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.
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.
authors.affiliation: Institute of Biotechnology, University of Cambridge, U.K.
authors.forename: S J
authors.initials: SJ
authors.lastname: Burton
authors.forename: C V
authors.initials: CV
authors.lastname: Stead
authors.forename: C R
authors.initials: CR
authors.lastname: Lowe
mesh_terms: D000227:Adenine Nucleotides / Q000378:metabolism*; D000426:Alcohol Dehydrogenase / Q000032:analysis / Q000378:metabolism*; D000818:Animals; D000880:Anthraquinones / Q000378:metabolism; D002846:Chromatography, Affinity / Q000379:methods; D004396:Coloring Agents / Q000378:metabolism; D006736:Horses; D008099:Liver / Q000201:enzymology*; D014227:Triazines / Q000378:metabolism
chemical_list: D000227:Adenine Nucleotides; D000880:Anthraquinones; D004396:Coloring Agents; D014227:Triazines; C012842:Cibacron Blue F 3GA; D000426:Alcohol Dehydrogenase