TY  - JOUR
AU  - Malatesti, Nela
AU  - Harej, Anja
AU  - Kraljević Pavelić, Sandra
AU  - Lončarić, M.
AU  - Zorc, H.
AU  - Wittine, Karlo
AU  - Anđelković, Uroš
AU  - Josić, Djuro
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6916
AB  - 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.
PB  - Elsevier
T2  - Photodiagnosis and Photodynamic Therapy
T1  - 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
VL  - 15
SP  - 115
EP  - 126
DO  - 10.1016/j.pdpdt.2016.07.003
ER  - 

@article{
author = "Malatesti, Nela and Harej, Anja and Kraljević Pavelić, Sandra and Lončarić, M. and Zorc, H. and Wittine, Karlo and Anđelković, Uroš and Josić, Djuro",
year = "2016",
abstract = "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.",
publisher = "Elsevier",
journal = "Photodiagnosis and Photodynamic Therapy",
title = "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",
volume = "15",
pages = "115-126",
doi = "10.1016/j.pdpdt.2016.07.003"
}

Malatesti, N., Harej, A., Kraljević Pavelić, S., Lončarić, M., Zorc, H., Wittine, K., Anđelković, U.,& Josić, D.. (2016). 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. in Photodiagnosis and Photodynamic Therapy
Elsevier., 15, 115-126.
https://doi.org/10.1016/j.pdpdt.2016.07.003

Malatesti N, Harej A, Kraljević Pavelić S, Lončarić M, Zorc H, Wittine K, Anđelković U, Josić D. 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. in Photodiagnosis and Photodynamic Therapy. 2016;15:115-126.
doi:10.1016/j.pdpdt.2016.07.003 .

Malatesti, Nela, Harej, Anja, Kraljević Pavelić, Sandra, Lončarić, M., Zorc, H., Wittine, Karlo, Anđelković, Uroš, Josić, Djuro, "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" in Photodiagnosis and Photodynamic Therapy, 15 (2016):115-126,
https://doi.org/10.1016/j.pdpdt.2016.07.003 . .