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

Abstract

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.

ZIF‐8 MOF Encapsulated Co‐porphyrin, an Efficient Electrocatalyst for Water Oxidation in a Wide pH Range: Works Better at Neutral pH

“…In other words, due to the modified microenvironment around the CoTMPP molecule inside the ZIF‐8 cage, the CoTMPP may undergo supramolecular interaction with ZIF‐8 surface. This can cause a weakening of the transition dipole moment of the Q‐band and also positional shifting of the Soret and Q bands (Figure 2a) [52] . In our earlier works, similar prominent effects of the interaction between ZIF‐8 and encapsulated guest species could be observed in the electronic spectra of the composite [2] .…”

Polyethylene Glycol-Coated Gold Nanoparticles as DNA and Atorvastatin Delivery Systems and Cytotoxicity Evaluation

“…On the other hand, the drug cellular uptake by using the gold nanoparticles as carriers is greater in the larger nanoparticles, in contrast with the transfection results obtained; however, it was demonstrated that the free atorvastatin cannot enter into the cells (0% of cell uptake) which besides confirms that both types of AuNPs are effectively performing the role of drug carriers (69.39% and 75.12% of drug cell uptake, respectively). Cellular uptake studies of fluorescent drugs [32]. Currently, nanocarriers have been used due to the physical and chemical advantages that they have.…”

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

“…Mesoporphyrinic complex, Zn(II)P was synthesized by the classical methods [18] that involves refluxing of equimolar ratios of the porphyrinic ligand [30] and metal salt in the presence of a basic catalyst. The structural evaluation of Zn(II)P was performed by elemental analysis, NMR, FT-IR and UV-Vis spectrometry.…”

“…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.…”