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Biofouling
The Journal of Bioadhesion and Biofilm Research
Volume 27, 2011 - Issue 1
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Original Articles

Evaluation of the antifouling properties of 3-alyklpyridine compounds

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Pages 99-109 | Received 15 Sep 2010, Accepted 19 Nov 2010, Published online: 21 Dec 2010

References

  • Abarzua , S and Jakubowski , S . 1995 . Biotechnological investigation for the prevention of biofouling.1. Biological and biochemical principles for the prevention of biofouling . Mar Ecol Prog Ser , 123 : 301 – 312 .
  • Abarzua , S , Jakubowski , S , Eckert , S and Fuchs , P . 1999 . Biotechnological investigation for the prevention of marine biofouling II. Blue-green algae as potential producers of biogenic agents for the growth inhibition of microfouling organisms . Bot Mar , 42 : 459 – 465 .
  • Alvarez , R and de Lera , A R . 1998 . Synthesis of haminol-A and haminol-B, polyenic alarm pheromones of cephalaspidean molluscs . Tetrahedron: Asymmetry , 9 : 3065 – 3072 .
  • Angarano , M B , McMahon , R D and Schertz , J A . 2009 . Cannabinoids as inhibitors of zebra mussel (Dreissena polymorpha) byssal attachment: a potentially green antifouling technology . Biofouling , 25 : 127 – 138 .
  • Angarano , M B , McMahon , R F , Hawkins , D L and Schetz , J A . 2007 . Exploration of structure-antifouling relationships of capsaicin-like compounds that inhibit zebra mussel (Dreissena polymorpha) macrofouling . Biofouling , 23 : 295 – 305 .
  • Briand , J F . 2009 . Marine antifouling laboratory bioassays: an overview of their diversity . Biofouling , 25 : 297 – 311 .
  • Caprioli , V , Cimino , G , De , Giulio A , Madaio , A , Scognamiglio , G and Trivellone , E . 1992 . Selected biological activities of saraines . Comp Biochem Physiol , 103B : 293 – 296 .
  • Chang , W C , Huang , L C , Wang , Y S , Peng , E P , Chang , H C , Hsu , N Y , Yang , W B and Chen , C H . 2007 . Matrix-assisted laser desorption/ionization (MALDI) mechanism revisited . Anal Chim Acta , 582 : 1 – 9 .
  • Chelossi , E , Mancini , I , Sepcic , K , Turk , T and Faimali , M . 2006 . Comparative antibacterial activity of polymeric 3-alkylpyridinium salts isolated from the Mediterranean sponge Reniera sarai and their synthetic analogues . Biomol Eng , 23 : 317 – 323 .
  • Cimino , G , De , Stefano S , Scognamiglio , G , Sodano , G and Trivellone , E . 1986 . Sarains: a new class of alkaloids from the marine sponge Reniera sarai . Bull Soc Chim Belges , 95 : 783
  • Cimino , G , Passeggio , A , Sodano , G , Spinella , A and Villani , G . 1991 . Alarm pheromones from the Mediterranean opisthobranch Haminoea navicula . Cell Mol Life Sci , 47 : 61 – 63 .
  • Cimino , G , Puliti , R , Scognamiglio , G , Spinella , A , Trivellone , E , Mattia , C A and Mazzarella , L . 1989 . Amazing new alkaloid skeletons from the marine sponge Reniera sarai . Pure Appl Chem , 61 : 535 – 538 .
  • Clare , A S . 1996 . Marine natural product antifoulants: status and potential . Biofouling , 9 : 211 – 229 .
  • Clare , A S , Rittschof , D , Gerhart , D J , Hooper , I R and Bonaventura , J . 1999 . Antisettlement and narcotic action of analogues of diterpene marine natural product antifoulants from octocorals . Mar Biotechnol , 1 : 427 – 436 .
