The Synthesis And Antibacterial Activity Of Novel Quaternary Phosphonium Salts And Novel Imidazolium Salts

Infectious diseases have a serious impact on human health and social production.For a long time,various antibacterial drugs have played an important role in the treatment of infectious diseases.However,the widespread and inappropriate use of antibiotics and disinfectants have induced new drug-resistant strains of microorganisms,leading to a dramatic increase in difficulties for antibacterial problems.The development of novel antibacterial agents has become increasingly important.In this study,different long-chain PEGs and p-toluenesulfonyl chloride were used as starting materials to synthesize p-toluene sulfonic acid esters containing PEG chains.Then they were carried out with triphenylphosphine and N-n-butylimidazole,respectively to get novel quaternary phosphonium salts containing PEG chains,N-n-butylimidazolium salts and N-n-tetradecylimidazolium salts.Their structures were characterized by ¹HNMR,³¹PNMR and MS.And these novel quaternary phosphonium salts containing PEG chains and N-n-tetradecylimidazole salts were evaluated for their antibacterial properties and in vitro cytotoxicity.The solubility of N-butylimidazolium salts to cellulose were also studied.The following parts were concluded in summary:（1）A new type of quaternary phosphonium salt and imidazolium salt with anion of p-toluene sulfonate is successfully synthesized.The synthesis step is simple and does not require costly column chromatography and is suitable for large-scale production.（2）Antibacterial activity test results showed that the antibacterial effect of DGME-TPPS was good,and as the length of the hydrophilic long-chain PEG was increased,the antibacterial effect was gradually reduced.The N-n-tetradecylimidazole salt containing PEG chain has a significant antibacterial effect against gram-negative bacteria（E.coil）and gram-positive bacteria（S.aureus）.Antibacterial mechanism studies have shown that such quaternary phosphonium salts and N-n-tetradecylimidazole salts work through sterilization.（3）In vitro cytotoxicity tests showed that mPEG₇₅₀-TPPS and N-n-butyl imidazolium salt had extremely low toxicity to 3T3 cells and good biocompatibility.DGME-TPPS has good anti-tumor activity against HepG2 cells.The N-n-tetradecylimidazole salt containing PEG chain has significant anti-tumor effect on human hepatoma cells HepG2,breast cancer cells MCF-7and cervical cancer cells Hela.Therefore,DGME-TPPS synthesized in this study and N-n-tetradecylimidazole salt containing PEG chain are expected to become a new class of antibacterial agents and anti-tumor drugs.mPEG₇₅₀-TPPS and N-n-butyl imidazolium salt with PEG chain have good biocompatibility and are a potential carriers for drug delivery.