Cucurbit[n]urils (n = 6–8) used as host molecules on supramolecular complexes formed with two different drugs: Emodin and indomethacin

Corda, Elisa; Hernández, Margarita; Sánchez-Cortés, Santiago; Sevilla, Pablo

doi:10.1016/j.colsurfa.2018.04.068

Cited by 11 publications

(5 citation statements)

References 53 publications

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“…These results indicated that the assemblies had characteristic absorption peaks of monomer components and the characteristic peak shift of the assemblies mostly occurred at 260 and 430 nm. It was speculated that the weak intermolecular interaction affected the n−π* and π–π* transitions of intramolecular electrons. , …”

Section: Resultsmentioning

confidence: 99%

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Natural Small-Molecule-Based Carrier-Free Self-Assembly Library Originated from Traditional Chinese Herbal Medicine

et al. 2022

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The carrier-free self-assembly of small molecules opens a new window for the development of nanomaterials. This study is dedicated to developing binary small-molecular self-assemblies derived from phytochemicals in traditional Chinese herbal medicine. Among them, Rhei Radix et Rhizoma and Coptidis Rhizoma are a common pair used in clinics for thousands of years. Here, we found that there were numerous spherical supramolecular nanoparticles (NPs) originated from Rhei Radix et Rhizoma and Coptidis Rhizoma decoction. Ultra-performance liquid chromatography/ tandem mass spectrometry (UPLC-MS/MS) was used to analyze the composition of the supramolecules, and a total of 119 phytochemicals were identified (23 anthraquinones, 31 alkaloids, 24 organic acids, 8 tannins, and other components). Isothermal titration calorimetry (ITC) showed that the interaction between Rhei Radix et Rhizoma and Coptidis Rhizoma was a spontaneous exothermic reaction, indicating that their phytochemicals had the property of self-assembly and interacted to form supramolecules in the decocting process. Furthermore, scanning electron microscopy (SEM), UV, IR, NMR, and ITC were used to verify that rhein and coptisine could self-assemble into nanofibers (Rhe-Cop NFs), while emodin and coptisine could self-assemble into nanoparticles (Emo-Cop NPs). The formation mechanism analysis of the self-assemblies revealed that they were induced by electrostatic attraction, hydrogen bonding, and π−π stacking, forming nanospheres of about 50 nm and nanofibers. The current study not only provides an idea of discovering carrier-free self-assemblies from traditional herbal medicine decoction but also supplies a reference for the design of binary self-assembly of small molecules in the future.

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Section: Resultsmentioning

confidence: 99%

“…It was speculated that the weak intermolecular interaction affected the n−π* and π–π* transitions of intramolecular electrons. 65 , 66 …”

Section: Resultsunclassified

Natural Small-Molecule-Based Carrier-Free Self-Assembly Library Originated from Traditional Chinese Herbal Medicine

et al. 2022

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“…Recently, CB[n] compounds are widely interest for drug delivery applications through host-guest formation because the CB [n] and their derivatives are non-toxic [20]. There are numerous reports focusing on drug delivery of the CB[n] [21][22][23][24][25][26]. Moreover, the different aspects of the CB[n] chemistry, such as catalysis [27], materials [28] and other potential application in supramolecular [29] have been also reported.…”

Section: Cucurbit[n]uril (Cb[n]mentioning

confidence: 99%

Theoretical investigation of the complexation, structural, and electronic properties of complexes between oseltamivir drug and cucurbit[n = 6–9]urils

et al. 2022

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The structural geometries of cucurbit [n]uril with n = 6-9 and their complexes with oseltamivir (OST) drug were obtained using the density functional theory computations. The stationary points of the most stable complexes were con rmed using vibrational frequency calculation. The complexation energies and electronic properties of CB[n]/OST complexes were investigated. The calculated results indicate that the intermolecular interactions in all the studied complexes occurring via a large number of dipole-dipole interactions, especially hydrogen bonds between oxygen atoms of CB[n] and hydrogen atoms of amine of oseltamivir drug. The negative complexation energies of CB[n]/OST complexes in both gas and water phases indicate that the host-guest complexes are exothermic process and the complexes are more stable than its bare CB [n]. In addition, the CB[7]/OST complex is more stable than that of all studied CB[n]/OST complexes. The frequency calculation results of the most stable complexes for each of CBs indicate that complexations are occurred via a spontaneous process. The NBO analysis of complexes shows the transferring of partial charge from CB[n]s to oseltamivir which correspond to their MEP contours. The HOMO and the LUMO orbitals are localized on the oseltamivir in CB[n]/OST complexes.After drug complexation, the electronic properties also display that, the energy gaps of CB[n] are signi cantly changed. All of the complexation properties point out here that CB[n]s can act as a host for appropriately oseltamivir guest, even in aqueous solution.

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“…[30][31][32][33] Nevertheless, their bioavailability is severely constrained by limited water solubility. It is known that the encapsulation of drug molecules using Q[n]s can improve the solubility of the guest, [34][35][36][37] we expected to use TMeQ [6] as a drug carrier for benzimidazole drug molecules to encapsulate the drug in order to augment its solubility, prolong the release time, enhance the efficacy, and achieve other desirable outcomes. Hence, it is of utmost signicance to investigate the interactions between Q[n]s and benzimidazole derivatives in the context of host-guest chemistry.…”

Section: Introductionmentioning

confidence: 99%

Study on the host–guest interactions between tetramethyl cucurbit[6]uril and 2-heterocyclic-substituted benzimidazoles

Ye,

Ma,

et al. 2024

RSC Adv.

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Cucurbit[n]urils (n = 6–8) used as host molecules on supramolecular complexes formed with two different drugs: Emodin and indomethacin

Cited by 11 publications

References 53 publications

Natural Small-Molecule-Based Carrier-Free Self-Assembly Library Originated from Traditional Chinese Herbal Medicine

Natural Small-Molecule-Based Carrier-Free Self-Assembly Library Originated from Traditional Chinese Herbal Medicine

Theoretical investigation of the complexation, structural, and electronic properties of complexes between oseltamivir drug and cucurbit[n = 6–9]urils

Study on the host–guest interactions between tetramethyl cucurbit[6]uril and 2-heterocyclic-substituted benzimidazoles

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Cucurbit[n]urils (n = 6–8) used as host molecules on supramolecular complexes formed with two different drugs: Emodin and indomethacin

Cited by 11 publications

References 53 publications

Natural Small-Molecule-Based Carrier-Free Self-Assembly Library Originated from Traditional Chinese Herbal Medicine

Natural Small-Molecule-Based Carrier-Free Self-Assembly Library Originated from Traditional Chinese Herbal Medicine

Theoretical investigation of the complexation, structural, and electronic properties of complexes between oseltamivir drug and cucurbit[n = 6–9]urils

Study on the host–guest interactions between tetramethyl cucurbit[6]uril and 2-heterocyclic-substituted benzimidazoles

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Cucurbit[n]urils (n = 6–8) used as host molecules on supramolecular complexes formed with two different drugs: Emodin and indomethacin