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Thermostabilization, Expression, Purification, and Crystallization of the Human Serotonin Transporter Bound to S-citalopram

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Multi-equilibrium system based on sertraline and β-cyclodextrin supramolecular complex in aqueous solution.

Joel J Passos¹, Frederico B De Sousa, Ivana S Lula

¹Laboratório de Encapsulamento Molecular e Biomateriais - Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, MG, Brazil.

International Journal of Pharmaceutics

|October 4, 2011

Summary

This study enhances sertraline (SRT) solubility using beta-cyclodextrin (βCD) complexation. The developed multi-equilibrium system significantly improves SRT solubility in various media, aiding oral drug delivery.

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Published on: August 15, 2016

Area of Science:

Pharmaceutical Sciences
Physical Chemistry
Materials Science

Background:

Sertraline (SRT), a common antidepressant, suffers from poor water solubility, hindering oral administration.
Beta-cyclodextrin (βCD) is a potential host molecule for improving drug solubility through inclusion complexation.

Purpose of the Study:

To evaluate a multi-equilibrium system involving βCD and SRT to enhance SRT solubility.
To characterize the inclusion compounds (ICs) formed between SRT and βCD.
To assess the in vitro solubility of SRT in the presence of βCD in aqueous and biomimetic media.

Main Methods:

Infrared spectroscopy (FTIR-HATR)
Isothermal titration calorimetry (ITC)
(1)H and 2D ROESY nuclear magnetic resonance (NMR) spectroscopy
Job's plot analysis
In vitro solubility studies
Theoretical calculations

Main Results:

SRT solubility was significantly increased in the presence of βCD at 1:1 and 1:2 molar ratios in all tested media.
FTIR-HATR indicated interactions between SRT and βCD.
ITC revealed a spontaneous, exothermic interaction with high affinity (K=14,726 M⁻¹) and a stoichiometry coefficient (n) of 1.63.
NMR and theoretical calculations confirmed the formation of inclusion compounds with multiple SRT binding sites within the βCD cavity, favoring the 1:2 complex.

Conclusions:

The βCD-SRT system effectively forms inclusion compounds, enhancing SRT solubility.
The multi-equilibrium nature of the system was confirmed, with a high affinity and favorable stoichiometry for complexation.
This approach offers a promising strategy for improving the oral bioavailability of sertraline.