Potential of synthetic chalcone derivatives to prevent marine biofouling

Abstract

Biofouling represents a major economic, environmental and health concern for which new eco-friendly solutions are needed. International legislation has restricted the use of biocidal-based antifouling coatings, and increasing efforts have been applied in the search for environmentally friendly antifouling agents. This research work deals with the assessment of the interest of a series of synthetic chalcone derivatives for antifouling applications. Six- teen chalcone derivatives were synthesized with moderate yields (38–85%). Antifouling bioactivity of these com- pounds was assessed at different levels of biological organization using both anti-macrofouling and anti- microfouling bioassays, namely an anti-settlement assay using mussel (Mytilus galloprovincialis) larvae, as well as marine bacteria and microalgal biofilms growth inhibition bioassays. Results showed that three compounds (11, 12, and 16) were particularly active against the settlement of mussel larvae (EC50 7.24–34.63 μM), being compounds 12 and 16 also able to inhibit the growth of microfouling species (EC50 4.09–20.31 μM). Moreover, the most potent compounds 12 and 16 were found to be non-toxic to the non-target species Artemia salina (b10% mortality at 25 μM). A quantitative structure-activity relationship model predicted that descriptors de- scribing the ability of molecules to form hydrogen bonds and encoding the shape, branching ratio and constitu- tional diversity of the molecule were implied in the antifouling activity against the settlement of mussel larvae. This work elucidates for the first time the relevance of synthesizing chalcone derivatives to generate new non- toxic products to prevent marine biofouling.