Disulfide-bridge dimeric porphyrin and their reference compounds for glutathione-based specific tumor-activation

Alpugan S., TOPKAYA TAŞKIRAN D., DUMOULIN F.

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, vol.21, no.12, pp.918-924, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 21 Issue: 12
  • Publication Date: 2017
  • Doi Number: 10.1142/s1088424617500961
  • Journal Name: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED)
  • Page Numbers: pp.918-924
  • Keywords: photodynamic therapy, porphyrin, tumor-activatable photosensitizer, disulfide, dimeric, TARGETED PHOTODYNAMIC THERAPY, PHOTOSENSITIZER, PHTHALOCYANINE, DELIVERY, METALLOPORPHYRINS, FLUORESCENT, GENERATION, CONJUGATE, LOGIC
  • Acibadem Mehmet Ali Aydinlar University Affiliated: Yes

Abstract

The tumor micro-environment is rich in glutathione. To exploit this feature for tumor-activatable porphyrin-based photosensitizers, a dimeric disulfide-bridged porphyrin has been designed and prepared, together with two reference derivatives, a non-cleavable dimer and a monomer. The three compounds have been investigated from a photochemical and photophysical point of view. It appears that the disulfide-bridged derivative exhibited intramolecular aggregation, but to an insufficient extent to induce a satisfying self-quenching of its photoproperties. Unlike expected, the non-cleavable dimer behaved like the monomeric derivative, due to the superior flexibility of the alkyl bridge over the disulfide bridge.