Surprising Antibacterial Activity and Selectivity of Hydrophilic Polyphosphoniums Featuring Sugar and Hydroxy Substituents

Abstract

There is currently an urgent need for the development of new antibacterial agents to combat the spread of antibiotic-resistant bacteria. We explored the synthesis and antibacterial activities of novel, sugar-functionalized phosphonium polymers.While these compounds exhibited antibacterial activity,w eu nexpectedly found that the control polymer poly(tris(hydroxypropyl)vinylbenzylphosphonium chloride) showed very high activity against both Gram-negative Escherichiac oli and Gram-positive Staphylococcus aureus and very low haemolytic activity against red blood cells.T hese results challenge the conventional wisdom in the field that lipophilic alkyls ubstituents are required for high antibacterial activity and opens prospects for new classes of antibacterial polymers.

Synthetic Polypeptide Polymers as Simplified Analogues of Antimicrobial Peptides

“…140 Apart from chemical functions involving nitrogen atoms, antimicrobial cationic polymers carrying other cationic groups were also found effective against several bacteria: this mainly includes side chains bearing sulphur 132 or phosphorus atoms. 133,141 For instance, Endo et al…”

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

“…To this aim, the derivatization of glucose is mainly based on a selective reaction at the anomeric position, which can be made directly on the unprotected sugar 36 or after its peracetylation ( Scheme 19 ). The two main strategies involve: (a) The introduction of halogenated alkyl chain [ 32 , 54 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 ], and (b) the substitution of the hydroxyl group with bromine ( Scheme 19 ) [ 82 , 83 , 84 , 85 , 86 , 87 , 88 ].…”

“…A slightly different approach, albeit conceptually similar, entails the introduction of an allyl substituent. This procedure was used by Cuthberth et al in 2018 [ 80 ] for synthesizing polymeric ionic compounds ( Scheme 20 ). In this specific case, the synthesis started with preparing peracetylated α-allyl glucoside 91 through a Fisher glycosylation of glucose followed by a peracetylation of the sugar [ 89 , 90 ].…”

“…The obtained halo-sugar is used for further derivatizations through S N 2 reactions that directly introduce the final nitrogen-containing cationic group (imidazole or pyridine) through a quaternization reaction, or a functionalized side-chain, which will be further derivatized to obtain the final ionic derivative [ 80 , 82 , 83 , 84 , 85 , 87 , 88 ].…”

“…d -mannose, a C-2 epimer of d -glucose, is an important monosaccharide for human metabolism, and it is primarily found in mannan, cellulose, and hemicellulose [ 113 ]. d -mannose has not been widely used as a starting material for synthesizing ILs: From 2011 to now, only a handful of reports can be found in the literature [ 32 , 33 , 80 , 100 ].…”