhibit the growth of the marine biofilm-forming bacterial strains tested. Xanthones 4, 6, 8, 16, 19, 21, and 23 were found to be non-toxic to the marine non-target species Artemia salina (<10% mortality at 50 μM). Insights on the antifouling mode of action of the hit xanthones 21 and 23 suggest that these two compounds affected similar molecular targets and cellular processes in mussel larvae, including that related to mussel adhesion capacity. This work exposes for the first time the relevance of C-1 aminated xanthones with a 3,4-dioxygenated pattern of substitution as new non-toxic products to prevent marine biofouling.

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Section: Introductionmentioning

confidence: 68%

Section: Structure-anti-settlement Activity Relationship Of Xanthone Derivativesmentioning

confidence: 90%

“…In this direction in this work, we proceeded with efforts to explore the structure-antifouling activity relationship (SAR) of xanthones and achieve optimized xanthone-derived antifoulants. Our findings revealed that the presence of hydroxyl groups at positions 3 and 4 was not crucial for activity since derivatives with methoxy groups at these positions were also active [14]. In this work, a library of 24 In an attempt to further explore the potential of xanthone derivatives for antifouling purposes, we explored for the first time the antifouling activity of a series of nineteen synthetic analogs [13].…”

Section: Introductionmentioning

confidence: 91%

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From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents

et al. 2021

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“…This could be achieved by, for example, microencapsulation of 1 . , Alternatively, methods to immobilize 1 in, or on, a coating could be considered. Immobilization in marine coatings has been successfully applied for the antifouling biocide 4-bromo-2-(4-chlorophenyl)-5-(trifluoro-methyl)-1 H pyrrole-3-carbonitrile (ECONEA) and to nature-inspired synthetic compounds. , …”

Section: Resultsmentioning

confidence: 99%

Nature-Inspired Peptide Antifouling Biocide: Coating Compatibility, Field Validation, and Environmental Stability

Cahill,

Grant,

Rennison

et al. 2023

ACS Appl. Bio Mater.

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This study reports the development of a class of eco-friendly antifouling biocides based on a cyclic dipeptide scaffold, 2,5-diketopiperazine (2,5-DKP). The lead compound cyclo(N-Bip-l-Arg-N-Bip-l-Arg) (1) was synthesized in gram amounts and used to assess the compatibility with an ablation/hydration coating, efficacy against biofouling, and biodegradation. Leaching of 1 from the coating into seawater was assessed via a rotating drum method, revealing relatively stable and predictable leaching rates under dynamic shear stress conditions (36.1 ± 19.7 to 25.2 ± 9.1 ng–1 cm–2 day–1) but low or no leaching under static conditions. The coatings were further analyzed using time-of-flight secondary ion mass spectrometry (ToF-SIMS), with 1 seen to localize at the surface of the coating in a surfactant-like fashion. When coatings were deployed in the ocean, detectable reductions in biofouling development were measured for up to 11 weeks. After this time, biofouling overwhelmed the performance of the coating, consistent with leaching kinetics. Biodegradation of 1 in seawater was assessed using theoretical oxygen demand and analytical quantification. Masking effects were observed at higher concentrations of 1 due to antimicrobial properties, but half-lives were calculated ranging from 13.4 to 16.2 days. The results can rationally inform future development toward commercial antifouling products.

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“…New antifouling biocides are transforming into less toxic products [ 4 ], with a low tendency to bioaccumulate [ 5 ], and a low toxicity to non-target organisms [ 6 , 7 ]. However, most of the research works focused on the evaluation of the chemical, physical, and mechanical properties of antifouling coatings without considering their environmental and economic impact [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Environmental and Economic Impact of an Innovative Biocide-Free Antifouling Coating for Naval Applications

et al. 2023

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The work provides an economic sustainability and environmental impact analysis for the validation of a biocide-free antifouling coating for marine applications able to reduce fuel consumption during navigation, CO2 emissions, and the overall environmental impacts associated with shipping, thanks to the reduction of incrustation and the avoidance of biocides release into the water. The results, related to the life cycle of the coating of a motor yacht, with an average sailing life of 25 years, show around 8.8% reduction in overall costs compared to a conventional paint, thanks to a more efficient antifouling action, which reduces the annual fuel consumption by ~13,700 kg/y, or ~9.6%. This leads to a reduction in CO2 emissions, associated with fuel consumption, of ~43.3 ton/y, as well as a lowering of the overall environmental impacts associated with the life cycle of the paint, by almost 10% for the most impactful damage classes, ensuring a greater environmental sustainability of the innovative coating, for the overall service life of the yacht on which it is applied.

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

Cited by 17 publications

References 34 publications

From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents

From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents

Nature-Inspired Peptide Antifouling Biocide: Coating Compatibility, Field Validation, and Environmental Stability

Environmental and Economic Impact of an Innovative Biocide-Free Antifouling Coating for Naval Applications

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