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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 and spectroscopic characterization of epiisopiloturine-metal complexes, and anthelmintic activity vs. S-mansoni

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Author(s):
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Portes, Marcelo Cecconi [1] ; De Moraes, Josue [2] ; Costa Veras, Leiz Maria [3] ; Leite, Jose Roberto [3] ; Mafud, Ana Carolina [4] ; Mascarenhas, Yvonne Primerano [4] ; Virgino Luz, Adamor Eleiel [5] ; Dalmatti Alves De Lima, Filipe Camargo [5] ; Do Nascimento, Rafael Rodrigues [5] ; Petrilli, Helena Maria [5] ; Silva Pinto, Pedro Luiz [6] ; Althoff, Gerhard [7] ; Da Costa Ferreira, Ana Maria [1]
Total Authors: 13
Affiliation:
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Sao Paulo - Brazil
[2] Nucleo Pesquisas Doencas Negligenciadas, Fac Ciencias Guarulhos FACIG, Guarulhos - Brazil
[3] Univ Fed Piaui, BIOTEC, Nucleo Pesquisa Biodiversidade & Biotecnol, Campus Parnaiba, Parnaiba - Brazil
[4] Univ Sao Paulo, Inst Fis Sao Carlos, Dept Fis & Ciencia Interdisciplinar, Sao Carlos, SP - Brazil
[5] Univ Sao Paulo, Inst Fis, Dept Fis Mat & Mecan, CP 20516, BR-01498 Sao Paulo - Brazil
[6] Adolfo Lutz Inst, Nucleo Enteroparasitas, Sao Paulo - Brazil
[7] NMR Applicat Grp, Bruker Instruments, Rheinstetten - Germany
Total Affiliations: 7
Document type: Journal article
Source: Journal of Coordination Chemistry; v. 69, n. 10, p. 1663-1683, 2016.
Web of Science Citations: 2
Abstract

Epiisopiloturine (EPI), extracted from leaves of Pilocarpus microphyllus, a plant originally from the Amazon and Savanna regions in Brazil, was described as a potential drug against Schistosomiasis, a neglected severe disease. Herein, EPI was complexed with copper(II) or zinc(II) salts and the isolated species, {[}Cu(epi)(4)](ClO4)(2) (1) and {[}Zn(epi)(2)Cl-2] (2), were structurally and spectroscopically characterized. By using X-ray diffraction, the crystal structures of both metal complexes were determined, indicating a square pyramidal geometry for copper for 1 and a tetrahedral environment around zinc for 2. EPR spectra of 1 show a typical tetragonal environment around the central metal ion with some tetrahedral distortion, both in the solid state and in frozen acetonitrile solution, in accordance with crystallographic data. For 2, NMR spectra have bands consistent with a tetrahedral species in solid state or in DMSO-d(6) solution. These spectroscopic characterization data were further supported by Density Functional Theory calculations, showing that these metal complexes are also stable in solution. Those metal complexes were tested against adult worms of Schistosoma mansoni, in comparison to the free alkaloid as anthelmintic agent. Coordination with copper(II) improved the alkaloid schistosomicidal properties, while binding to zinc(II) decreased its activity. {[}GRAPHICS] . (AU)

FAPESP's process: 11/50318-1 - Development of compounds with pharmacological or medicinal interest and of systems for their transport, detection and recognition in biological media
Grantee:Ana Maria da Costa Ferreira
Support type: Research Projects - Thematic Grants
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 type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 12/02326-8 - Computational modeling of solid-molecule interaction in systems with nanotechnology interests
Grantee:Filipe Camargo Dalmatti Alves Lima
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 13/07937-8 - Redoxome - Redox Processes in Biomedicine
Grantee:Ohara Augusto
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC