Does thermotropic liquid crystalline self-assembly control biological activity in amphiphilic amino acids? - tyrosine ILCs as a case study

Publikationstyp
Journal Article
Publikationsdatum
2023-06-27
Sprache
English
Author
Grunwald, Marco André 
Hagenlocher, Selina Emilie
Turkanovic, Larissa
Bauch, Soeren Magnus
Wachsmann, Sebastian Benedikt
Altevogt, Luca Alexa
Ebert, Max 
Knöller, Julius Agamemnon 
Raab, Aileen Rebecca 
Schulz, Finn 
Kolmangadi, Mohamed A. 
Zens, Anna 
Huber, Patrick orcid-logo
Material- und Röntgenphysik M-2 
Schönhals, Andreas 
Bilitiewski, Ursula
Laschat, Sabine 
TORE-URI
https://hdl.handle.net/11420/42323
Enthalten in
Physical chemistry, chemical physics 
Volume
25
Start Page
17639
End Page
17656
Citation
Physical Chemistry Chemical Physics 25: 17639-17656 (2023)
Publisher DOI
10.1039/d3cp00485f
Scopus ID
2-s2.0-85164239960
Amphiphilic amino acids represent promising scaffolds for biologically active soft matter. In order to understand the bulk self-assembly of amphiphilic amino acids into thermotropic liquid crystalline phases and their biological properties a series of tyrosine ionic liquid crystals (ILCs) was synthesized, carrying a benzoate unit with 0-3 alkoxy chains at the tyrosine unit and a cationic guanidinium head group. Investigation of the mesomorphic properties by polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (WAXS, SAXS) revealed smectic A bilayers (SmAd) for ILCs with 4-alkoxy- and 3,4-dialkoxybenzoates, whereas ILCs with 3,4,5-trisalkoxybenzoates showed hexagonal columnar mesophases (Colh), while different counterions had only a minor influence. Dielectric measurements revealed a slightly higher dipole moment of non-mesomorphic tyrosine-benzoates as compared to their mesomorphic counterparts. The absence of lipophilic side chains on the benzoate unit was important for the biological activity. Thus, non-mesomorphic tyrosine benzoates and crown ether benzoates devoid of additional side chains at the benzoate unit displayed the highest cytotoxicities (against L929 mouse fibroblast cell line) and antimicrobial activity (against Escherichia coli ΔTolC and Staphylococcus aureus) and promising selectivity ratio in favour of antimicrobial activity.