title: Anti-barnacle Activity of Isocyanides Derived from Amino Acids.
abstract: 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 EC50values of 0.07 - 10.34 μg/ml after 120 h exposure without significant toxicity. In addition, seven compounds showed more than 95% settlement inhibition of the cypris larvae at 10 μg/ml after 120 h exposure without any mortality observed. Considering their structure, these amino acid-isocyanides would eventually be biodegraded to their original nontoxic amino acids. These should be useful for further research focused on the development of environmentally friendly antifoulants.
authors.affiliation: Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo, 183-8509, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Fukuda
authors.affiliation: Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo, 183-8509, Japan.
authors.forename: Hideki
authors.initials: H
authors.lastname: Wagatsuma
authors.affiliation: Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo, 183-8509, Japan.
authors.forename: Yoshifumi
authors.initials: Y
authors.lastname: Kominami
authors.affiliation: Environmental Science Research Laboratory, Central Research Institute of Electric Power Industry, 1646 Abiko, Abiko-shi, Chiba, 270-1194, Japan.
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Nogata
authors.affiliation: CERES Inc., 1-4-5 Midori, Abiko-shi, Chiba, 270-1153, Japan.
authors.forename: Erina
authors.initials: E
authors.lastname: Yoshimura
authors.affiliation: Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo, 183-8509, Japan.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Chiba
authors.affiliation: Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo, 183-8509, Japan.
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Kitano
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000818:Animals; D057219:Biofouling / Q000517:prevention & control*; D003486:Cyanides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015394:Molecular Structure; D001468:Thoracica / Q000187:drug effects*
chemical_list: D000596:Amino Acids; D003486:Cyanides
keywords: Amino acids; Antifouling activity; Barnacle; Isocyanide; Structure-activity relationships