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Molecules 2017, 22(11), 1815; doi:10.3390/molecules22111815

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

1
Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia St., 020956 Bucharest, Romania
2
“Victor Babeş” National Institute of Pathology, 99-101 Splaiul Independentei, 050096 Bucharest, Romania
3
“Ilie Murgulescu” Institute of Physical Chemistry, Romanian Academy, 202 Splaiul Independentei, 060021 Bucharest, Romania
4
Centro de Química-Física Molecular, Institute of Nanosciences and Nanotechnology, Instituto Superior Técnico Av. Rovisco Pais 1049-001, Lisboa, Portugal
5
Polytechnic Institute of Portalegre, P-7300-110 Portalegre, Portugal
6
Dokumar, Teknopark Blvd No 1 Pendik 34906, Istanbul, Turkey
7
Molecular Biology Genetics & Bioengineering Program, Faculty of Engineering & Natural Sciences, Sabanci University, Orhanli 34956 Tuzla, Istanbul, Turkey
*
Authors to whom correspondence should be addressed.
Received: 6 September 2017 / Revised: 18 October 2017 / Accepted: 22 October 2017 / Published: 25 October 2017
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Abstract

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. View Full-Text
Keywords: unsymmetrical porphyrins; singlet oxygen formation quantum yield; fluorescence quantum yields; cytotoxicity; human colon carcinoma HT-29 cells; mouse L929 fibroblasts; peripheral blood mononuclear cells unsymmetrical porphyrins; singlet oxygen formation quantum yield; fluorescence quantum yields; cytotoxicity; human colon carcinoma HT-29 cells; mouse L929 fibroblasts; peripheral blood mononuclear cells
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Boscencu, R.; Manda, G.; Radulea, N.; Socoteanu, R.P.; Ceafalan, L.C.; Neagoe, I.V.; Ferreira Machado, I.; Basaga, S.H.; Vieira Ferreira, L.F. Studies on the Synthesis, Photophysical and Biological Evaluation of Some Unsymmetrical Meso-Tetrasubstituted Phenyl Porphyrins. Molecules 2017, 22, 1815.

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