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Title: Investigating the effect of supramolecular gel phase crystallization on gel nucleation

Abstract

Supramolecular gel phase crystallization offers a new strategy for drug polymorph screening and discovery. In this method, the crystallization outcome depends on the interaction between solute and gel fibre. While supramolecular gels have shown success in producing new polymorphs and crystals with novel morphologies, role of the gel and nature of gel–solute interaction remains largely unexplored. The present study aims to provide a comprehensive picture of the structural evolution of a supramolecular gel produced from a bis(urea) based gelator (G) in the presence of a polymorphic drug carbamazepine (CBZ). The structural aspects of the gel have been assessed by single crystal X-ray analysis, X-ray powder diffraction (XRPD) and solid state NMR spectroscopy. Small Angle Neutron Scattering (SANS) has been used to follow the changes in gel structure in the presence of CBZ. Visual evidence from morphological study and structural evolution observed at a macroscopic level from rheological measurements, shows good agreement with the SANS results. The concentration of the gelator and the relative proportion of G to CBZ were found to be crucial factors in determining the competitive nucleation events involving gelation and crystallization. At a critical G to CBZ ratio the effect of CBZ on gel structure was maximummore » and fiber bundling in the gel was found to be critically affected. Here, this study offers important information about how the interplay of gelator assembly and gel–solute interactions can fine-tune the nucleation events in a supramolecular gel phase crystallization.« less

Authors:
ORCiD logo [1]; ORCiD logo [1];  [2];  [2]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [1]
  1. Univ. of Cincinnati, Cincinnati, OH (United States)
  2. Durham Univ., Durham (United Kingdom)
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1509551
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Soft Matter
Additional Journal Information:
Journal Volume: 14; Journal Issue: 46; Journal ID: ISSN 1744-683X
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Dawn, Arnab, Mirzamani, Marzieh S., Jones, Christopher D., Yufit, Dmitry S., Qian, Shuo, Steed, Jonathan W., and Kumari, Harshita. Investigating the effect of supramolecular gel phase crystallization on gel nucleation. United States: N. p., 2018. Web. doi:10.1039/c8sm01916a.
Dawn, Arnab, Mirzamani, Marzieh S., Jones, Christopher D., Yufit, Dmitry S., Qian, Shuo, Steed, Jonathan W., & Kumari, Harshita. Investigating the effect of supramolecular gel phase crystallization on gel nucleation. United States. doi:10.1039/c8sm01916a.
Dawn, Arnab, Mirzamani, Marzieh S., Jones, Christopher D., Yufit, Dmitry S., Qian, Shuo, Steed, Jonathan W., and Kumari, Harshita. Thu . "Investigating the effect of supramolecular gel phase crystallization on gel nucleation". United States. doi:10.1039/c8sm01916a. https://www.osti.gov/servlets/purl/1509551.
@article{osti_1509551,
title = {Investigating the effect of supramolecular gel phase crystallization on gel nucleation},
author = {Dawn, Arnab and Mirzamani, Marzieh S. and Jones, Christopher D. and Yufit, Dmitry S. and Qian, Shuo and Steed, Jonathan W. and Kumari, Harshita},
abstractNote = {Supramolecular gel phase crystallization offers a new strategy for drug polymorph screening and discovery. In this method, the crystallization outcome depends on the interaction between solute and gel fibre. While supramolecular gels have shown success in producing new polymorphs and crystals with novel morphologies, role of the gel and nature of gel–solute interaction remains largely unexplored. The present study aims to provide a comprehensive picture of the structural evolution of a supramolecular gel produced from a bis(urea) based gelator (G) in the presence of a polymorphic drug carbamazepine (CBZ). The structural aspects of the gel have been assessed by single crystal X-ray analysis, X-ray powder diffraction (XRPD) and solid state NMR spectroscopy. Small Angle Neutron Scattering (SANS) has been used to follow the changes in gel structure in the presence of CBZ. Visual evidence from morphological study and structural evolution observed at a macroscopic level from rheological measurements, shows good agreement with the SANS results. The concentration of the gelator and the relative proportion of G to CBZ were found to be crucial factors in determining the competitive nucleation events involving gelation and crystallization. At a critical G to CBZ ratio the effect of CBZ on gel structure was maximum and fiber bundling in the gel was found to be critically affected. Here, this study offers important information about how the interplay of gelator assembly and gel–solute interactions can fine-tune the nucleation events in a supramolecular gel phase crystallization.},
doi = {10.1039/c8sm01916a},
journal = {Soft Matter},
number = 46,
volume = 14,
place = {United States},
year = {2018},
month = {11}
}

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    Works referencing / citing this record:

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    • Dawn, Arnab; Mirzamani, Marzieh; Jones, Christopher D.
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    What Kind of “Soft Materials” Can We Design from Molecular Gels?
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    • Dawn, Arnab; Shiraki, Tomohiro; Haraguchi, Shuichi
    • Chemistry - An Asian Journal, Vol. 6, Issue 2
    • DOI: 10.1002/asia.201000217

    Two-Component Gel-Phase Materials—Highly Tunable Self-Assembling Systems
    journal, September 2005

    • Hirst, Andrew R.; Smith, David K.
    • Chemistry - A European Journal, Vol. 11, Issue 19
    • DOI: 10.1002/chem.200500241

    Supramolecular Amino Acid Based Hydrogels: Probing the Contribution of Additive Molecules using NMR Spectroscopy
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    • Ramalhete, Susana M.; Nartowski, Karol P.; Sarathchandra, Nichola
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    • DOI: 10.1002/jps.10093

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    • DOI: 10.1038/nchem.859

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    • Sangeetha, Neralagatta M.; Maitra, Uday
    • Chemical Society Reviews, Vol. 34, Issue 10
    • DOI: 10.1039/b417081b

    Cyclohexane bis-urea compounds for the gelation of water and aqueous solutions
    journal, January 2005

    • de Loos, Maaike; Friggeri, Arianna; van Esch, Jan
    • Organic & Biomolecular Chemistry, Vol. 3, Issue 9
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    Correlations between structure, material properties and bioproperties in self-assembled β-hairpin peptide hydrogels
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    • Faraday Discussions, Vol. 139
    • DOI: 10.1039/b717616c

    Gelation is crucially dependent on functional group orientation and may be tuned by anion binding
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    • Piepenbrock, Marc-Oliver M.; Lloyd, Gareth O.; Clarke, Nigel
    • Chemical Communications, Issue 23
    • DOI: 10.1039/b804259d

    A strategy for producing predicted polymorphs: catemeric carbamazepine form V
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    • Arlin, Jean-Baptiste; Price, Louise S.; Price, Sarah L.
    • Chemical Communications, Vol. 47, Issue 25
    • DOI: 10.1039/c1cc11634g

    Supramolecular gels formed from multi-component low molecular weight species
    journal, January 2012

    • Buerkle, Lauren E.; Rowan, Stuart J.
    • Chemical Society Reviews, Vol. 41, Issue 18
    • DOI: 10.1039/c2cs35106d

    Characterization of supramolecular gels
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    • The Journal of Chemical Physics, Vol. 97, Issue 9
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