Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, Ocean University of China, Qingdao, 266003, China.
Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, Ocean University of China, Qingdao, 266003, China; Open Studio for Marine Corrosion and Protection, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao, 266237, China.
Ecotoxicol Environ Saf. 2019 Oct 30;182:109423. doi: 10.1016/j.ecoenv.2019.109423. Epub 2019 Jul 17.
Indole derivatives derived from the secondary metabolites of marine organisms possess the excellent antifouling property to inhibit the biofouling. These compounds and their analogues are simple in structure and have been proven to have low toxicity and bioaccumulation. Therefore, the active indole antifoulants are expected to replace the potentially toxic antifoulants which are widely used in current antifouling coatings. Seven indole derivatives were synthesized via the Friedel-Crafts alkylation reaction and were characterized by IR spectra, H NMR, C NMR and elemental analysis. Inhibition experiments against marine algae and bacteria were conducted, and the partial inhibition rates of algae and bacteria were more than 90%. This outcome indicates that indole derivatives possess excellent properties suitable for use as targeting anti-fouling compound for algae and bacteria. Non-invasive Micro-test Technology (NMT) reveals that the Ca efflux of Platymonas subcordiformis dramatically increased in the presence of indole derivatives, which is inferred to be the molecular mechanism for inhibiting the growth of marine algae. The antifouling coatings containing indole derivatives were prepared and subjected to an antifouling test in a marine environment, and the results show that N-(1-H-5-bromo-indole-3-ylmethyl) benzamide and N-(1-H-2-phenyl-indole-3-ylmethyl) benzamide possess better antifouling performance compared to copper pyrithione (CuPT). According to these results, indole derivatives in this study might become novel and promising antifoulants.
从海洋生物次生代谢产物中衍生出的吲哚衍生物具有优异的防污性能，可以抑制生物污损。这些化合物及其类似物结构简单，已被证明具有低毒性和低生物累积性。因此，活性吲哚防污剂有望替代目前广泛应用于防污涂料中的潜在有毒防污剂。通过 Friedel-Crafts 烷基化反应合成了 7 种吲哚衍生物，并通过红外光谱、H NMR、C NMR 和元素分析对其进行了表征。对海洋藻类和细菌进行了抑制实验，藻类和细菌的部分抑制率均超过 90%。这一结果表明，吲哚衍生物具有良好的性能，适合用作针对藻类和细菌的靶向防污化合物。非侵入式微量测试技术（NMT）表明，吲哚衍生物的 Platymonas subcordiformis 钙离子外流显著增加，这被推断为抑制海洋藻类生长的分子机制。制备了含有吲哚衍生物的防污涂料，并在海洋环境中进行了防污测试，结果表明，N-(1-H-5-溴-吲哚-3-基甲基)苯甲酰胺和 N-(1-H-2-苯基-吲哚-3-基甲基)苯甲酰胺的防污性能优于铜吡啶硫酮（CuPT）。根据这些结果，本研究中的吲哚衍生物可能成为新型、有前途的防污剂。
