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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

1
,
2
,
2
,
1
,
1
,
2
 and
2,*
1 ISMAR—CNR Institute of Marine Science, U.O.S. Genova, Via De Marini 6, 16149 Genova, Italy 2 Department of Biology, Biotechnical Faculty, University of Ljubljana, Večna pot 111, Ljubljana 1000, Slovenia
* Author to whom correspondence should be addressed.
Received: 23 December 2013 / Revised: 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 (CC BY 3.0).

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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.

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