title: Synthesis and application of a water-soluble near-infrared dye for cancer detection using optical imaging.
abstract: A novel water-soluble 2-[2-(2-chloro-3-{2-[3,3-dimethyl-5-sulfo-1-(4-sulfo-butyl)-3H-indol-2-yl]-vinyl}-cyclohex-2-enylidene)-ethylidene]-3,3-dimethyl-1-(4-sulfo-butyl)-2,3-dihydro-1H-indole-5-carboxylic acid (dye 2) was developed via an asymmetric approach. With an additional sulfonate group, the near-infrared feature of this dye exhibited a 2-fold increase in quantum yield compared to the previous generation. The current synthetic strategy provided a single carboxylic group as a handle for conjugation, thus allowing selectivity for bioconjugation. The stability of this dye was demonstrated by labeling peptides via solid-phase peptide chemistry. The in vivo optical imaging showed potential and broad applications of this dye in developing molecular-based beacons for cancer detection.
authors.affiliation: Athinoula A. Martinos Center for Biomedical Imaging, Department of Radiology, Massachusetts General Hospital, Charlestown, Massachusetts 02129, USA.
authors.forename: Wellington
authors.initials: W
authors.lastname: Pham
authors.forename: Zdravka
authors.initials: Z
authors.lastname: Medarova
authors.forename: Anna
authors.initials: A
authors.lastname: Moore
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D004396:Coloring Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects*; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D003952:Diagnostic Imaging / Q000295:instrumentation* / Q000379:methods*; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007259:Infrared Rays; D051379:Mice; D008819:Mice, Nude; D008856:Microscopy, Fluorescence; D015394:Molecular Structure; D009369:Neoplasms / Q000175:diagnosis*; D012995:Solubility; D013050:Spectrometry, Fluorescence; D014867:Water / Q000737:chemistry*
chemical_list: C503267:2-(2-(2-chloro-3-(2-(3,3-dimethyl-5-sulfo-1-(4-sulfo-butyl)-3H-indol-2-yl)-vinyl)-cyclohex-2-enylidene)-ethylidene)-3,3-dimethyl-1-(4-sulfo-butyl)-2,3-dihydro-1H-indole-5-carboxylic acid; D004396:Coloring Agents; D003510:Cyclohexanes; D007211:Indoles; D014867:Water