  • Cutignano , A , Cimino , G , Giordano , A , d'Ippolito , G and Fontana , A . 2004 . Polyketide origin of 3-alkylpyridines in the marine mollusc Haminoea orbignyana . Tetrahedron Lett , 45 : 2627 – 2629 .
  • Cutignano , A , Tramice , A , De , Caro S , Villani , G , Cimino , G and Fontana , A . 2003 . Biogenesis of 3-alkylpyridine alkaloids in the marine mollusc Haminoea orbignyana . Angew Chem Int Ed , 42 : 2633 – 2636 .
  • Cutignano , A , Blihoghe , D , Fontana , A , Villani , G , d'Ippolito , G and Cimino , G . 2007 . Fusarypyrones, novel polypropionates from Mediterranean mollusc Haminoea fusari . Tetrahedron , 63 : 12935 – 12939 .
  • Da , Gama BA , Pereira , R C , Carvalho , A GV , Coutinho , R and Yoneshigue-Valentin , Y . 2002 . The effects of seaweed secondary metabolites on biofouling . Biofouling , 18 : 13 – 20 .
  • Davies-Coleman , M T , Faulkner , D J , Dubowchik , G M , Roth , G P , Polson , C and Fairchild , C . 1993 . A new EGF-active polymeric pyridinium alkaloid from the sponge Callyspongia fibrosa . J Org Chem , 58 : 5925 – 5930 .
  • Eleršek , T , Kosi , G , Turk , T , Pohleven , F and Sepčić , K . 2008 . Influence of polymeric 3-alkylpyridinium salts from the marine sponge Reniera sarai on the growth of algae and wood decay fungi . Biofouling , 24 : 137 – 143 .
  • Ellman , G L , Courtney , K D , Andres , V J and Featherstone , R M . 1961 . A new rapid colorimetric determination of acetylcholinesterase activity . Biochem Pharmacol , 7 : 88 – 95 .
  • Evans , S M . 1999 . TBT or not TBT? That is the question . Biofouling , 14 : 117 – 129 .
  • Faimali , M , Sepcic , K , Turk , T and Geraci , S . 2003a . Non-toxic antifouling activity of polymeric 3-alkylpyridinium salts from the Mediterranean sponge Reniera sarai (Pulitzer-Finali) . Biofouling , 19 : 47 – 56 .
  • Faimali , M , Falugi , C , Gallus , L , Piazza , V and Tagliafierro , G . 2003b . Involvement of acetylcholine in settlement of Balanus amphitrite . Biofouling , 19 : 213 – 220 .
  • Faimali , M , Garaventa , F , Mancini , I , Sicurelli , A , Guella , G , Piazza , V and Greco , G . 2005 . Antisettlement activity of synthetic analogues of polymeric 3-alkylpyridinium salts isolated from the sponge Reniera sarai . Biofouling , 21 : 49 – 57 .
  • Faimali , M , Garaventa , F , Piazza , V , Greco , G , Corra , C , Magillo , F , Pittore , M , Giacco , E , Gallus , L , Falugi , C and Tagliafierro , G . 2006 . Swimming speed alteration of larvae of Balanus amphitrite as a behavioral end-point for laboratory toxicological bioassays . Mar Biol , 149 : 87 – 96 .
  • Feng , D Q , Ke , C H , Lu , C Y and Li , S J . 2009 . Herbal plants as a promising source of natural antifoulants: evidence from barnacle settlement inhibition . Biofouling , 25 : 181 – 190 .
  • Ferdous , Z and Muktadir , A KM . 2009 . A review: potentiality of zooplankton as bioindicator . Am J Appl Sci , 6 : 1815 – 1819 .
  • Fusetani , N . 2004 . Biofouling and antifouling . Nat Prod Rep , 21 : 94 – 104 .
