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Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study

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Published on: August 15, 2016

Structural and theoretical-experimental physicochemical study of trimethoprim/randomly methylated-β-cyclodextrin

Daniela Kubota¹, Osmir Fabiano Lopes Macedo, George Ricardo Santana Andrade

¹Núcleo de Pós-graduação em Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus Universitário Prof. José Aloísio de Campos, CEP 49100-000 São Cristovão, SE, Brazil.

Carbohydrate Research

|October 26, 2011

Summary

This study characterizes trimethoprim

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Area of Science:

Pharmaceutical Chemistry
Supramolecular Chemistry

Background:

Trimethoprim is an antibiotic.
Beta-cyclodextrins are used to improve drug solubility and delivery.

Purpose of the Study:

To structurally characterize the inclusion complex of trimethoprim with randomly methylated beta-cyclodextrin (RAMEB).
To investigate the inclusion mechanism and stoichiometry.

Main Methods:

Phase-solubility studies at pH 7.0.
Stoichiometric determination using the continuous variation method.
Spectroscopic analysis (FTIR, 1D and 2D 1H NMR).
Semiempirical molecular modeling.

Main Results:

A 1:1 stoichiometry was confirmed for the trimethoprim-RAMEB complex.
Spectroscopic data indicated inclusion of the trimethoprim's trimethoxyphenyl ring within the RAMEB cavity.
Interactions between trimethoprim and RAMEB's methyl groups were observed.
Molecular modeling supported the proposed inclusion structure.

Conclusions:

Trimethoprim forms a 1:1 inclusion complex with randomly methylated beta-cyclodextrin.
The trimethoprim molecule is primarily included via its trimethoxyphenyl ring.
This complexation enhances understanding of drug-cyclodextrin interactions for potential pharmaceutical applications.