Bioactivity and Structural Properties of Novel Synthetic Analogues of the Protozoan Toxin Climacostol
AbstractClimacostol (5-[(2Z)-non-2-en-1-yl]benzene-1,3-diol) is a resorcinol produced by the protozoan Climacostomum virens for defence against predators. It exerts a potent antimicrobial activity against bacterial and fungal pathogens, inhibits the growth of several human and rodent tumour cells, and is now available by chemical synthesis. In this study, we chemically synthesized two novel analogues of climacostol, namely, 2-methyl-5 [(2Z)-non-2-en-1-yl]benzene-1,3-diol (AN1) and 5-[(2Z)-non-2-en-1-yl]benzene-1,2,3-triol (AN2), with the aim to increase the activity of the native toxin, evaluating their effects on prokaryotic and free-living protists and on mammalian tumour cells. The results demonstrated that the analogue bearing a methyl group (AN1) in the aromatic ring exhibited appreciably higher toxicity against pathogen microbes and protists than climacostol. On the other hand, the analogue bearing an additional hydroxyl group (AN2) in the aromatic ring revealed its ability to induce programmed cell death in protistan cells. Overall, the data collected demonstrate that the introduction of a methyl or a hydroxyl moiety to the aromatic ring of climacostol can effectively modulate its potency and its mechanism of action. View Full-Text
Share & Cite This Article
Buonanno, F.; Catalani, E.; Cervia, D.; Proietti Serafini, F.; Picchietti, S.; Fausto, A.M.; Giorgi, S.; Lupidi, G.; Rossi, F.V.; Marcantoni, E.; Petrelli, D.; Ortenzi, C. Bioactivity and Structural Properties of Novel Synthetic Analogues of the Protozoan Toxin Climacostol. Toxins 2019, 11, 42.
Buonanno F, Catalani E, Cervia D, Proietti Serafini F, Picchietti S, Fausto AM, Giorgi S, Lupidi G, Rossi FV, Marcantoni E, Petrelli D, Ortenzi C. Bioactivity and Structural Properties of Novel Synthetic Analogues of the Protozoan Toxin Climacostol. Toxins. 2019; 11(1):42.Chicago/Turabian Style
Buonanno, Federico; Catalani, Elisabetta; Cervia, Davide; Proietti Serafini, Francesca; Picchietti, Simona; Fausto, Anna M.; Giorgi, Simone; Lupidi, Gabriele; Rossi, Federico V.; Marcantoni, Enrico; Petrelli, Dezemona; Ortenzi, Claudio. 2019. "Bioactivity and Structural Properties of Novel Synthetic Analogues of the Protozoan Toxin Climacostol." Toxins 11, no. 1: 42.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.