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Cahill, P. L., Moodie, L. W., Hertzer, C., Pinori, E., Pavia, H., Hellio, C., . . . Svenson, J. (2024). Creating New Antifoulants Using the Tools and Tactics of Medicinal Chemistry. Accounts of Chemical Research, 57, 399
Åpne denne publikasjonen i ny fane eller vindu >>Creating New Antifoulants Using the Tools and Tactics of Medicinal Chemistry
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2024 (engelsk)Inngår i: Accounts of Chemical Research, ISSN 0001-4842, E-ISSN 1520-4898, Vol. 57, s. 399-Artikkel i tidsskrift (Fagfellevurdert) Epub ahead of print
Abstract [en]

Conspectus The unwanted accumulation of marine micro- and macroorganisms such as algae and barnacles on submerged man-made structures and vessel hulls is a major challenge for any marine operation. Known as biofouling, this problem leads to reduced hydrodynamic efficiency, significantly increased fuel usage, microbially induced corrosion, and, if not managed appropriately, eventual loss of both performance and structural integrity. Ship hull biofouling in the international maritime transport network conservatively accounts for 0.6% of global carbon emissions, highlighting the global scale and the importance of this problem. Improved antifouling strategies to limit surface colonization are paramount for essential activities such as shipping, aquaculture, desalination, and the marine renewable energy sector, representing both a multibillion dollar cost and a substantial practical challenge. From an ecological perspective, biofouling is a primary contributor to the global spread of invasive marine species, which has extensive implications for the marine environment. Historically, heavy metal-based toxic biocides have been used to control biofouling. However, their unwanted collateral ecological damage on nontarget species and bioaccumulation has led to recent global bans. With expanding human activities within aquaculture and offshore energy, it is both urgent and apparent that environmentally friendly surface protection remains key for maintaining the function of both moving and stationary marine structures. Biofouling communities are typically a highly complex network of both micro- and macroorganisms, representing a broad section of life from bacteria to macrophytes and animals. Given this diversity, it is unrealistic to expect that a single antifouling “silver bullet” will prevent colonization with the exception of generally toxic biocides. For that reason, modern and future antifouling solutions are anticipated to rely on novel coating technologies and “combination therapies” where mixtures of narrow-spectrum bioactive components are used to provide coverage across fouling species. In contrast to the existing cohort of outdated, toxic antifouling strategies, such as copper- and tributyltin-releasing paints, modern drug discovery techniques are increasingly being employed for the rational design of effective yet safe alternatives. The challenge for a medicinal chemistry approach is to effectively account for the large taxonomic diversity among fouling organisms combined with a lack of well-defined conserved molecular targets within most taxa. The current Account summarizes our work employing the tools of modern medicinal chemistry to discover, modify, and develop optimized and scalable antifouling solutions based on naturally occurring antifouling and repelling compounds from both marine and terrestrial sources. Inspiration for rational design comes from targeted studies on allelopathic natural products, natural repelling peptides, and secondary metabolites from sessile marine organisms with clean exteriors, which has yielded several efficient and promising antifouling leads.

sted, utgiver, år, opplag, sider
American Chemical Society, 2024
Emneord
Animals, Aquatic Organisms, Biofouling, Biological Products, Chemistry, Pharmaceutical, Disinfectants, Humans, biological product, disinfectant agent, animal, aquatic species, human, medicinal chemistry, prevention and control
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-71934 (URN)10.1021/acs.accounts.3c00733 (DOI)2-s2.0-85184302554 (Scopus ID)
Tilgjengelig fra: 2024-02-27 Laget: 2024-02-27 Sist oppdatert: 2024-02-27bibliografisk kontrollert
Berglin, M., Cavanagh, J. P., Caous, J. S., Thakkar, B. S., Vasquez, J. M., Stensen, W., . . . Svenson, J. (2023). Flexible and Biocompatible Antifouling Polyurethane Surfaces Incorporating Tethered Antimicrobial Peptides through Click Reactions. Macromolecular Bioscience
Åpne denne publikasjonen i ny fane eller vindu >>Flexible and Biocompatible Antifouling Polyurethane Surfaces Incorporating Tethered Antimicrobial Peptides through Click Reactions
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2023 (engelsk)Inngår i: Macromolecular Bioscience, ISSN 1616-5187, E-ISSN 1616-5195Artikkel i tidsskrift (Fagfellevurdert) Epub ahead of print
Abstract [en]

