Design and synthesis of a DNA-crosslinking azinomycin analogues

Casely-Hayford, Maxwell A. and Pors, Klaus and James, Colin H. and Patterson, Laurence H. and Hartley, John A. and Searcey, Mark (2005) Design and synthesis of a DNA-crosslinking azinomycin analogues. Organic & Biomolecular Chemistry, 3 (19). pp. 3585-3589. ISSN 1477-0520. (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

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The azinomycins are potent antitumour antibiotics 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
Projects: [52] Development of DNA-crosslinking anticancer agents
Uncontrolled keywords: antitumour antibiotics; sequence selectivity; carzinophilin; cytotoxicity; alkylation; naphthoate; mechanism; cleavage; agent
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > Medway School of Pharmacy
Depositing User: Maxwell Casely-Hayford
Date Deposited: 15 Sep 2008 21:40
Last Modified: 01 May 2014 09:20
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