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Photosensitizers for Anticancer Photodynamic Therapy

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Photosensitizers for Anticancer Photodynamic Therapy ( photosensitizers-anticancer-photodynamic-therapy )

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molecules Article Synthesis and Evaluation of New Potential Benzo[a]phenoxazinium Photosensitizers for Anticancer Photodynamic Therapy Juan Zhang 1,2, Wellington Tavares de Sousa Júnior 2, Victor Carlos Mello da Silva 2, Mosar Correa Rodrigues 2,3, José Athayde Vasconcelos Morais 2,3 ID , Jia-Li Song 1, Zhi-Qiang Cheng 1, João Paulo Figueiró Longo 3 ID , Ricardo Bentes Azevedo 3, Cheng-Shi Jiang 1,* ID , Luís Alexandre Muehlmann 2,* and Hua Zhang 1,* 1 2 3 jplongo82@gmail.com (J.P.F.L.); razevedo@unb.br (R.B.A.) * Correspondence: jiangchengshi-20@163.com (C.-S.J.); luismuehlmann88@gmail.com (L.A.M.); bio_zhangh@ujn.edu.cn (H.Z.); Tel.: +86-0531-8973-6199 (H.Z.) Received: 16 May 2018; Accepted: 8 June 2018; Published: 13 June 2018 School of Biological Science and Technology, University of Jinan, Jinan 250022, China; zjandzq@163.com (J.Z.); 13285419800@163.com (J.-L.S.); czq13515312897@163.com (Z.-Q.C.) Faculty of Ceilandia, University of Brasília, Brasilia 72220275, Brazil; wellingtonjunior123@hotmail.com (W.T.d.S.J.); victooormellooo@gmail.com (V.C.M.d.S.); mosarcr@gmail.com (M.C.R.); joseathayde_9@hotmail.com (J.A.V.M.); Institute of Biological Sciences, University of Brasília, Brasilia 70910900, Brazil; Abstract: The use of photodynamic therapy (PDT) and development of novel photosensitizers (PSs) for cancer treatment have received more and more attention nowadays. In the present work, five benzo[a]phenoxazinium derivatives have been prepared and evaluated for their in vitro anticancer photodynamic activity for the first time. They are red light absorbers and show low fluorescence quantum yield. Of these compounds, PS4 exhibited a higher quantum yield for reactive oxygen species (ROS) generation. The assays with cells in vitro showed that PS1 and PS4 were not significantly toxic in the dark, but was robustly toxic against the murine breast adenocarcinoma cells 4T1 and normal murine fibroblast cells NIH-3T3 upon photoactivation. More interestingly, PS5 was particularly selective towards 4T1 cancer cells and nearly non-phototoxic to non-cancerous NIH-3T3 cells. The results described in this report suggest that these new benzo[a]phenoxazinium derivatives are potential candidates as PSs for anticancer PDT. Further investigation of benzo[a]phenoxaziniums for anticancer PDT is warranted. Keywords: benzo[a]phenoxazinium; photosensitizer; reactive oxygen species; photodynamic therapy; anticancer 1. Introduction Photodynamic therapy (PDT) is a minimally invasive protocol that has been used in anticancer therapy for a long time [1]. PDT is based on the focal photoactivation of photosensitizers (PSs), which can directly act on the target tissues and then elicit photochemical reactions that eventually lead to oxidative stress [2]. The main consequences of these events include direct cytotoxicity, collapse of the tumor microvasculature, and/or activation of immune response against tumor antigens [3]. A particularly important benefit of PDT as a cancer therapy is the possibility to restrict its effects to the irradiated site, sparing the normal tissues. Although PDT has been successfully applied in the treatment of skin, gynecological, gastrointestinal, and some head and neck cancers for a long time, only a few PSs (e.g., porfimer sodium, temoporfin, aminolevulinic acid and photofrin) have been put 􏰁􏰂􏰃 􏰅􏰆􏰇 􏰈􏰉􏰊􏰋􏰌􏰂􏰍 Molecules 2018, 23, 1436; doi:10.3390/molecules23061436 www.mdpi.com/journal/molecules

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