Efficient, simple antibacterial materials to combat implant-associated infections are much in demand. Herein, the development of polyurethanes, both cross-linked thermoset and flexible and versatile thermoplastic, suitable for “click on demand” attachment of antibacterial compounds enabled via incorporation of an alkyne-containing diol monomer in the polymer backbone, is described. By employing different polyolic polytetrahydrofurans, isocyanates, and chain extenders, a robust and flexible material comparable to commercial thermoplastic polyurethane is prepared. A series of short synthetic antimicrobial peptides are designed, synthesized, and covalently attached in a single coupling step to generate a homogenous coating. The lead material is shown to be biocompatible and does not display any toxicity against either mouse fibroblasts or reconstructed human epidermis according to ISO and OECD guidelines. The repelling performance of the peptide-coated materials is illustrated against colonization and biofilm formation by Staphylococcus aureus and Staphylococcus epidermidis on coated plastic films and finally, on coated commercial central venous catheters employing LIVE/DEAD staining, confocal laser scanning microscopy, and bacterial counts. This study presents the successful development of a versatile and scalable polyurethane with the potential for use in the medical field to reduce the impact of bacterial biofilms. 

sted, utgiver, år, opplag, sider
John Wiley and Sons Inc, 2023
Emneord
Bacteria; Biocompatibility; Biofilms; Cell culture; Coated materials; Crosslinking; Peptides; Plastic coatings; Reinforced plastics; Anti-foulings; Antibacterial materials; Antimicrobial peptide; Biocompatible; Click chemistry; Click reaction; Flexible; Implant-associated infection; On demands; Simple++; Polyurethanes
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-68814 (URN)10.1002/mabi.202300425 (DOI)2-s2.0-85178409798 (Scopus ID)
Merknad

This study was financed by Amicoat A/S. The authors are grateful for the analytical assistance from RISE scientists L. Brive, P. Borchardt, K. Johansson, and J. Somertune.

Tilgjengelig fra: 2024-01-08 Laget: 2024-01-08 Sist oppdatert: 2024-01-15bibliografisk kontrollert
Cahill, P., Grant, T., Rennison, D., Champeau, O., Boundy, M., Passfield, E., . . . Svenson, J. (2023). Nature-Inspired Peptide Antifouling Biocide: Coating Compatibility, Field Validation, and Environmental Stability. ACS Applied Bio Materials, 6(6), 2415-2425
Åpne denne publikasjonen i ny fane eller vindu >>Nature-Inspired Peptide Antifouling Biocide: Coating Compatibility, Field Validation, and Environmental Stability
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2023 (engelsk)Inngår i: ACS Applied Bio Materials, E-ISSN 2576-6422, Vol. 6, nr 6, s. 2415-2425Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

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. 

sted, utgiver, år, opplag, sider
American Chemical Society, 2023
Emneord
2, 5-diketopiperazine, antifouling, biocide, eco-friendly, peptide, Biofouling, Disinfectants, Kinetics, Peptides, Biocides, Biomimetics, Coatings, Leaching, Lead compounds, Seawater, Secondary ion mass spectrometry, Shear stress, disinfectant agent, Anti-foulings, Antifouling biocides, Cyclic dipeptide, Diketopiperazines, Environmental stability, Field validation, Rotating drums, Synthesised, chemistry, prevention and control
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-65667 (URN)10.1021/acsabm.3c00226 (DOI)2-s2.0-85163305141 (Scopus ID)
Merknad

This project was funded by the New Zealand Ministry for Business, Innovation, and Employment (Contract: CAWX1805, “Next generation marine antifouling using designer peptides”).

