Novel hydrophilic galactose-conjugated chlorin e6 derivatives for photodynamic therapy and fluorescence imaging |
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| Institution: | 1. Institute of Chemistry of the Komi Science Centre, Ural Division of Russian Academy of Sciences, 167000, 48 Pervomayskaya st., Syktyvkar, Russia;2. Institute of Biology of Komi Scientific Centre of the Ural Branch of the Russian Academy of Sciences, 167000, 28 Kommunisticheskaya st., Syktyvkar, Russia;1. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Wenhua Road 103, Shenyang 110016, China;2. Tianjin Vocational College of Bioengineering, Tianjin 300462, China;1. Laboratório de Terapia Fotodinâmica, Instituto de Pesquisa e desenvolvimento, Univap-Universidade do Vale do Paraíba, Av. Shishima Hifumi, 2911, 12244-000 São José dos Campos, SP, Brazil;2. Laboratório de Parasitologia e Biotecnologia, Instituto de Pesquisa e desenvolvimento, Univap-Universidade do Vale do Paraíba, Av. Shishima Hifumi, 2911, 12244-000 São José dos Campos, SP, Brazil;3. Laboratório de Biofotônica, Instituto de Física, USP-Universidade de São Paulo, USP São Carlos-Campus 1, Avenida Trabalhador São-Carlense, 400—Parque Arnold Schimidt, São Carlos, SP 13566, Brazil;4. Laboratório de Nanossensores, Instituto de Pesquisa e desenvolvimento, Univap-Universidade do Vale do Paraíba, Av. Shishima Hifumi, 2911, 12244-000 São José dos Campos, SP, Brazil;1. Dipartimento di Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Palermo, Italy;2. Dipartimento di Biopatologia e Biotecnologie Mediche e Forensi (Di.Bi.Me.F.), Università di Palermo, Palermo, Italy;3. Dipartimento di Biotecnologie Cellulari ed Ematologia, Sapienza Università di Roma, Rome, Italy;1. Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan;2. Department of Bioscience, Fukui Prefectural University, Yoshida-Gun, Fukui 910-1195, Japan;1. CLCC Eugène Marquis, INSERM, Univ Rennes 1, UMR1242, rue Bataille Flandres Dunkerque, 35042 Rennes, France;2. Equipe Ligue Contre Le Cancer, rue Bataille Flandres Dunkerque, 35042 Rennes, France;3. Université de Bordeaux, 146 rue Léo Saignat, 33076 Bordeaux, France;4. INSERM U1218, 229 cours de l’Argonne, 33076 Bordeaux Cedex, France;5. Bioprojet Biotech, 4 rue du Chesnay Beauregard, 35760 Saint-Grégoire, France |
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| Abstract: | We synthesized new hydrophilic chlorin e6 derivatives with two and four galactose fragments conjugated to the macrocycle via carbon atom in position 6 of the galactose fragment. Galactose fragments were inserted by alkylation of the amino groups of chlorin e6 amides with one and two ethylene diamine fragments on the macrocycle periphery with triflate of diacetone galactose, followed by removal of diisopropylidene protection by 70% aqueous trifluoroacetic acid. The synthesized compounds were shown to be capable of penetrating the membrane of HeLa cells; they have intense red fluorescence inside the cell and have phototoxic properties towards HeLa cells (upon LED irradiation at 660 nm and light exposure value of 12 J/cm2). These properties, along with water solubility, allow us to consider the synthesized compounds to be promising as potential antitumor PSs and diagnostic compounds for visualizing malignant tumors and creating on their basis preparations for simultaneous diagnostics and therapy of oncological diseases. |
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| Keywords: | Cytotoxicity Amide |
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