The effect of alkyl chain length of (R)-3-Hydroxybutyric alkyl ester on antibacterial activity and its antibacterial mechanism

Abstract

This work describes the relationship between the antibacterial activity and the ester chain length (C1-C8) of ( R)-3-Hydroxybutyric (( R)-3-HB) alkyl esters that synthesized from ( R)-3-HB acid (( R)-3-HBA) by esterification reaction. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) decrease as the length of the ( R)-3-HB alkyl ester chain increases from 1 to 6, but ( R)-3-HB-C7 and ( R)-3-HB-C8 have their own rules for different microorganisms. Among them, the ( R)-3HB-C6 has the relatively best antibacterial and antifungal properties, which MIC were 1.95 mg mL−1 against E. coli and S. aureus; 0.98 mg mL−1 against C. albicans and B. subtilis; 0.49 mg mL−1 against A. niger. Finally, the antimicrobial mechanisms of the ( R)-3HB-C6 are revealed, and these include disruption of biofilm and the bacterial wall/membrane, leakage of the intracellular content, and change in the transmembrane potential. These results imply the potential application of ( R)-3-HB alkyl ester as new antimicrobial agents; future research can use this as an antibacterial element to synthesize new polymer materials or agents with high-efficiency antibacterial activity.

Progress of polymer-based strategies in fungal disease management: Designed for different roles

“…Similar results were observed with nylon-3 copolymers which decreased the MIC of azoles and AmB against some selected fungi, highlighting the potential of combination therapy (Rank et al, 2017). A study of aliphatic polyesters found that hydrophobic interaction induced the damage of fungal cell walls and membranes (Cheng et al, 2022). Mohamed et al (2015) highlighted the antimicrobial activity of cations by demonstrating that a higher degree of quaternization and glutaraldehyde cross-linking of the hydrogel resulted in a strengthened positive charge and more antibacterial activity.…”

“…Similar results were observed with nylon-3 copolymers which decreased the MIC of azoles and AmB against some selected fungi, highlighting the potential of combination therapy ( Rank et al., 2017 ). A study of aliphatic polyesters found that hydrophobic interaction induced the damage of fungal cell walls and membranes ( Cheng et al., 2022 ). Mohamed et al.…”

Polyhydroxyalkanoates (PHAs) from Endophytic Bacterial Strains as Potential Biocontrol Agents against Postharvest Diseases of Apples

“…Not all PHAs possess antimicrobial or antiviral activity. The possible mechanisms of biocontrol activity can be related to the destruction of the microbial wall/membrane and the leakage of intracellular contents and changes in transmembrane potential [38,39]. The antimicrobial properties of PHAs are believed to be related to their monomers-hydroxylsubstituted fatty acids, which act as anionic surfactants.…”

“…flavescens D5 strain as biocontrol agents, three treatments of apple fruits were proposed: combined inoculation of PHA and the phytopathogen P. expansum, preventive treatment of PHA 24 h before inoculation of the phytopathogen, and therapeutic treatment with PHA 24 h after Not all PHAs possess antimicrobial or antiviral activity. The possible mechanisms of biocontrol activity can be related to the destruction of the microbial wall/membrane and the leakage of intracellular contents and changes in transmembrane potential [38,39]. The antimicrobial properties of PHAs are believed to be related to their monomers-hydroxylsubstituted fatty acids, which act as anionic surfactants.…”