From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects.
Anna SykulaElżbieta Łodyga-ChruścińskaEugenio GarribbaDorota KręgielAliaksandr DzeikalaElżbieta KlewickaLidia Piekarska-RadzikPublished in: Molecules (Basel, Switzerland) (2022)
Microorganisms are able to give rise to biofilm formation on food matrixes and along food industry infrastructures or medical equipment. This growth may be reduced by the application of molecules preventing bacterial adhesion on these surfaces. A new Schiff base ligand, derivative of hesperetin, HABH (2-amino-N'-(2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-ylidene)benzohydrazide), and its copper complex, CuHABH [CuLH 2 (OAc)], were designed, synthesized and analyzed in terms of their structure and physicochemical properties, and tested as antibacterial agents. Their structures both in a solid state and in solution were established using several methods: FT-IR, 1 H NMR, 13 C NMR, UV-Vis, FAB MS, EPR, ESI-MS and potentiometry. Coordination binding of the copper(II) complex dominating at the physiological pH region in the solution was found to be the same as that detected in the solid state. Furthermore, the interaction between the HABH and CuHABH with calf-thymus DNA (CT-DNA) were investigated. These interactions were tracked by UV-Vis, CD (circular dichroism) and spectrofluorimetry. The results indicate a stronger interaction of the CuHABH with the CT-DNA than the HABH. It can be assumed that the nature of the interactions is of the intercalating type, but in the high concentration range, the complex can bind to the DNA externally to phosphate residues or to a minor/major groove. The prepared compounds possess antibacterial and antibiofilm activities against Gram-positive and Gram-negative bacteria. Their antagonistic activity depends on the factor-strain test system. The glass was selected as a model surface for the experiments on antibiofilm activity. The adhesion of bacterial cells to the glass surface in the presence of the compounds was traced by luminometry and the best antiadhesive action against both bacterial strains was detected for the CuHABH complex. This molecule may play a crucial role in disrupting exopolymers (DNA/proteins) in biofilm formation and can be used to prevent bacterial adhesion especially on glass equipment.
Keyphrases
- biofilm formation
- solid state
- staphylococcus aureus
- pseudomonas aeruginosa
- circulating tumor
- escherichia coli
- candida albicans
- cell free
- single molecule
- ms ms
- computed tomography
- multiple sclerosis
- mass spectrometry
- nucleic acid
- high resolution
- magnetic resonance
- healthcare
- induced apoptosis
- image quality
- silver nanoparticles
- cell cycle arrest
- oxide nanoparticles
- circulating tumor cells
- multidrug resistant
- oxidative stress
- pi k akt
- contrast enhanced
- aqueous solution
- dna binding
- binding protein
- endoplasmic reticulum stress