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    Two structurally related diaziridinylbenzoquinones preferentially cross-link DNA at different sites upon reduction with DT-diaphorase.

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    Authors
    Berardini, M D
    Souhami, R L
    Lee, C S
    Gibson, N W
    Butler, John
    Hartley, John A
    Affiliation
    Department of Oncology, University College & Middlesex School of Medicine, London, U.K.
    Issue Date
    1993-04-06
    
    Metadata
    Show full item record
    Abstract
    The nucleotide sequence preferences for the formation of interstrand cross-links induced in DNA by 2,5-diaziridinyl-1,4-benzoquinone (DZQ) and 3,6-dimethyl-2,5-diaziridinyl-1,4-benzoquinone (MeDZQ) were studied using synthetic duplex oligonucleotides and denaturing polyacrylamide gel electrophoresis (PAGE). Reaction of these bifunctional alkylating agents with a DNA duplex containing several potential cross-linking sites resulted in the formation of cross-linked DNAs with different electrophoretic mobilities. Analysis of the principal cross-linked products by piperidine fragmentation revealed that the preferential site of cross-linking was altered from a 5'-GNC to a 5'-GC sequence upon reduction of DZQ to the hydroquinone form by the enzyme DT-diaphorase. In contrast, the reduced form of MeDZQ was found to preferentially cross-link at 5'-GNC sites within the same sequence. These preferences were confirmed in duplex oligonucleotides containing single potential cross-linking sites. Additional minor cross-linked products were characterized and revealed that DZQ and MeDZQ are both capable of cross-linking across four base pairs in a 5'-GNNC sequence.
    Citation
    Two structurally related diaziridinylbenzoquinones preferentially cross-link DNA at different sites upon reduction with DT-diaphorase. 1993, 32 (13):3306-12 Biochemistry
    Journal
    Biochemistry
    URI
    http://hdl.handle.net/10541/100397
    DOI
    10.1021/bi00064a013
    PubMed ID
    8461296
    Type
    Article
    Language
    en
    ISSN
    0006-2960
    ae974a485f413a2113503eed53cd6c53
    10.1021/bi00064a013
    Scopus Count
    Collections
    All Paterson Institute for Cancer Research

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    Related articles

    • Molecular dynamics simulations provide a structural basis for the experimentally observed nucleotide preferences for DNA interstrand cross-links induced by aziridinylbenzoquinones.
    • Authors: Haworth IS, Lee CS, Yuki M, Gibson NW
    • Issue date: 1993 Nov 30
    • 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
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    • 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
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    • Relationship between DT-diaphorase-mediated metabolism of a series of aziridinylbenzoquinones and DNA damage and cytotoxicity.
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    • Issue date: 1992 Sep
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