Asymmetrical, water-soluble phthalocyanine dyes for covalent labeling of oligonucleotides.
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.
Hammer
Robert P
RP
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803-1804, USA. rphammer@lsu.edu
Owens
Clyde V
CV
Hwang
Seok-Hwan
SH
Sayes
Christie M
CM
Soper
Steven A
SA
D002851:Chromatography, High Pressure Liquid; D004396:Coloring Agents / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D007211:Indoles / Q000032:analysis / Q000737:chemistry*; D054833:Isoindoles; D015394:Molecular Structure; D009841:Oligonucleotides / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D013054:Spectrophotometry, Atomic; D013056:Spectrophotometry, Ultraviolet; D013194:Staining and Labeling / Q000379:methods*
D004396:Coloring Agents; D007211:Indoles; D054833:Isoindoles; D009841:Oligonucleotides; C013647:phthalocyanine