Chirality Inversion on the Carbon Dot Surface via Covalent Surface Conjugation of Cyclic α-Amino Acid Capping Agents

Fatemeh Ostadhossein, Gururaja Vulugundam, Santosh K. Misra, Indrajit Srivastava, Dipanjan Pan

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

Manipulating the chiroptical properties at the nanoscale is of great importance in stereoselective reactions, enantioseparation, self-assembly, and biological phenomena. In recent years, carbon dots have garnered great attention because of their favorable properties such as tunable fluorescence, high biocompatibility, and facile, scalable synthetic procedures. Herein, we report for the first time the unusual behavior of cyclic amino acids on the surface of carbon dots prepared via microwave-based carbonization. Various amino acids were introduced on the surface of carbon dots via EDC/NHS conjugation at room temperature. Circular dichroism results revealed that although most of the surface conjugated amino acids can preserve their chirality on negatively charged, "bare" carbon dots, the "handedness" of cyclic α-amino acids can be flipped when covalently attached on carbon dots. Moreover, these chiroptical carbon dots were found to interact with the cellular membrane or its mimic in a highly selective manner due to their acquired asymmetric selectivity. A comprehensive inhibitor study was conducted to investigate the pathway of cellular trafficking of these carbon dots. Overall, it was concluded that the chirality of the amino acid on the surface of carbon dots could regulate many of the cellular processes.

Original languageEnglish (US)
Pages (from-to)3913-3922
Number of pages10
JournalBioconjugate Chemistry
Volume29
Issue number11
DOIs
StatePublished - Nov 21 2018

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

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