Tilgjengelig fra: 2023-08-10 Laget: 2023-08-10 Sist oppdatert: 2023-08-10bibliografisk kontrollert
Vinagre, P., Lindén, J. B., Mardaras, E., Pinori, E. & Svenson, J. (2022). Probing the correlation between corrosion resistance and biofouling of thermally sprayed metallic substrata in the field. Biofouling (Print), 38(2), 147-161
Åpne denne publikasjonen i ny fane eller vindu >>Probing the correlation between corrosion resistance and biofouling of thermally sprayed metallic substrata in the field
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2022 (engelsk)Inngår i: Biofouling (Print), ISSN 0892-7014, E-ISSN 1029-2454, Vol. 38, nr 2, s. 147-161Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The correlation between inherent corrosion resistance and biofouling was investigated for five different metallic coatings. Steel panels thermally spray-coated with either aluminium, Monel, bronze or different aluminium alloys were tested in controlled salt mist conditions and electrochemical corrosion tests and subsequently employed at sea. The biofouling of the panels was monitored at different depths (5, 10 and 15 m) at periods ranging from 5 to 12 months. The main macrofouling organisms were quantified and analysed using permutational multivariate analysis. The results indicate a significant difference in fouling pressure between depths and the geographic sites used. No statistically significant link between high corrosion resistance and lower biofouling pressure was observed, indicating that the main marine macrofoulers settled equally well on corrosion resistant and corrosion prone metallic surfaces. This work sheds light on biofouling of thermally sprayed metallic substrata and it characterizes and compares biofouling assemblages from different biogeographical regions in Europe. 

sted, utgiver, år, opplag, sider
Taylor and Francis Ltd., 2022
Emneord
alloy, Biofouling, corrosion, macrofouling, salt water, thermal spray
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-58901 (URN)10.1080/08927014.2022.2033736 (DOI)2-s2.0-85125370934 (Scopus ID)
Tilgjengelig fra: 2022-03-25 Laget: 2022-03-25 Sist oppdatert: 2023-05-16bibliografisk kontrollert
Karlsen, E., Stensen, W., Juskewitz, E., Svenson, J., Berglin, M. & Svendsen, J. S. (2021). Anti-colonization effect of au surfaces with self-assembled molecular monolayers functionalized with antimicrobial peptides on s. Epidermidis. Antibiotics, 10(12), Article ID 1516.
Åpne denne publikasjonen i ny fane eller vindu >>Anti-colonization effect of au surfaces with self-assembled molecular monolayers functionalized with antimicrobial peptides on s. Epidermidis
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2021 (engelsk)Inngår i: Antibiotics, ISSN 0066-4774, E-ISSN 2079-6382, Vol. 10, nr 12, artikkel-id 1516Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Medical devices with an effective anti-colonization surface are important tools for com-batting healthcare-associated infections. Here, we investigated the anti-colonization efficacy of antimicrobial peptides covalently attached to a gold model surface. The gold surface was modified by a self-assembled polyethylene glycol monolayer with an acetylene terminus. The peptides were covalently connected to the surface through a copper-catalyzed [3 + 2] azide-acetylene coupling (CuAAC). The anti-colonization efficacy of the surfaces varied as a function of the antimicrobial activity of the peptides, and very effective surfaces could be prepared with a 6 log unit reduction in bacterial colonization. © 2021 by the authors. 

sted, utgiver, år, opplag, sider
MDPI, 2021
Emneord
Anti-colonization, Antifouling, Antimicrobial peptide, Antimicrobial surface, Certika, Self-assembled monolayer, ToF-SIMS imaging, acetylene, copper, dichloromethane, gold, macrogol, macrogol 200, macrogol 400, phenylalanine, polypeptide antibiotic agent, self assembled monolayer, tryptophan, antibiotic sensitivity, antimicrobial activity, Article, bacterial colonization, colony forming unit, column chromatography, drug synthesis, electrospray mass spectrometry, Escherichia coli, Gram negative bacterium, healthcare associated infection, high performance liquid chromatography, lipophilicity, minimum inhibitory concentration, nonhuman, proton nuclear magnetic resonance, Staphylococcus epidermidis, time of flight mass spectrometry
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-57900 (URN)10.3390/antibiotics10121516 (DOI)2-s2.0-85121753149 (Scopus ID)
Merknad

 Funding details: Norges Forskningsråd, 283272; Funding text 1: This research was funded by Amicoat AS and the Research Council of Norway, grant number 283272.

