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Pharmaceutical polymorph control in a drug-mimetic supramolecular gel

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.
1478-6524
78-84
Foster, Jonathan A.
c65a60d4-6770-497b-82ce-0656dceb97ec
Damodaran, Krishna K.
24603524-476f-45f4-a657-fb547b921c17
Maurin, Antoine
d5060c18-8aff-43aa-a5d4-9f102df62a56
Day, Graeme
e3be79ba-ad12-4461-b735-74d5c4355636
Thompson, Hugh P.G.
be3bf8ed-7503-4b64-9851-5116134859c3
Cameron, Gart J.
56e11a29-7b44-4e42-b3f6-5b180412f67f
Bernal, Jenifer Cuesta
cad93aba-aaa7-4d7f-8de5-b8bfba23bfea
Steed, Jonathan W.
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Foster, Jonathan A.
c65a60d4-6770-497b-82ce-0656dceb97ec
Damodaran, Krishna K.
24603524-476f-45f4-a657-fb547b921c17
Maurin, Antoine
d5060c18-8aff-43aa-a5d4-9f102df62a56
Day, Graeme
e3be79ba-ad12-4461-b735-74d5c4355636
Thompson, Hugh P.G.
be3bf8ed-7503-4b64-9851-5116134859c3
Cameron, Gart J.
56e11a29-7b44-4e42-b3f6-5b180412f67f
Bernal, Jenifer Cuesta
cad93aba-aaa7-4d7f-8de5-b8bfba23bfea
Steed, Jonathan W.
97a5b8f6-b374-454d-a0b4-0bcaf37aa962

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, 78-84. (doi:10.1039/C6SC04126D).

Record type: Article

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.

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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
ORCID for Graeme Day: ORCID iD orcid.org/0000-0001-8396-2771

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Date deposited: 11 Oct 2016 15:38
Last modified: 15 Sep 2021 01:59

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Contributors

Author: Jonathan A. Foster
Author: Krishna K. Damodaran
Author: Antoine Maurin
Author: Graeme Day ORCID iD
Author: Hugh P.G. Thompson
Author: Gart J. Cameron
Author: Jenifer Cuesta Bernal
Author: Jonathan W. Steed

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