Influence of Carbohydrate Residues on Antibacterial Activity of Vancomycin

Samaszko-Fiertek, Justyna; Szulc, Monika; Dmochowska, Barbara; Jaśkiewicz, Maciej; Kamysz, Wojciech; Ślusarz, Rafał; Madaj, Janusz

doi:10.2174/1570178616666190329225748

Cited by 3 publications

(7 citation statements)

References 31 publications

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“…As they suggest, the mechanism of action of such antibiotics could be different from the interaction with the terminal peptidoglycan fragment. This possibility is also confirmed by our research on the activity of aglycone against some reference strains, which, despite the presence of full structure of the cyclic heptapeptide, shows a significantly reduced effectiveness [12]. An additional mechanism of vancomycin's action has been described in the literature that involves the inhibition of ribonucleic acid synthesis by changing the permeability of the bacterial cell membrane [13].…”

Section: Introductionsupporting

confidence: 74%

NMR and MD Analysis of the Bonding Interaction of Vancomycin with Muramyl Pentapeptide

Ślusarz

Dmochowska

Samaszko-Fiertek

et al. 2022

IJMS

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The article describes an NMR spectroscopy study of interactions between vancomycin and a muramyl pentapeptide in two complexes: vancomycin and a native muramyl pentapeptide ended with D-alanine (MPP-D-Ala), and vancomycin and a modified muramyl pentapeptide ended with D-serine (MPP-D-Ser). The measurements were made in a 9:1 mixture of H2O and D2O. The obtained results confirmed the presence of hydrogen bonds previously described in the literature. At the same time, thanks to the pentapeptide model used, we were able to prove the presence of two more hydrogen bonds formed by the side chain amino group of L-lysine and oxygen atoms from the vancomycin carboxyl and amide groups. This type of interaction has not been described before. The existence of these hydrogen bonds was confirmed by the 1H NMR and molecular modeling. The formation of these bonds incurs additional through-space interactions, visible in the NOESY spectrum, between the protons of the L-lysine amino group and a vancomycin-facing hydrogen atom in the benzylic position. The presence of such interactions was also confirmed by molecular dynamics trajectory analysis.

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Section: Introductionsupporting

confidence: 74%

NMR and MD Analysis of the Bonding Interaction of Vancomycin with Muramyl Pentapeptide

Ślusarz

Dmochowska

Samaszko-Fiertek

et al. 2022

IJMS

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“…A study on the effect of carbohydrate residues on the antibacterial activity of a glycopeptidic antibiotic, viz., vancomycin has been carried out [84] . The presence of the sugar residues in the vancomycin derivative reduces the toxicity of the drug as compared to that of the vancomycin alone.…”

Section: Bio‐medical Applicationsmentioning

confidence: 99%

“…A study on the effect of carbohydrate residues on the antibacterial activity of a glycopeptidic antibiotic, viz., vancomycin has been carried out. [84] The presence of the sugar residues in the vancomycin derivative reduces the toxicity of the drug as compared to that of the vancomycin alone. Three types of vancomycin derivatives were synthesized, viz., vancomycin aglycon, modification of amino group of vancosamine and through sugar modification of the carboxyl group.…”

Section: Bio-medical Applicationsmentioning

confidence: 99%

Glyco‐Conjugate Design and Demonstration as Receptors for the Species of Biological, Ecological and Medical Importance: Support from Spectroscopy and Microscopy

Areti¹,

Nag

Rao

2021

ChemistrySelect

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This review article mainly provides a critical evaluation of the ion and molecular recognition aspects along with the biomedical applications of the conjugates of carbohydrates published in the literature during the past ten years. Thus, the article primarily deals with the derivatives of carbohydrates, wherein these were selective towards the species of biological and ecological relevance as well as their utility in the medical research. The recognition has been monitored by different spectral techniques, such as, fluorescence and absorption spectroscopy and in some cases even visual colour changes. These were further supported by 1H‐Nuclear Magnetic Resonance, electrospray ionization mass spectrometry (ESI MS) and microscopy data. Over the past one decade, there has been a surge in the development and applications of the conjugates of carbohydrates in the field of chemosensors. The accelerated interest is mainly due to their water solubility, biocompatibility and selective and sensitive interactions exhibited by these towards ions and molecules of the type of examples included in this article. Owing to the presence of protein‐carbohydrate interactions, the carbohydrate conjugates have been employed for different biomedical applications such as antimicrobial activity, cell imaging and specific targeting. Therefore, in this article, the sensing and medical applications of the carbohydrate conjugates have also been discussed. For clarity, the main features have been conveniently divided into four sections, sensing of guest species, viz., metal ion, anion or amino acid and bio‐medical applications. While discussing the biomedical applications, such as, the imaging, specific targeting and anti‐disease activity of these conjugates in solution as well when they are attached onto solid surfaces have been covered. Overall, this article deals with the analysis of more than three dozen glyco‐based receptors demonstrated for selective sening of ions and molecular species along with their applications towards disease diagnosis and or prevention. Enough efforts were put to place these on a common platform and to compare these accordingly.

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“…Rutin is composed of aglycone and sugar residue (Figure 1). The aglycone part is composed of quercetin linked with an O-glycosidic bond with rutinose, which is a disaccharide [9,10]. Rutinoside was first isolated from the common rue herb (Ruta graveolens L.), from which the name of the organic chemical compound is derived.…”

Section: Introductionmentioning

confidence: 99%

“…), among many others. Rutin is also commonly found in vegetables and fruits, mainly citrus fruits, and plant-based drinks [9]. Pure rutin takes the form of a yellow powder with a structure of fine crystals.…”

Section: Introductionmentioning

confidence: 99%

The Direction of the Antibacterial Effect of Rutin Hydrate and Amikacin

Miklasińska-Majdanik,

Kępa,

Wąsik

et al. 2023

Antibiotics

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The aim of the presented study was to examine the in vitro antimicrobial activity of rutin hydrate (RH) alone and in combination with amikacin against 12 reference strains of Gram-positive and Gram-negative bacteria. The antibacterial activity assay was evaluated in the concentration range of 2–2048 µg/mL. A serial microdilution method was used to determine the minimal inhibitory concentration (MIC) of the examined compound against reference strains. RH showed varying potential against the tested strains with MICs ranging from 128 to 1024 µg/mL. In order to examine the combinatory profile of RH and amikacin, the fractional inhibitory concentrations (FICs) were determined. The RH–amikacin combination was more active against Gram-negative bacteria where four synergism and two additive interactions were noted. For four out of six Gram-positive isolates, an indifferent effect of RH and amikacin was demonstrated, and for two strains, the tested combination had an additive effect. The results of this study showed that RH possesses antimicrobial potential in vitro towards the tested reference isolates. Moreover, it shows a promising combined effect with amikacin against Gram-negative bacteria.

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Influence of Carbohydrate Residues on Antibacterial Activity of Vancomycin

Cited by 3 publications

References 31 publications

NMR and MD Analysis of the Bonding Interaction of Vancomycin with Muramyl Pentapeptide

NMR and MD Analysis of the Bonding Interaction of Vancomycin with Muramyl Pentapeptide

Glyco‐Conjugate Design and Demonstration as Receptors for the Species of Biological, Ecological and Medical Importance: Support from Spectroscopy and Microscopy

The Direction of the Antibacterial Effect of Rutin Hydrate and Amikacin

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