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

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 synthe...

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Bibliographic Details
Published in:	Physical chemistry chemical physics : PCCP Vol. 25; no. 26; p. 17639
Main Authors:	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, Schönhals, Andreas, Bilitiewski, Ursula, Laschat, Sabine
Format:	Journal Article
Language:	English
Published:	England 05-07-2023
Subjects:	Amines Amino Acids Animals Anti-Infective Agents Benzoates - chemistry Ionic Liquids Liquid Crystals - chemistry Mice Scattering, Small Angle Tyrosine X-Ray Diffraction
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Summary:	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 (SmA ) for ILCs with 4-alkoxy- and 3,4-dialkoxybenzoates, whereas ILCs with 3,4,5-trisalkoxybenzoates showed hexagonal columnar mesophases (Col ), 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 ΔTolC and ) and promising selectivity ratio in favour of antimicrobial activity.
ISSN:	1463-9084
DOI:	10.1039/d3cp00485f