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Eight analogues of the bioherbicides macrocidin A ( 1 ) and Z ( 2 ) with structural variance in the size of the macrocycle, its para - or meta -cyclophane character, and its functional groups were synthesized on two modular routes and tested for herbicidal, antibiotic, and antibiofilm activities. Apart from the lead compounds 1 and 2 , the structurally simplified dihydromacrocidin Z ( 3 ) and normacrocidin Z ( 4 ) showed high herbicidal activity in either thistles, dandelions or in both. The derivatives 2 , 3 , and dibromide 9 also inhibited the growth of Staphylococcus aureus biofilms by ca 70% when applied at subtoxic concentrations as low as ca 20 µM, which are unlikely to induce bacterial resistance. They also led to the dispersion of preformed biofilms of S. aureus , exceeding a similar effect by microporenic acid A, a known biofilm inhibitor. Compounds 3 and 9 showed no noticeable cytotoxicity against human cancer and endothelial cells at concentrations below 50 µM, making them conceivable candidates for application as anti-biofilm agents in a medicinal context.

Dual Agents: Fungal Macrocidins and Synthetic Analogues with Herbicidal and Antibiofilm Activities