Conjugation-Induced Fluorescent Labeling of Proteins and Polymers Using Dithiomaleimides

• Published in: Journal of the American Chemical Society Vol. 135; no. 8; pp. 2875 - 2878
• Main Authors: Robin, Mathew P, Wilson, Paul, Mabire, Anne B, Kiviaho, Jenny K, Raymond, Jeffery E, Haddleton, David M, O’Reilly, Rachel K
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 27-02-2013
• Subjects: Chromatography, High Pressure Liquid; Fluorescent Dyes - chemistry; Maleimides - chemistry; Polyethylene Glycols - chemistry; Polymers - chemistry; Proteins - chemistry; Solubility; Spectrometry, Fluorescence; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Spectrophotometry, Ultraviolet
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja3105494

Dithiomaleimides (DTMs) with alkyl substituents are shown to be a novel class of highly emissive fluorophores. Variable solubility and further functionalization can easily be tailored through the choice of N and S substituents. Inclusion of a DTM unit into a ROP/RAFT initiator or insertion into the disulfide bond of salmon calcitonin (sCT) demonstrates the utility for fluorescent labeling of polymers and proteins. Simultaneous PEGylation and fluorescent labeling of sCT is also demonstrated, using the DTM unit as both a linker and a fluorophore. It is anticipated that DTMs will offer an attractive alternative to commonly used bulky, planar fluorophores.