Light-Controlled Anticancer Activity and Cellular Uptake of a Photoswitchable Cisplatin Analogue
A photoactive analogue of cisplatin was synthesized with two arylazopyrazole ligands, able to undergo trans–cis/cis–trans photoisomerizations. The cis photoisomer showed a dark half-life of 9 days. The cytotoxicities of both photoisomers of the complex were determined in several cancer and normal ce...
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| Veröffentlicht in: | Journal of medicinal chemistry 2024-11, Vol.67 (21), p.19103-19120 |
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| container_title | Journal of medicinal chemistry |
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| creator | Stolarek, Marta Kaminski, Kamil Kaczor-Kamińska, Marta Obłoza, Magdalena Bonarek, Piotr Czaja, Anna Datta, Magdalena Łach, Wojciech Brela, Mateusz Sikorski, Artur Rak, Janusz Nowakowska, Maria Szczubiałka, Krzysztof |
| description | A photoactive analogue of cisplatin was synthesized with two arylazopyrazole ligands, able to undergo trans–cis/cis–trans photoisomerizations. The cis photoisomer showed a dark half-life of 9 days. The cytotoxicities of both photoisomers of the complex were determined in several cancer and normal cell lines and compared to that of cisplatin. The trans photoisomer of the complex was much more cytotoxic than both the cis photoisomer and cisplatin, and was more toxic for cancer (4T1) than for normal (NMuMG) murine breast cells. 4T1 cell death occurred through necrosis. Photoisomerization of the trans and cis photoisomers internalized by the 4T1 cells increased and decreased their viability, respectively. The cellular uptake of the trans photoisomer was stronger than that of both the cis photoisomer and cisplatin. Both photoisomers interacted with DNA faster than cisplatin. The trans photoisomer was bound stronger by bovine serum albumin and induced a greater decrease in cellular glutathione levels than the cis photoisomer. |
| doi_str_mv | 10.1021/acs.jmedchem.4c01575 |
| format | Article |
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The cis photoisomer showed a dark half-life of 9 days. The cytotoxicities of both photoisomers of the complex were determined in several cancer and normal cell lines and compared to that of cisplatin. The trans photoisomer of the complex was much more cytotoxic than both the cis photoisomer and cisplatin, and was more toxic for cancer (4T1) than for normal (NMuMG) murine breast cells. 4T1 cell death occurred through necrosis. Photoisomerization of the trans and cis photoisomers internalized by the 4T1 cells increased and decreased their viability, respectively. The cellular uptake of the trans photoisomer was stronger than that of both the cis photoisomer and cisplatin. Both photoisomers interacted with DNA faster than cisplatin. 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| title | Light-Controlled Anticancer Activity and Cellular Uptake of a Photoswitchable Cisplatin Analogue |
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