Tilgjengelig fra: 2022-01-10 Laget: 2022-01-10 Sist oppdatert: 2023-05-25bibliografisk kontrollert
Herzberg, M., Berglin, M., Eliahu, S., Bodin, L., Agrenius, K., Zlotkin, A. & Svenson, J. (2021). Efficient prevention of marine biofilm formation employing a surface-grafted repellent marine peptide. ACS Applied Bio Materials, 4(4), 3360-3373
Åpne denne publikasjonen i ny fane eller vindu >>Efficient prevention of marine biofilm formation employing a surface-grafted repellent marine peptide
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2021 (engelsk)Inngår i: ACS Applied Bio Materials, E-ISSN 2576-6422, Vol. 4, nr 4, s. 3360-3373Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Creation of surfaces resistant to the formation of microbial biofilms via biomimicry has been heralded as a promising strategy to protect a range of different materials ranging from boat hulls to medical devices and surgical instruments. In our current study, we describe the successful transfer of a highly effective natural marine biofilm inhibitor to the 2D surface format. A series of cyclic peptides inspired by the natural equinatoxin II protein produced by Beadlet anemone (Actinia equine) have been evaluated for their ability to inhibit the formation of a mixed marine microbial consortium on polyamide reverse osmosis membranes. In solution, the peptides are shown to effectively inhibit settlement and biofilm formation in a nontoxic manner down to 1 nM concentrations. In addition, our study also illustrates how the peptides can be applied to disperse already established biofilms. Attachment of a hydrophobic palmitic acid tail generates a peptide suited for strong noncovalent surface interactions and allows the generation of stable noncovalent coatings. These adsorbed peptides remain attached to the surface at significant shear stress and also remain active, effectively preventing the biofilm formation over 24 h. Finally, the covalent attachment of the peptides to an acrylate surface was also evaluated and the prepared coatings display a remarkable ability to prevent surface colonization at surface loadings of 55 ng/cm2 over 48 h. The ability to retain the nontoxic antibiofilm activity, documented in solution, in the covalent 2D-format is unprecedented, and this natural peptide motif displays high potential in several material application areas.

sted, utgiver, år, opplag, sider
American Chemical Society, 2021
Emneord
Antifouling, Marine biofilm, Nontoxic, Peptide, Reverse osmosis, Surface grafting, Biofilms, Biomimetics, Boat instruments, Coatings, Osmosis membranes, Palmitic acid, Shear stress, Surgical equipment, Biofilm formation, Covalent attachment, Material application, Microbial biofilm, Microbial consortia, Noncovalent surfaces, Surface colonization, Surgical instrument, Peptides
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-52974 (URN)10.1021/acsabm.0c01672 (DOI)2-s2.0-85103788257 (Scopus ID)
Tilgjengelig fra: 2021-04-21 Laget: 2021-04-21 Sist oppdatert: 2023-12-22bibliografisk kontrollert
Håkansson, J., Cavanagh, J. P., Stensen, W., Mortensen, B., Svendsen, J.-S. -. & Svenson, J. (2021). In vitro and in vivo antibacterial properties of peptide AMC-109 impregnated wound dressings and gels. Journal of Antibiotics, 74, 337-345
Åpne denne publikasjonen i ny fane eller vindu >>In vitro and in vivo antibacterial properties of peptide AMC-109 impregnated wound dressings and gels
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2021 (engelsk)Inngår i: Journal of Antibiotics, ISSN 0021-8820, E-ISSN 1881-1469, Vol. 74, s. 337-345Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Synthetic mimics of antimicrobial peptides (AMPs) is a promising class of molecules for a variety of antimicrobial applications. Several hurdles must be passed before effective systemic infection therapies with AMPs can be achieved, but the path to effective topical treatment of skin, nail, and soft tissue infections appears less challenging to navigate. Skin and soft tissue infection is closely coupled to the emergence of antibiotic resistance and represents a major burden to the healthcare system. The present study evaluates the promising synthetic cationic AMP mimic, AMC-109, for treatment of skin infections in vivo. The compound is evaluated both in impregnated cotton wound dressings and in a gel formulation against skin infections caused by Staphylococcus aureus and methicillin resistant S. aureus. Both the ability to prevent colonization and formation of an infection, as well as eradicate an ongoing infection in vivo with a high bacterial load, were evaluated. The present work demonstrates that AMC-109 displays a significantly higher antibacterial activity with up to a seven-log reduction in bacterial loads compared to current clinical standard therapy; Altargo cream (1% retapamulin) and Fucidin cream (2% fusidic acid) in the in vivo wound models. It is thus concluded that AMC-109 represents a promising entry in the development of new and effective remedies for various skin infections. © 2021, The Author(s)

sted, utgiver, år, opplag, sider
Springer Nature, 2021
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-52240 (URN)10.1038/s41429-021-00406-5 (DOI)2-s2.0-85099971826 (Scopus ID)
Merknad

Funding details: Norges Forskningsråd; Funding text 1: Acknowledgements This work was partly supported by the BIA— User-driven Research-based Innovation Project Program (Grant Number 281949) from the Research Council of Norway.

