Measurement of the Adhesion Force of a Living Sessile Organism on Antifouling Coating Surfaces Prepared with Polysulfobetaine-Grafted Particles.

An antifouling polymer brush-like structure was fabricated by a simple and versatile dip-coating method of sulfobetaine containing copolymer-grafted silica nanoparticles (SiNPs) and alkyl diiodide cross-linkers. Surface-initiated atom transfer radical copolymerization of 3-(-2-methacryloyloxyethyl--dimethyl)ammonatopropanesulfonate (MAPS) and -dimethylaminoethyl methacrylate (DMAEMA) was carried out from initiator-immobilized SiNPs to give poly(MAPS--DMAEMA)-grafted SiNPs (MAPS/DMAEMA = 9/1, mol/mol) with diameters of 150-170 nm. The SiNP--copolymer/2,2,2-trifluoroethanol solution was dip-coated on silicon and glass substrates.

Anti-Barnacle Activities of Isothiocyanates Derived from β-Citronellol and Their Structure-Activity Relationships.

Antifouling agents with low toxicity are in high demand for sustaining marine industries and the environment. This study aimed to synthesize 15 isothiocyanates derived from β-citronellol and evaluate their antifouling activities and toxicities against cypris larvae of the barnacle Amphibalanus amphitrite. The synthesized isothiocyanates exhibited effective antifouling activities (EC =0.

Effective Synthesis and Antifouling Activity of Dolastatin 16 Derivatives.

Some derivatives of dolastatin 16, a depsipeptide natural product first obtained from the sea hare , were synthesized through second-generation synthesis of two unusual amino acids, dolaphenvaline and dolamethylleuine. The second-generation synthesis enabled derivatizations such as functionalization of the aromatic ring in dolaphenvaline. The derivatives of fragments and whole structures were evaluated for antifouling activity against the cypris larvae of Small fragments inhibited the settlement of the cypris larvae at potent to moderate concentrations (EC = 0.

Bioactivities of Lyngbyabellins from Cyanobacteria of and Genera.

Cyanobacteria are reported as rich sources of secondary metabolites that provide biological activities such as enzyme inhibition and cytotoxicity. Ten depsipeptide derivatives (lyngbyabellins) were isolated from a Malaysian and a Red Sea sp.: lyngbyabellins G (), O (), P (), H (), A (), 27-deoxylyngbyabellin A (), and homohydroxydolabellin ().

Seasonal alternation of the ontogenetic development of the moon jellyfish Aurelia coerulea in Maizuru Bay, Japan.

Outbreaks of moon jellyfish Aurelia spp. are frequently reported from many parts of the world's coastal areas. Aurelia spp.

Synthesis and Structure-Activity Relationship of Omaezallene Derivatives.

Omaezallene derivatives (nor-bromoallene, nor-bromodiene, and bromoenynes) were successfully synthesized. Their antifouling activity and toxicity to the cypris larvae of the barnacle Amphibalanus amphitrite and ecotoxicity to the marine crustacean Tigriopus japonicus were studied. It was revealed that the two side chains of omaezallene were essential to its antifouling activity because the activities of nor-bromoallene and nor-bromodiene were significantly diminished.

Isocyanides Derived from α,α-Disubstituted Amino Acids: Synthesis and Antifouling Activity Assessment.

Herein, we contribute to the development of environmentally friendly antifoulants by synthesizing eighteen isocyanides derived from α,α-disubstituted amino acids and evaluating their antifouling activity/toxicity against the cypris larvae of the Balanus amphitrite barnacle. Almost all isocyanides showed good antifouling activity without significant toxicity and exhibited EC values of 0.07 - 7.

Serinolamides and Lyngbyabellins from an Okeania sp. Cyanobacterium Collected from the Red Sea.

NMR- and MS-guided fractionation of an extract of an Okeania sp. marine cyanobacterium, collected from the Red Sea, led to the isolation of four new metabolites, including serinolamides C (1) and D (2) and lyngbyabellins O (3) and P (4), together with the three known substances lyngbyabellins F (5) and G (6) and dolastatin 16 (7). The planar structures of the new compounds were determined using NMR and MS analyses.

New Marine Antifouling Compounds from the Red Alga Laurencia sp.

Six new compounds, omaezol, intricatriol, hachijojimallenes A and B, debromoaplysinal, and 11,12-dihydro-3-hydroxyretinol have been isolated from four collections of sp. These structures were determined by MS and NMR analyses. Their antifouling activities were evaluated together with eight previously known compounds isolated from the same samples.

Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides.

Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls and fishing nets, is a serious economic issue whose effects include oil wastage and clogged nets. Organotin compounds were utilized since the 1960s as an antifouling material; however, the use of such compounds was later banned by the International Maritime Organization (IMO) due to their high toxicity toward marine organisms, resulting in masculinization and imposex. Since the ban, there have been extensive efforts to develop environmentally benign antifoulants.

Total synthesis and biological activity of dolastatin 16.

The total synthesis of dolastatin 16, a macrocyclic depsipeptide first isolated from the sea hare Dolabella auricularia as a potential antineoplastic metabolite by Pettit et al., was achieved in a convergent manner. Dolastatin 16 was reported by Tan to exhibit strong antifouling activity, and thus shows promise for inhibiting the attachment of marine benthic organisms such as Amphibalanus amphitrite to ships and submerged artificial structures.

Anti-barnacle Activity of Isocyanides Derived from Amino Acids.

