title: Simple one-pot preparation of water-soluble, cysteine-reactive cyanine and merocyanine dyes for biological imaging.
abstract: A simple one-pot-procedure for preparation of protein-reactive, water-soluble merocyanine and cyanine dyes has been developed. The 1-(3-ammoniopropyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate bromide (1) was used as a common starting intermediate. The method allows easy preparation of dyes with chloro- and iodoacetamide side chains for covalent attachment to cysteine. By placing a sulfonato group directly on the dye fluorophore system, dyes with high fluorescence quantum yields in water were generated. Both iodo- and chloroacetamido derivatives were shown to be useful in protein labeling. Less reactive chloroacetamides will be preferential for selective labeling of the most reactive cysteines.
authors.affiliation: Department of Pharmacology and Lineberger Cancer Center, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA. alexei.toutchkine@sial.com
authors.forename: Alexei
authors.initials: A
authors.lastname: Toutchkine
authors.forename: Dan-Vinh
authors.initials: DV
authors.lastname: Nguyen
authors.forename: Klaus M
authors.initials: KM
authors.lastname: Hahn
mesh_terms: D002232:Carbocyanines / Q000737:chemistry* / Q000378:metabolism; D003545:Cysteine / Q000737:chemistry; D003952:Diagnostic Imaging; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D049452:Green Fluorescent Proteins / Q000378:metabolism; D019950:Mitogen-Activated Protein Kinase 1 / Q000378:metabolism; D011744:Pyrimidinones / Q000737:chemistry* / Q000378:metabolism; D011993:Recombinant Fusion Proteins / Q000378:metabolism; D012995:Solubility; D014867:Water
chemical_list: D002232:Carbocyanines; D005456:Fluorescent Dyes; D011744:Pyrimidinones; D011993:Recombinant Fusion Proteins; C485184:enhanced green fluorescent protein; D014867:Water; D049452:Green Fluorescent Proteins; C003954:merocyanine dye; D019950:Mitogen-Activated Protein Kinase 1; D003545:Cysteine