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Isolation and Characterization of Precise Dye/Dendrimer Ratios
Author(s) -
Dougherty Casey A.,
Furgal Joseph C.,
van Dongen Mallory A.,
Goodson Theodore,
Banaszak Holl Mark M.,
Mao Janet,
DiMaggio Stassi
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304854
Subject(s) - dendrimer , fluorescence spectroscopy , chemistry , high performance liquid chromatography , fluorescence , fluorescein , click chemistry , conjugated system , particle (ecology) , particle size , materials science , chromatography , polymer chemistry , polymer , organic chemistry , physics , oceanography , quantum mechanics , geology
Fluorescent dyes are commonly conjugated to nanomaterials for imaging applications using stochastic synthesis conditions that result in a Poisson distribution of dye/particle ratios and therefore a broad range of photophysical and biodistribution properties. We report the isolation and characterization of generation 5 poly(amidoamine) (G5 PAMAM) dendrimer samples containing 1, 2, 3, and 4 fluorescein (FC) or 6‐carboxytetramethylrhodamine succinimidyl ester (TAMRA) dyes per polymer particle. For the fluorescein case, this was achieved by stochastically functionalizing dendrimer with a cyclooctyne “click” ligand, separation into sample containing precisely defined “click” ligand/particle ratios using reverse‐phase high performance liquid chromatography (RP‐HPLC), followed by reaction with excess azide‐functionalized fluorescein dye. For the TAMRA samples, stochastically functionalized dendrimer was directly separated into precise dye/particle ratios using RP‐HPLC. These materials were characterized using 1 H and 19 F NMR spectroscopy, RP‐HPLC, UV/Vis and fluorescence spectroscopy, lifetime measurements, and MALDI.