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ANTIPARASITIC AND IMMUNOMODULATORY ACTIVITIES OF 1,1-BIS(4-HYDROXYPHENYL)-2-PHENYL-BUT-1-ENE AND ITS PROTECTED AND FREE 2-FERROCENYL DERIVATIVES
Author
Affilliation
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil / Hospital São Rafael. Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil / Hospital São Rafael. Salvador, BA, Brasil
École Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, France
École Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, France
Instituto de Química e Biotecnologia. UFAL. Maceió, Al, Brasil
Instituto de Química e Biotecnologia. UFAL. Maceió, Al, Brasil
École Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, France
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil / Hospital São Rafael. Salvador, BA, Brasil
École Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, France
École Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, France
Instituto de Química e Biotecnologia. UFAL. Maceió, Al, Brasil
Instituto de Química e Biotecnologia. UFAL. Maceió, Al, Brasil
École Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, France
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.
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