ORCiD
Nejat Düzgüneş: 0000-0001-6159-1391
Department
Biomedical Sciences
Document Type
Article
Publication Title
Bioorganic Chemistry
ISSN
0045-2068
Volume
96
DOI
10.1016/j.bioorg.2020.103634
Publication Date
3-1-2020
Abstract
An important subgroup within the porphyrazine (Pz) family constitutes seco-porphyrazines, in the chemical structure of which one pyrrole unit is opened in the oxidative process. So far, there are only limited data on N-seco- and C-seco-Pzs. Here, the synthesis of a novel member of the Pzs seco-family, represented by an S-seco-tribenzoporphyrazine analogue, 22,23-bis(4-(3,5-dibutoxycarbonylphenoxy)butylsulfanyl)tribenzo[b,g,l]-22,23-dioxo-22,23-seco-porphyrazinato magnesium(II), is reported, with moderate 34% yield. The new derivative was characterized using NMR spectroscopy, UV–Vis spectroscopy, and mass spectrometry. In the photochemical study performed following the indirect chemical method with 1,3-diphenylisobenzofuran, S-seco-Pz revealed a high singlet oxygen quantum yield of 0.27 in DMF. Potential photocytotoxicity of S-seco-Pz was assessed in vitro on three cancer cell lines – two oral squamous cell carcinoma cell lines derived from the tongue (CAL 27, HSC-3) and human cervical epithelial adenocarcinoma cells (HeLa). In the biological study, the macrocycle was tested in its free form and after loading into liposomes. It is worth noting that S-seco-Pz was found to be non-toxic in the dark, with cell viability levels over 80%. The photocytotoxic IC50 values for free S-seco-Pz were 0.61, 0.18, and 4.1 µM for CAL 27, HSC-3 and HeLa cells, respectively. Four different liposomal compositions were analyzed, and the cationic liposomes revealed the highest photokilling efficacy, with the IC50 values for CAL 27, HSC-3, and HeLa cells at 0.24, 0.25, and 0.31 µM, respectively. The results of the photocytotoxicity study indicate that the new S-seco-tribenzoporphyrazine can be considered as a potential photosensitizer in photodynamic therapy of cancer, along with the developed cationic liposomal nanocarrier.
Recommended Citation
Mlynarczyk, D. T.,
Piskorz, J.,
Popenda, L.,
Stolarska, M.,
Szczolko, W.,
Konopka, K.,
Jurga, S.,
Sobotta, L.,
Mielcarek, J.,
Düzgüneş, N.,
&
Goslinski, T.
(2020).
S-seco-porphyrazine as a new member of the seco-porphyrazine family – Synthesis, characterization and photocytotoxicity against cancer cells.
Bioorganic Chemistry, 96,
DOI: 10.1016/j.bioorg.2020.103634
https://scholarlycommons.pacific.edu/dugoni-facarticles/590
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
