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Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones

Errington, Rachel J. ORCID:, Sadiq, Maria, Cosentino, Laura, Wiltshire, Marie, Sadiq, Omair, Sini, Marcella, Lizano, Enric, Pujol, Maria D., Morais, Goreti R. and Pors, Klaus 2018. Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones. Bioorganic and Medicinal Chemistry Letters 28 (8) , pp. 1274-1277. 10.1016/j.bmcl.2018.03.040

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Structural features from the anticancer prodrug nemorubicin (MMDX) and the DNA-binding molecule DRAQ5™ were used to prepare anthraquinone-based compounds, which were assessed for their potential to interrogate cytochrome P450 (CYP) functional activity and localisation. 1,4-disubstituted anthraquinone 8 was shown to be 5-fold more potent in EJ138 bladder cancer cells after CYP1A2 bioactivation. In contrast, 1,5-bis((2-morpholinoethyl)amino) substituted anthraquinone 10 was not CYP-bioactivated but was shown to be fluorescent and subsequently photo-activated by a light pulse (at a bandwidth 532–587 nm), resulting in punctuated foci accumulation in the cytoplasm. It also showed low toxicity in human osteosarcoma cells. These combined properties provide an interesting prospective approach for opto-tagging single or a sub-population of cells and seeking their location without the need for continuous monitoring.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Medicine
Publisher: Elsevier
ISSN: 0960-894X
Date of First Compliant Deposit: 11 May 2018
Date of Acceptance: 15 March 2018
Last Modified: 10 Nov 2023 10:35

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