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Mar. Drugs 2017, 15(7), 203; doi:10.3390/md15070203

Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides

1
Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, N10W5, Sapporo 060-0810, Japan
2
Environmental Science Research Laboratory, Central Research Institute of Electric Power Industry, 1646 Abiko, Abiko, Chiba 270-1194, Japan
3
CERES, Inc., 1-4-5 Midori, Abiko, Chiba 270-1153, Japan
*
Authors to whom correspondence should be addressed.
Received: 16 May 2017 / Revised: 12 June 2017 / Accepted: 21 June 2017 / Published: 29 June 2017
(This article belongs to the Special Issue Antifouling Marine Natural Products)
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Abstract

Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls and fishing nets, is a serious economic issue whose effects include oil wastage and clogged nets. Organotin compounds were utilized since the 1960s as an antifouling material; however, the use of such compounds was later banned by the International Maritime Organization (IMO) due to their high toxicity toward marine organisms, resulting in masculinization and imposex. Since the ban, there have been extensive efforts to develop environmentally benign antifoulants. Natural antifouling products obtained from marine creatures have been the subject of considerable attention due to their potent antifouling activity and low toxicity. These antifouling compounds often contain isocyano groups, which are well known to have natural antifouling properties. On the basis of our previous total synthesis of natural isocyanoterpenoids, we envisaged the installation of an isocyano functional group onto glucosamine to produce an environmentally friendly antifouling material. This paper describes an effective synthetic method for various glucosamine-based isocyanides and evaluation of their antifouling activity and toxicity against cypris larvae of the barnacle Amphibalanus amphitrite. Glucosamine isocyanides with an ether functionality at the anomeric position exhibited potent antifouling activity, with EC50 values below 1 μg/mL, without detectable toxicity even at a high concentration of 10 μg/mL. Two isocyanides had EC50 values of 0.23 and 0.25 μg/mL, comparable to that of CuSO4, which is used as a fouling inhibitor (EC50 = 0.27 μg/mL). View Full-Text
Keywords: antifouling; glucosamine; isocyanide antifouling; glucosamine; isocyanide
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Umezawa, T.; Hasegawa, Y.; Novita, I.S.; Suzuki, J.; Morozumi, T.; Nogata, Y.; Yoshimura, E.; Matsuda, F. Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides. Mar. Drugs 2017, 15, 203.

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