Microwave-assisted Synthesis of Unsymmetrical Tetrapyrrolic Compounds

Socoteanu, Radu; Boscencu, Rica; Nacea, Veronica; Oliveira, Anabela S.; Ferreira, L. F. Vieira

doi:10.37358/rc.08.9.1949

Cited by 7 publications

(9 citation statements)

References 13 publications

(12 reference statements)

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“…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.…”

Section: Resultssupporting

confidence: 92%

“…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.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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We designed three unsymmetrical meso-tetrasubstituted phenyl porphyrins for further development as theranostic agents for cancer photodynamic therapy (PDT): 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) and Cu(II)-5-(4-hydroxy-3-methoxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin (Cu(II)2.2). The porphyrinic compounds were synthesized and their structures were confirmed by elemental analysis, FT-IR, UV-Vis, EPR and NMR. The compounds had a good solubility in polar/nonpolar media. P2.2 and, to a lesser extent, Zn(II)2.2 were fluorescent, albeit with low fluoresence quantum yields. P2.2 and Zn(II)2.2 exhibited PDT-acceptable values of singlet oxygen generation. A “dark” cytotoxicity study was performed using cells that are relevant for the tumor niche (HT-29 colon carcinoma cells and L929 fibroblasts) and for blood (peripheral mononuclear cells). Cellular uptake of fluorescent compounds, cell viability/proliferation and death were evaluated. P2.2 was highlighted as a promising theranostic agent for PDT in solid tumors considering that P2.2 generated PDT-acceptable singlet oxygen yields, accumulated into tumor cells and less in blood cells, exhibited good fluorescence within cells for imagistic detection, and had no significant cytotoxicity in vitro against tumor and normal cells. Complexing of P2.2 with Zn(II) or Cu(II) altered several of its PDT-relevant properties. These are consistent arguments for further developing P2.2 in animal models of solid tumors for in vivo PDT.

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Section: Resultssupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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“…The important band frequencies of the ligand and copper complexes and corresponding assignments are presented in Table 1. The IR spectra of the porphyrinic ligands TCMPOH m and TCMP were analyzed in a previous paper [23]. The IR bands of the ligands at approx.…”

Section: Resultsmentioning

confidence: 99%

“…The intensities of the signals are described as weak (w), medium (m), strong (s) and very strong (v.s.) ; 1 Data for this compound were taken from [23]. …”

Section: Resultsmentioning

confidence: 99%

Microwave Synthesis, Basic Spectral and Biological Evaluation of Some Copper (II) Mesoporphyrinic Complexes

et al. 2010

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Cu(II) complexes with asymmetrical and symmetrical porphyrinic ligands were synthesized with superior yields using microwave irradiation. The paper presents the synthesis of 5-(3-hydroxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl)-21,23-Cu(II)-porphine in comparison to its symmetrical complex 5,10,15,20-meso-tetrakis-(4-carboxymethylphenyl)-21,23-Cu(II) porphine. The two compounds were characterized by FT-IR, UV-Vis and EPR spectroscopy, which fully confirmed the structures. The spectral molecular absorption properties of the porphyrinic complexes were studied in organic solvents (methanol, ethanol, iso-propanol, dimethyl sulfoxide, dimethylformamide and methylene chloride), and the influence of the solvent polarity on the absorbance maxima is described. In order to establish their future potential in biomedical applications preliminary toxicological studies consisting of viability and proliferation of standard tumor cell lines OPEN ACCESSMolecules 2010, 15 3732 (MCF7 and B16) testing was performed. The obtained results indicate a low toxicity for both compounds and further recommends them for testing in light activation protocols.

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“…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.…”

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confidence: 99%

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

Radulea¹,

Boscencu²,

Socoteanu³

et al. 2019

Rev. Chim.

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This study include in the same frame promising structures tailored as photoactive agents for photodynamic therapy of cancer versus one of the most versatile cell lines from experimental point of view, fibroblasts type, subcutaneous connective tissues- L929. Transmembrane potential was studied establishing important features in the behavior of chemical vectors against cultured cells via membranar media. Two amphiphilic porphyrins, 5,15-bis-(4-hydroxy-3-methoxyphenyl)-10,20-bis-(4-carboxymethylphenyl)porphyrin and Zn(II)-5,15-bis-(4-hydroxy-3-methoxyphenyl)-10,20-bis-(4-carboxymethylphenyl)porphyrin were assessed in terms of the effect on membrane potential. The comparative effect of free base porphyrin and metalloporphyrin with amphiphilic structure, reveal hyperpolarization phenomena and bring informations about consequences of active compound concentration against cell membrane.

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Microwave-assisted Synthesis of Unsymmetrical Tetrapyrrolic Compounds

Cited by 7 publications

References 13 publications

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

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

Microwave Synthesis, Basic Spectral and Biological Evaluation of Some Copper (II) Mesoporphyrinic Complexes

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

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