Selective Anticancer Materials by Self-Assembly of Synthetic Amphiphiles Based on N-Acetylneuraminic Acid.
ACS Appl Mater Interfaces
; 14(14): 16100-16107, 2022 Apr 13.
Article
in En
| MEDLINE
| ID: mdl-35377593
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.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
N-Acetylneuraminic Acid
Language:
En
Journal:
ACS Appl Mater Interfaces
Journal subject:
BIOTECNOLOGIA
/
ENGENHARIA BIOMEDICA
Year:
2022
Document type:
Article