Unsymmetrical Mesoporphyrinic Complexes of Copper (II) and Zinc (II). Microwave-Assisted Synthesis, Spectral Characterization and Cytotoxicity Evaluation

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.

Synthesis, Spectral Analysis and Preliminary in Vitro Evaluation of Some Tetrapyrrolic Complexes with 3d Metal Ions

“…The infrared spectral data obtained for the synthesized metalloporphyrins revealed the presence of typical vibration modes of both the tetrapyrrolic macrocycles and phenyl substituents. This is generally in agreement with results previously reported for similar porphyrinic structures [25,26,27,28,29,30]. The large band registered at about 3410 cm −1 can be assigned to the O–H stretching vibration of the –OH functional group, near the typical 3423 cm −1 of the N–H vibration.…”

“…Taking into account that localization at a subcellular level of the tetrapyrrolic structure is directly influenced by the polarity of the molecule and by the type of metallic ion [21,22], our research has been focused on obtaining porphyrins with various degrees of hydrophobic/hydrophilic substitutions that favor their uptake by cellular targets [23,24,25,26,27,28,29,30]. As a continuation of our research, in this study we describe the synthesis of some new asymmetrical tetrapyrrolic complexes, Zn(II)-5-(3-hydroxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin ( P1 ) and Cu(II)-5-(3-hydroxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin ( P2 ) (Figure 1), their spectral properties and a preliminary in vitro evaluation focused on their dark toxicity in the context of their potential use in the diagnosis and PDT of cancer.…”

Studies on the Synthesis, Photophysical and Biological Evaluation of Some Unsymmetrical Meso-Tetrasubstituted Phenyl Porphyrins

“…The changes observed in the spectral behavior were in agreement with our previous results obtained for other unsymmetrical porphyrins [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. Comparison of the absorption spectral parameters indicated that they were not significantly affected either by the type of peripheral substituents of the porphyrinic core, or by environmental polarity.…”

“…Therefore, changes in the molecular architecture of porphyrins by introducing polar and nonpolar substituients [ 14 , 15 ] or metallic ions [ 15 ] can improve their photophysical characteristics and pharmacological efficacy. Consequently, as part of our ongoing research on obtaining unsymmetrical meso -tetrasubstituted phenyl porphyrins [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ], we designed and synthesized three new unsymmetrical meso -tetrasubstituted phenyl porphyrins whose general structure is presented in Figure 1 : 5-(4-hydroxy-3-methoxyphenyl)-10,15,20- tris -(4-acetoxy-3-methoxyphenyl)porphyrin ( P2.2 ), Zn(II)-5-(4-hydroxy-3-methoxyphenyl)-10,15,20- tris -(4-acetoxy-3-methoxyphenyl)porphyrin ( Zn(II)2.2 ), Cu(II)-5-(4-hydroxy-3-methoxyphenyl)-10,15,20- tris -(4-acetoxy-3-methoxyphenyl)porphyrin ( Cu(II)2.2 ). These compounds are intended to be developed as theranostic agents for photodynamic therapy (PDT) in cancer.…”

The Effect of Some Amphiphilic Porphyrins on the Transmembrane Potential of Cultured L929 Cells

“…Continuing our researches regarding amphiphilic porphyrins with biomedical applications, [17][18][19][20][21][22][23][24][25][26][27][28][29], in this study we synthesized a new A 2 B 2 type porphyrinic complex, Zn(II)-5,15-bis-(4-hydroxy-3-methoxyphenyl)-10,20-bis-(4-carboxymethylphenyl)porphyrin (Zn(II)P) ( fig. 1), and assessed its effect on the transmembrane potential of L929 cultured cells.…”