Selective Anticancer Materials by Self-Assembly of Synthetic Amphiphiles Based on N-Acetylneuraminic Acid

Jiwon Hwang, Ye Rim Kim, Jung Yeon Park, Woo Hyun Nam, Jehan Kim, Jinhan Cho, Yongju Kim

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

N-Acetylneuraminic acid (Neu5Ac), one of the abundant types of sialic acid, is an emerging anticancer agent owing to its ability to target selectins in the plasma membrane of cancer cells. Considering the functionality of Neu5Ac, obtaining novel Neu5Ac-conjugated materials with a selective and an enhanced antitumor activity has remained a challenge. Herein, we report the supramolecular materials of three novel amphiphiles composed of Neu5Ac as a hydrophilic segment and pyrene or adamantane as a hydrophobic segment. The synthetic amphiphiles 1, 2, and 3 self-assembled into ribbons, vesicles, and irregular aggregates in an aqueous solution, respectively. Among the materials, vesicles of amphiphile 2 showed the most substantial selectivity toward cancer cells, followed by cell death due to the production of reactive oxygen species by the pyrene group. The dual advantage of Neu5Ac-selectivity and the pyrene-cytotoxicity of vesicles of amphiphile 2 can provide a strategy for effective anticancer materials.

Original languageEnglish
Pages (from-to)16100-16107
Number of pages8
JournalACS Applied Materials and Interfaces
Volume14
Issue number14
DOIs
Publication statusPublished - 2022 Apr 13

Bibliographical note

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

Keywords

  • N-acetylneuraminic acid
  • Neu5Ac
  • active targeting cancer therapy
  • anticancer materials
  • reactive oxygen species
  • sialic acid
  • supramolecular materials

ASJC Scopus subject areas

  • General Materials Science

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