Davletshin Rustam R, Kuryntseva Polina A, Gayneev Aidar M, Galieva Gulnaz Sh, Selivanovskaya Svetlana Yu, Davletshina Natal'ya V, Ivshin Kamil A, Islamov Daut R
A.M. Butlerov Institute of Chemistry, Kazan Federal University, Kazan, Russia.
Institute of Environmental Science and Biotechnology, Kazan Federal University, Kazan, Russia.
Curr Microbiol. 2025 Sep 8;82(10):496. doi: 10.1007/s00284-025-04480-y.
Phosphorylated structural analogs of Benzalkonium Chloride-diisopropoxyphosphorylmethane (dimethyldodecylammonium) bromide 1 (phosphorylated quaternary ammonium salt) and isopropoxyphosphorylmethane (dimethylalkylammonium) 2 (phosphorylated betaine) were synthesized. The structure of compound 1 was confirmed by single crystal X-ray diffraction study. The antibacterial, antifungal, and ecotoxicological profiles of the synthesized compounds were evaluated against aquatic organisms and flowering plants. Both compounds demonstrated comparable toxicity toward Paramecium caudatum (Protista) and Ceriodaphnia affinis (Cladocera), with EC values of compound 1-0.62 g/L (P. caudatum), 0.13 g/L (C. affinis) and compound 2-0.90 g/L (P. caudatum), 0.08 g/L (C. affinis). These values indicate significantly lower toxicity compared to Benzalkonium chloride (BC) control (EC = 110 μg/L for P. caudatum, 30 μg/L for C. affinis). Neither compound exhibited toxicity toward the green alga Chlorella vulgaris, whereas BC inhibited growth by 93%. However, both compounds 1 and 2 inhibited Raphanus sativus seed germination at 10.0 g/L, whereas BC exhibited only marginal phytotoxicity even at this high concentration (10 g/L). According to the disk diffusion method, compound 1 exhibited superior activity against all tested isolates Bacillus subtilis (Gram-positive), Pseudomonas fluorescens (Gram-negative) and Fusarium sp. (micromycete). Compound 2 showed activity only against B. subtilis and Fusarium sp. at 10.0 g/L. Compound 1 inhibited microbial growth significantly more effectively than BC across all three microorganisms, while compound 2 performance did not differ substantially from the control. Thus, the synthesized compound 1-demonstrates antimicrobial efficacy comparable to reference compounds (Miramistin, Benzalkonium Chloride) while exhibiting substantially lower ecotoxicity. This enhanced safety profile suggests its production and application would pose reduced environmental risks.
合成了苯扎氯铵 - 二异丙氧基磷酰甲烷（二甲基十二烷基铵）溴化物1（磷酸化季铵盐）和异丙氧基磷酰甲烷（二甲基烷基铵）2（磷酸化甜菜碱）的磷酸化结构类似物。通过单晶X射线衍射研究确定了化合物1的结构。评估了合成化合物对水生生物和开花植物的抗菌、抗真菌和生态毒理学特性。两种化合物对尾草履虫（原生生物）和近缘隆线溞（枝角类）均表现出相当的毒性，化合物1的EC值分别为0.62 g/L（尾草履虫）、0.13 g/L（近缘隆线溞），化合物2的EC值分别为0.90 g/L（尾草履虫）、0.08 g/L（近缘隆线溞）。这些值表明与苯扎氯铵（BC）对照相比毒性显著更低（尾草履虫的EC = 110 μg/L，近缘隆线溞的EC = 30 μg/L）。两种化合物对普通小球藻均未表现出毒性，而BC抑制其生长达93%。然而，化合物1和2在10.0 g/L时均抑制萝卜种子萌发，而BC即使在该高浓度（10 g/L）下仅表现出轻微的植物毒性。根据纸片扩散法，化合物1对所有测试菌株枯草芽孢杆菌（革兰氏阳性）、荧光假单胞菌（革兰氏阴性）和镰刀菌属（微真菌）均表现出优异的活性。化合物2仅在10.0 g/L时对枯草芽孢杆菌和镰刀菌属表现出活性。在所有三种微生物中，化合物1抑制微生物生长的效果明显优于BC，而化合物2的性能与对照相比无显著差异。因此，合成的化合物1显示出与参考化合物（聚维酮碘、苯扎氯铵）相当的抗菌功效，同时表现出显著更低的生态毒性。这种更高的安全性表明其生产和应用将降低环境风险。