Tilgjengelig fra: 2021-02-05 Laget: 2021-02-05 Sist oppdatert: 2023-05-22bibliografisk kontrollert
Greco, I., Molchanova, N., Holmedal, E., Jenssen, H., Hummel, B. D., Watts, J. L., . . . Svenson, J. (2020). Correlation between hemolytic activity, cytotoxicity and systemic in vivo toxicity of synthetic antimicrobial peptides.. Scientific Reports, 10(1), Article ID 13206.
Åpne denne publikasjonen i ny fane eller vindu >>Correlation between hemolytic activity, cytotoxicity and systemic in vivo toxicity of synthetic antimicrobial peptides.
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2020 (engelsk)Inngår i: Scientific Reports, E-ISSN 2045-2322, Vol. 10, nr 1, artikkel-id 13206Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The use of non-standard toxicity models is a hurdle in the early development of antimicrobial peptides towards clinical applications. Herein we report an extensive in vitro and in vivo toxicity study of a library of 24 peptide-based antimicrobials with narrow spectrum activity towards veterinary pathogens. The haemolytic activity of the compounds was evaluated against four different species and the relative sensitivity against the compounds was highest for canine erythrocytes, intermediate for rat and human cells and lowest for bovine cells. Selected peptides were additionally evaluated against HeLa, HaCaT and HepG2 cells which showed increased stability towards the peptides. Therapeutic indexes of 50-500 suggest significant cellular selectivity in comparison to bacterial cells. Three peptides were administered to rats in intravenous acute dose toxicity studies up to 2-8 × MIC. None of the injected compounds induced any systemic toxic effects in vivo at the concentrations employed illustrating that the correlation between the different assays is not obvious. This work sheds light on the in vitro and in vivo toxicity of this class of promising compounds and provides insights into the relationship between the different toxicity models often employed in different manners to evaluate the toxicity of novel bioactive compounds in general.

Emneord
Drug development, Drug discovery, Drug safety, Infectious diseases, Medical research, Medicinal chemistry, Pharmacology, Toxicology
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-46286 (URN)10.1038/s41598-020-69995-9 (DOI)32764602 (PubMedID)
Tilgjengelig fra: 2020-08-18 Laget: 2020-08-18 Sist oppdatert: 2023-05-22bibliografisk kontrollert
Vinagre, P., Simas, T., Cruz, E., Pinori, E. & Svenson, J. (2020). Marine biofouling: A European database for the marine renewable energy sector. Journal of Marine Science and Engineering, 8(8), Article ID 495.
Åpne denne publikasjonen i ny fane eller vindu >>Marine biofouling: A European database for the marine renewable energy sector
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2020 (engelsk)Inngår i: Journal of Marine Science and Engineering, E-ISSN 2077-1312, Vol. 8, nr 8, artikkel-id 495Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Biofouling is a major problem shared among all maritime sectors employing submerged structures where it leads to substantially increased costs and lowered operational lifespans if poorly addressed. Insight into the ongoing processes at the relevant marine locations is key to effective management of biofouling. Of specific concern for the marine renewable energy (MRE) sector is the fact that information on biofouling composition and magnitude across geographies is dispersed throughout published papers and consulting reports. To enable rapid access to relevant key biofouling events the present work describes a European biofouling database to support the MRE sector and other maritime industries. The database compiles in one document qualitative and quantitative data for challenging biofouling groups, including non-native species associated with MRE and related marine equipment, in different European Ecoregions. It provides information on the occurrence of fouling species and data on key biofouling parameters, such as biofouling thickness and weight. The database aims to aid the MRE sector and offshore industries in understanding which biofouling communities their devices are more susceptible to at a given site, to facilitate informed decisions. In addition, the biofouling mapping is useful for the development of biosecurity risk management plans as well as academic research. © 2020 by the authors.

sted, utgiver, år, opplag, sider
MDPI AG, 2020
Emneord
Biofouling, Colonization, Macrofouling, Mapping, Marine renewable energy, Maritime, Non-native species
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-46801 (URN)10.3390/JMSE8070495 (DOI)2-s2.0-85089279949 (Scopus ID)
Merknad

