Isolation and characterization of precise dye/dendrimer ratios

Casey A. Dougherty, Joseph C. Furgal, Mallory A. van Dongen, Theodore Goodson III, Mark M. Banaszak Holl, Janet Manono, Stassi Dimaggio

Research output: Contribution to journalArticleResearchpeer-review

Abstract

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 1H and 19F NMR spectroscopy, RP-HPLC, UV/Vis and fluorescence spectroscopy, lifetime measurements, and MALDI. High definition: Two approaches for the formation of generation 5 PAMAM samples containing precise dye/dendrimer ratios are presented. The first approach, using direct separation based on dye hydrophobicity, generated a set of TAMRA-containing dendrimers, and the second, using click chemistry, generated a set of fluorescein-containing dendrimer (see figure).

Original languageEnglish
Pages (from-to)4638-4645
Number of pages8
JournalChemistry - A European Journal
Volume20
Issue number16
DOIs
Publication statusPublished - 14 Apr 2014
Externally publishedYes

Keywords

  • click chemistry
  • dendrimers
  • dyes/pigments
  • fluorescent probes
  • nanostructures

Cite this

Dougherty, C. A., Furgal, J. C., van Dongen, M. A., Goodson III, T., Banaszak Holl, M. M., Manono, J., & Dimaggio, S. (2014). Isolation and characterization of precise dye/dendrimer ratios. Chemistry - A European Journal, 20(16), 4638-4645. https://doi.org/10.1002/chem.201304854
Dougherty, Casey A. ; Furgal, Joseph C. ; van Dongen, Mallory A. ; Goodson III, Theodore ; Banaszak Holl, Mark M. ; Manono, Janet ; Dimaggio, Stassi. / Isolation and characterization of precise dye/dendrimer ratios. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 16. pp. 4638-4645.
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Dougherty, CA, Furgal, JC, van Dongen, MA, Goodson III, T, Banaszak Holl, MM, Manono, J & Dimaggio, S 2014, 'Isolation and characterization of precise dye/dendrimer ratios' Chemistry - A European Journal, vol. 20, no. 16, pp. 4638-4645. https://doi.org/10.1002/chem.201304854

Isolation and characterization of precise dye/dendrimer ratios. / Dougherty, Casey A.; Furgal, Joseph C.; van Dongen, Mallory A.; Goodson III, Theodore; Banaszak Holl, Mark M.; Manono, Janet; Dimaggio, Stassi.

In: Chemistry - A European Journal, Vol. 20, No. 16, 14.04.2014, p. 4638-4645.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Isolation and characterization of precise dye/dendrimer ratios

AU - Dougherty, Casey A.

AU - Furgal, Joseph C.

AU - van Dongen, Mallory A.

AU - Goodson III, Theodore

AU - Banaszak Holl, Mark M.

AU - Manono, Janet

AU - Dimaggio, Stassi

PY - 2014/4/14

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KW - dyes/pigments

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Dougherty CA, Furgal JC, van Dongen MA, Goodson III T, Banaszak Holl MM, Manono J et al. Isolation and characterization of precise dye/dendrimer ratios. Chemistry - A European Journal. 2014 Apr 14;20(16):4638-4645. https://doi.org/10.1002/chem.201304854