Intermolecular interactions between cucurbit[7]uril and pilocarpine

Na'Il Saleh, Marieh B. Al-Handawi, Leena Al-Kaabi, Liaquat Ali, S. Salman Ashraf, Thies Thiemann, Bassam Al-Hindawi, Mohammed Meetani

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

The interactions between cucurbit[7]uril (CB7) macrocycles and pilocarpine (PIL) were investigated in aqueous solution by using 1H NMR and circular dichroism (CD) spectroscopic techniques. The characterizations of the freeze-drying solid complex were conducted by electrospray ionization mass spectroscopy (ESI-MS), Fourier transform-infrared spectroscopy (FT-IR), thermogravimetry, and differential scanning calorimetry (DSC) techniques. The DSC and thermogravimetry confirmed the production of a thermally stable solid complex. The NMR, CD and ESI-MS measurements confirmed asymmetric induction during the complexation reaction, in which the γ-lactone ring of PIL (not the imidazole nucleus) has been fully encapsulated within the cavity of CB7. The stability of the drug has significantly enhanced as evidenced by the high-performance liquid chromatographic (HPLC) method. The results are discussed in the context of utilizing non-conventional supramolecular host-guest approaches to enhance the chemical stability in aqueous media of hydrophilic PIL drugs as model compounds. The non-classical stereospecific interactions between CB7 and PIL drugs are also highlighted.

Original languageEnglish
Pages (from-to)53-62
Number of pages10
JournalInternational Journal of Pharmaceutics
Volume460
Issue number1-2
DOIs
Publication statusPublished - 2014

Keywords

  • Diasteroisomeric products
  • ESI-MS
  • HPLC
  • Pilocarpine
  • Polarimetry
  • Stability

ASJC Scopus subject areas

  • Pharmaceutical Science

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