Investigation of the Binding of Roxatidine Acetate Hydrochloride with Cyclomaltoheptaose (B-Cyclodextrin) Using Ir and Nmr Spectroscopy
Carbohydrate Research 346 (2011) 1809–1813
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Investigation of the binding of roxatidine acetate hydrochloride with cyclomaltoheptaose (b-cyclodextrin) using IR and NMR spectroscopy
Arti Maheshwari a,⇑, Manisha Sharma a, Deepak Sharma b a b
Department of Chemistry, IET, Mangalayatan University, Beswan, Aligarh, India Department of Physics, IET, Mangalayatan University, Beswan, Aligarh, India
a r t i c l e
i n f o
a b s t r a c t
NMR chemical shift changes of the cyclomaltoheptaose (b-cyclodextrin, b-CD) cavity protons as well as roxatidine acetate hydrochloride aromatic ring protons revealed the formation of a RAH–b-CD inclusion complex. Detailed FTIR and NMR spectroscopic (1H NMR, COSY, NOESY, ROESY) studies have been done. The stoichiometry of the complex was determined to be 1:1, and the overall binding constant was also determined by Scott’s method. The NOESY spectrum confirmed the selective penetration of the aromatic ring of RAH into the b-CD cavity in comparison to that of the piperidine ring. The mode of penetration of the guest into the CD cavity and structure of the complex has been established. Ó 2011 Elsevier Ltd. All rights reserved.
Article history: Received 1 June 2011 Received in revised form 5 July 2011 Accepted 6 July 2011 Available online 18 July 2011 Keywords: Roxatidine acetate hydrochloride b-Cyclodextrin COSY NOESY ROESY
1. Introduction Cyclomaltooligosaccharides (cyclodextrins, CDs) are oligosaccharides composed of six to eight glucopyranose units bound by a-(1?4) linkages that are commonly named a-, b-, and c-CD, respectively. b-CD, in particular, has an internal cavity shaped like a truncated cone. By virtue of their shape and the hydrophobic nature of the cavity, CDS accommodate a variety of hydrophobic molecules, or parts of them, inside their cavity through noncovalent interactions to form inclusion
Contents lists available at ScienceDirect
Carbohydrate Research journal homepage: www.elsevier.com/locate/carres
Investigation of the binding of roxatidine acetate hydrochloride with cyclomaltoheptaose (b-cyclodextrin) using IR and NMR spectroscopy
Arti Maheshwari a,⇑, Manisha Sharma a, Deepak Sharma b a b
Department of Chemistry, IET, Mangalayatan University, Beswan, Aligarh, India Department of Physics, IET, Mangalayatan University, Beswan, Aligarh, India
a r t i c l e
i n f o
a b s t r a c t
NMR chemical shift changes of the cyclomaltoheptaose (b-cyclodextrin, b-CD) cavity protons as well as roxatidine acetate hydrochloride aromatic ring protons revealed the formation of a RAH–b-CD inclusion complex. Detailed FTIR and NMR spectroscopic (1H NMR, COSY, NOESY, ROESY) studies have been done. The stoichiometry of the complex was determined to be 1:1, and the overall binding constant was also determined by Scott’s method. The NOESY spectrum confirmed the selective penetration of the aromatic ring of RAH into the b-CD cavity in comparison to that of the piperidine ring. The mode of penetration of the guest into the CD cavity and structure of the complex has been established. Ó 2011 Elsevier Ltd. All rights reserved.
Article history: Received 1 June 2011 Received in revised form 5 July 2011 Accepted 6 July 2011 Available online 18 July 2011 Keywords: Roxatidine acetate hydrochloride b-Cyclodextrin COSY NOESY ROESY
1. Introduction Cyclomaltooligosaccharides (cyclodextrins, CDs) are oligosaccharides composed of six to eight glucopyranose units bound by a-(1?4) linkages that are commonly named a-, b-, and c-CD, respectively. b-CD, in particular, has an internal cavity shaped like a truncated cone. By virtue of their shape and the hydrophobic nature of the cavity, CDS accommodate a variety of hydrophobic molecules, or parts of them, inside their cavity through noncovalent interactions to form inclusion
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