用于寡核苷酸共价标记的不对称水溶性酞菁染料。
Asymmetrical, water-soluble phthalocyanine dyes for covalent labeling of oligonucleotides.
作者信息
Hammer Robert P, Owens Clyde V, Hwang Seok-Hwan, Sayes Christie M, Soper Steven A
机构信息
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803-1804, USA.
出版信息
Bioconjug Chem. 2002 Nov-Dec;13(6):1244-52. doi: 10.1021/bc0155869.
Two new water-soluble, porphyrazine (Pz) dyes containing an isothiocyanate function for covalent linking have each been prepared by cross condensation of two different aromatic dinitriles, one containing carboxylates for solubilizing purposes and the other containing a nitro group for conversion into the labeling function. The initial mononitrotricarboxylato Pzs have been purified to homogeneity from the mixture of Pz congeners formed in the condensation reaction by anion exchange chromatography. The phthalocyanine dye 1 has an absorption maxima at 683 nm while the trinaphthoporphyrazine dye 2 has an absorption maxima at 755 nm, due to the increased size of the aromatic system. Both dyes were successfully conjugated to oligonucleotide primers, showing their potential for use in near-infrared-based DNA diagnostic applications.
通过两种不同芳香族二腈的交叉缩合反应，分别制备了两种新型的、含有用于共价连接的异硫氰酸酯官能团的水溶性卟吩嗪（Pz）染料。其中一种芳香族二腈含有羧酸盐用于增溶，另一种含有硝基用于转化为标记官能团。通过阴离子交换色谱法，从缩合反应中形成的Pz同系物混合物中，将初始的单硝基三羧基Pz纯化至同质。酞菁染料1在683nm处有最大吸收峰，而三萘并卟吩嗪染料2在755nm处有最大吸收峰，这是由于芳香体系尺寸增大所致。两种染料均成功与寡核苷酸引物偶联，显示出它们在基于近红外的DNA诊断应用中的潜力。
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