Design and synthesis of a DNA-crosslinking azinomycin analogue

Casely-Hayford, Maxwell A., Pors, Klaus, James, Colin H., Patterson, Laurence H., Hartley, John A. and Searcey, Mark ORCID: (2005) Design and synthesis of a DNA-crosslinking azinomycin analogue. Organic & Biomolecular Chemistry, 3 (19). pp. 3585-3589. ISSN 1477-0520

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The azinomycins are potent antitumour that are able to crosslink DNA, but are relatively unstable and unlikely to progress as therapeutic candidates. A prototype analogue 4 with more clinical potential has been designed and synthesised and incorporates the epoxide function of the azinomycins and a nitrogen mustard. Two further analogues 5 and 6 that can alkylate DNA but cannot crosslink the duplex have also been synthesised. Compound 4 crosslinks DNA efficiently at nM concentrations. Compounds 4-6 were submitted to the NCI 60 cell line screen and have similar antitumour activity, although 4 is slightly less active than the non-crosslinking compounds. These observations will be important in the design of further azinomycin analogues with antitumour activity.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
UEA Research Groups: Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017)
Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Depositing User: Rachel Smith
Date Deposited: 13 Jun 2011 13:35
Last Modified: 24 Oct 2022 02:16
DOI: 10.1039/b508908e

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