Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives

Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil / Hospital São Rafael. Salvador, BA, Brasil

Access type:openAccess
Publication Date:2010
Main Author: Soares, Milena Botelho Pereira
Other Authors: Costa, José Fernando Oliveira, Sá, Matheus Santos de, Santos, Ricardo Ribeiro dos, Pigeon, Pascal, Jaouen, Gérard, Santana, Antônio Euzébio Goulart, Goulart, Marilia Oliveira Fonseca, Hillard, Elizabeth
Document type: Article
Language:eng
Published: Wiley-Liss, INC
Online Access:https://www.arca.fiocruz.br/handle/icict/9025
Citation:SOARES, M. B. P. et al. Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives. Drug Development Research, v. 71, p. 69–75, 2010.
English abstract:The ferrocenyl diphenol 1 [1,1-bis(4-hydroxyphenyl)-2-ferrocenyl-but-1-ene] displays strong cytotoxic effects against a variety of cancer cells. In the present study we have evaluated the immunomodulatory and antiparasitic activities of compound 1 and its protected dipalmitate analogue 2. We have furthermore compared the antiparasitic results of 1 and 2 with the organic analogue, 3 [1,1-bis(4- hydroxyphenyl)-2-phenyl-but-1-ene], where the ferrocenyl group has been replaced by a phenyl ring. When assayed against normal (noncancerous) splenocytes, all compounds were considered nontoxic. Compound 1 inhibited NO production by macrophages, inhibited concanavalin A-induced lymphoproliferation, and was active against Leishmania amazonensis and Trypanosoma cruzi. Compound 2 had lower activity in all assays performed. Surprisingly, compounds 1 and 2 exhibited similar and significant activity against Plasmodium falciparum, with IC50 values of 3.50 and 1.33 mM, respectively. Compound 3 showed an inverse activity profile, being active against T. cruzi but far less active against P. falciparum.