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  • Title: Design and applications of biomimetic anthraquinone dyes. III. Anthraquinone-immobilised C.I. reactive blue 2 analogues and their interaction with horse liver alcohol dehydrogenase and other adenine nucleotide-binding proteins.
    Author: Burton SJ, Stead CV, Lowe CR.
    Journal: J Chromatogr; 1990 May 25; 508(1):109-25. PubMed ID: 2380311.
    Abstract:
    C.I. Reactive Blue 2 analogues were bonded onto an agarose support matrix by a novel method which entailed immobilisation by the anthraquinone ring 1-amino group as opposed to the usual triazine ring coupling methods. Dyes with spacer arms attached to the anthraquinone ring 1-amino group were synthesised by reacting methoxytriazine analogues of C.I. Reactive Blue 2 with chloroacetyl chloride and ethylenediamine. Unlike the blue parent dyes, all C.I. Reactive Blue 2 analogues with derivatised anthraquinone ring 1-amino groups were of a characteristic red colour. This change of chromaticity was entirely expected since the anthraquinone ring 1-amino group is an important component of the C.I. Reactive Blue 2 chromophore. Chromatographic studies indicated that, in comparison to adsorbents comprising triazine ring-immobilised dyes, adsorbents formed from C.I. Reactive Blue 2 analogues immobilised by the anthraquinone ring were better suited to the isolation of horse liver alcohol dehydrogenase and other adenine nucleotide-requiring enzymes. Similarities between C.I. Reactive Blue 2 analogues immobilised by the anthraquinone ring and N6-(6-aminohexyl)adenine nucleotide derivatives could be identified which may account for these observations. These studies confirm that highly effective affinity ligands based on synthetic textile dyes can be designed in a rational manner.
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