TY - JOUR
T1 - Structural optimization and evaluation of butenolides as potent antifouling agents: modification of the side chain affects the biological activities of compounds
AU - Li, Yongxin
AU - Zhang, Fengying
AU - Xu, Ying
AU - Matsumura, Kiyotaka
AU - Han, Zhuang
AU - Liu, Lingli
AU - Lin, Wenhan
AU - Jia, Yanxing
AU - Qian, Pei-Yuan
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): SA-C0040, UK-C0016
Acknowledgements: This study was supported by a grant (DY125-15-T-02) from the China Ocean Mineral Resources Research and Development Association, a joint research grant from the Research Grants Council of the HKSAR and the National Natural Science Foundation of China (N_HKUST602/09), and award SA-C0040/UK-C0016 from the King Abdullah University of Science and Technology to P.Y. Qian.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.
PY - 2012/8/24
Y1 - 2012/8/24
N2 - A recent global ban on the use of organotin compounds as antifouling agents has increased the need for safe and effective antifouling compounds. In this study, a series of new butenolide derivatives with various amine side chains was synthesized and evaluated for their anti-larval settlement activities in the barnacle, Balanus amphitrite. Side chain modification of butenolide resulted in butenolides 3c-3d, which possessed desirable physico-chemical properties and demonstrated highly effective non-toxic anti-larval settlement efficacy. A structure-activity relationship analysis revealed that varying the alkyl side chain had a notable effect on anti-larval settlement activity and that seven to eight carbon alkyl side chains with a tert-butyloxycarbonyl (Boc) substituent on an amine terminal were optimal in terms of bioactivity. Analysis of the physico-chemical profile of butenolide analogues indicated that lipophilicity is a very important physico-chemical parameter contributing to bioactivity. © 2012 Copyright Taylor and Francis Group, LLC.
AB - A recent global ban on the use of organotin compounds as antifouling agents has increased the need for safe and effective antifouling compounds. In this study, a series of new butenolide derivatives with various amine side chains was synthesized and evaluated for their anti-larval settlement activities in the barnacle, Balanus amphitrite. Side chain modification of butenolide resulted in butenolides 3c-3d, which possessed desirable physico-chemical properties and demonstrated highly effective non-toxic anti-larval settlement efficacy. A structure-activity relationship analysis revealed that varying the alkyl side chain had a notable effect on anti-larval settlement activity and that seven to eight carbon alkyl side chains with a tert-butyloxycarbonyl (Boc) substituent on an amine terminal were optimal in terms of bioactivity. Analysis of the physico-chemical profile of butenolide analogues indicated that lipophilicity is a very important physico-chemical parameter contributing to bioactivity. © 2012 Copyright Taylor and Francis Group, LLC.
UR - http://hdl.handle.net/10754/600222
UR - https://www.tandfonline.com/doi/full/10.1080/08927014.2012.717071
UR - http://www.scopus.com/inward/record.url?scp=84865540117&partnerID=8YFLogxK
U2 - 10.1080/08927014.2012.717071
DO - 10.1080/08927014.2012.717071
M3 - Article
C2 - 22920194
SN - 0892-7014
VL - 28
SP - 857
EP - 864
JO - Biofouling
JF - Biofouling
IS - 8
ER -