Funding details: Steadman Philippon Research Institute, SPRI; Funding details: Centre for Industrial Technological Development, CDTI; Funding details: Energimyndigheten; Funding details: IK4-Azterlan, OCEANERA/0005/2014; Funding details: Eusko Jaurlaritza; Funding details: Fundação para a Ciência e a Tecnologia, FCT; Funding text 1: This research was funded by FCT (Portuguese Foundation for Science and Technology), SWEA (Swedish Energy Agency), SPRI (Basque Business Development Agency), EVE (Energy Agency of the Basque Government) and CDTI (Spanish Centre for the Development of Industrial Technology) throughOCEANERA-NET(Ocean Energy European Research Network) under the reference OCEANERA/0005/2014. The authors thank the OCEANIC partners CorPower Ocean (H?gersten, Sweden), Gaiker (Zamudio, Spain), IK4-Azterlan (Durango, Spain), Repol (Almazora, Spain), RISE (Bor?s, Sweden), WavEC (Lisboa, Portugal), Skandinavisk Ytf?r?dling (Esl?v, Sweden) and Recubrimientos Mikra (Idiazabal, Spain)for the support during the project.

Tilgjengelig fra: 2020-08-24 Laget: 2020-08-24 Sist oppdatert: 2023-05-16bibliografisk kontrollert
Labriere, C., Elumalai, V., Staffansson, J., Cervin, G., Le Norcy, T., Denardou, H., . . . Svenson, J. (2020). Phidianidine A and synthetic analogues as naturally inspired marine antifoulants. Journal of Natural Products, 83(11), 3413-3423
Åpne denne publikasjonen i ny fane eller vindu >>Phidianidine A and synthetic analogues as naturally inspired marine antifoulants
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2020 (engelsk)Inngår i: Journal of Natural Products, ISSN 0163-3864, E-ISSN 1520-6025, Vol. 83, nr 11, s. 3413-3423Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Stationary and slow-moving marine organisms regularly employ a natural product chemical defense to prevent being colonized by marine micro- and macroorganisms. While these natural antifoulants can be structurally diverse, they often display highly conserved chemistries and physicochemical properties, suggesting a natural marine antifouling pharmacophore. In our current report, we investigate the marine natural product phidianidine A, which displays several chemical properties found in highly potent marine antifoulants. Phidianidine A and synthetic analogues were screened against the settlement and metamorphosis of Amphibalanus improvisus cyprids, and several of the compounds displayed inhibitory activities at low micromolar concentrations with IC50 values down to 0.7 μg/mL observed. The settlement study highlights that phidianidine A is a potent natural antifoulant and that the scaffold can be tuned to generate simpler and improved synthetic analogues. The bioactivity is closely linked to the size of the compound and to its basicity. The study also illustrates that active analogues can be prepared in the absence of the natural constrained 1,2,4-oxadiazole ring. A synthetic lead analogue of phidianidine A was incorporated in a coating and included in antifouling field trials, where it was shown that the coating induced potent inhibition of marine bacteria and microalgae settlement.

sted, utgiver, år, opplag, sider
American Chemical Society, 2020
HSV kategori
Identifikatorer
urn:nbn:se:ri:diva-50996 (URN)10.1021/acs.jnatprod.0c00881 (DOI)2-s2.0-85096227269 (Scopus ID)
Merknad

Funding details: Göteborgs Universitet; Funding details: Norges Forskningsråd, ES508288, 275043; Funding text 1: For C.L., J.H.H., J.S., and V.E., this work was partly supported with grants from the Norwegian Research Council (ES508288 and 275043 CasCat). L.W.K.M. acknowledges the Uppsala Antibiotic Centre for support. H.P. and G.C. were supported by the Centre for Marine Chemical Ecology ( http://www.cemace.science.gu.se ) at the University of Gothenburg. Finally, the authors are grateful to V. Bhave (TOC) for providing the image of Phidiana militaris.

Tilgjengelig fra: 2020-12-10 Laget: 2020-12-10 Sist oppdatert: 2021-03-26bibliografisk kontrollert
Organisasjoner
Identifikatorer
ORCID-id: ORCID iD iconorcid.org/0000-0002-4729-9359
v. 2.41.0