Abstract
‘Onium’ compounds, including ammonium and phosphonium salts, have been employed as antiseptics and disinfectants. These cationic biocides have been incorporated into multiple materials, principally to avoid bacterial attachment. In this work, we selected 20 alkyl-triphenylphosphonium salts, differing mainly in the length and functionalization of their alkyl chains, in fulfilment of two main objectives: 1) to provide a comprehensive evaluation of the antifouling profile of these molecules with relevant marine fouling organisms; and 2) to shed new light on their potential applications, beyond their classic use as broad-spectrum biocides. In this regard, we demonstrate for the first time that these compounds are also able to act as non-toxic quorum sensing disruptors in two different bacterial models (Chromobacterium violaceum and Vibrio harveyi) as well as repellents in the mussel Mytilus galloprovincialis. In addition, their inhibitory activity on a fouling-relevant enzymatic model (tyrosinase) is characterized. An analysis of the structure-activity relationships of these compounds for antifouling purposes is provided, which may result useful in the design of targeted antifouling solutions with these molecules. Altogether, the findings reported herein provide a different perspective on the biological activities of phosphonium compounds that is particularly focused on, but, as the reader will realize, is not limited to their use as antifouling agents.
Highlights
Marine biofouling is a deleterious process that imposes a plethora of costly problems to human activities in the ocean, to the shipping industry [1]
We demonstrate for the first time that these compounds are able to act as non-toxic quorum sensing disruptors in two different bacterial models (Chromobacterium violaceum and Vibrio harveyi) as well as repellents in the mussel Mytilus galloprovincialis
The antifouling profile of a collection of 20 alkyl triphenylphosphonium salts has been evaluated in detail
Summary
Marine biofouling is a deleterious process that imposes a plethora of costly problems to human activities in the ocean, to the shipping industry [1]. Biofouling is a complex phenomenon that involves a wide array of organisms, from microbes to invertebrates It is often depicted as a successional process with four main stages, illustrated with an hypothetical material surface that is submerged in the sea (Fig 1): 1) adsorption, from the first seconds after immersion, of organic particles onto the submerged surface, with the development of a so-called ‘conditioning film’ that constitutes the molecular fouling and promotes the 2) arrival of primary colonizers, initially (first 24 h) pioneer motile bacteria and, within the first days, an array of microorganisms, with bacteria and benthic diatoms as the main representatives, that form complex multispecies biofilms (microfouling) and tend to promote the 3) settlement of macroalgal zoospores (e.g. ulvophycean) and 4) invertebrate larvae (e.g. mussel pediveligers, barnacle cyprids) that end up forming a complex macroscopic fouling community. That increasing concern led to a stepwise prohibition of organotin compounds in antifouling paint formulations that was established by the International Maritime Organization and fully entered into force in September 2008
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