Asymmetricallymeso-substituted porphyrin derivative containing the triazole group: Synthesis, characterization and photo-physicochemical properties

Abstract

In this study, a novel asymmetrically meso-substituted AB3 porphyrins derivative including one triazole group to enhance the anticancer activity of the molecule and three bromophenyl groups to improve photochemical properties has been synthesized and characterized. Our objectives were to generate a system with triazole and bromophenyl groups that enhance the singlet oxygen generation and exhibits an anti-cancer effect. Therefore, photophysical and photochemical properties of this asymmetric porphyrin derivative (AB[Formula: see text] and the symmetric derivative (B[Formula: see text] were investigated in THF. The substituent effect on fluorescence quantum yield and singlet oxygen generation was evaluated for efficiency in photodynamic therapy (PDT) as a photosensitizer. The molecules exhibited no aggregation tendency, solubility in common organic solvents and high singlet oxygen quantum yield in THF therefore these favorable properties make them good candidates as a photosensitizer for PDT.

New AB3-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

“…33 An asymmetrical AB 3 -type porphyrin having one triazole and three bromophenyl groups has been recently reported by our group. 25 It was revealed from the study that the AB 3 -type porphyrin motif showed no aggregation tendency, solubility in common organic solvents and a high singlet oxygen quantum yield. 25…”

“…25 It was revealed from the study that the AB 3 -type porphyrin motif showed no aggregation tendency, solubility in common organic solvents and a high singlet oxygen quantum yield. 25…”

“…33 An asymmetrical AB 3 -type porphyrin having one triazole and three bromophenyl groups has been recently reported by our group. 25 It was revealed from the study that the AB 3 -type porphyrin motif showed no aggregation tendency, solubility in common organic solvents and a high singlet oxygen quantum yield. 25 Piperidine, morpholine and their derivatives are important nitrogen and oxygen containing heterocyclic compounds, which in many cases show potent biological activity.…”

“…25 It was revealed from the study that the AB 3 -type porphyrin motif showed no aggregation tendency, solubility in common organic solvents and a high singlet oxygen quantum yield. 25 Piperidine, morpholine and their derivatives are important nitrogen and oxygen containing heterocyclic compounds, which in many cases show potent biological activity. 34,35 For example, Nyokong et al currently reported the synthesis of morpholine substituted Zn porphyrin derivatives for their photodynamic therapy activity against the MCF-7 cancer cell line and found that morpholine linked porphyrins showed promising PDT activity.…”

“…[21][22][23] Another significant application of AB 3 -type porphyrins is that these compounds are employed as photosensitizers in the area of photodynamic therapy (PDT), which is a useful technique for the treatment of a wide range of diseases. 24,25 Photodynamic therapy involves the activation of a photosensitizer (PS) by visible light in the presence of molecular oxygen which generates cytotoxic reactive oxygen species (ROS) that lead to oxidative cell damage. 26,27 The main advantage of photodynamic therapy is that it has high selectivity and fewer side effects in the management or treatment of specific malignant neoplastic diseases.…”