Multifunctionalized Polyamides Prepared by Facile Ugi Reaction as Thermosensitive, Biocompatible and Antibacterial Biomaterials

Abstract

A series of multifunctionalized polyamides were facilely prepared by Ugi four‐component polymerization (Ugi‐4CP) in one‐pot method at room temperature using several diacids, aldehydes, 1,4 bis‐(3‐aminopropyl) piperazine and tert‐butyl isocyanide as monomers. The simple combination of monomers in Ugi‐4CP led to formation of nine thermosensitive polyamides in water, and their lower critical solution temperatures (LCSTs) were in range of 13.1‐70.1°C. The LCSTs for the subsequently‐quaternized polyamides (PBA‐800‐Br, PIA‐800‐Br and PCA‐800‐Br) were easily readjusted to the desired value in the inorganic salt solutions. PBA‐800‐Br and PIA‐800‐Br exhibited high antibacterial activity against Gram negative E. coli and Gram positive S. aureus. Confocal laser scanning microscope (CLSM) manifested the clear internalization into the cellular inside for the fluorescent molecule‐labelled polyamides. After 24–72 hours of incubation in polyamide solution, the viability rate of HeLa cells reached up to 80–141%, indicating the excellent biocompatibility. In conclusion, the thermosensitive, antibacterial and biocompatible polyamides have great potential to be used as biomaterials.

Imine-based multicomponent polymerization: Concepts, structural diversity and applications

“…6A, Deng 2020). [53] High molar masses were obtained (Mn up to 46 kg/mol) which is not surprising given the use of PEG macromonomers. The polymers exhibited thermoresponsive behaviour that could be tuned by changing the lengths of the PEG segment or by changing the hydrophobicity of the aldehyde which constituted the pendant group.…”

Progress in Isocyanide‐Based Step‐Growth Polymerization

“…Thus, these multifunctional polyamides are potential applicable in drug release and biological bactericidal materials. [ 36 ] In 2020, Chen et al. prepared redox‐responsive cationic polypeptoids for intracellular protein delivery via the U‐4CP of dicarboxylic acids containing SS bond, 1,6‐diisocyanidohexane, isobutyraldehyde, and different tertiary amines.…”

“…Thus, these multifunctional polyamides are potential applicable in drug release and biological bactericidal materials. [36] In 2020, Chen et al prepared redox-responsive cationic polypeptoids for intracellular protein delivery via the U-4CP of dicarboxylic acids containing S-S bond, 1,6-diisocyanidohexane, isobutyraldehyde, and different tertiary amines. [37] These cationic polypeptoids could co-assemble with anionic proteins to form nanocomplexes with smaller size characteristics, which could enter the cells by macropinocytosis and caveolae-mediated endocytosis.…”

Crystal structure, computational study, optical and vibrational properties of a new luminescent material based on bismuth(III): (C10H28N4)[Bi2Cl10]

“…Bismuth compounds are considered nontoxic and safe. Due to their properties, they have been widely used in medicine and their main applications are associated with ulcers, bacterial infections, and different gastrointestinal disorders [20]. The combination of bismuth complexes with the 1,4-bis (3aminopropyl)piperazine could confer to the hybrid, biological features, due to the properties, not only of the bismuth, but also of the amine [21].…”