کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1410250 1501852 2009 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Characterization of cyclodextrin complexes of camostat mesylate by ESI mass spectrometry and NMR spectroscopy
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Characterization of cyclodextrin complexes of camostat mesylate by ESI mass spectrometry and NMR spectroscopy
چکیده انگلیسی

Supramolecular interactions between camostat mesylate, a serine protease inhibitor (1), with α-, β-, and γ-cyclodextrin (CD) in water were investigated using electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR) spectroscopy. ESI mass spectral analysis revealed that the 1:1 stoichiometry in all the complexes was formed. The binding constants (Kst) calculated by linear equations constructed from the ESI mass spectra of all the complexes indicated that γ-CD was most favorable complexing agent for the binding with 1 among the CDs. Pronounced changes in the 1H chemical shift upon complex formation with γ-CD were observed for the protons of the two aromatic rings of 1, with much larger chemical shift changes observed for the protons of the guanidinyl group-linked aromatic ring of 1. These results suggest that the cavity of γ-CD rather than that of α- or β-CD is large enough to accommodate the guanidine group of 1. Spatial geometry of 1 within the cavity of γ-CD was further identified with two-dimensional rotating frame nuclear Overhauser effect spectroscopy (2D ROESY) experiment. The observed ROESY cross peaks indicated intermolecular dipolar interactions between the two aromatic ring protons of 1 and the protons within the cavity of γ-CD. Based on the 1:1 stoichiometry of the complex, ROESY cross peaks suggest that two types of 1:1 complexes of γ-CD with 1 exist simultaneously in solution with different geometries.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 938, Issues 1–3, 16 December 2009, Pages 192–197
نویسندگان
, , , , , , , ,