Microwave Synthesis Under Solvent-Free Conditions and Spectral Studies of Some Mesoporphyrinic Complexes

Boscencu, Rica

doi:10.3390/molecules17055592

Cited by 13 publications

(14 citation statements)

References 30 publications

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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%

“…Moreover, we selected for this study the synthesis and evaluation of A 3 B isomer complexes with zinc or copper ions. The A 4 type metalloporphyrins have been described by us previously [ 19 ].…”

Section: Resultsmentioning

confidence: 99%

“…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: Resultsmentioning

confidence: 99%

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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“…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.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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Abstract:In this paper, two tetrapyrrolic complexes, Zn(II)-5-(3-hydroxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin and Cu(II)-5-(3-hydroxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin were synthesized, and characterized from a spectral and biological point of view. The study provided data concerning the behavior of identical external substituents vs. two different core insertions. Some of the properties of the proposed tetrapyrrolic structures were highlighted, having photodynamic therapy of cancer as a targeted biomedical application. Elemental analysis, NMR, FTIR and UV-Vis data in various solvents were provided. A preliminary in vitro study on normal and cancer cultured cells was carried out for biocompatibility assessment in dark conditions. The preliminary in vitro study OPEN ACCESSMolecules 2015, 20 15489 performed on human peripheral mononuclear cells exposed to tetrapyrrolic compounds (2 µM) showed that the proposed compounds had a convenient cytotoxic profile on human normal peripheral blood mononuclear cells under dark conditions. Meanwhile, the investigated compounds reduced the number of metabolically active breast tumor MCF-7 cells, with the exception of Zn(II) complex-containing a symmetrical ligand. Accordingly, preliminary in vitro data suggest that the proposed tetrapyrrolic compounds are good candidates for PDT, as they limit tumor expansion even under dark conditions, whilst sparing normal cells.

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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.…”

mentioning

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 Synthesis Under Solvent-Free Conditions and Spectral Studies of Some Mesoporphyrinic Complexes

Cited by 13 publications

References 30 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

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

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

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