Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones
dc.contributor.author | Errington, R.J. | * |
dc.contributor.author | Sadiq, M. | * |
dc.contributor.author | Cosentino, L. | * |
dc.contributor.author | Wiltshire, M. | * |
dc.contributor.author | Sadiq, O. | * |
dc.contributor.author | Sini, Marcella | * |
dc.contributor.author | Lizano, E. | * |
dc.contributor.author | Pujol, M.D. | * |
dc.contributor.author | Ribeiro Morais, Goreti | * |
dc.contributor.author | Pors, Klaus | * |
dc.date.accessioned | 2018-06-06T09:22:33Z | |
dc.date.available | 2018-06-06T09:22:33Z | |
dc.date.issued | 2018-05-01 | |
dc.identifier.citation | Errington RJ, Sadiq M, Cosentino L et al (2018) Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones. Bioorganic & Medicinal Chemistry Letters. 28(8): 1274-1277. | en_US |
dc.identifier.uri | http://hdl.handle.net/10454/16100 | |
dc.description | Yes | en_US |
dc.description.abstract | 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. | en_US |
dc.language.iso | en | en_US |
dc.rights | © 2018 Elsevier. Reproduced in accordance with the publisher's self-archiving policy. This manuscript version is made available under the CC-BY-NC-ND 4.0 license. | en_US |
dc.subject | Anthraquinone | en_US |
dc.subject | Nemorubicin | en_US |
dc.subject | MMDX | en_US |
dc.subject | DRAQ5 | en_US |
dc.subject | Cytochrome P450 | en_US |
dc.subject | CYP1A2 | en_US |
dc.subject | Fluorophore | en_US |
dc.subject | Cancer | en_US |
dc.title | Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones | en_US |
dc.status.refereed | Yes | en_US |
dc.date.Accepted | 2018-03-15 | |
dc.date.application | 2018-03-16 | |
dc.type | Article | en_US |
dc.type.version | Accepted Manuscript | en_US |
dc.identifier.doi | https://doi.org/10.1016/j.bmcl.2018.03.040 |