TY - JOUR
T1 - Intermolecular interactions between cucurbit[7]uril and pilocarpine
AU - Saleh, Na'Il
AU - Al-Handawi, Marieh B.
AU - Al-Kaabi, Leena
AU - Ali, Liaquat
AU - Salman Ashraf, S.
AU - Thiemann, Thies
AU - Al-Hindawi, Bassam
AU - Meetani, Mohammed
N1 - Funding Information:
N.S. would like to acknowledge the United Arab Emirates University for their support under the grant numbers 31S074 , within the framework of National Research Foundation (NRF).
PY - 2014
Y1 - 2014
N2 - 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.
AB - 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.
KW - Diasteroisomeric products
KW - ESI-MS
KW - HPLC
KW - Pilocarpine
KW - Polarimetry
KW - Stability
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U2 - 10.1016/j.ijpharm.2013.11.010
DO - 10.1016/j.ijpharm.2013.11.010
M3 - Article
C2 - 24239578
AN - SCOPUS:84888248792
SN - 0378-5173
VL - 460
SP - 53
EP - 62
JO - International Journal of Pharmaceutics
JF - International Journal of Pharmaceutics
IS - 1-2
ER -