Intermolecular interactions between cucurbit[7]uril and pilocarpine

Saleh, Na’il; Al‐Handawi, Marieh B.; Al-Kaabi, Leena; Ali, Liaquat; Ashraf, S. Salman; Thiemann, Thies; al‐Hindawi, Bassam; Meetani, Mohammed A.

doi:10.1016/j.ijpharm.2013.11.010

Cited by 21 publications

(17 citation statements)

References 42 publications

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“…Moreover, Q[ n ]s can enhance the physical stability [ 17 – 18 ] and increase the solubility [ 19 – 20 ] of drug molecules. After Q[ n ]s forms a host–guest complex with drug molecules, it can also improve the bioavailability and delivery capacity [ 21 ], can help to reduce the side effects and toxicity of the drug [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

Zeng¹,

Xie²,

Luo³

et al. 2020

Beilstein J. Org. Chem.

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In this study, we investigated the host–guest interactions between oroxin A (OA) and cucurbit[8]uril (Q[8]) using 1H NMR, MS, UV–vis and IR spectroscopy. The results showed that OA and Q[8] formed an inclusion compound (OA@Q[8]) with a molar ratio of 1:1 and a binding constant of 1.299 × 107 L·mol−1. In addition, the effect of Q[8] on the properties of OA was investigated through comparative experiments. The solubility of OA in water increased 22.47-fold when the concentration of Q[8] was 1 × 10−4 mol·L−1. Q[8] hardly affected the antioxidant capacity of OA, while the cumulative release of OA in gastric juice increased 2.3-fold after forming the inclusion compound with Q[8].

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Section: Introductionmentioning

confidence: 99%

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

Zeng¹,

Xie²,

Luo³

et al. 2020

Beilstein J. Org. Chem.

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“…Upon encapsulation by CB[7] with the binding constant K = (2.00 ± 0.09) × 10 3 M –1 , the half‐life of TMZ increased from 3 to 5 h, suggesting that complexation could slow the formation of MTIC by stabilizing TMZ, which favored the biouptake of the drug . Meanwhile, CB[7] stabilized pilocarpine (PIL, a natural imidazole alkaloid that is used in ocular medicine) and minimized the formation of its degradation products . HPLC analysis of PIL (2.5 mM) at pH 7.4 and room temperature in the absence and presence of CB[7] (5 mM) for a period of 8 weeks showed one peak and three peaks corresponding to the degradation products, in PIL–CB[7] and PIL alone, respectively .…”

Section: Effect On the Stability Of Complexed Drugsmentioning

confidence: 99%

“…31 HPLC analysis of PIL (2.5 mM) at pH 7.4 and room temperature in the absence and presence of CB [7] (5 mM) for a period of 8 weeks showed one peak and three peaks corresponding to the degradation products, in PIL-CB [7] and PIL alone, respectively. 31 CB [7] has also been found to stabilize antioxidant anthocyanins, such as 3 ,4 ,7-trimethoxyflavylium (B-TMF), as monitored by their color changes. At pH 3 or above, the flavylium cation form (F + ) of anthocyanins undergoes a series of transformations exhibiting a color change.…”

Section: Effect On the Stability Of Complexed Drugsmentioning

confidence: 99%

“…Meanwhile, CB[7] stabilized pilocarpine (PIL, a natural imidazole alkaloid that is used in ocular medicine) and minimized the formation of its degradation products . HPLC analysis of PIL (2.5 mM) at pH 7.4 and room temperature in the absence and presence of CB[7] (5 mM) for a period of 8 weeks showed one peak and three peaks corresponding to the degradation products, in PIL–CB[7] and PIL alone, respectively . CB[7] has also been found to stabilize antioxidant anthocyanins, such as 3′,4′,7‐trimethoxyflavylium (B‐TMF), as monitored by their color changes.…”

Section: Effect On the Stability Of Complexed Drugsmentioning

confidence: 99%

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Cucurbit[7]uril: an emerging candidate for pharmaceutical excipients

Kuok

Wyman

et al. 2017

Annals of the New York Academy of Sciences

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Cucurbit[7]uril (CB[7]), belonging to the cucurbit[n]uril family (CB[n], n = 5-8, 10, or 13-15), may form host-guest complexes with a variety of small molecules of biomedical interest. The physical and chemical properties of the complexed drugs are often improved as a result of this complexation, suggesting the potential application of CB[7] as a pharmaceutical excipient. This review has summarized the most recent research progress reported between 2011 and early 2017 regarding the biocompatibility of CB[7] and the influence of CB[7] on the stability, solubility, biouptake, and biological activities (including therapeutic efficacies and toxicities) of guest drug molecules. Through this systemic summary and analysis, we intend to stimulate further research efforts in this area and promote the use of CB[7] as an emerging pharmaceutical excipient to improve various properties of drug molecules (or active pharmaceutical ingredients).

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“…However, the important advantage of CDs is their ability to increase the solubility of poorly soluble drugs 5 . Our group 10 – 12 among others 13 – 16 have utilized CBs-induced p K a shifts to simulate natural receptors in their modulation of acid-base equilibrium 17 that is displayed by some potential bioactive molecules 10 , 13 , pharmaceutical drugs 11 , 12 , 14 , 15 and hormones 16 . Generally, supramolecular approach utilizing CBs and CDs has also been employed to control several biological phenomena such as enzymatic activities 18 , or chemical sensing in fish 19 , just to name a few.…”

Section: Introductionmentioning

confidence: 99%

Host-guest complexes of imazalil with cucurbit[8]uril and β-cyclodextrin and their effect on plant pathogenic fungi

Al-Dubaili

El‐Tarabily

Saleh

2018

Sci Rep

Self Cite

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We report the control of imazalil (IMZ) antifungal activity utilizing its non-covalent assembly with β-cyclodextrins (β-CD) and cucurbit[8]uril (CB8) macrocycles, as well as its stimuli-responsive disassembly with cadaverine. The NMR results are consistent with inclusion of a single IMZ molecule inside the cavities of either CB8 from its aromatic site or β-CD from its aliphatic end. Efficient complex formation with both host molecules and controlled released upon the addition of cadaverine is supported by NMR measurements. The stimuli-responsiveness of the same host-guest assemblies with cadaverine was validated against seven economically important plant pathogenic fungi which cause agriculturally important plant diseases across the globe. While loading the drug into macrocycles cavities suppressed its activity, subsequent adding of cadaverine efficiently restored it up. The results in the present paper enable researchers working in the area of mycology and plant pathology to inhibit or reduce the fungal growth on demand in order to control these economically important plant pathogenic fungi.

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Intermolecular interactions between cucurbit[7]uril and pilocarpine

Cited by 21 publications

References 42 publications

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

Cucurbit[7]uril: an emerging candidate for pharmaceutical excipients

Host-guest complexes of imazalil with cucurbit[8]uril and β-cyclodextrin and their effect on plant pathogenic fungi

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