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Antifouling activity of synthetic alkylpyridinium polymers using the barnacle model.
Mar Drugs. 2014 Apr 02; 12(4):1959-76.MD

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.

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Authors+Show Affiliations

Piazza V
ISMAR-CNR Institute of Marine Science, U.O.S. Genova, Via De Marini 6, 16149 Genova, Italy. veronica.piazza@ge.ismar.cnr.it.
Dragić I
Department of Biology, Biotechnical Faculty, University of Ljubljana, Večna pot 111, Ljubljana 1000, Slovenia. ivana84@gmail.com.
Sepčić K
Department of Biology, Biotechnical Faculty, University of Ljubljana, Večna pot 111, Ljubljana 1000, Slovenia. kristina.sepcic@bf.uni-lj.si.
Faimali M
ISMAR-CNR Institute of Marine Science, U.O.S. Genova, Via De Marini 6, 16149 Genova, Italy. marco.faimali@ismar.cnr.it.
Garaventa F
ISMAR-CNR Institute of Marine Science, U.O.S. Genova, Via De Marini 6, 16149 Genova, Italy. francesca.garaventa@ismar.cnr.it.
Turk T
Department of Biology, Biotechnical Faculty, University of Ljubljana, Večna pot 111, Ljubljana 1000, Slovenia. tom.turk@bf.uni-lj.si.
Berne S
Department of Biology, Biotechnical Faculty, University of Ljubljana, Večna pot 111, Ljubljana 1000, Slovenia. sabina.berne@bf.uni-lj.si.

MeSH

AnimalsBiofoulingHaliclonaInhibitory Concentration 50LarvaMediterranean SeaPolymersPyridinium CompoundsThoracicaToxicity Tests, AcuteToxicity Tests, Subacute

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24699112

Citation

Piazza, Veronica, et al. "Antifouling Activity of Synthetic Alkylpyridinium Polymers Using the Barnacle Model." Marine Drugs, vol. 12, no. 4, 2014, pp. 1959-76.
Piazza V, Dragić I, Sepčić K, et al. Antifouling activity of synthetic alkylpyridinium polymers using the barnacle model. Mar Drugs. 2014;12(4):1959-76.
Piazza, V., Dragić, I., Sepčić, K., Faimali, M., Garaventa, F., Turk, T., & Berne, S. (2014). Antifouling activity of synthetic alkylpyridinium polymers using the barnacle model. Marine Drugs, 12(4), 1959-76. https://doi.org/10.3390/md12041959
Piazza V, et al. Antifouling Activity of Synthetic Alkylpyridinium Polymers Using the Barnacle Model. Mar Drugs. 2014 Apr 2;12(4):1959-76. PubMed PMID: 24699112.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antifouling activity of synthetic alkylpyridinium polymers using the barnacle model. AU - Piazza,Veronica, AU - Dragić,Ivanka, AU - Sepčić,Kristina, AU - Faimali,Marco, AU - Garaventa,Francesca, AU - Turk,Tom, AU - Berne,Sabina, Y1 - 2014/04/02/ PY - 2013/12/23/received PY - 2014/02/26/revised PY - 2014/02/26/accepted PY - 2014/4/5/entrez PY - 2014/4/5/pubmed PY - 2014/12/15/medline SP - 1959 EP - 76 JF - Marine drugs JO - Mar Drugs VL - 12 IS - 4 N2 - 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. SN - 1660-3397 UR - https://www.unboundmedicine.com/medline/citation/24699112/Antifouling_activity_of_synthetic_alkylpyridinium_polymers_using_the_barnacle_model_ DB - PRIME DP - Unbound Medicine ER -