SYNTHESIS AND PHOTOPHYSICAL EVALUATION OF <i>meso</i>-PHENYL-1,4-DIHYDROPYRIDINE AND PYRIDINE-PORPHYRIN HYBRIDS

Авторы

  • Lais Danciguer Guanaes Departamento de Farmácia, Universidade Federal do Paraná, Av. Lothario Meissner, 3400, Jardim Botânico, Curitiba, Paraná, Brazil
  • Matheus Murmel Guimarães Departamento de Farmácia, Universidade Federal do Paraná, Av. Lothario Meissner, 3400, Jardim Botânico, Curitiba, Paraná, Brazil
  • Diogo R. B. Ducatti Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, P. O. Box 19046, Curitiba, Paraná, Brazil
  • Maria Eugênia R. Duarte Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, P. O. Box 19046, Curitiba, Paraná, Brazil
  • Sandra M. W. Barreira Departamento de Farmácia, Universidade Federal do Paraná, Av. Lothario Meissner, 3400, Jardim Botânico, Curitiba, Paraná, Brazil
  • Miguel D. Noseda Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, P. O. Box 19046, Curitiba, Paraná, Brazil
  • Alan Guilherme Gonçalves Departamento de Farmácia, Universidade Federal do Paraná, Av. Lothario Meissner, 3400, Jardim Botânico, Curitiba, Paraná, Brazil

DOI:

https://doi.org/10.1007/6292

Ключевые слова:

1, 4-dihydropyridine, porphyrin, pyridine, photosensitizer, photostability, singlet oxygen, UV-vis spectrum.

Аннотация

In the present work, we have synthesized new molecular hybrids consisting of porphyrin ring system connected at the meso positions with phenyl groups and/or, through p-phenylene linkers, with 1,4-dihydropyridine or pyridine moieties. In general, the directed use of dihydropyridine aldehyde, under time-modified Adler–Longo procedures, gave the best overall yields of the following meso-substituted dihydropyridine-porphyrins of general formula A1B3, A2B2, or A4, where A stands for phenyl-dihydropyridine and B for phenyl substituents. The corresponding meso-substituted pyridine-porphyrin hybrids were obtained from oxidation of the dihydropyridineporphyrins with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The UV-vis spectra bands of the A4 dihydropyridine-porphyrin were unexpectedly red-shifted, having a rhodoporphyrin Q-bands profile. It was also found that an increased production of 1O2 correlates with a higher number of dihydropyridine or pyridine moieties in the hybrid molecule. All porphyrin hybrids were considered adequate candidates to be employed in photodynamic therapy.

Опубликован

2021-12-15

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Раздел

Оригинальные статьи