title: Structural optimization and evaluation of butenolides as potent antifouling agents: modification of the side chain affects the biological activities of compounds.
abstract: 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.
authors.affiliation: KAUST Global Collaborative Research, Division of Life Science, Hong Kong University of Science and Technology , Clear Water Bay , Hong Kong , PR China.
authors.forename: Yongxin
authors.initials: Y
authors.lastname: Li
authors.forename: Fengying
authors.initials: F
authors.lastname: Zhang
authors.forename: Ying
authors.initials: Y
authors.lastname: Xu
authors.forename: Kiyotaka
authors.initials: K
authors.lastname: Matsumura
authors.forename: Zhuang
authors.initials: Z
authors.lastname: Han
authors.forename: Lingli
authors.initials: L
authors.lastname: Liu
authors.forename: Wenhan
authors.initials: W
authors.lastname: Lin
authors.forename: Yanxing
authors.initials: Y
authors.lastname: Jia
authors.forename: Pei-Yuan
authors.initials: PY
authors.lastname: Qian
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D057219:Biofouling / Q000517:prevention & control*; D002013:Bryozoa; D007814:Larva; D013329:Structure-Activity Relationship; D001468:Thoracica
chemical_list: C004511:butenolide; D015107:4-Butyrolactone