Anion-switchable supramolecular gels for controlling pharmaceutical crystal growth

Nat Chem. 2010 Dec;2(12):1037-43. doi: 10.1038/nchem.859. Epub 2010 Oct 10.

Abstract

We describe the use of low-molecular-weight supramolecular gels as media for the growth of molecular crystals. Growth of a range of crystals of organic compounds, including pharmaceuticals, was achieved in bis(urea) gels. Low-molecular-weight supramolecular gelators allow access to an unlimited range of solvent systems, in contrast to conventional aqueous gels such as gelatin and agarose. A detailed study of carbamazepine crystal growth in four different bis(urea) gelators, including a metallogelator, is reported. The crystallization of a range of other drug substances, namely sparfloxacin, piroxicam, theophylline, caffeine, ibuprofen, acetaminophen (paracetamol), sulindac and indomethacin, was also achieved in supramolecular gel media without co-crystal formation. In many cases, crystals can be conveniently recovered from the gels by using supramolecular anion-triggered gel dissolution; however, crystals of substances that themselves bind to anions are dissolved by them. Overall, supramolecular gel-phase crystallization offers an extremely versatile new tool in pharmaceutical polymorph screening.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry*
  • Carbamazepine / chemistry
  • Crystallization
  • Gelatin / chemistry
  • Gels / chemistry*
  • Pharmaceutical Preparations / chemistry*
  • Sepharose / chemistry
  • Solvents / chemistry

Substances

  • Anions
  • Gels
  • Pharmaceutical Preparations
  • Solvents
  • Carbamazepine
  • Gelatin
  • Sepharose

Associated data

  • PubChem-Substance/99343611
  • PubChem-Substance/99343612
  • PubChem-Substance/99343613
  • PubChem-Substance/99343614
  • PubChem-Substance/99343615
  • PubChem-Substance/99343616
  • PubChem-Substance/99343617
  • PubChem-Substance/99343618
  • PubChem-Substance/99343619