Crystal Habit Modification of Metronidazole by Supramolecular Gels with Complementary Functionality

Sreejith Sudhakaran Jayabhavan, Jonathan W. Steed, Krishna K. Damodaran*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A series of bis(urea) compounds with complementary functional groups similar to the pharmaceutical drug metronidazole and a structural isomer isometronidazole have been synthesized. The gelation properties of these compounds were studied in various solvent/solvent mixtures. The mechanical strength of the isomeric gelators was compared using rheology, and the morphologies of the xerogels were analyzed by scanning electron microscopy. These gels were used as media for metronidazole crystallization resulting in a marked habit modification of the metronidazole crystals in the drug-mimicking gels. However, crystallization in the nonmimetic isomeric gel resulted in morphologies similar to the solution state. These results indicate that the drug-mimetic gels interact with the surface of the drug crystal giving rise to new morphologies.

Original languageEnglish
Pages (from-to)5383-5393
Number of pages11
JournalCrystal Growth and Design
Volume21
Issue number9
DOIs
Publication statusPublished - 1 Sept 2021

Bibliographical note

Funding Information:
We thank University of Iceland Research Fund and Science Institute for funding. S.S.J. thanks the University of Iceland for the doctoral research grant. We thankfully acknowledge Dr. Dmitry S. Yufit, Department of Chemistry, Durham University, U.K., for face indexing the crystals from different gelators. We also acknowledge Dr. Sigríđur Jónsdóttir and Dr. Friđrik Magnus, University of Iceland, for NMR/mass spectroscopy and powder X-ray diffraction analysis, respectively. We thank Rannís Iceland for infrastructure grants (150998-0031 and 191763-0031) for a single-crystal X-ray diffractometer and rheometer.

Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.

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