A Convenient Synthesis of Cyanine Dyes: Reagents for the Labeling of Biomolecules

Abstract

Four tetramethylindo(di)carbocyanine‐derived carboxylicacids have been prepared using a modified one‐pot procedure for the dye assembly. The acids were converted into oxysuccinimide esters and phosphoramidite reagents. The efficiency of the reagents in the labeling of oligonucleotides and proteins has been demonstrated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Cyanine-based 1-amino-1-deoxyglucose as fluorescent probes for glucose transporter mediated bioimaging

“…Cy3 and Cy5 were prepared according to the literature procedure [21]. The other starting material, 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine, was prepared by the literature method [22].…”

Nucleotides and Nucleic Acids; Oligo- and Polynucleotides

“…551 Cyanine dyes find wide application in fluorescence applications, and some new cyanine analogues have been reported. The synthesis of four cyanine dyes suitable for labelling oligonucleotides and other biomolecules have been reported, 552 and Cy3 attached to dU via a rigid, rather than the more common flexible linker has been described. 553 Huang and Coull have described a system of generating a hemicyanine dye in situ (Scheme 2).…”

Silent, fluorescent labeling of native neuronal receptors

“…Selective Boc-deprotection of 2 using dichloroacetic acid 38 afforded primary amine 3 that was then coupled to the carboxylic acid of previously-reported tethered acrylamide 4 39 using HATU/HOAt and collidine to yield 5. Next, tert-butyl ester 5 was treated with TFA to afford the carboxylic acid 6 and this was coupled to the amine-functionalized Cy3 7 40 using HATU/HOAt and collidine to afford 8. The methyl ester of 8 was then hydrolyzed to afford compound 9, a portion of which is used as a control molecule for electrophysiological and imaging experiments.…”

“…Compound 12 (580 mg, 1.26 mmol) 40 was dissolved in dry DMF (5 mL) and treated with EDC HCl (274 mg, 1.39 mmol), HOBt (166 mg, 1.23 mmol), and DIPEA (491 mg, 3.80 mmol) (Scheme 2). The reaction mixture was stirred for 30 min at room temperature.…”