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Title: Bioactivity and Structural Properties of Novel Synthetic Analogues of the Protozoan Toxin Climacostol
Authors: Buonanno, Federico
Catalani, Elisabetta
Cervia, Davide 
Proietti Serafini, Francesca
Picchietti, Simona 
Fausto, Anna Maria 
Giorgi, Simone
Lupidi, Gabriele
Rossi, Federico Vittorio
Marcantoni, Enrico
Petrelli, Dezemona
Ortenzi, Claudio
Journal: TOXINS 
Issue Date: 2019
Climacostol (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.
ISSN: 2072-6651
DOI: 10.3390/toxins11010042
Rights: Attribution 4.0 International
Appears in Collections:A1. Articolo in rivista

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