Chiral Transport in Nanochannel Based Artificial Drug Transporters

Small. 2023 Feb;19(6):e2205274. doi: 10.1002/smll.202205274. Epub 2022 Dec 4.

Abstract

The precise regulation of chiral drug transmembrane transport can be achieved through drug transporters in living organisms. However, implementing this process in vitro is still a formidable challenge due to the complexity of the biological systems that control drug enantiomeric transport. Herein, a facile and feasible strategy is employed to construct chiral L-tyrosine-modified nanochannels (L-Tyr nanochannels) based on polyethylene terephthalate film, which could enhance the chiral recognition of propranolol isomers (R-/S-PPL) for transmembrane transport. Moreover, conventional fluorescence spectroscopy, patch-clamp technology, laser scanning confocal microscopy, and picoammeter technology are employed to evaluate the performance of nanochannels. The results show that the L-Tyr nanochannel have better chiral selectivity for R-/S-PPL compared with the L-tryptophan (L-Trp) channel, and the chiral selectivity coefficient is improved by about 4.21-fold. Finally, a detailed theoretical analysis of the chirality selectivity mechanism is carried out. The findings would not only enrich the basic theory research related to chiral drug transmembrane transport, but also provide a new idea for constructing artificial channels to separate chiral drugs.

Keywords: biomimetic nanochannels; chirality; drug transport; gate effect; propranolol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Transport
  • Stereoisomerism
  • Tryptophan*

Substances

  • Tryptophan