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For developing novel photosensitizers with therapeutic potential in non-malignant and malignant cutaneous disorders, the unsymmetrical porphyrin, 5-(2-hydroxy-3-methoxyphenyl)-10, 15, 20-tris-(4-carboxymethylphenyl) porphyrin, was evaluated in silico and in vitro. The cellular uptake of the investigated porphyrin and its ability to perform photodynamic therapy were investigated in terms of the viability, proliferation, and necrosis of human HaCaT keratinocytes and human Hs27 skin fibroblasts, in correlation with the predictions regarding diffusion through cell membranes, ADMET profile (absorption, distribution, metabolism, elimination, toxicity), and potential pharmacological mechanism. Molecular docking and 250 ns molecular dynamics simulations revealed that P5.2 has the potential to form a relatively stable complex with the carbonic anhydrase IX catalytic site, the lowest predicted free energy of binding (MM/PBSA) being −39.097 kcal/mol. The results of the in vitro study showed that P5.2 is incorporated within 24 h in the investigated cells, especially in HaCaT keratinocytes, indicating its photosensitizing ability. Nevertheless, P5.2 does not exert significant cytotoxicity in "dark" conditions. In turn, PDT induced a decrease in the number of metabolically active HaCaT keratinocytes within 24 h, accompanied by a 4-fold increase in lactate dehydrogenase release, indicating its ability to perform PDT in human skin cells. The experimental results suggest that the asymmetrical porphyrin is a promising candidate theranostics agent for skin disorders. [ABSTRACT FROM AUTHOR]

A novel, carbazole-substituted, asymmetrical porphyrin derivatives, 5-[p-hydroxyl phenyl]-10, 15, 20–tricarbazole porphyrin and its metal (Zn, Dy) complexes have been synthesized and characterized by means of UV-vis spectra, IR spectra,1H NMR spectra, and MS. Luminescent properties were discussed by fluorescent spectrum, and their high thermal stability was explained by thermal analytical results. The oxidation and reduction properties of the compounds were investigated by cyclic voltammetry. [ABSTRACT FROM AUTHOR]

A new asymmetrical 5-[p-(4-flourobenzoyloxy)-m-ethyloxy] phenyl-10, 15, 20-triphenyl porphyrin and its transition metal (Zn, Cu, Ni, Co, Mn) complexes were synthesized. Their constitute and structure were characterized by elemental analyses, UV-vis, IR, molar conductances and 1H NMR. Optical properties were discussed by fluorescence spectrum, and their high thermal stability was explained by thermal analytical results. [ABSTRACT FROM AUTHOR]