TBT or not TBT?: That is the question

Evans, Stewart M.

doi:10.1080/08927019909378403

Cited by 62 publications

(46 citation statements)

References 112 publications

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“…7 Consequently, the International Maritime Organization (IMO) prohibited the use of TBT-based antifouling paints on ships in 2008. 8 Currently, TBT-based paints have been replaced by copper-based antifouling agents, but these require a high concentration of copper and a co-biocide to achieve the same efficacy. Concerns about copper toxicity have led several countries to review their existing copper environmental risk assessments in coastal waters, and a number of countries have already banned copper-based antifouling paints in areas with a high density of boats.…”

Section: Introductionmentioning

confidence: 99%

Total synthesis and biological activity of dolastatin 16

et al. 2017

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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. Therefore, dolastatin 16 is a potential compound for a new, environmentally friendly antifouling material to replace banned tributyltin-based antifouling paints. The synthesis of dolastatin 16 involved the use of prolinol to prevent formation of a diketopiperazine composed of L-proline and N-methyl-D-valine during peptide coupling. This strategy for the elongation of peptide chains allowed the efficient and scalable synthesis of one segment, which was subsequently coupled with a second segment and cyclized to form the macrocyclic framework of dolastatin 16. The synthetic dolastatin 16 exhibited potent antifouling activity similar to that of natural dolastatin 16 toward cypris larvae of Amphibalanus amphitrite.

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Section: Introductionmentioning

confidence: 99%

Total synthesis and biological activity of dolastatin 16

et al. 2017

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“…Both micro-and macrofouling in the world's oceans cause huge material and economic losses in maintenance of mariculture, shipping industries, naval vessels, and seawater pipelines (Yebra et al 2004). In order to minimise the impacts of foulers, many underwater structures are protected by toxic antifouling coatings (Evans, 1999;Yebra et al 2004). The International Maritime Organisation (IMO) and Marine Environmental Protection Committee (MEPC) decided to ban the usage of TBT or other substances containing tin as biocides in antifouling paints, effective in January 2008.…”

Section: Introductionmentioning

confidence: 99%

Antifouling diketopiperazines produced by a deep-sea bacterium,Streptomyces fungicidicus

et al. 2006

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Modern antifouling coatings use heavy metals and toxic organic molecules to prevent biofouling, the undesirable growth of marine organisms on man-made substrata. In an ongoing survey of deep-sea microorganisms aimed at finding low toxic antifouling metabolites, an actinomycete bacterium was isolated from the Pacific sediment at the depth of about 5000 m. The bacterium was closely related to Streptomyces fungicidicus (99% similarity) according to 16S ribosomal RNA sequence information. The spent culture medium of this bacterium inhibited barnacle larval attachment. Bioassay-guided fractionation was employed to isolate antifouling compounds. The ethyl acetate extract was fractionated by using an open silica gel column. Active fractions were further purified on a HPLC C 18 column., and cyclo-(L-Leu-L-Val) were isolated for the first time from a deep sea bacterium, and the structures of the compounds were elucidated by nuclear magnetic resonance spectroscopy and mass spectrometry. The pure diketopiperazines were tested for antilarval activity using the barnacle Balanus amphitrite. Effective concentrations that inhibited 50% larval attachment (EC 50 ) after 24 h ranged from 0.10 -0.27 mM. The data suggest that diketopiperazines and other compounds from deep-sea bacteria may be used as novel antifoulants.

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“…TBT was banned for antifouling paints from 2003 and should not be used on ships' hulls from 2008 (Champ, 2003 andEvans, 1999). Nevertheless one company still uses this biocide for sensor biofouling protection.…”

Section: An "Uncontrolled" Biocide Generation System Based On Copper mentioning

confidence: 99%

Biofouling protection for marine environmental sensors

2010

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Abstract. These days, many marine autonomous environment monitoring networks are set up in the world. These systems take advantage of existing superstructures such as offshore platforms, lightships, piers, breakwaters or are placed on specially designed buoys or underwater oceanographic structures. These systems commonly use various sensors to measure parameters such as dissolved oxygen, turbidity, conductivity, pH or fluorescence. Emphasis has to be put on the long term quality of measurements, yet sensors may face very short-term biofouling effects. Biofouling can disrupt the quality of the measurements, sometimes in less than a week.Many techniques to prevent biofouling on instrumentation are listed and studied by researchers and manufacturers. Very few of them are implemented on instruments and of those very few have been tested in situ on oceanographic sensors for deployment of at least one or two months. This paper presents a review of techniques used to protect against biofouling of in situ sensors and gives a short list and description of promising techniques.

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TBT or not TBT?: That is the question

Cited by 62 publications

References 112 publications

Total synthesis and biological activity of dolastatin 16

Total synthesis and biological activity of dolastatin 16

Antifouling diketopiperazines produced by a deep-sea bacterium,Streptomyces fungicidicus

Biofouling protection for marine environmental sensors

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