Abstract
New unsymmetrical mesoporphyrinic complexes, namely 5-(4-hydroxyphenyl)-10,15,20–tris-(4-carboxymethylphenyl)–21,23-Zn(II)-porphine and 5-(4-hydroxyphenyl)-10,15,20–tris-(4-carboxymethylphenyl)–21,23-Cu(II)-porphine, were synthesized using a microwave irradiation method. The structures of the porphyrinic complexes were confirmed using FT-IR, UV–Vis, EPR and NMR spectral data. The spectral absorption and emission properties of the porphyrinic complexes were studied in organic solvents of different polarities and the influence of solvent polarity on the wavelengths of the absorbance and fluorescence band maxima is described. The cytotoxicity evaluation of the porphyrinic complexes was performed on human colon adenocarcinoma cell line HT29 for different doses and incubation times. The obtained result indicates a lack of or low toxicity for both compounds, thus recommending them for further testing in light activation protocols.
Highlights
IntroductionPhotodynamic therapy as a selective treatment method that involves the administration of a pharmaceutical formulation containing a tetrapyrrolic photosensitizer, its selective localization at the cellular level, followed by generation by irradiation with light in the red region of the visible spectrum of cytotoxic species such as singlet oxygen (1O2) that destroys the sick cells [11,12,13,14,15]
This paper reports the microwave-assisted synthesis of some new unsymmetrical porphyrinic complexes, namely 5-(4-hydroxyphenyl)-10,15,20–tris-(4-carboxymethylphenyl)–21,23-Zn(II)-porphine (denoted as Zn(II)TCMPOHp - Figure 1) and 5-(4-hydroxyphenyl)-10,15,20–tris-(4-carboxymethylphenyl)–21,23-Cu(II)-porphine (denoted as Cu(II)TCMPOHp - Figure 1), their spectral properties and cytotoxicity evaluation with a view to assessing their possible use in the photodiagnosis and photodynamic therapy of cancer
The synthetic reactions have been successfully repeated several times with identical results and the porphyrinic complexes formed were characterized by elemental analysis, IR, UV–Vis, NMR, EPR spectrometry and evaluated in terms of cytotoxicity using HT29 cell line for different doses and incubation times
Summary
Photodynamic therapy as a selective treatment method that involves the administration of a pharmaceutical formulation containing a tetrapyrrolic photosensitizer, its selective localization at the cellular level, followed by generation by irradiation with light in the red region of the visible spectrum of cytotoxic species such as singlet oxygen (1O2) that destroys the sick cells [11,12,13,14,15]. By modifying the charge density and its distribution at the periphery of the tetrapyrrolic macrocycle it is possible to control the route of these compounds to the target cells [24,25] The purity of these compounds is very important because the presence of trace amounts of impurities can introduce significant errors in the photodynamic activity
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