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자료유형
학술저널
저자정보
Pavani, Christiane (Departamento de Quimica, FFCLRP, Universidade de Sao Paulo) Uchoa, Adjaci F. (Departamento de Bioquimica, Instituto de Quimica, Universidade de Sao Paulo) Oliveira, Carla S. (Departamento de Bioquimica, Instituto de Quimica, Universidade de Sao Paulo) Iamamoto, Yassuko (Departamento de Quimica, FFCLRP, Universidade de Sao Paulo) Baptista, Mauricio S. (Departamento de Bioquimica, Instituto de Qu´ımica, Universidade de Sao Paulo)
저널정보
한국광과학회 Photochemical & photobiological sciences : an international journal Photochemical & photobiological sciences : an international journal 제8권 제2호
발행연도
2009.1
수록면
233 - 240 (8page)

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A series of photosensitizers (PS), which are meso-substituted tetra-cationic porphyrins, was synthesized in order to study the role of amphiphilicity and zinc insertion in photodynamic therapy (PDT) efficacy. Several properties of the PS were evaluated and compared within the series including photophysical properties (absorption spectra, fluorescence quantum yield $\Phi_f$, and singlet oxygen quantum yield $\Phi_{\Delta}$), uptake by vesicles, mitochondria and HeLa cells, dark and phototoxicity in HeLa cells. The photophysical properties of all compounds are quite similar ($\Phi_f\;{\leq}\;0.02$; $\Phi_{\Delta}\;{\sim}\;0.8$). An increase in lipophilicity and the presence of zinc in the porphyrin ring result in higher vesicle and cell uptake. Binding in mitochondria is dependent on the PS lipophilicity and on the electrochemical membrane potential, i.e., in uncoupled mitochondria PS binding decreases by up to 53%. The porphyrin substituted with octyl groups (TC8PyP) is the compound that is most enriched in mitochondria, and its zinc derivative (ZnTC8PyP) has the highest global uptake. The stronger membrane interaction of the zinc-substituted porphyrins is attributed to a complexing effect with phosphate groups of the phospholipids. Zinc insertion was also shown to decrease the interaction with isolated mitochondria and with the mitochondria of HeLa cells, an effect that has been explained by the particular characteristics of the mitochondrial internal membrane. Phototoxicity was shown to increase proportionally with membrane binding efficiency, which is attributed to favorable membrane interactions which allow more efficient membrane photooxidation. For this series of compounds, photodynamic efficiency is directly proportional to the membrane binding and cell uptake, but it is not totally related to mitochondrial targeting.

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