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

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.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Errington RJ,Sadiq M,Cosentino L,Wiltshire M,Sadiq O,Sini M,Lizano E,Pujol MD,Morais GR,Pors K

doi

10.1016/j.bmcl.2018.03.040

subject

Has Abstract

pub_date

2018-05-01 00:00:00

pages

1274-1277

issue

8

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(18)30231-2

journal_volume

28

pub_type

杂志文章

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