Supramolecular encapsulation of benzimidazole-derived drugs by cucurbit[7]uril

Apurba L. Koner, Indrajit Ghosh, Nail Saleh, Werner M. Nau

Research output: Contribution to journalArticlepeer-review

118 Citations (Scopus)

Abstract

UV-vis and NMR spectroscopic techniques were employed to demonstrate the ability of the synthetic macrocyclic host cucurbit[7]uril (CB7) to solubilize and stabilize widely used fungicides and anthelmintic drugs of the benzimidazole family in water, namely, albendazole (ABZ), carbendazim (CBZ), thiabendazole (TBZ), fuberidazole (FBZ), and the parent benzimidazole (BZ). CB7 binds the protonated forms of these guests very strongly (e.g., K = 2.6 × 107 L/mol for ABZ) but their neutral forms significantly more weakly (e.g., K = 6.5 × 104 L/mol for ABZ), which reflects a complexation-induced increase of their pKa values by 2.6 units for ABZ, 2.5 units for CBZ, 4.0 units for TBZ, 3.8 units for FBZ, and 3.5 units for BZ. The absolute drug solubilities increased upon complexation from 0.003 to 0.300 mmol/L for ABZ, from 0.160 to 1.12 mmol/L for CBZ, from 0.110 to 1.11 mmol/L for TBZ, and from 0.25 to 0.75 mmol/L for FBZ (for BZ, the solubility enhancement was found to be insignificant). Complexation by CB7 further improves the photostability of the drugs and alters their photophysical properties.

Original languageEnglish
Pages (from-to)139-147
Number of pages9
JournalCanadian Journal of Chemistry
Volume89
Issue number2
DOIs
Publication statusPublished - 2011

Keywords

  • Benzimidazole drugs
  • Cucurbit[ n ]urils
  • Drug delivery
  • P K shifts
  • Photostability
  • Solubility enhancement
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Supramolecular encapsulation of benzimidazole-derived drugs by cucurbit[7]uril'. Together they form a unique fingerprint.

Cite this