Next Article in Journal
The Individual and Combined Effects of the Cyanotoxins, Anatoxin-a and Microcystin-LR, on the Growth, Toxin Production, and Nitrogen Fixation of Prokaryotic and Eukaryotic Algae
Previous Article in Journal
Osmotic-Adaptation Response of sakA/hogA Gene to Aflatoxin Biosynthesis, Morphology Development and Pathogenicity in Aspergillus flavus
Article Menu
Issue 1 (January) cover image

Export Article

Open AccessArticle
Toxins 2019, 11(1), 42; https://doi.org/10.3390/toxins11010042

Bioactivity and Structural Properties of Novel Synthetic Analogues of the Protozoan Toxin Climacostol

1
Laboratory of Protistology and Biology Education, Department of Education, Cultural Heritage, and Tourism (ECHT), Università degli Studi di Macerata, 62100 Macerata, Italy
2
Department for Innovation in Biological, Agro-food and Forest systems (DIBAF), Università degli Studi della Tuscia, 01100 Viterbo, Italy
3
School of Sciences and Technologies, Section of Chemistry, Università degli Studi di Camerino, 62032 Camerino, Italy
4
School of Biosciences and Veterinary Medicine, Università degli Studi di Camerino, 62032 Camerino, Italy
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 12 December 2018 / Revised: 7 January 2019 / Accepted: 8 January 2019 / Published: 15 January 2019
(This article belongs to the Section Marine and Freshwater Toxins)
Full-Text   |   PDF [6858 KB, uploaded 15 January 2019]   |  

Abstract

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. View Full-Text
Keywords: Climacostomum virens; secondary metabolites; resorcinolic lipids; protists; ciliates; apoptosis Climacostomum virens; secondary metabolites; resorcinolic lipids; protists; ciliates; apoptosis
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
SciFeed

Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Toxins EISSN 2072-6651 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top