  • Fontana , A . 2006 . “ Biogenetic proposals and biosynthetic studies on secondary metabolites of marine molluscs ” . In Marine molecular biotechnology. Series Progress in molecular and subcellular biology, Vol. Molluscs , Edited by: Cimino , G and Gavagnin , M. 303 – 332 . Heidelberg , Germany : Springer .
  • Garaventa , F , Faimali , M , Sepcic , K and Geraci , S . 2003 . Laboratory analysis of antimicrofouling activity of poly-APS extracted from Reniera sarai (Porifera: Demospongiae) . Biol Mar Mediterr , 10 : 565 – 567 .
  • Garaventa , F , Gambardella , C , Di , Fino A , Pittore , M and Faimali , M . 2010 . Swimming speed alteration of Artemia sp. and Brachionus plicatilis as a sub-lethal behavioural end-point for ecotoxicological surveys . Ecotoxicology , 19 : 512 – 519 .
  • Green , A S , Chandler , G T and Piegorsch , W W . 1996 . Life-stage-specific toxicity of sediment-associated chlorpyrifos to a marine, infaunal copepod . Environ Toxicol Chem , 15 : 1182 – 1188 .
  • Hellio , C , Bourgougnon , N and Le Gal , Y . 2000 . Phenoloxidase from Mytilus edulis byssus gland: purification,partial characterization and application for screening products with potential antifouling activities . Biofouling , 16 : 235 – 244 .
  • Houssen , W E , Lu , Z , Edrada-Ebel , R A , Chatzi , C , Tucker , S J , Sepčić , K , Turk , T , Zovko , A , Shen , S Mancini , I . 2010 . Chemical synthesis and biological activities of 3-alkyl pyridinium polymeric analogues of marine toxins . J Chem Biol , 3 : 113 – 125 .
  • Lee , K W , Raisuddin , S , Hwang , D S , Park , H G and Lee , J S . 2007 . Acute toxicities of trace metals and common xenobiotics to the marine copepod Tigriopus japonicus: evaluation of its use as a benchmark species for routine ecotoxicity tests in Western Pacific coastal regions . Environ Toxicol , 22 : 532 – 538 .
  • Lee , K W , Raisuddin , S , Hwang , D S , Park , H G , Dahms , H U , Ahn , I Y and Lee , J S . 2008 . Two-generation toxicity study on the copepod model species Tigriopus japonicas . Chemosphere , 72 : 1359 – 1365 .
  • Malovrh , P , Sepčić , K , Turk , T and Maček , P . 1999 . Characterization of haemolytic activity of 3-alkylpyridinium polymers from the marine sponge Reniera sarai . Comp Biochem Physiol , 124C : 221 – 226 .
  • Marin , A , Alvarez , L A , Cimino , G and Spinella , A . 1999 . Chemical defence in cephalaspidean gastropods: origin, anatomical location and ecological roles . J Molluscan Stud , 65 : 121 – 131 .
  • Miliou , H , Verriopoulos , G , Maroulis , D , Bouloukos , D and Moraitou-Apostolopoulou , M . 2000 . Influence of life-history adaptations on the fidelity of laboratory bioassays for the impact of heavy metals (Co2+ and Cr6+) on tolerance and population dynamics of Tisbe holothuriae . Mar Pollut Bull , 40 : 352 – 359 .
  • Onae , M . 2003 . General aspects of tin-free antifouling paints . Chem Rev , 103 : 3431 – 3448 .
  • Paleari , L , Trombino , S , Falugi , C , Gallus , L , Carlone , S , Angelini , C , Sepčić , K , Turk , T , Faimali , M Noonan , D M . 2006 . Marine sponge-derived polymeric alkylpyridinium salts as a novel tumor chemotherapeutic targeting the cholinergic system in lung tumors . Int J Oncol , 29 : 1381 – 1388 .
