Synthesis, photochemical and in vitro cytotoxic evaluation of benzoselenazole-based aminosquaraines
Squaraine dyes have recently attracted interest as potential second generation photosensitizers for photo-dynamic therapy. Several cationic aminosquaraine dyes bearing benzoselenazole terminal nuclei were synthezised and their cytotoxic activity was tested against four different human tumor cell lin...
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| Veröffentlicht in: | Photochemical & photobiological sciences 2019, Vol.18 (2), p.336-342 |
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| creator | Magalhães, Álvaro F. Graça, Vânia C. Calhelha, Ricardo C. Ferreira Machado, I. L. Ferreira, L. F. Vieira Ferreira, Isabel C. F. R. Santos, Paulo F. |
| description | Squaraine dyes have recently attracted interest as potential second generation photosensitizers for photo-dynamic therapy. Several cationic aminosquaraine dyes bearing benzoselenazole terminal nuclei were synthezised and their cytotoxic activity was tested against four different human tumor cell lines – breast (MCF-7), non-small cell lung (NCI-H460), cervical (HeLa) and hepatocellular (HepG2) carcinomas – and against a non-tumor porcine liver primary cell line (PLP2), both in the absence of light and under irradiation. All dyes, which displayed strong absorption within the phototherapeutic window, were found to exhibit photodynamic activity and were shown to be, in most cases, more cytotoxic, both in the dark and upon irradiation, than their benzothiazole analogues. |
| doi_str_mv | 10.1039/c8pp00201k |
| format | Article |
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L.</creatorcontrib><creatorcontrib>Ferreira, L. F. Vieira</creatorcontrib><creatorcontrib>Ferreira, Isabel C. F. R.</creatorcontrib><creatorcontrib>Santos, Paulo F.</creatorcontrib><title>Synthesis, photochemical and in vitro cytotoxic evaluation of benzoselenazole-based aminosquaraines</title><title>Photochemical & photobiological sciences</title><addtitle>Photochem Photobiol Sci</addtitle><addtitle>Photochem Photobiol Sci</addtitle><description>Squaraine dyes have recently attracted interest as potential second generation photosensitizers for photo-dynamic therapy. Several cationic aminosquaraine dyes bearing benzoselenazole terminal nuclei were synthezised and their cytotoxic activity was tested against four different human tumor cell lines – breast (MCF-7), non-small cell lung (NCI-H460), cervical (HeLa) and hepatocellular (HepG2) carcinomas – and against a non-tumor porcine liver primary cell line (PLP2), both in the absence of light and under irradiation. All dyes, which displayed strong absorption within the phototherapeutic window, were found to exhibit photodynamic activity and were shown to be, in most cases, more cytotoxic, both in the dark and upon irradiation, than their benzothiazole analogues.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Benzothiazole</subject><subject>Biochemistry</subject><subject>Biomaterials</subject><subject>Cell Line, Tumor</subject><subject>Cervix</subject><subject>Chemistry</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Cyclobutanes - chemical synthesis</subject><subject>Cyclobutanes - chemistry</subject><subject>Cyclobutanes - pharmacology</subject><subject>Cytotoxicity</subject><subject>Dyes</subject><subject>Hepatocellular carcinoma</subject><subject>Hepatocytes</subject><subject>Humans</subject><subject>Irradiation</subject><subject>Liver</subject><subject>Lungs</subject><subject>Phenols - chemical synthesis</subject><subject>Phenols - chemistry</subject><subject>Phenols - pharmacology</subject><subject>Photochemical Processes</subject><subject>Photochemicals</subject><subject>Photodynamic therapy</subject><subject>Physical Chemistry</subject><subject>Plant Sciences</subject><subject>Radiation</subject><subject>Selenium - chemistry</subject><subject>Tumor cell lines</subject><subject>Tumors</subject><issn>1474-905X</issn><issn>1474-9092</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1L5TAUBuAwjIx6dTM_YAjMRtSOSdMmzVLELxBczAjuykl6OjfaJjVpxeuvn8p1FMRVAufJm8NLyHfOfnEm9JGthoGxnPH7L2SLF6rINNP517d7ebtJtlO6Y4yXhVTfyKZggjPNxRaxv1d-XGJy6ZAOyzAGu8TeWego-IY6Tx_dGAO1q3GePTlL8RG6CUYXPA0tNeifQ8IOPTyHDjMDCRsKvfMhPUwQwXlMO2SjhS7h7uu5IDdnp39OLrKr6_PLk-OrzBZcjJnRyE3ODWijTCtUYcumlQpMg5ArKCRDhY3QEqUQklm0lVCyMoBlYTFHsSB769whhocJ01j3LlnsOvAYplTnnGvNZTU_X5CfH-hdmKKft5uVqlRV6FLOan-tbAwpRWzrIboe4qrmrH6pvn6vfsY_XiMn02PzRv93PYODNUjzyP_F-P7nJ3H_AFTyj_0</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Magalhães, Álvaro F.</creator><creator>Graça, Vânia C.</creator><creator>Calhelha, Ricardo C.</creator><creator>Ferreira Machado, I. L.</creator><creator>Ferreira, L. F. Vieira</creator><creator>Ferreira, Isabel C. F. R.</creator><creator>Santos, Paulo F.</creator><general>Springer International Publishing</general><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>2019</creationdate><title>Synthesis, photochemical and in vitro cytotoxic evaluation of benzoselenazole-based aminosquaraines</title><author>Magalhães, Álvaro F. ; Graça, Vânia C. ; Calhelha, Ricardo C. ; Ferreira Machado, I. L. ; Ferreira, L. F. Vieira ; Ferreira, Isabel C. F. 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| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Benzothiazole Biochemistry Biomaterials Cell Line, Tumor Cervix Chemistry Chemistry Techniques, Synthetic Cyclobutanes - chemical synthesis Cyclobutanes - chemistry Cyclobutanes - pharmacology Cytotoxicity Dyes Hepatocellular carcinoma Hepatocytes Humans Irradiation Liver Lungs Phenols - chemical synthesis Phenols - chemistry Phenols - pharmacology Photochemical Processes Photochemicals Photodynamic therapy Physical Chemistry Plant Sciences Radiation Selenium - chemistry Tumor cell lines Tumors |
| title | Synthesis, photochemical and in vitro cytotoxic evaluation of benzoselenazole-based aminosquaraines |
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