Issue 1, 2017

Pharmaceutical polymorph control in a drug-mimetic supramolecular gel

Abstract

We report the synthesis of a bis(urea) gelator designed to specifically mimic the chemical structure of the highly polymorphic drug substance ROY. Crystallization of ROY from toluene gels of this gelator results in the formation of the metastable red form instead of the thermodynamic yellow polymorph. In contrast, all other gels and solution control experiments give the yellow form. Conformational and crystal structure prediction methods have been used to propose the structure of the gel and show that the templation of the red form by the targeted gel results from conformational matching of the gelator to the ROY substrate coupled with overgrowth of ROY onto the local periodic structure of the gel fibres.

Graphical abstract: Pharmaceutical polymorph control in a drug-mimetic supramolecular gel

Supplementary files

Article information

Article type
Edge Article
Submitted
14 Sep 2016
Accepted
07 Oct 2016
First published
07 Oct 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 78-84

Pharmaceutical polymorph control in a drug-mimetic supramolecular gel

J. A. Foster, K. K. Damodaran, A. Maurin, G. M. Day, H. P. G. Thompson, G. J. Cameron, J. C. Bernal and J. W. Steed, Chem. Sci., 2017, 8, 78 DOI: 10.1039/C6SC04126D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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