Synthesis, spectroscopic characterization, antibacterial activity and antiproliferative profile of a new silver(I) complex of 5-fluorocytosine

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Pereira, Gabriele de Menezes ; Nunes, Julia H. Bormio ; Cruz, Allefe B. ; Pereira, Douglas Henrique ; Buglio, Kaio Eduardo ; Ruiz, Ana Lucia T. G. ; de Carvalho, Joao Ernesto ; Frajacomo, Silmara Cristina L. ; Lustri, Wilton R. ; Bergamini, Fernando R. G. ; Corbi, Pedro Paulo

• Tipo de documento: Artigo Científico
• Fonte: JOURNAL OF FLUORINE CHEMISTRY; v. 266, p. 9-pg., 2023-02-01.

Resumo

In this paper, we report the synthesis, structural characterization, and explore the potential antibacterial and antiproliferative activities of a new silver(I) complex of the nucleotide analogue 5-fluorocytosine, Ag-5FC. Elemental and thermogravimetric (TGA) analyses led to the minimal formula AgC4H4FN3O center dot H2O. Infrared (FT-IR) and solid-state C-13 nuclear magnetic resonance (NMR) spectroscopic analyses indicate that the ligand coordinates to the metal ion by its nitrogen and oxygen atoms. High resolution mass spectrometric (HRMS) data confirmed the proposed composition of the complex as well as the presence of recombination species in solution. Molecular modeling reinforces the proposed N,O-coordination of 5FC to silver as indicated by IR data with a possible structure of the complex in a dimeric form, of coordination formula [Ag(C4H4FN3O)(OH2)](2). The complex showed a modest antimicrobial activity (MIC = 4.3 mmol.L-1) against Gram-negative (Pseudomonas aeruginosa and Escherichia coli) and Gram-positive (Staphylococcus aureus and Bacillus cereus) strains. Despite the low solubility, the Ag-5FC complex totally inhibited the proliferation of colon (HT-29), multidrug resistant ovarian (NCI/ADR-RES), prostate (PC-3), and renal (786-0) tumor cell lines in a concentration range of 6.2 to 9.3 mu mol L-1. Further studies are necessary to confirm efficiency and safety for continuing the pre-clinical evaluation of the Ag-5FC complex. (AU)

• Processo FAPESP: 21/08717-8 - Síntese de complexos de cobre, prata e ouro envolvendo análogos de nucleotídeos na busca por novas alternativas para o tratamento do câncer de ovário
• Beneficiário: Pedro Paulo Corbi
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 21/07458-9 - Uso de fontes de nutrientes variadas e resíduos agroindustriais na produção de celulose bacteriana para aplicação tópica como suporte de liberação sustentada de (metalo) fármacos antibacterianos e antitumorais
• Beneficiário: Wilton Rogério Lustri
• Modalidade de apoio: Auxílio à Pesquisa - Regular