Zeta potential shifting nanoemulsions comprising single and gemini tyrosine-based surfactants

Andrea Fürst; Iram Shahzadi; Zeynep Burcu Akkuş-Dağdeviren; Anna Maria Schöpf; Ronald Gust; Andreas Bernkop-Schnürch

doi:10.1016/j.ejps.2023.106538

Zeta potential shifting nanoemulsions comprising single and gemini tyrosine-based surfactants

Eur J Pharm Sci. 2023 Oct 1:189:106538. doi: 10.1016/j.ejps.2023.106538. Epub 2023 Jul 24.

Authors

Andrea Fürst¹, Iram Shahzadi¹, Zeynep Burcu Akkuş-Dağdeviren¹, Anna Maria Schöpf², Ronald Gust², Andreas Bernkop-Schnürch³

Affiliations

¹ Center for Chemistry and Biomedicine, Department of Pharmaceutical Technology, Institute of Pharmacy, University of Innsbruck, Innrain 80/82, 6020, Innsbruck, Austria.
² Center for Chemistry and Biomedicine, Department of Pharmaceutical Chemistry, Institute of Pharmacy, University of Innsbruck, Innrain 80/82, 6020, Innsbruck, Austria.
³ Center for Chemistry and Biomedicine, Department of Pharmaceutical Technology, Institute of Pharmacy, University of Innsbruck, Innrain 80/82, 6020, Innsbruck, Austria. Electronic address: Andreas.Bernkop@uibk.ac.at.

PMID: 37495057
DOI: 10.1016/j.ejps.2023.106538

Abstract

Aim: This study aims to design and evaluate zeta potential shifting nanoemulsions comprising single and gemini type tyrosine-based surfactants for specific cleavage by tyrosine phosphatase.

Methods: Tyrosine-based surfactants, either single 4-(2-amino-3-(dodecylamino)-3-oxopropyl)phenyl dihydrogen phosphate (AF1) or gemini 4-(2-amino-3-((1-(dodecylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)amino)-3-oxopropyl)phenyl dihydrogen phosphate (AF2) type were synthesized via amide bond formation of tyrosine with dodecylamine followed by phosphorylation. These surfactants were incorporated into nanoemulsions. Nanoemulsions were monitored by incubation with isolated tyrosine phosphatase as well as secreted tyrosine phosphatase of Escherichia coli in terms of phosphate release and zeta potential change.

Results: Via isolated tyrosine phosphatase, and mediated by E. coli, phosphate groups of either single or gemini tyrosine-based surfactants could be cleaved by secreted tyrosine phosphatase. Nanoemulsions comprising a single tyrosine-based surfactant resulted in a charge shift from - 13.46 mV to - 4.41 mV employing isolated tyrosine phosphatase whilst nanoemulsions consisting of a gemini tyrosine-based surfactant showed a shift in zeta potential from - 15.92 mV to - 5.86 mV, respectively.

Conclusion: Nanoemulsions containing tyrosine-based surfactants represent promising zeta potential shifting nanocarrier systems targeting tyrosine phosphatase secreting bacteria.

Keywords: Enzyme; Lipid-based formulations; Nanoemulsions; Surfactants; Tyrosine phosphatase; Zeta potential shift.