Physicochemical and in vitro cytotoxicity studies of inclusion complex between gemcitabine and cucurbit[7]uril host

Buczkowski, Adam; Gorzkiewicz, Michał; Stępniak, Artur; Malinowska-Michalak, Małgorzata; Tokarz, Paweł; Urbaniak, Paweł; Йонов, Максим; Klajnert‐Maculewicz, Barbara; Pałecz, Bartłomiej

doi:10.1016/j.bioorg.2020.103843

Cited by 7 publications

(4 citation statements)

References 93 publications

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“…When the drug interacts with the carrier, a reduction of diffusion coefficients is generally observed related to the size modification or the strength of interaction. For example, supramolecular complex formation of a cytostatic drug, gemcitabine, with its cucurbuturil nanocontainer was proved by PFG-NMR by the reduction of gemcitabine diffusion coefficient when complexes as well as the possible impact of ethanol consumption [62,63]. Similarly, the covalent attachment of an antiinflammatory and anti-cancer drug, the histone deacetylase inhibitor valproic acid, to its polymeric nanocontainer was demonstrated with PFG-NMR [64].…”

Section: Interaction Drug-nanomedicinementioning

confidence: 99%

NMR diffusometry: A new perspective for nanomedicine exploration

Franconi

Lemaire

Gimel

et al. 2021

Journal of Controlled Release

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Nuclear Magnetic Resonance (NMR) based diffusion methods open new perspectives for nanomedicine characterization and their bioenvironment interaction understanding. This review summarizes the theoretical background of diffusion phenomena. Self-diffusion and mutual diffusion coefficient notions are featured. Principles, advantages, drawbacks, and key challenges of NMR diffusometry spectroscopic and imaging methods are presented. This review article also gives an overview of representative applicative works to the nanomedicine field that can contribute to elucidate important issues. Examples of in vitro characterizations such as identification of formulated species, process monitoring, drug release follow-up, 2 / 29 nanomedicine interactions with biological barriers are presented as well as possible transpositions for studying in vivo nanomedicine fate.

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Section: Interaction Drug-nanomedicinementioning

confidence: 99%

NMR diffusometry: A new perspective for nanomedicine exploration

Franconi

Lemaire

Gimel

et al. 2021

Journal of Controlled Release

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“…Quantitative analysis successfully determined the concentrations of individual components in the mixtures of tobaccospecific N-nitrosamines NNN and NNK, even in the presence of an order-of-a-magnitude higher concentration of nicotine interferent. 63 Porphyrins exhibit excellent phytophysical properties and find extensive application in imaging and diagnosis. But in aqueous media, these molecules aggregate because of their hydrophobicity and π−π stacking interactions, which limits their cellular uptake.…”

Section: ■ Use Of Cb[n] In Diagnosismentioning

confidence: 99%

“…The assays required only simple laboratory instrumentation, yet displayed excellent recognition profiles for a large number of guests (2 probes recognized 13 guests) in a qualitative as well as quantitative manner. Quantitative analysis successfully determined the concentrations of individual components in the mixtures of tobacco-specific N-nitrosamines NNN and NNK, even in the presence of an order-of-a-magnitude higher concentration of nicotine interferent . Porphyrins exhibit excellent phytophysical properties and find extensive application in imaging and diagnosis.…”

Section: Use Of Cb[n] In Diagnosismentioning

confidence: 99%

Supramolecular Chemotherapy with Cucurbit[n]urils as Encapsulating Hosts

Shukla

Sagar

Sood

et al. 2023

ACS Appl. Bio Mater.

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The cucurbit[n]urils (CB[n]) belong to the field of relatively young supramolecules which act as containers for a large variety of guests and are being explored extensively for their numerous biomedical applications. This includes drug formulation and delivery, controlled drug release, photodynamic therapy, sensing for bioanalytical purposes, etc. These supramolecular host–guest systems have distinctive recognition properties and have successfully been shown to enhance the in vitro and in vivo utility of various chemotherapeutic agents. The CB[n]s are tailored to optimize their application in payload delivery and diagnostics and in lowering the toxicity of existing drugs. This review has listed the recent studies on working mechanisms and host–guest complexation of the biologically vital molecules with CB[n] and highlighted their implementation in anticancer therapeutics. Various modifications in CB-drug inclusion compounds like CB supramolecular nanoarchitectures along with application in photodynamic therapy, which has shown potential as targeted drug delivery vehicles in cancer chemotherapy, have also been discussed.

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“…In the past cucurbiturils have been used as drug delivery vehicles for cisplatin, pro avine, and doxorubicin [16][17][18][19]. Adam Buczkowski et al have carried out an in vitro cell viability study on tumor cell lines MOLT4, THP-1, and U937 and found that free gemcitabine and gemcitabine complexed by Q [7] show equal cytotoxicity when exposed for 24 h and 72 hours [20]. The complexation of gemcitabine and cucurbit [7]uril in highly acidic aqueous conditions.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the gemcitabine drug complexation with cucurbit[n]urils (n = 6–8): a computational analysis

2023

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In this work, the DFT-D3 method was employed to investigate the complex formation capability of gemcitabine drug with host cucurbit [n]uril Q[n] (n = 6,7 and8) molecules. The density functional theory studies demonstrate that the most stable con guration is a fully encapsulated complex. In the gemcitabine@[6] and gemcitabine@[7] encapsulated systems the gemcitabine amino -NH 2 and the alcoholic group in the carbohydrate bonds with the carbonyl units of Q [n]. The addition of sodium ions leads to the partial exclusion of the gemcitabine molecule and the sodium atoms lie close to the carbonyl portal of Q [7]. Thermodynamic parameters computed for the complexation process exhibit high negative entropy change implying that the encapsulation process is spontaneous and is an enthalpy-driven process. Frontier molecular orbitals are located mainly on the gemcitabine uracil ring, before and after encapsulation formation, indicating that the encapsulation happens by pure physical adsorption. Quantitative molecular electrostatic potentials demonstrate a shift in charge occurs during the complex formation and is more pronounced in gemcitabine@Q [7]. AIM topological analysis illustrates that these complexes are stabilized by various noncovalent interactions including HBs and C•••F interactions. The 2D RDG plots exhibit the presence of strong HBs and weak van der Waals interactions and the presence of steric repulsion. The isosurface NCI diagram shows predominant steric interaction in the gemcitabine@Q[6] complex.The NCI isosurface for gemcitabine encapsulated complexes with Q[7] and Q[8] host displays that the green patches are uniformly distributed in all directions. Finally, EDA results demonstrate Paulis repulsive energy is predominant in the gemcitabine@Q[6] complex, while the orbital and dispersion energies stabilize the gemcitabine@Q[7] complex.

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Physicochemical and in vitro cytotoxicity studies of inclusion complex between gemcitabine and cucurbit[7]uril host

Cited by 7 publications

References 93 publications

NMR diffusometry: A new perspective for nanomedicine exploration

NMR diffusometry: A new perspective for nanomedicine exploration

Supramolecular Chemotherapy with Cucurbit[n]urils as Encapsulating Hosts

Unveiling the gemcitabine drug complexation with cucurbit[n]urils (n = 6–8): a computational analysis

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