Effect of the structure of chitosan quaternary ammonium salts with different spacer groups on antibacterial and antibiofilm activities.

In this study, three types of dodecyl chitosan quaternary ammonium salts, each with different spacer groups were synthesized. These chitosan derivatives are N',N'-dimethyl-N'-dodecyl-ammonium chloride-N-amino-acetyl chitosan (DMDAC), N'-dodecyl-N-isonicotinyl chitosan chloride (DINCC) and N',N'-dimethyl-N'-dodecyl-ammonium chloride-N-benzoyl chitosan (DMDBC). The synthesized products were characterized using Fourier transform infrared spectrometers, nuclear magnetic resonance, thermogravimetric analysis, and elemental analysis. The antibacterial and antibiofilm activities against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were investigated. The experimental results indicated that the introduction of hydrophobic groups of spacer groups could enhance the antibacterial and antibiofilm activities of the chitosan derivatives. The antibacterial rates of the chitosan derivatives were over 90 % for both E. coli and S. aureus at a concentration of 0.5 mg/mL. The chitosan derivatives removed >50 % of the mature biofilm of E. coli and over 90 % of the mature biofilm of S. aureus at a concentration of 2.5 mg/mL. Further, the synthesized chitosan derivatives were determined to be non-toxic to L929 cells. Among them, DMDBC exhibited the most promising overall performance and show potential for wide-ranging applications in food preservation, disinfectants, medical, and other fields.

Evaluating the antibacterial and antibiofilm activities of chitosan derivatives containing six-membered heterocyclics against E. coli and S. aureus.

Chitosan exhibits good biocompatibility and some antibacterial activity, making it a popular choice in biomedicine, personal care products, and food packaging. Despite its advantages, the limited antibacterial effectiveness of chitosan hinders its widespread use. Introducing a six-membered heterocyclic structure through chemical modification can significantly enhance its antimicrobial properties and broaden its potential applications. In order to explore the effect of six-membered heterocyclic structure on the antibacterial and antibiofilm activities of chitosan. In this study, seven chitosan derivatives containing six-membered heterocyclics were prepared. They were characterized using Fourier transform infrared (FT-IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and elemental analysis. Cell viability assay showed that they were non-toxic. The antibacterial and antibiofilm activities against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were evaluated. Our research findings demonstrate that increasing the hydrophobicity, alkalinity and charge density of the substitute groups improved the antibacterial and antibiofilm activities of chitosan. This study also offers valuable insights into the quantitative structure-activity relationships of chitosan derivatives in terms of antibacterial and antibiofilm activities.

Preparation of citric acid cross-linked chitosan quaternary phosphonium/polyvinyl alcohol composite film and its application in strawberry preservation.

Chitosan quaternary phosphine salts (NPCS) were synthesized with enhanced antimicrobial properties using a two-step method. Composite films (CNSP) were prepared by incorporating NPCS and polyvinyl alcohol (PVA) as the base material, citric acid as the crosslinker and functional additive, exhibiting antibacterial and UV-blocking properties. The composite film showed a maximum tensile strength of 20.4 MPa, an elongation at break of 677%, and a UV light barrier transmittance of 70%. Application of these composite membranes in preserving strawberries demonstrated effectiveness in maintaining freshness by preventing water loss, inhibiting microbial growth, and extending shelf life. In addition, the composite film demonstrated biosafety. These results indicate that CNSP composite films holds significant promise for safe and sustainable food packaging applications.

Synthesis of N-isonicotinic sulfonate chitosan and its antibiofilm activity against E. coli and S.aureus.

N-(sodium 2-hydroxypropylsulfonate) chitosan (HSCS), N-sulfonate chitosan (SCS) and N-isonicotinic sulfonate chitosan (ISCS) were prepared. The structures of the prepared chitosan derivatives were characterized by nuclear magnetic resonance (1H NMR) spectroscopy, Fourier transform infrared (FTIR) spectroscopy, ultraviolet-visible (UV-vis) spectroscopy and elemental analysis (EA). Antibacterial and antibiofilm activities of these chitosan derivatives were evaluated in vitro. The minimum inhibitory concentration (MIC) of HSCS and SCS against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were 0.625 mg/mL and 0.156 mg/mL, respectively. ISCS exhibited MIC values of 0.313 mg/mL and 0.078 mg/mL against E. coli and S. aureus, respectively. ISCS demonstrated superior antibacterial and antibiofilm properties compared to SCS and HSCS. These findings suggest that the incorporation of a pyridine structure into sulfonate chitosan enhances its antibacterial and antibiofilm activities, and the prepared ISCS has a promising application prospect for controlling the reproduction of microorganisms in the field of food packaging.

Preparation of biguanidine quaternary ammonium salts grafted chitosan with enhanced antibacterial and antibiofilm activities.

