Structural characterization of fondaparinux interaction with per-6-amino-beta-cyclodextrin: An NMR and MS study
نویسندگان
چکیده
The highly anionic synthetic pentasaccharide fondaparinux (FDPX) – representing the antithrombin binding sequence of heparin is in clinical use as a potent anticoagulant. Contrary to unfractionated heparin, FDPX lacks antidote completely reversing its anticoagulant activity, therefore it great importance identify new structures exhibiting strong intermolecular interactions towards FDPX. polycationic heptakis(6-amino-6-deoxy)-beta-cyclodextrin (NH2-β-CD) can serve an excellent model compound mimic these between oppositely charged oligosaccharides. Herein, extensive NMR spectroscopic and nano-electrospray ionization mass spectrometric (nESI-MS) studies were conducted understand molecular-level - NH2-β-CD systems. experiments performed at pD 7.4 2.0. Job’s method continuous variation 1H titration suggested formation FDPX∙NH2-β-CD complex 7.4, while presence multiple complexes was assumed Stability constants determined by separate titrations, yielding log β11=3.65 ± 0.02 β11 ≥ 4.9 value high-affinity system 2D NOESY indicated spatial proximities anomeric resonance α-l-iduronic acid residue cyclodextrin’s methylene unit proximity cationic amino function. Acidic degradation investigated MS for first time detail confirming that desulfation occurs involving one two sulfate moieties. inhibited cyclodextrin case equimolar ratio This report on stabilizing effect complexation degradation.
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ژورنال
عنوان ژورنال: Journal of Pharmaceutical and Biomedical Analysis
سال: 2021
ISSN: ['0731-7085', '1873-264X']
DOI: https://doi.org/10.1016/j.jpba.2021.113947