Comparison between cucurbiturils and β-cyclodextrin interactions with cholesterol molecules present in Langmuir monolayers used as a biomembrane model

Tovani, Camila Bussola; Souza, João Francisco Ventrici de; Cavallini, Thiago de Souza; Demets, Grégoire Jean-François; Ito, Amando Siuiti; Barioni, Marina Berardi; Pazin, Wallance Moreira; Zaniquelli, Maria Elisabete Darbello

doi:10.1016/j.colsurfb.2013.05.006

Cited by 16 publications

(7 citation statements)

References 31 publications

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“…CB[ n ]s are also not toxic, cheap and resistant to microorganisms, which makes them excellent candidates to replace cyclodextrins for most applications. Our own contribution to this field includes the stabilization of reactive species and drug carriers, and the use of CB[ n ] as structural elements in hybrid composites, as templates for nanoparticle synthesis, or to develop special catalysts and coatings, sensors and specialty polymers . Their ability to host a wide range of substrates is mainly due to the hydrophobicity of the inner cavity lacking hydrogen bond donor/acceptor moieties.…”

Section: Soluble Supramolecular Assembliesmentioning

confidence: 99%

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Correia

Chowdhury

Ramos

et al. 2018

Polymer International

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This review article focuses on supramolecular assemblies involving cucurbit[n]uril‐based containers and viologen guests as key building elements. Cucurbit[n]urils (CB[n], n = 5–8,10) are fascinating hosts forming a wide range of inclusion complexes (caviplexes) with 4,4′‐bipyridinium salts, known as viologens, either as discrete 1:1 inclusion compounds with CB[7] or as ternary inclusion compounds involving two hosts or two guests (2:1 with CB[7] and 1:2 or 1:1:1 with CB[8]). This property is currently being actively exploited to design and prepare self‐assembled dynamic stimuli‐responsive supramolecular polymers including gels, vesicles, films and organized arrays of polymeric microspheres or nanoparticles. This review highlights the main benefits of such polymers and gives an overview of the achievements and progress made in this field over the past decades. © 2018 Society of Chemical Industry

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Section: Soluble Supramolecular Assembliesmentioning

confidence: 99%

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Correia

Chowdhury

Ramos

et al. 2018

Polymer International

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“…CyDs can release cholesterol from the erythrocyte membrane, thereby causing hemolysis [13]. It is known that CB [7] and other homologues (with the exception of CB [5] and CB [6]) can also bind cholesterol molecules [31], so the hemolytic effect of cucurbiturils may be similar to the effects of cyclodextrins.…”

Section: Discussionmentioning

confidence: 99%

Assessment of the Biocompatibility of Cucurbiturils in Blood Cells

et al. 2021

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Currently, cucurbiturils are being actively researched all over the world. Research is focused on the ways of improving the solubility and selectivity of cucurbiturils, increasing the stability of the complexes with other particles in various media and enhancing their ability to bind and release various substances. The most significant area of our research is the assessment of safety, studying the biological properties and synergistic effects of cucurbiturils during complexation with drugs. In this article, the hemocompatibility of erythrocytes and leukocytes with cucurbiturils was investigated. We demonstrated that cucurbiturils have no cytotoxic effect, even at high concentrations (1 mM) and do not affect the viability of PBMCs. However, cucurbiturils can increase the level of the early apoptosis of lymphocytes and cucurbit[7]uril enhances hemolysis in biologically relevant media. Despite this, cucurbiturils are fairly safe organic molecules in concentrations up to 0.3 mM. Thus, we believe that it will become possible to use polymer nanostructures as drug delivery systems in clinical practice, since cucurbiturils can be modified to improve pharmacological properties.

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“…Three types of micelles were prepared from amphiphilic molecules with different charges: anionic sodium dodecyl sulfate (SDS), cationic hexadecyltrimethylammonium bromide (CTAB) and zwitterionic n‐hexadecyl‐n,n‐dimethyl‐3‐ammonio‐1‐propanesulfonate (HPS). More closely related to the membranes, PC bilayers have been extensively employed as a model for the basic structure of cell membranes and as a nonspecific target for the action of amphiphilic molecules with therapeutic effects . Large unilamellar vesicles (LUVs) with different surface charges were prepared, using the zwitterionic phospholipid DMPC, the negative phospholipid 1,2‐dimyristoyl‐sn‐glycero‐3‐[Phospho‐rac(1‐glycerol)] (DMPG) and the cationic lipid dimethyl dioctadecyl ammonium bromide (DODAB).…”

Section: Introductionmentioning

confidence: 99%

pH and Charge Effects Behind the Interaction of Artepillin C, the Major Component of Green Propolis, With Amphiphilic Aggregates: Optical Absorption and Fluorescence Spectroscopy Studies

Camuri

Costa

Ito

et al. 2019

Photochem & Photobiology

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Brazilian green propolis is one of the bee products most consumed in the world to prevent diseases, owing antioxidant, antimicrobial, anti‐inflammatory and antitumor activities. The major component of Brazilian green propolis is Artepillin C (ArtC), a cinnamic acid derivative with two prenylated groups that improve the affinity of the compound for lipophilic environment. Here, we have employed optical absorption and fluorescence techniques to draw conclusions on how ArtC interacts with amphiphilic aggregates commonly used as model membranes having different charges in the polar head group. Optical absorption spectra were representative of the protonation state of ArtC, dictated by the local pH at the surface of micelles and lipid vesicles. Fluorescence results showed that, in the presence of micelles and vesicles, the polarizability around ArtC was modified, compared to the value in aqueous medium, and the molecule should be located preferentially on the surface region of the model membranes, with an enhanced interaction with the less ordered state of the lipid vesicles.

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Comparison between cucurbiturils and β-cyclodextrin interactions with cholesterol molecules present in Langmuir monolayers used as a biomembrane model

Cited by 16 publications

References 31 publications

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Assessment of the Biocompatibility of Cucurbiturils in Blood Cells

pH and Charge Effects Behind the Interaction of Artepillin C, the Major Component of Green Propolis, With Amphiphilic Aggregates: Optical Absorption and Fluorescence Spectroscopy Studies

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