  • Pane , L , Giacco , E and Mariottini , G L . 2005 . “ Acute and chronic heavy metal bioassay on Tigriopus fulvus Fischer (Copepoda: Harpacticoida) ” . In 13th Symposium PRIMO 13, Pollutant response in marine organisms 113 Alessandria , , Italy
  • Pane , L , Giacco , E , Corrà , C , Greco , G , Mariottini , G L , Varisco , F and Faimali , M . 2008 . Ecotoxicological evaluation of harbour sediments using marine organisms from different trophic levels . J Soils Sedim , 8 : 74 – 79 .
  • Pelttari , E , Matikainen , J and Elo , H . 2002 . Antimicrobial activity of the marine alkaloids haminol and pulo'upone and related compounds . Z Naturforsch , 57c : 548 – 552 .
  • Qian , P Y , Xu , Y and Fusetani , N . 2010 . Natural products as antifouling compounds: recent progress and future perspectives . Biofouling , 26 : 223 – 234 .
  • Raisuddin , S , Kwok , K WH , Leung , K MY , Schlenk , D and Lee , J S . 2007 . The copepod Tigriopus: a promising marine model organism for ecotoxicology and environmental genomics . Aquat Toxicol , 83 : 161 – 173 .
  • Rittschof , D , Lai , C H , Kok , L M and Teo , S LM . 2003 . Pharmaceuticals as antifoulants: concept and principles . Biofouling , 19 : 207 – 212 .
  • Rittschof , D , Sasikumar , N , Murlless , D , Clare , A S , Gerhart , D and Bonaventura , J . 1994 . “ Mixture interactions of lactones, furans, and a commercial biocide: toxicity and antibarnacle settlement activity ” . In Recent developments in biofouling control , Edited by: Thompson , M F , Nagabhushanam , R , Sarojini , R and Fingerman , M . 269 – 274 . New Delhi : M-F Oxford and IBH Publ. Co .
  • Scott , R H , Whyment , A D , Foster , A , Gordon , K H , Milne , BF and Jaspars , M . 2000 . Analysis of the structure and electrophysiological actions of halitoxins: 1,3 alkyl-pyridinium salts from Callyspongia ridleyi . J Membr Biol , 176 : 119 – 131 .
  • Sepčić , K and Turk , T . 2006 . “ 3-Alkylpyridinium compounds as potential non-toxic antifouling agents ” . In Marine molecular biotechnology, antifouling compounds , Edited by: Fusetani , N and Calre , A S . 105 – 127 . Berlin , Heidelberg : Springer-Verlag .
  • Sepčić , K , Batista , U , Vacelet , J , Macek , P and Turk , T . 1997a . Biological activities of aqueous extracts from marine sponges and cytotoxic effects of 3-alkylpyridinium polymers from Reniera sarai . Comp Biochem Phys C , 117 : 47 – 53 .
  • Sepčić , K , Marcel , V , Klaebe , A , Turk , T , Šuput , D and Fournier , D . 1998 . Inhibition of acetylcholinesterase by an alkylpyridinium polymer from the marine sponge, Reniera sarai . BBA-Protein Struct M , 1387 : 217 – 225 .
  • Sepčić , K , Poklar , N , Vesnaver , G , Fournier , D , Turk , T and Macek , P . 1999 . Interaction of 3-alkylpyridinium polymers from the sea sponge Reniera sarai with insect acetylcholinesterase . J Prot Chem , 18 : 251 – 257 .
  • Sepčić , K , Guella , G , Mancini , I , Pietra , F , DallaSerra , M , Menestrina , G , Tubbs , K , Macek , P and Turk , T . 1997b . Characterization of anticholinesterase-active 3-alkylpyridinium polymers from the marine sponge Reniera sarai in aqueous solutions . J Nat Prod , 60 : 991 – 996 .
  • Spinella , A , Alvarez , L A and Cimino , G . 1993a . Predator-prey relationship between Navanax inermis and Bulla gouldiana: a chemical approach . Tetrahedron , 49 : 3203 – 3210 .
