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High-temperature resistant water-soluble polymers derived from exotic amino acids.

ABSTRACT: High-performance water-soluble polymers have a wide range of applications from engineering materials to biomedical plastics. However, existing materials are either natural polymers that lack high thermostability or rigid synthetic polymers. Therefore, we design an amino acid-derived building block, 4,4'-diamino-α-truxillate dianion (4ATA^2-), that induces water solubility in high-performance polymers. Polyimides containing 4ATA^2- units are intrinsically water-soluble and are processed into films cast from an aqueous solution. The resulting polyimide films exhibit exceptional transparency and extremely high thermal stability. In addition, the films can be made insoluble in water by simple post-treatment using weak acid or multivalent metal ions such as calcium. The synthesized polyimide's derived from bio-based resources are useful for yielding waterborne polymeric high-performance applications.

SUBMITTER: Dwivedi S

PROVIDER: S-EPMC9057247 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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High-temperature resistant water-soluble polymers derived from exotic amino acids.

Dwivedi Sumant S Nag Aniruddha A Sakamoto Shigeki S Funahashi Yasuyoshi Y Harimoto Toyohiro T Takada Kenji K Kaneko Tatsuo T

RSC advances 20201015 62

High-performance water-soluble polymers have a wide range of applications from engineering materials to biomedical plastics. However, existing materials are either natural polymers that lack high thermostability or rigid synthetic polymers. Therefore, we design an amino acid-derived building block, 4,4'-diamino-α-truxillate dianion (4ATA<sup>2-</sup>), that induces water solubility in high-performance polymers. Polyimides containing 4ATA<sup>2-</sup> units are intrinsically water-soluble and are ...[more]

PMID: 35515151

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Project description:Amino acids have shown promising abilities to form complexes with poorly water-soluble drugs and improve their physicochemical properties for a better dissolution profile through molecular interactions. Salt formation via ionization between acidic drugs and basic amino acids is known as the major contributor to solubility enhancement. However, the mechanism of solubility enhancement due to non-ionic interactions, which is less pH-dependent, remains unclear. The aim of this study is to evaluate non-ionic interactions between a model acidic drug, indomethacin (IND), and basic amino acids, arginine, lysine and histidine, in water. At low concentrations of amino acids, IND-arginine and IND-lysine complexes have shown a linear relationship (AL-type phase solubility diagram) between IND solubility and amino acid concentration, producing ∼1 : 1 stoichiometry of drug-amino acid complexes as expected due to the strong electrostatic interactions. However, IND-histidine complexes have shown a nonlinear relationship with lower improvement in IND solubility due to the weaker electrostatic interactions when compared to arginine and lysine. Interestingly, the results have also shown that at high arginine concentrations, the linearity was lost between IND solubility and amino acid concentration with a negative diversion from linearity, following the type-AN phase solubility. This is indicative that the electrostatic interaction is being interrupted by non-electrostatic interactions, as seen with histidine. The IND-lysine complex, on the other hand, showed a complex curvature phase solubility diagram (type BS) as lysine self-assembles and polymerizes at higher concentrations. The freeze-dried drug-amino acid solids were further characterized using thermal analysis and infrared spectroscopy, with results showing the involvement of weak non-ionic interactions. This study shows that the solubility improvement of an insoluble drug in the presence of basic amino acids was due to both non-ionic and ionic interactions.

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High-temperature resistant water-soluble polymers derived from exotic amino acids.

Publications

High-temperature resistant water-soluble polymers derived from exotic amino acids.

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