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

doi:10.1016/j.ijpharm.2013.11.010

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

Chemistry

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

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 language	British English
Pages (from-to)	53-62
Number of pages	10
Journal	International Journal of Pharmaceutics
Volume	460
Issue number	1-2
DOIs	https://doi.org/10.1016/j.ijpharm.2013.11.010
State	Published - 2014

Keywords

Diasteroisomeric products
ESI-MS
HPLC
Pilocarpine
Polarimetry
Stability

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10.1016/j.ijpharm.2013.11.010

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@article{03a6c6482fc042a38f0790b4bde15952,

title = "Intermolecular interactions between cucurbit[7]uril and pilocarpine",

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.",

keywords = "Diasteroisomeric products, ESI-MS, HPLC, Pilocarpine, Polarimetry, Stability",

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

note = "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). ",

year = "2014",

doi = "10.1016/j.ijpharm.2013.11.010",

language = "British English",

volume = "460",

pages = "53--62",

journal = "International Journal of Pharmaceutics",

issn = "0378-5173",

publisher = "Elsevier B.V.",

number = "1-2",

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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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DO - 10.1016/j.ijpharm.2013.11.010

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VL - 460

SP - 53

EP - 62

JO - International Journal of Pharmaceutics

JF - International Journal of Pharmaceutics

IS - 1-2

ER -

Intermolecular interactions between cucurbit[7]uril and pilocarpine

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Keywords

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