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 |
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| Affiliation: | 1. Department of Biotechnology, Centre for high-throughput technologies, University of Rijeka, Radmile Matejčić 2, 51000 Rijeka, Croatia;2. Laboratory for Photonics and Quantum Optics, Division of Experimental Physics, Ruđer Bošković Institute, Bijenička cesta 54, 10002 Zagreb, Croatia;3. Laboratory of Optics and Optical Thin Films, Division of Materials Physics, Ruđer Bošković Institute, Bijenička cesta 54, 10002 Zagreb, Croatia;1. São Carlos Institute of Physics, University of São Paulo, PO Box 13560-970, Sao Carlos, SP, Brazil;2. Department of Veterinary Clinic and Surgery, Faculty of Agriculture and Veterinary Sciences, São Paulo State University (UNESP), Jaboticabal, SP, Brazil;1. University of Belgrade, Faculty of Chemistry, Studentski trg 12-16, Belgrade, 11158, Serbia;2. Plasma Chemistry Research Group, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1117 Budapest, Magyar tudósok krt. 2, Hungary;3. Centre of Excellence in Environmental Chemistry and Engineering, ICTM, University of Belgrade, Njegoševa 12, Belgrade, 11158, Serbia;4. University of Novi Sad, Faculty of Technology, Bulevar cara Lazara 1, 21000, Novi Sad, Serbia;1. Cancer Center, Southern Medical University, Guangzhou 510315, China;2. Traditional Chinese Medicine-Integrated Hospital, Southern Medical University, Guangzhou 510315, China;3. Department of Oncology, Jiujiang First Hospital, Jiujiang, China;4. Department of Endoscopy, Cancer Center of Guangzhou Medical University, China;5. The Third Hospital of Wenzhou Medical University, Ruian, Zhejiang 325200, China |
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| 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. |
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| Keywords: | Cationic porphyrin Amphiphilic structure Photodynamic therapy Low light dose Cancer |
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