PEG-coumarin based biocompatible self-assembled fluorescent nanoaggregates synthesized via click reactions and studies of aggregation behavior

Gautam Behl, Manisha Sikka, Aruna Chhikara, Madhu Chopra

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

Hypothesis: Click chemistry has found wide application in drug discovery, bioconjugation reactions, polymer chemistry and synthesis of amphiphilic materials with pharmaceutical and biomedical applications. Triazole substitution via a click reaction alters photophysical properties of coumarin. Both coumarin and triazole moieties participate in π-π stacking interactions. Hence it should be possible to prepare fluorescent self-assembly systems by conjugation of coumarin to poly (ethylene glycol) (PEG) via click reactions exhibiting hydrophilic, hydrophobic and π-π stacking interactions. Moreover, the materials can be suitable platforms to assess fluorescence modulation effect of triazole substitution on coumarins. Experiments: PEG supported coumarin conjugates were synthesized and the fluorescence modulation effect of the formation of triazole on coumarin was assessed. Their aggregation properties were studied by surface tension measurements, dynamic light scattering (DLS), transmission electron microscopy (TEM), fluorescence and 1H NMR spectroscopy. Findings: The conjugates were found to form nanoaggregates in the size range of 100-120nm with a negative free energy of micellization (~-27kJmol-1) confirming aggregation and self-assembly. The Quantum yield of 4-methyl-7-propargylcoumarin (7P4MC) was enhanced after triazole formation with azide functionalized PEG (methoxy-PEG350 azide). The conjugates were found to exhibit π-π stacking interactions in addition to hydrophilic and hydrophobic interactions. They were found to be biocompatible with human pancreatic cancer cells.

Original languageEnglish
Pages (from-to)151-160
Number of pages10
JournalJournal of Colloid and Interface Science
Volume416
DOIs
Publication statusPublished - 15 Feb 2014
Externally publishedYes

Keywords

  • Biocompatible
  • CAC
  • Click reaction
  • Coumarin
  • Fluorescence
  • Nanoaggregates
  • PEG
  • Self-assembly
  • Stacking

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