Creation of new potent antifouling active compounds is important for the development of environmentally friendly antifouling agents. Fifteen isocyanide congeners derived from proteinogenic amino acids were synthesized, and the antifouling activity and toxicity of these compounds against cypris larvae of the barnacle Balanus amphitrite were investigated. All synthesized amino acid-isocyanides exhibited potent anti-barnacle activity with EC values of 0.

Wewakazole B, a Cytotoxic Cyanobactin from the Cyanobacterium Moorea producens Collected in the Red Sea.

A mass spectrometry (MS)-guided isolation has led to the purification of a new cyanobactin, wewakazole B (1), along with the known compound curacin D from a Red Sea Moorea producens. The planar structure of 1 was elucidated using a combination of NMR and MS techniques. After ozonolysis and acid hydrolysis, the absolute configurations of the amino acid components of 1 were determined by chiral-phase LC-MS and HPLC analyses.

Omaezallene from red alga Laurencia sp.: structure elucidation, total synthesis, and antifouling activity.

Natural antifouling products have been the subject of considerable attention. We screened marine algae for antifouling activity and discovered omaezallenes, the new bromoallene-containing natural products isolated from the red alga Laurencia sp. Described is the isolation, structure elucidation, and total syntheses of omaezallenes.

Prolonged morphometric study of barnacles grown on soft substrata of hydrogels and elastomers.

A long-term investigation of the shell shape and the basal morphology of barnacles grown on tough, double-network (DN) hydrogels and polydimethylsiloxane (PDMS) elastomer was conducted in a laboratory environment. The elastic modulus of these soft substrata varied between 0.01 and 0.

The mode of action of isocyanide in three aquatic organisms, Balanus amphitrite, Bugula neritina and Danio rerio.

Isocyanide is a potential antifouling compound in marine environments. In this study, we investigated its mode of action in three aquatic organisms. Two of them, the bryozoan Bugula neritina and the barnacle Balanus amphitrite, are major marine fouling invertebrates, and the other organism is the non-target species zebrafish Danio rerio.

Total synthesis of 10-isocyano-4-cadinene and its stereoisomers and evaluations of antifouling activities.

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, and determination of its absolute stereochemistry were achieved. 10-Isocyano-4-cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, intermolecular Diels-Alder reaction and samarium diiodide induced Barbier-type cyclization were employed as key steps.

Poly-ethers from Winogradskyella poriferorum: Antifouling potential, time-course study of production and natural abundance.

A sponge-associated bacterium, Winogradskyella poriferorum strain UST030701-295T was cultured up to 100l for extraction of antifouling bioactive compounds. Five poly-ethers were isolated and partially characterized based on nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS); two of them showed inhibitory effects on biofilm formation of marine bacteria and larval settlement of macro-foulers but did not produce any adverse effects on the phenotypes of zebra fish embryos at a concentration of 5μg ml(-1). The effect of culture duration on the production of the poly-ethers and the bioactivity of the relevant extracts was monitored over a period of 12 days.

Anti-barnacle activity of novel simple alkyl isocyanides derived from citronellol.

Twenty novel simple alkyl isocyanides derived from citronellol were synthesized and evaluated for their antifouling activity and toxicity against cypris larvae of the barnacle, Balanus amphitrite. The anti-barnacle activity of the synthesized isocyanides was in the EC(50) range of 0.08-1.

Species-specific detection and quantification of common barnacle larvae from the Japanese coast using quantitative real-time PCR.

Species-specific detection and quantification methods for barnacle larvae using quantitative real-time polymerase chain reaction (qPCR) were developed. Species-specific primers for qPCR were designed for 13 barnacle species in the mitochondrial 12S ribosomal RNA gene region. Primer specificity was examined by PCR using template DNA extracted from each of the 13 barnacle species, other unidentified barnacle species, and field collected zooplankton samples.

Total synthesis of 10-isocyano-4-cadinene and determination of its absolute configuration.

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels-Alder reaction and a SmI(2)-induced Barbier-type reaction were employed as key steps.

Purification and partial amino acid sequence analysis of the larval settlement-inducing pheromone from adult extracts of the barnacle, Balanus amphitrite (=Amphibalanus amphitrite).

A previously undescribed larval settlement-inducing protein was purified from adult extracts of the barnacle, Balanus amphitrite (=Amphibalanus amphitrite). Results of SDS-PAGE indicated that the relative molecular mass of the protein in reduced and denatured form is 31,600 +/- 500 kDa, and that it is distinct from the Settlement Inducing Protein Complex (SIPC) which has previously been determined as a larval settlement-inducing pheromone. The N-terminal 33-residue sequence of the intact protein showed no similarity with previously reported proteins in the EMBL/Genbank/DDBJ databases.

Larval development and settlement of a whale barnacle.

Larval development and settlement of whale barnacles have not previously been described, unlike intertidal barnacles. Indeed, the mechanisms of the association between barnacles and whales have not been studied. Here we describe the larval development and settlement of the whale barnacle, Coronula diadema, and possible involvement of a cue from the host in inducing larval settlement.

Synthesis and anti-barnacle activities of novel isocyanocyclohexane compounds containing an ester or an ether functional group.

Ten novel isocyanocyclohexane compounds that possess an oxygenic functional group at the 4-position were synthesized and evaluated for their antifouling activity against the larvae of the barnacle Balanus amphitrite with the aim of exploring the structure-activity relationships further. The anti-barnacle effect of the synthesized compounds was in the EC50 range of 0.0096-17.

Antifouling activity of simple synthetic isocyanides against larvae of the barnacle Balanus amphitrite.

Twelve simple linear isocyanides were synthesized and examined for antifouling activity and toxicity against cyprid larvae of the barnacle, Balanus amphitrite. Larval settlement was inhibited, with EC50 values of 0.046-1.