Meso-tetra-(piridil)-porfirinas com complexos periféricos de paládio: busca por novos compostos com ação fotodinâmica
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2020-12-16
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Universidade Federal de Goiás
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The present dissertation had as objective at the synthesis of new photosensitizing compounds for use in Photodynamic Therapy through the modification of meso-tetra (4-pyridyl) porphyrin (TPyP). For that, phosphine binders containing palladium atoms were inserted: 1,2-bis(diphenylphosphine)ethane (dppe), 1,3-bis(diphenylphosphine) propane (dppp), 1,4-bis(diphenylphosphine)butane (dppb) and 1,1'-bis (diphenylphosphine)ferrocene (dppf), dating in porphyrins: {TPyP[PdCl(dppe)]4}(PF6)4, {TPyP[PdCl(dppp)]4}(PF6)4, {TPyP[PdCl(dppb)]4}(PF6)4 e {TPyP[PdCl(dppf)]4}(PF6)4, respectively. After synthesis, structural characterization was performed using infrared spectroscopic techniques (FTIR), elementar analysis and 1H, 13C{1H} e 31P{1H} nuclear magnetic resonance (NMR). X-ray diffraction (XRD) was used to prove a structure for obtaining monocrystal porphyrin {TPyP[PdCl(dppb)]4}BF4. Through spectroscopicUV-Vis absorption, fluorescent emission and flash-photolysis techniques, it was possible to determine the lipophilicity of the molar absorption coefficients (), the lifetime of the triplet state and the fluorescence (Φf) and oxygen production quantum singlet (ΦΔ). In addition, an interaction with DNA was evaluated through spectrophotometric titration and viscosity. Finally, phototoxicity and cytotoxicity in the tumor cell line MDA-MB231 and healthy HACAT were evaluated. Biological tests were performed on two cell lines: MDA-MB231 and MCF-10A. The experiments were carried out in the dark and in the presence of irradiation, to determine the photodynamic efficiency of the synthesized compounds. The porphyrin-derived complexes exhibited IC50 values similar to that presented by cisplatin, in the MDA-MB231 breast cell, however, with respect to the non-tumoral breast cell, MCF-10A, they were more cytotoxic than the commercial drug, so that the selectivity index values were much lower for porphyrins than that presented by cisplatin.
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ALVES, K. M. Meso-tetra-(piridil)-porfirinas com complexos periféricos de paládio: busca por novos compostos com ação fotodinâmica. 2020. 111 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Goiânia, 2020.