title: General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability.
abstract: To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg9. The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg9Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described.
authors.affiliation: Department of Chemistry, Washington University in St Louis, St. Louis, MO 63130, USA.
authors.forename: Xiaoxu
authors.initials: X
authors.lastname: Li
authors.forename: John Stephen
authors.initials: JS
authors.lastname: Taylor
mesh_terms: D000478:Alkylation; D002462:Cell Membrane / Q000378:metabolism*; D002463:Cell Membrane Permeability; D015195:Drug Design; D004355:Drug Stability; D004952:Esters / Q000737:chemistry*; D019793:Fluorescein / Q000737:chemistry; D005453:Fluorescence; D006863:Hydrogen-Ion Concentration; D008301:Maleimides / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013057:Spectrum Analysis
chemical_list: D004952:Esters; D008301:Maleimides; D010455:Peptides; D011355:Prodrugs; C043592:maleimide; D019793:Fluorescein