title: From broad-spectrum biocides to quorum sensing disruptors and mussel repellents: antifouling profile of alkyl triphenylphosphonium salts.
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.
authors.affiliation: Institute for Bioorganic Chemistry "Antonio González", Center for Biomedical Research of the Canary Islands (CIBICAN), Department of Organic Chemistry, University of La Laguna, Av. Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain; Oceanic Platform of the Canary Islands (PLOCAN), Carretera de Taliarte s/n, 35214 Telde, Gran Canaria, Spain.
authors.forename: Alberto J
authors.initials: AJ
authors.lastname: Martín-Rodríguez
authors.affiliation: Department of Biotechnology and Aquaculture, Instituto de Investigaciones Marinas CSIC, Eduardo Cabello 6, 36208 Vigo, Spain.
authors.forename: Jose M F
authors.initials: JM
authors.lastname: Babarro
authors.affiliation: Department of Fundamental & Experimental Physics, Faculty of Sciences, University of La Laguna, Av. Astrofísico Francisco Sánchez s/n, 38206 La Laguna, Tenerife, Spain.
authors.forename: Fernando
authors.initials: F
authors.lastname: Lahoz
authors.affiliation: Department of Botany, Ecology and Plant Physiology, Faculty of Sciences, University of La Laguna, Av. Astrofísico Francisco Sánchez s/n, 38206 La Laguna, Tenerife, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Sansón
authors.affiliation: Institute for Bioorganic Chemistry "Antonio González", Center for Biomedical Research of the Canary Islands (CIBICAN), Department of Organic Chemistry, University of La Laguna, Av. Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: Víctor S
authors.initials: VS
authors.lastname: Martín
authors.affiliation: Institute for Bioorganic Chemistry "Antonio González", Center for Biomedical Research of the Canary Islands (CIBICAN), Department of Organic Chemistry, University of La Laguna, Av. Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: Manuel
authors.initials: M
authors.lastname: Norte
authors.affiliation: Institute for Bioorganic Chemistry "Antonio González", Center for Biomedical Research of the Canary Islands (CIBICAN), Department of Organic Chemistry, University of La Laguna, Av. Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: José J
authors.initials: JJ
authors.lastname: Fernández
mesh_terms: D000818:Animals; D001156:Artemia / Q000187:drug effects / Q000502:physiology; D057219:Biofouling; D002861:Chromobacterium / Q000187:drug effects / Q000502:physiology; D017377:Diatoms / Q000187:drug effects / Q000502:physiology; D004202:Disinfectants / Q000737:chemistry / Q000494:pharmacology*; D005656:Fungal Proteins / Q000037:antagonists & inhibitors / Q000737:chemistry; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000737:chemistry; D049878:Mytilus / Q000187:drug effects / Q000502:physiology; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000494:pharmacology*; D053038:Quorum Sensing / Q000187:drug effects; D012624:Seaweed / Q000187:drug effects / Q000502:physiology; D013329:Structure-Activity Relationship; D014733:Vibrio / Q000187:drug effects / Q000502:physiology
chemical_list: D004202:Disinfectants; D005656:Fungal Proteins; D009943:Organophosphorus Compounds; D014442:Monophenol Monooxygenase