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Issue 4, 2015
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Tailoring the dissolution rate enhancement of aminoglutethimide by functionalization of MCM-41 silica: a hydrogen bonding propensity approach

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Abstract

The adsorption and in vitro release properties of the poorly soluble cytostatic agent DL-aminoglutethimide (AGT) on pristine MCM-41, 3-aminopropyl and a novel N-propyl-2-sulfanylacetamide functionalized MCM-41 material were studied. The mesostructured supports and hybrid samples were characterized by small- and wide-angle X-ray diffraction, FT-IR spectroscopy, thermogravimetric and calorimetric analyses, SEM-EDX and N2 adsorption–desorption isotherms. The drug uptake was found to be strongly influenced by its ionization state and solution pH. Drug release experiments show a spectacular increase in the dissolution rate of the therapeutic agent for all hybrid samples, indicating that aminoglutethimide encapsulation into the mesopores of MCM-41-type supports is a viable strategy for dissolution rate enhancement. Using a knowledge-based logit hydrogen bonding propensity model to assess the relative strengths of drug–support supramolecular interactions, we have proposed that a Si–OH⋯Cl AGT+ mechanism is responsible for the increased drug adsorption in acid media and release rate enhancement at physiological pH.

Graphical abstract: Tailoring the dissolution rate enhancement of aminoglutethimide by functionalization of MCM-41 silica: a hydrogen bonding propensity approach

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Publication details

The article was received on 25 Sep 2014, accepted on 02 Dec 2014 and first published on 02 Dec 2014


Article type: Paper
DOI: 10.1039/C4RA11224E
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RSC Adv., 2015,5, 2592-2601

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    Tailoring the dissolution rate enhancement of aminoglutethimide by functionalization of MCM-41 silica: a hydrogen bonding propensity approach

    R. Mitran, S. Nastase, C. Matei and D. Berger, RSC Adv., 2015, 5, 2592
    DOI: 10.1039/C4RA11224E

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