Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 41-819 Zabrze, Poland.
Faculty of Science and Technology, Jan Długosz University in Czestochowa, 13/15 Armii Krajowej Av., 42-200 Czestochowa, Poland.
Int J Mol Sci. 2024 Feb 22;25(5):2576. doi: 10.3390/ijms25052576.
The work presents the synthesis of a series of linear polyamidoamines by polycondensation of sebacoyl dichloride with endogenous polyamines: putrescine, spermidine, spermine, and norspermidine-a biogenic polyamine not found in the human body. During the synthesis carried out via interfacial reaction, hydrophilic, semi-crystalline polymers with an average viscosity molecular weight of approximately 20,000 g/mol and a melting point of approx. 130 °C were obtained. The structure and composition of the synthesized polymers were confirmed based on NMR and FTIR studies. The cytotoxicity tests performed on human fibroblasts and keratinocytes showed that the polymers obtained with spermine and norspermidine were strongly cytotoxic, but only in high concentrations. All the other examined polymers did not show cytotoxicity even at concentrations of 2000 µg/mL. Simultaneously, the antibacterial activity of the obtained polyamides was confirmed. These polymers are particularly active against , and virtually all the polymers obtained demonstrated a strong inhibitory effect on the growth of cells of this strain. Antimicrobial activity of the tested polymer was found against strains like , , and . The broadest spectrum of bactericidal action was demonstrated by polyamidoamines obtained from spermine, which contains two amino groups in the repeating unit of the chain. The obtained polymers can be used as a material for forming drug carriers and other biologically active compounds in the form of micro- and nanoparticles, especially as a component of bactericidal creams and ointments used in dermatology or cosmetology.
这项工作展示了通过癸二酰二氯与内源性多胺(腐胺、精胺、亚精胺和降亚精胺)的缩聚反应合成一系列线性聚酰胺胺。降亚精胺是一种在人体中不存在的生物多胺。在通过界面反应进行的合成过程中,得到了具有约 20,000 g/mol 的平均粘均分子量和约 130°C 的熔点的亲水性、半结晶聚合物。基于 NMR 和 FTIR 研究证实了所合成聚合物的结构和组成。对人成纤维细胞和角质形成细胞进行的细胞毒性测试表明,用精胺和降亚精胺获得的聚合物具有很强的细胞毒性,但仅在高浓度下。所有其他检查的聚合物即使在 2000 µg/mL 的浓度下也没有显示出细胞毒性。同时,还证实了所得到的聚酰胺的抗菌活性。这些聚合物对 特别有效,并且实际上所有获得的聚合物对该菌株的细胞生长都具有很强的抑制作用。测试聚合物对 、 和 等菌株具有抗菌活性。含有链重复单元中两个氨基的精胺得到的聚酰胺胺表现出最广泛的杀菌作用。所得聚合物可用作形成药物载体和其他形式的微纳米级生物活性化合物的材料,特别是作为用于皮肤病学或美容学的杀菌乳膏和软膏的组成部分。