title: Combining aminocyanine dyes with polyamide dendrons: a promising strategy for imaging in the near-infrared region.
abstract: Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S(NR)1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.
authors.affiliation: Molecular Design Institute, Department of Chemistry, New York University, 31 Washington Place, New York, NY 10003-6688, USA.
authors.forename: Cátia
authors.initials: C
authors.lastname: Ornelas
authors.forename: Rachelle
authors.initials: R
authors.lastname: Lodescar
authors.forename: Alexander
authors.initials: A
authors.lastname: Durandin
authors.forename: James W
authors.initials: JW
authors.lastname: Canary
authors.forename: Ryan
authors.initials: R
authors.lastname: Pennell
authors.forename: Leonard F
authors.initials: LF
authors.lastname: Liebes
authors.forename: Marcus
authors.initials: M
authors.lastname: Weck
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002232:Carbocyanines / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D004396:Coloring Agents / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D050091:Dendrimers / Q000737:chemistry*; D003952:Diagnostic Imaging; D005456:Fluorescent Dyes / Q000737:chemistry*; D015394:Molecular Structure; D019265:Spectroscopy, Near-Infrared
chemical_list: D000480:Alkynes; D002232:Carbocyanines; D004396:Coloring Agents; D050091:Dendrimers; D005456:Fluorescent Dyes; D003300:Copper