Pharmaceutical polymorph control in a drug-mimetic supramolecular gel
Pharmaceutical polymorph control in a drug-mimetic supramolecular gel
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 shows that the templation of the red form by the targetted gel results from conformational matching of the gelator to the ROY substrate coupled with overgorwth of ROY onto the local periodic structure of the gel fibres.
78-84
Foster, Jonathan A.
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Damodaran, Krishna K.
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Maurin, Antoine
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Day, Graeme
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Thompson, Hugh P.G.
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Cameron, Gart J.
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Bernal, Jenifer Cuesta
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Steed, Jonathan W.
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Foster, Jonathan A.
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Damodaran, Krishna K.
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Maurin, Antoine
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Day, Graeme
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Thompson, Hugh P.G.
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Cameron, Gart J.
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Bernal, Jenifer Cuesta
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Steed, Jonathan W.
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Foster, Jonathan A., Damodaran, Krishna K., Maurin, Antoine, Day, Graeme, Thompson, Hugh P.G., Cameron, Gart J., Bernal, Jenifer Cuesta and Steed, Jonathan W.
(2016)
Pharmaceutical polymorph control in a drug-mimetic supramolecular gel.
Chemical Science, 8, .
(doi:10.1039/C6SC04126D).
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 shows that the templation of the red form by the targetted gel results from conformational matching of the gelator to the ROY substrate coupled with overgorwth of ROY onto the local periodic structure of the gel fibres.
Text
ROY RSC v4 referees.pdf
- Accepted Manuscript
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Accepted/In Press date: 7 October 2016
e-pub ahead of print date: 7 October 2016
Organisations:
Chemistry
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Local EPrints ID: 401303
URI: http://eprints.soton.ac.uk/id/eprint/401303
ISSN: 1478-6524
PURE UUID: 9ae82738-f02b-40ac-bc9a-084eddd91b33
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Date deposited: 11 Oct 2016 15:38
Last modified: 15 Mar 2024 03:44
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Contributors
Author:
Jonathan A. Foster
Author:
Krishna K. Damodaran
Author:
Antoine Maurin
Author:
Hugh P.G. Thompson
Author:
Gart J. Cameron
Author:
Jenifer Cuesta Bernal
Author:
Jonathan W. Steed
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