Synthesis of cyclodextrin derivatives with monosaccharides and their binding with ampicillin and selected lectins

Abstract

β-and γ-Cyclodextrins connected on their narrow side via 6 bond-linkers with monosaccharides (Man, GlcNAc) suitable for bacterial lectin recognition, along with reference mono-analogues were prepared. The resulting compounds: (a) posses a functional cavity forming inclusion complexes with a model guest molecule and with the antibiotic ampicillin; (b) inhibit by more than 30% the hydrolysis of ampicillin in the presence of the enzyme β-lactamase; (c) interact stronger with surface immobilized lectins than the reference mono-analogues. The present work suggests that combining the lectin recognition property of the compounds with their ability to encapsulate antibiotics could be used to target and kill bacteria.

Synthesis, Characterization of Some Copper (II) Complexes with Ampicillin Derivatives and Study their Biological Activity

“…The bands present in the ampicillin due to NH2 (3511 cm-1) OH (3447 cm -1 ) C-H aromatic (3039 cm -1 ) amide C = O (1774 cm-1). The NH2 and OH were disappeared in compounds (1, 2) and (3,4) respectively as shown in Table 2. U.V -Visible Spectra was measureed.…”

“…Ampicillin is known as (2S,5R,6R)-6-[[(2R)-2amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid with molecular formula C16H19N3O4S [1]. It has biological activity against bacteria [2][3][4][5][6] and microbial [7][8]. Ampicillin has primary amine, which can be used to prepare many chemical derivatives to improve its pharmacological properties such as Schiff base [9] or amide bond [10] and carboxylic group [11].…”

Mono-6-Substituted Cyclodextrins—Synthesis and Applications

“…Lampropoulou et al [ 128 ] also synthesized a negatively charged β-CD. The authors utilized 3-mercaptopropanoic acid in DMF with NaH as a base.…”

In Vitro Glycosylation of Membrane Proteins Using N-Glycosyltransferase

“…15 Simple saccharides have also been conjugated with bovine serum albumin using commercially available linkers. 16 Similarly, ribonuclease A was conjugated with a naturally derived mannopentose via reductive amination of the oligosaccharide followed by coupling using an azide heterobifunctional reagent. 17 As an alternative approach, Yuan and co-workers have developed a convergent chemical method to develop a stable acyl donor to enable glycopeptide−glycopeptide ligation.…”

“…This simple strategy has been used to make a majority of neoglycoproteins reported in the literature. − For example, glycoconjugates of bovine serum albumin were synthesized using the Amadori reaction with dextran . Simple saccharides have also been conjugated with bovine serum albumin using commercially available linkers . Similarly, ribonuclease A was conjugated with a naturally derived mannopentose via reductive amination of the oligosaccharide followed by coupling using an azide heterobifunctional reagent .…”