Intermolecular interactions between cucurbit[7]uril and pilocarpine

Reversible non-covalent host–guest formation of pilocarpine with CB7 excipient enhanced the chemical stability of the drug. 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...

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Bibliographic Details
Published in:International journal of pharmaceutics 2014-01, Vol.460 (1-2), p.53-62
Main Authors: Saleh, Na’il, Al-Handawi, Marieh B., Al-Kaabi, Leena, Ali, Liaquat, Salman Ashraf, S., Thiemann, Thies, al-Hindawi, Bassam, Meetani, Mohammed
Format: Article
Language:English
Subjects:
Bridged-Ring Compounds - chemistry
Chromatography, High Pressure Liquid
Circular Dichroism
Diasteroisomeric products
ESI-MS
HPLC
Imidazoles - chemistry
Magnetic Resonance Spectroscopy
Pilocarpine
Pilocarpine - chemistry
Polarimetry
Spectrometry, Mass, Electrospray Ionization
Spectroscopy, Fourier Transform Infrared
Stability
Thermogravimetry
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Summary:Reversible non-covalent host–guest formation of pilocarpine with CB7 excipient enhanced the chemical stability of the drug. 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.
ISSN:0378-5173
1873-3476
DOI:10.1016/j.ijpharm.2013.11.010