Synthesis and Spectral Evaluation of Some Unsymmetrical Mesoporphyrinic Complexes

Abstract

Synthesis and spectral evaluation of new zinc and copper unsymmetrical mesoporphyrinic complexes are reported. Zn(II)-5-(4-acetoxy-3-methoxyphenyl)-10,15,20- tris-(4-carboxymethylphenyl)porphyrin, Zn(II)-5-[(3,4-methylenedioxy)phenyl]-10,15,20- tris-(4-carboxymethylphenyl)porphyrin, Cu(II)-5-(4-acetoxy-3-methoxyphenyl)-10,15,20- tris-(4-carboxymethylphenyl)porphyrin and Cu(II)-5-[(3,4-methylenedioxy)phenyl]-10,15,20- tris-(4-carboxymethylphenyl)porphyrin were synthesized using microwave-assisted synthesis. The complexes were characterized by elemental analysis, FT-IR, UV-Vis, EPR and NMR spectroscopy, which fully confirmed their structure. The spectral absorption properties of the porphyrinic complexes were studied in solvents with different polarities. Fluorescence emission and singlet oxygen formation quantum yields were evaluated for the compounds under study, revealing high yields for the zinc derivatives. The copper complexes are not emissive and only display residual capacity for singlet oxygen formation.

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.…”

Synthesis and physico-chemical properties of a H-cardanol triazole zinc porphyrin conjugate

“…UV spectra of equimolar mixtures of ZP 7 and HTC 8 were recorded in all six solvents to nd out if there was an associative interaction between these two units with a change in the nature of the solvent, but the spectra did not reveal any shis. The zinc porphyrin 7, as anticipated for metalloporphyrins, 33 displayed only moderate effects upon changing the solvent polarity. The bathochromic shi of the Soret band of 5 by 7 nm when the solvent was changed from hexane to DMF was in agreement with the similar shi seen for the parent 7.…”

AFM imaging, fractal analysis and in vitro cytotoxicity evaluation of Zn(II) vs. Cu(II) porphyrins

“…In this paper it is comparatively examined the morphology of the two type of M (II)-porphyrinic complexes, Zn(II)-5-(4-acetoxy-3-methoxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl) porphyrin (Zn(II)TCMPOMo) http and Cu(II)-5-(4-acetoxy-3-methoxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl) porphyrin (Cu(II)TCMPOMo) [9] (as presented in Fig. 1) and it has been studied the selfsimilarity of copper and zinc porphyrins using systematic fractal analysis performed on AFM micrographs.…”