Cross-linking and sequence specific alkylation of DNA by aziridinyl quinones. 2. Structure requirements for sequence selectivity.
AffiliationCRC Department of Biophysical Chemistry, Drug Development, Paterson Institute for Cancer Research, Christie Hospital NHS Trust, Manchester, U.K.
MetadataShow full item record
AbstractThe cytotoxicities and DNA sequence selectivity for guanine-N7 alkylation of 22 mono- and disubstituted 2,5-diaziridinyl-1,4-benzoquinones have been investigated. Several quinones produced patterns of alkylation following reduction with a selectivity for 5'-TGC-3' sequences. This sequence selectivity appeared to be dependent only on the presence of a hydrogen in position-6 of the quinone. A computer model, based on published crystallographic data, was used to explain this selectivity. The sequence selective quinones were generally more cytotoxic that the quinones which reacted randomly.
CitationCross-linking and sequence specific alkylation of DNA by aziridinyl quinones. 2. Structure requirements for sequence selectivity. 1997, 40 (3):357-61 J. Med. Chem.
JournalJournal of Medicinal Chemistry
- Cross-linking and sequence-specific alkylation of DNA by aziridinylquinones. 3. Effects of alkyl substituents.
- Authors: Hargreaves RH, O'Hare CC, Hartley JA, Ross D, Butler J
- Issue date: 1999 Jun 17
- Alteration in DNA cross-linking and sequence selectivity of a series of aziridinylbenzoquinones after enzymatic reduction by DT-diaphorase.
- Authors: Lee CS, Hartley JA, Berardini MD, Butler J, Siegel D, Ross D, Gibson NW
- Issue date: 1992 Mar 24
- DNA cross-linking and sequence selectivity of aziridinylbenzoquinones: a unique reaction at 5'-GC-3' sequences with 2,5-diaziridinyl-1,4-benzoquinone upon reduction.
- Authors: Hartley JA, Berardini M, Ponti M, Gibson NW, Thompson AS, Thurston DE, Hoey BM, Butler J
- Issue date: 1991 Dec 17
- Cross-linking and sequence specific alkylation of DNA BY aziridinylquinones. 1. Quinone methides.
- Authors: Mayalarp SP, Hargreaves RH, Butler J, O'Hare CC, Hartley JA
- Issue date: 1996 Jan 19
- DNA-Directed alkylating agents. 7. Synthesis, DNA interaction, and antitumor activity of bis(hydroxymethyl)- and bis(carbamate)-substituted pyrrolizines and imidazoles.
- Authors: Atwell GJ, Fan JY, Tan K, Denny WA
- Issue date: 1998 Nov 19