A New Nonconjugated Naphthalene Derivative ofMeso‐tetra‐(3‐hydroxy)‐phenyl‐porphyrin as a Potential Sensitizer for Photodynamic Therapy

Abstract

A new 5,10,15,20-tetra-(phenoxy-3-carbonyl-1-amino-naphthyl)-porphyrin was prepared by an isocyanate condensation reaction and its photophysical properties fully evaluated, both in terms of photostability and singlet oxygen production. It shows considerably enhanced photostability when compared with the parent 5,10,15,20-tetra-(3-hydroxy-phenyl)-porphyrin, with the photodegradation quantum yields for T(NAF)PP and T(OH)PP being 4.65×10(-4) and 5.19×10(-3) , respectively. Its photodynamic effect in human carcinoma HT-29 cells was evaluated. The new porphyrin showed good properties as a sensitizer in photodynamic therapy with an in vitro cytotoxicity IC(50) value of 6.80μg mL(-1) for a 24h incubation. In addition to the potential of this compound, the synthetic route used provides possibilities of extension to a wide range of new sensitizers.

Photosensitization Reactions In Vitro and In Vivo

“…Pd‐bacteriopheophorbide 14 had greater stability than 13 and 15 , and also produced more reactive oxygen species (ROS) thereby generating hydroperoxides. Another porphyrin system was studied, namely 5,10,15,20‐tetra‐(phenoxy‐3‐carbonyl‐1‐aminonaphthyl)‐porphyrin ( 16 ), which was synthesized by a naphthylisocyanate condensation reaction (9). The absorption of the 4th Q‐band extended out to ca 670 nm, while the triplet porphyrin and singlet oxygen quantum yields were found to be enhanced compared to the parent 5,10,15,20‐tetra‐(3‐hydroxyphenyl)‐porphyrin.…”

Co-protoporphyrin IX and Sn-protoporphyrin IX inactivate Zika, Chikungunya and other arboviruses by targeting the viral envelope

“…Porphyrins are a large class of natural and synthetic organic heterocyclic molecules that can bear a metal atom in the center of their tetrapyrrolic structure. Some of these molecules can be photosensitized and are often used in photodynamic therapy for microorganism killing 26 – 29 . Additionally, antimicrobial activity of some porphyrinic compounds has also been described in the absence of light stimuli 27 .…”

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

“…Compound 20 ( Figure 6), possessing an amide-naphthyl moiety, was synthesised and its photodynamic activities were evaluated against HT-29 cells. It showed low dark cytotoxicity and the best in vitro activity (IC50 ¼ 4.848 mM) when incubated with light between 600 and 800 nm 44 . Additionally, silicon is considered to have potential for improving photochemical efficiencies and has been introduced as a metal centre in phthalocyanine, and the results have shown it to be a promising PS for PDT 45,46 .…”