N-(4-N'-pyridine-benzylcarbonyl chloride) chitosan (CBPyC), N-p-biguanidine benzoyl chitosan (CSBG), and N-(p-biguanidine -1-pyridine-4-benzylcarbonyl chloride) chitosan (CSQPG) were synthesized. The structures of prepared chitosan derivatives were characterized using nuclear magnetic resonance spectroscopy (NMR) and ultraviolet-visible (UV-vis) spectroscopy, and the degree of substitution was determined through elemental analysis (EA) and evaluated on the basis of the integral values in 1H NMR. The antibacterial activities of chitosan derivatives against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were investigated in vitro using antibacterial rate, minimal inhibitory concentration and minimum bacterial concentration assays. The antibiofilm activity was also assessed using the crystal violet assay. CSQPC exhibited higher antibacterial and antibiofilm activities against E. coli and S. aureus compared to CBPyC and CSBG. The antibacterial rate of CSQPG against E. coli and S. aureus at a concentration of 0.5 mg/mL was 43.3% and 100%, respectively. The biofilm inhibition rate of CSQPG at 0.5 MIC against E. coli and S. aureus was 56.5% and 69.1%, respectively. At a concentration of 2.5 mg/mL, the biofilm removal rates of E. coli and S. aureus were 72.9% and 90.1%, respectively. The antibacterial and antibiofilm activities of CSQPG were better than CSBG and CBPyC, and the combination of guanidine and quaternary ammonium further improved the positive charge density of chitosan and enhanced its antibacterial activity.

Effect of the structure of chitosan quaternary phosphonium salt and chitosan quaternary ammonium salt on the antibacterial and antibiofilm activity.

N-(4-N', N', N'-trimethylphosphonium chloride) benzoyl chitosan (TMPCS), N-(4-N', N', N'-triphenylphosphonium chloride) benzoyl chitosan (TPPCS), and N-(4-N', N', N'-trimethylmethanaminium chloride) benzoyl chitosan (TMACS) were synthesized. The structures of the products were characterized by Fourier transform infrared spectroscopy, Nuclear magnetic resonance spectroscopy and ultraviolet-visible spectroscopy. Their antibacterial activities against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were investigated in vitro using the antibacterial rate, minimal inhibitory concentration (MIC) and minimum bactericidal concentration (MBC), the antibiofilm activity was investigated by crystal violet assay. The antibacterial assessment revealed that the chitosan quaternary phosphonium salts of similar structure had superior antibacterial activity than chitosan quaternary ammonium salt. The antibacterial rate of CS, TMPCS, TPPCS and TMACS against E. coli at 0.5 mg/mL was 10.4 %, 42.0 %, 58.5 % and 21.6 % respectively. At the same concentration, the antibacterial rate of TMPCS, TPPCS and TMACS against S.aureus was all up to 100 %. The biofilm inhibition rate of CS, TMPCS, TPPCS and TMACS at a half of MIC against E.coli was 28.4 %, 33.9 %, 56.6 % and 57.6 % respectively, and against S.aureus was 30.8 %, 53.8 %, 62.2 % and 58.5 % respectively. The biofilm removal rate of CS, TMPCS, TPPCS, TMACS against E.coli at 2.5 mg/mL was 20.6 %, 46.4 %, 48.9 % and 41.6 % respectively, and against S.aureus at 2.5 mg/mL was 41.5 %, 60.4 %, 69.9 % and 59.01 % respectively.

Synthesis, characterization, and antibacterial activity of N,O-quaternary ammonium chitosan.

N,N,N-Trimethyl O-(2-hydroxy-3-trimethylammonium propyl) chitosans (TMHTMAPC) with different degrees of O-substitution were synthesized by reacting O-methyl-free N,N,N-trimethyl chitosan (TMC) with 3-chloro-2-hydroxy-propyl trimethyl ammonium chloride (CHPTMAC). The products were characterized by (1)H NMR, FTIR and TGA, and investigated for antibacterial activity against Staphylococcus aureus and Escherichia coli under weakly acidic (pH 5.5) and weakly basic (pH 7.2) conditions. TMHTMAPC exhibited enhanced antibacterial activity compared with TMC, and the activity of TMHTMAPC increased with an increase in the degree of substitution. Divalent cations (Ba(2+) and Ca(2+)) strongly reduced the antibacterial activity of chitosan, O-carboxymethyl chitosan and N,N,N-trimethyl-O-carboxymethyl chitosan, but the repression on the antibacterial activity of TMC and TMHTMAPC was weaker. This indicates that the free amino group on chitosan backbone is the main functional group interacting with divalent cations. The existence of 100 mM Na(+) slightly reduced the antibacterial activity of both chitosan and its derivatives.

Relationship between N,N-dialkyl chitosan monolayer and corresponding vesicle.

The properties of N,N-dialkyl chitosan monolayers and corresponding vesicles have been studied by LB technique and drug-release experiment. With increasing molecular weight of chitosan backbone and/or length of alkyl chain, both the compressibility and collapse pressure of N,N-dialkyl chitosan monolayer are enhanced. The experiments on drug-release behavior of N,N-dialkyl chitosan vesicles show that the drug-release rate and the equilibrium drug-release ratio are decreased with increasing the compressibility of corresponding monolayer. It is worth noticing that there is a linear relationship between the compressibility of N,N-dialkyl chitosan monolayers and the equilibrium drug-release ratio of the vesicles.