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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Structural parameters, molecular properties, and biological evaluation of some terpenes targeting Schistosoma mansoni parasite

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Author(s):
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Mafud, Ana C. [1] ; Silva, Marcos P. N. [2] ; Monteiro, Daniela C. [2] ; Oliveira, Maria F. [2] ; Resende, Joao G. [2] ; Coelho, Mayara L. [3] ; de Sousa, Damiao P. [4] ; Mendonca, Ronaldo Z. [5, 2] ; Pinto, Pedro L. S. [6] ; Freitas, Rivelilson M. [3] ; Mascarenhas, Yvonne P. [1] ; de Moraes, Josue [2]
Total Authors: 12
Affiliation:
[1] Univ Sao Paulo, Inst Fis Sao Carlos, Sao Carlos, SP - Brazil
[2] Univ Guarulhos, Nucl Pesquisa Doencas Negligenciadas, Guarulhos, SP - Brazil
[3] Univ Fed Piaui, Rede Nordeste Biotecnol, Programa Posgrad Biotecnol, Teresina, PI - Brazil
[4] Univ Fed Paraiba, Dept Ciencias Farmaceut, BR-58059900 Joao Pessoa, Paraiba - Brazil
[5] Inst Butantan, Lab Parasitol, Sao Paulo, SP - Brazil
[6] Adolfo Lutz Inst, Nucl Enteroparasitas, Sao Paulo, SP - Brazil
Total Affiliations: 6
Document type: Journal article
Source: Chemico-Biological Interactions; v. 244, p. 129-139, JAN 25 2016.
Web of Science Citations: 16
Abstract

The use of natural products has a long tradition in medicine, and they have proven to be an important source of lead compounds in the development of new drugs. Among the natural compounds, terpenoids present broad-spectrum activity against infective agents such as viruses, bacteria, fungi, protozoan and helminth parasites. In this study, we report a biological screening of 38 chemically characterized terpenes from different classes, which have a hydroxyl group connected by hydrophobic chain or an acceptor site, against the blood fluke Schistosoma mansoni, the parasite responsible for schistosomiasis mansoni. In vitro bioassays revealed that 3,7-dimethyl-1-octanol (dihydrocitronellol) (10) was the most active terpene (IC50 values of 13-52 mu M) and, thus, we investigated its antischistosomal activity in greater detail. Confocal laser scanning microscopy revealed that compound 10 induced severe tegumental damage in adult schistosomes and a correlation between viability and tegumental changes was observed. Furthermore, we compared all the inactive compounds with dihydrocitronellol structurally by using shape and charge modeling. Lipophilicity (miLogP) and other molecular properties (e.g. molecular polar surface area, molecular electrostatic potential) were also calculated. From the 38 terpenes studied, compound 10 is the one with the greatest flexibility, with a sufficient apolar region by which it may interact in a hydrophobic active site. In conclusion, the integration of biological and chemical analysis indicates the potential of the terpene dihydrocitronellol as an antiparasitic agent. (C) 2015 Elsevier Ireland Ltd. All rights reserved. (AU)

FAPESP's process: 14/02282-6 - Structure-activity relationship studies about of Pilocarpus microphyllus (Rutaceae) alkaloid derivatives against Schistosoma mansoni
Grantee:Ana Carolina Mafud
Support Opportunities: Scholarships in Brazil - Post-Doctoral