Combined A3 coupling and click chemistry approach for the synthesis of dendrimer-based biological tools

Anjali Sharma, Diana Mejía, Aurélie Regnaud, Nick Uhlig, Chao Jun Li, Dusica Maysinger, Ashok Kakkar

Research output: Contribution to journalArticle

Abstract

We report a versatile approach in which two highly efficient chemical reactions, multicomponent A3coupling and alkyne-azide click chemistry, are combined to construct dendrimer-based tools for applications in biology. Using a convergent approach, dendrons with desired architecture and an alkyne at the focal point are first assembled and then stitched together via multicomponent A3 coupling reaction. The desired functional groups, including a stealth agent, imaging dye, and drug molecules, could be easily covalently linked to the surfaces of these hyperbranched macromolecules using alkyne-azide click chemistry. These A3-click dendrimers are noncytotoxic at concentrations as high as 1 μM and in fact reduce the toxicity of the drug. The dye-coated dendrimers specifically target and localize in lipid droplets. This unison methodology represents an attractive chemical strategy in exploiting the untapped potential of A3 coupling and facilitating the development of nanodevices for imaging and drug delivery. (Figure Presented).

Original languageEnglish (US)
Pages (from-to)1079-1083
Number of pages5
JournalACS Macro Letters
Volume3
Issue number10
DOIs
StatePublished - Oct 21 2014
Externally publishedYes

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Dendrimers
Alkynes
Azides
Dyes
Imaging techniques
Coloring Agents
Macromolecules
Drug delivery
Lipids
Functional groups
Toxicity
Chemical reactions
Pharmaceutical Preparations
Molecules

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Combined A3 coupling and click chemistry approach for the synthesis of dendrimer-based biological tools. / Sharma, Anjali; Mejía, Diana; Regnaud, Aurélie; Uhlig, Nick; Li, Chao Jun; Maysinger, Dusica; Kakkar, Ashok.

In: ACS Macro Letters, Vol. 3, No. 10, 21.10.2014, p. 1079-1083.

Research output: Contribution to journalArticle

Sharma, A, Mejía, D, Regnaud, A, Uhlig, N, Li, CJ, Maysinger, D & Kakkar, A 2014, 'Combined A3 coupling and click chemistry approach for the synthesis of dendrimer-based biological tools', ACS Macro Letters, vol. 3, no. 10, pp. 1079-1083. https://doi.org/10.1021/mz5006298
Sharma, Anjali ; Mejía, Diana ; Regnaud, Aurélie ; Uhlig, Nick ; Li, Chao Jun ; Maysinger, Dusica ; Kakkar, Ashok. / Combined A3 coupling and click chemistry approach for the synthesis of dendrimer-based biological tools. In: ACS Macro Letters. 2014 ; Vol. 3, No. 10. pp. 1079-1083.
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