Intermolecular interactions between cucurbit[7]uril and pilocarpine

详细信息    查看全文

• 作者：Na鈥檌l Saleh ; Marieh B. Al-H ; awi ; Leena Al-Kaabi ; Liaquat Ali ; S. Salman Ashraf ; Thies Thiemann ; Bassam al-Hindawi ; Mohammed Meetani
• 关键词：Pilocarpine ; Stability ; Diasteroisomeric products ; Polarimetry ; HPLC ; ESI-MS
• 刊名：International Journal of Pharmaceutics
• 出版年：2 January, 2014
• 年：2014
• 卷：460
• 期：1-2
• 页码：53-62
• 全文大小：1298 K

文摘

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 纬-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.