title: Synthesis of near-IR fluorescent oxazine dyes with esterase-labile sulfonate esters.
abstract: Near-IR oxazine dyes are reported that contain sulfonate esters which are rapidly cleaved by esterase activity to unmask highly polar anionic sulfonates. Strategies for the synthesis of these dyes included the development of milder dye condensation conditions with improved functional compatibility and the use of an alkyl halide that allows for the introduction of esterase-labile sulfonates without the need for sulfonation of the target molecule.
authors: Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, Worcester, Massachusetts 01655, USA.
authors: Steven M
authors: SM
authors: Pauff
authors: Stephen C
authors: SC
authors: Miller
mesh_terms: D000476:Alkanesulfonates / Q000737:chemistry*; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry; D004950:Esterases / Q000378:metabolism*; D004952:Esters; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D000476:Alkanesulfonates; D004396:Coloring Agents; D004952:Esters; D005456:Fluorescent Dyes; D010078:Oxazines; D013451:Sulfonic Acids; D004950:Esterases