  • Spinella , A , Alvarez , L A , Passeggio , A and Cimino , G . 1993b . New 3-alkylpyridines from 3 Mediterranean cephalaspidean mollusks – structure, ecological role and taxonomic relevance . Tetrahedron , 49 : 1307 – 1314 .
  • Steinberg , P D and de , Nys R . 2002 . Chemical mediation of colonization of seaweed surfaces . J Phycol , 38 : 621 – 629 .
  • Sjögren , M , Dahlström , M , Hedner , E , Jonsson , P R , Vik , A , Gundersen , L L and Bohlin , L . 2008 . Antifouling activity of the sponge metabolite agelasine D and synthesised analogs on Balanus improvisus . Biofouling , 24 : 251 – 258 .
  • Thomas , K V and Brooks , S . 2010 . The environmental fate and effects of antifouling paint biocides . Biofouling , 26 : 73 – 88 .
  • Thomason , J C , Hills , J M , Clare , A S , Neville , A and Richardson , M . 1998 . Hydrodynamic consequences of barnacle colonization . Hydrobiology , 375 : 191 – 201 .
  • Turk , T , Frangež , R and Sepčić , K . 2007 . Mechanisms of toxicity of 3-alkylpyridinium polymers from marine sponge Reniera sarai . Mar Drugs , 5 : 157 – 167 .
  • Turk , T , Sepčić , K , Mancini , I and Guella , G . 2008 . 3-Alkylpyridinium and 3-alkylpyridine compounds from marine sponges, their synthesis, biological activities and potential use. In: Atta-ur-Rahman, editor . Stud Nat Prod Chem , 35 : 355 – 397 .
  • Tsoukatou , M , Marechal , J P , Hellio , C , Novakovic , I , Tufegdzie , S , Sladic , D , Gasic , M J , Clare , A S , Vagias , C and Roussis , V . 2007 . Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms . Molecules , 12 : 1022 – 1034 .
  • Vitalina , S , Avelin , S , Rittschof , D , Sarojoni , R and Nagabhushanam , R . 1991 . “ Compounds from octocorals that inhibit barnacle settlement: isolation and biological potency ” . In Bioactive compounds from marine organisms , Edited by: Thompson , M F , Sorojini , R and Nagabhushanam , R . 331 – 339 . New Delhi : Oxford and IBH Publ. Co .
  • Villa , F , Albanese , D , Giussani , B , Stewart , P S , Daffonchio , D and Cappitelli , F . 2010 . Hindering biofilm formation with zosteric acid . Biofouling , 26 : 739 – 752 .
  • Wahl , M . 1989 . Marine epibiosis. 1. Fouling and antifouling – some basic aspects . Mar Ecol Prog Ser , 58 : 175 – 189 .
  • Wang , G YS , Kuramoto , M , Daisuke , U , Yamada , A , Yamaguchi , K and Yazawa , K . 1996 . Three novel anti-microfouling nitroalkyl pyridine alkaloids from the okinawan marine sponge Callyspongia sp . Tetrahedron Lett , 37 : 1813 – 1816 .
  • Wang , M and Wang , G . 2010 . Oxidative damage effects in the copepod Tigriopus japonicus Mori experimentally exposed to nickel . Ecotoxicology , 19 : 273 – 284 .
  • Zhou , X , Xu , Y , Jin , C and Qian , P Y . 2009a . Reversible anti-settlement activity against Amphibalanus (=Balanus) amphitrite, Bugula neritina, and Hydroides elegans by a nontoxic pharmaceutical compound, mizolastine . Biofouling , 25 : 739 – 747 .
  • Zhou , X , Zhang , Z , Xu , Y , Jin , C , He , H , Hao , X and Qian , Pei-Yuan . 2009b . Flavone and isoflavone derivatives of terrestrial plants as larval settlement inhibitors of the barnacle Balanus amphitrite . Biofouling , 25 : 69 – 76 .

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