Scientific paper - Original scientific paper
Synthesis, characterisation and in vitro investigation of photodynamic activity of 5-(4- octadecanamidophenyl)-10, 15, 20-tris(N- methylpyridinium-3-yl)porphyrin trichloride on HeLa cells using low light fluence rate
Title (English) Synthesis, characterisation and in vitro investigation of photodynamic activity of 5-(4- octadecanamidophenyl)-10, 15, 20-tris(N- methylpyridinium-3-yl)porphyrin trichloride on HeLa cells using low light fluence rate
Author Malatesti, Nela Harej, Anja Kraljević Pavelić, Sandra Lončarić, Martin Zorc, Hrvoje Wittine, Karlo Anđelković, Uroš Josić, Đuro
Photodynamic therapy (PDT) is a treatment that aims to kill cancer cells by reactive oxygen species, mainly singlet oxygen, produced through light activation of a photosensitiser (PS). Amongst photosensitisers that attracted the most attention in the last decade are cationic and amphiphilic molecules based on porphyrin, chlorin and phthalocyanine structures. Our aim was to join this search for more optimal balance of the lipophilic and hydrophilic moieties in a PS. A new amphiphilic porphyrin, 5-(4-octadecanamidophenyl)-10, 15, 20- tris(N-methylpyridinium-3-yl)porphyrin trichloride (5) was synthesised and characterised by 1H NMR, UV–vis and fluorescence spectroscopy, and by MALDI-TOF/TOF spectrometry. In vitro photodynamic activity of 5 was evaluated on HeLa cell lines and compared to the activity of the hydrophilic 5-(4- acetamidophenyl)-10, 15, 20-tris(N- methylpyridinium-3-yl)porphyrin trichloride (7). Low fluence rate (2 mW cm−2) of red light (643 nm) was used for the activation, and both porphyrins showed a drug dose-response as well as a light dose-response relationship, but the amphiphilic porphyrin was presented with significantly lower IC50 values. The obtained IC50 values for 5 were 1.4 μM at 15 min irradiation time and 0.7 μM when the time of irradiation was 30 min, while for 7 these values were 37 and 6 times higher, respectively. These results confirm the importance of the lipophilic component in a PS and show a potential for 5 to be used as a PS in PDT applications.
Keywords (English) Cationic porphyrin Amphiphilic structure Photodynamic therapy Low light dose Cancer
Publication type scientific paper - original scientific paper
Publication status published
Peer review peer review - international
Journal title Photodiagnosis and Photodynamic Therapy
Numbering 2016, Vol. 15, pp 115-126
Date publication: 2016.
DOI identifier 10.1016/j.pdpdt.2016.07.003
Article URL http://bib.irb.hr/830506
Scientific field INTERDISCIPLINARY AREAS OF KNOWLEDGE Biotechnology in Biomedicine (natural science, biomedicine and healthcare, bioethics area
Institution University of Rijeka (Department of Biotechnology)