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Mar. Drugs 2014, 12(4), 1959-1976; doi:10.3390/md12041959
Article

Antifouling Activity of Synthetic Alkylpyridinium Polymers Using the Barnacle Model

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Received: 23 December 2013; in revised form: 26 February 2014 / Accepted: 26 February 2014 / Published: 2 April 2014
(This article belongs to the Special Issue Advances and New Perspectives in Marine Biotechnology)
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Abstract: Polymeric alkylpyridinium salts (poly-APS) isolated from the Mediterranean marine sponge, Haliclona (Rhizoniera) sarai, effectively inhibit barnacle larva settlement and natural marine biofilm formation through a non-toxic and reversible mechanism. Potential use of poly-APS-like compounds as antifouling agents led to the chemical synthesis of monomeric and oligomeric 3-alkylpyridinium analogues. However, these are less efficient in settlement assays and have greater toxicity than the natural polymers. Recently, a new chemical synthesis method enabled the production of poly-APS analogues with antibacterial, antifungal and anti-acetylcholinesterase activities. The present study examines the antifouling properties and toxicity of six of these synthetic poly-APS using the barnacle (Amphibalanus amphitrite) as a model (cyprids and II stage nauplii larvae) in settlement, acute and sub-acute toxicity assays. Two compounds, APS8 and APS12-3, show antifouling effects very similar to natural poly-APS, with an anti-settlement effective concentration that inhibits 50% of the cyprid population settlement (EC50) after 24 h of 0.32 mg/L and 0.89 mg/L, respectively. The toxicity of APS8 is negligible, while APS12-3 is three-fold more toxic (24-h LC50: nauplii, 11.60 mg/L; cyprids, 61.13 mg/L) than natural poly-APS. This toxicity of APS12-3 towards nauplii is, however, 60-fold and 1200-fold lower than that of the common co-biocides, Zn- and Cu-pyrithione, respectively. Additionally, exposure to APS12-3 for 24 and 48 h inhibits the naupliar swimming ability with respective IC50 of 4.83 and 1.86 mg/L.
Keywords: Amphibalanus amphitrite; antifouling; natural product antifoulants; alkylpyridinium polymers; Haliclona (Rhizoniera) sarai; barnacle; settlement assay; toxicity assay; swimming inhibition assay Amphibalanus amphitrite; antifouling; natural product antifoulants; alkylpyridinium polymers; Haliclona (Rhizoniera) sarai; barnacle; settlement assay; toxicity assay; swimming inhibition assay
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Piazza, V.; Dragić, I.; Sepčić, K.; Faimali, M.; Garaventa, F.; Turk, T.; Berne, S. Antifouling Activity of Synthetic Alkylpyridinium Polymers Using the Barnacle Model. Mar. Drugs 2014, 12, 1959-1976.

AMA Style

Piazza V, Dragić I, Sepčić K, Faimali M, Garaventa F, Turk T, Berne S. Antifouling Activity of Synthetic Alkylpyridinium Polymers Using the Barnacle Model. Marine Drugs. 2014; 12(4):1959-1976.

Chicago/Turabian Style

Piazza, Veronica; Dragić, Ivanka; Sepčić, Kristina; Faimali, Marco; Garaventa, Francesca; Turk, Tom; Berne, Sabina. 2014. "Antifouling Activity of Synthetic Alkylpyridinium Polymers Using the Barnacle Model." Mar. Drugs 12, no. 4: 1959-1976.


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