Isocyanides Derived from α,α‐Disubstituted Amino Acids: Synthesis and Antifouling Activity Assessment

Herein, we contribute to the development of environmentally friendly antifoulants by synthesizing eighteen isocyanides derived from α,α‐disubstituted amino acids and evaluating their antifouling activity/toxicity against the cypris larvae of the Balanus amphitrite barnacle. Almost all isocyanides sh...

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Bibliographic Details
Published in:Chemistry & biodiversity 2018-03, Vol.15 (3), p.e1700571-n/a
Main Authors: Inoue, Yuki, Takashima, Shuhei, Nogata, Yasuyuki, Yoshimura, Erina, Chiba, Kazuhiro, Kitano, Yoshikazu
Format: Article
Language:English
Subjects:
Amino acids
Antifoulants
Antifouling
antifouling activity
Antifouling substances
barnacle
isocyanides
Larvae
Methionine
Phenylalanine
structure–activity relationship
Toxicity
Valine
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Summary:Herein, we contribute to the development of environmentally friendly antifoulants by synthesizing eighteen isocyanides derived from α,α‐disubstituted amino acids and evaluating their antifouling activity/toxicity against the cypris larvae of the Balanus amphitrite barnacle. Almost all isocyanides showed good antifouling activity without significant toxicity and exhibited EC50 values of 0.07 – 7.30 μg/mL after 120‐h exposure. The lowest EC50 values were observed for valine‐, methionine‐, and phenylalanine‐derived isocyanides, which achieved > 95% cypris larvae settlement inhibition at concentrations of less than 30 μg/mL without exhibiting significant toxicity. Thus, the prepared isocyanides should be useful for further research focused on the development of environmentally friendly antifouling agents.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.201700571