Anti-barnacle Activity of Isocyanides Derived from Amino Acids

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 larva...

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Bibliographic Details
Published in:Chemistry & biodiversity 2016-11, Vol.13 (11), p.1502-1510
Main Authors: Fukuda, Takuya, Wagatsuma, Hideki, Kominami, Yoshifumi, Nogata, Yasuyuki, Yoshimura, Erina, Chiba, Kazuhiro, Kitano, Yoshikazu
Format: Article
Language:English
Subjects:
Amino acids
Amino Acids - chemistry
Animals
Antifouling activity
Balanus amphitrite
Barnacle
Biofouling - prevention & control
Cyanides - chemistry
Cyanides - isolation & purification
Cyanides - pharmacology
Cypris
Isocyanide
Molecular Structure
Structure-activity relationships
Thoracica - drug effects
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Summary: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 EC50 values 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.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.201600063