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Search for "cyclodextrins" in Full Text gives 184 result(s) in Beilstein Journal of Organic Chemistry.

Spatial arrangements of cyclodextrin host–guest complexes in solution studied by 13C NMR and molecular modelling

  • Konstantin Lebedinskiy,
  • Ivan Barvík,
  • Zdeněk Tošner,
  • Ivana Císařová,
  • Jindřich Jindřich and
  • Radim Hrdina

Beilstein J. Org. Chem. 2024, 20, 331–335, doi:10.3762/bjoc.20.33

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  • crystallization of host–guest complexes and their crystallographic analysis. Keywords: anisotropy; 13C NMR; cyclodextrin; host–guest complexes; Introduction Complexation of organic and inorganic compounds with α-, β-, or γ-cyclodextrins and their derivatives [1] is an established tool used in medicine for drug
  • ). Having established the method, we chose various cyclic compounds (noradamantane, adamantane, cyclohexane derivatives) with desired symmetry and measured NMR spectra of these guest molecules (2–8) in α-cyclodextrin and cyclodextrins with a larger cavity (β-CD and γ-CD, Figure 4). In all cases, the 1H NMR
  • compound 4, we were thus able to select representative conformations of the guest molecule in all types of cyclodextrins (Figure 5) using the spatial densities gained from classical MD simulations. Compounds 1–8 (as hydrochloride salts or free bases), were attempted to co-crystallize with α-, β- and γ
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Published 20 Feb 2024

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

  • Ghenwa Nasr,
  • Hélène Greige-Gerges,
  • Sophie Fourmentin,
  • Abdelhamid Elaissari and
  • Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

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  • , France, Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV, UR 4492), SFR Condorcet FR CNRS 3417, Université du Littoral Côte d'Opale, 145 Av. M.Schumann, 9140 Dunkirk, France 10.3762/bjoc.19.115 Abstract Cyclodextrins (CDs) are known for their ability to extract lipid components from
  • content membrane increase. Keywords: cholesterol; cyclodextrins; liposome; membrane permeability; Introduction Cyclodextrins (CDs) are a family of cyclic oligosaccharides made of glucopyranose units connected by α-1,4-glycosidic bonds. They possess a cone-shaped molecular structure with a hydrophobic
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Published 17 Oct 2023

CO2 complexation with cyclodextrins

  • Cecilie Høgfeldt Jessen,
  • Jesper Bendix,
  • Theis Brock Nannestad,
  • Heloisa Bordallo,
  • Martin Jæger Pedersen,
  • Christian Marcus Pedersen and
  • Mikael Bols

Beilstein J. Org. Chem. 2023, 19, 1021–1027, doi:10.3762/bjoc.19.78

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  • from industrial processes, power generation, and transportation contribute significantly to global warming and climate change. Carbon capture and storage (CCS) technologies are essential to reduce these emissions and mitigate the effects of climate change. Cyclodextrins (CDs), cyclic oligosaccharides
  • , are studied as potential CO2 capture agents due to their unique molecular structures and high selectivity towards CO2. In this paper we have investigated binding efficiency of a number of cyclodextrins towards CO2. It is found that the crystal structure of α-cyclodextrin with CO2 has a 1:1
  • stoichioimetry and that a number of simple and modified cyclodextrins bind CO2 in water with a Kg of 0.18–1.2 bar−1 (7–35 M−1) with per-O-methyl α-cyclodextrin having the highest CO2 affinity. Keywords: carbon dioxide; crystals; cyclodextrin; gas binding; Introduction The concentration of carbon dioxide (CO2
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Published 17 Jul 2023

Cyclodextrins as building blocks for new materials

  • Miriana Kfoury and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

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  • Miriana Kfoury Sophie Fourmentin Université du Littoral Côte d'Opale, Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV, UR 4492), 59140 Dunkerque, France 10.3762/bjoc.19.66 Keywords: building blocks; cyclodextrins; new materials; The continuous increase in the number of
  • publications carried out on cyclodextrins (CDs) and their market growth are clear evidence of the undying interest in these macrocycles discovered in 1891 [1]. It seems that these supramolecules still have not revealed all their secrets and are still stimulating curiosity in fundamental and applied research
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Published 19 Jun 2023

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

  • Nan Yang,
  • Yi-Yan Zhu,
  • Wei-Xiu Lin,
  • Yi-Long Lu and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

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  • supramolecular systems derived from water-soluble macrocycles, including cyclodextrins (CDs), calix[n]arenes (CXs), cucurbiturils (CBs), and pillararenes have been widely studied [2][6][7][8]. Similar to those macrocyclic acceptors, tribenzotriquinacene (TBTQ) derivatives, a class of versatile host molecules
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Published 08 May 2023

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

  • Nicoleta G. Hădărugă,
  • Gabriela Popescu,
  • Dina Gligor (Pane),
  • Cristina L. Mitroi,
  • Sorin M. Stanciu and
  • Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

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  • Cyclodextrins (CDs) are studied for more than one hundred years due to their unique properties related to their spatial macrocyclic structure that comprises six to eight α-ᴅ-glucopyranose (Glcp) units for the natural α-, β-, and γ-CD [1][2][3]. All hydroxy groups are oriented to the exterior of the macrocycle
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Published 28 Mar 2023

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

  • János Máté Orosz,
  • Dóra Ujj,
  • Petr Kasal,
  • Gábor Benkovics and
  • Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

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  • ; monosubstitution; reduction; Introduction Cyclodextrins (CDs), as cyclic oligosaccharides, consist of a macrocyclic ring of glucose subunits linked by α-1,4-glycosidic bonds [1]. They are widely used in pharmaceutical, food and chemical industries, as well as in agriculture. It has been known for decades, that CD
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Published 09 Mar 2023

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

  • Sedat Ünal,
  • Gamze Varan,
  • Juan M. Benito,
  • Yeşim Aktaş and
  • Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

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  • our group, and detailed studies were carried out to elucidate the mechanism. Both the results of our studies and the literature emphasize that cyclodextrins show high affinity for lipid-based molecules such as cholesterol and phospholipids in biological membranes [50][55][56]. Furthermore, it was
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Published 13 Feb 2023

Preparation of β-cyclodextrin/polysaccharide foams using saponin

  • Max Petitjean and
  • José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

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  • Max Petitjean Jose Ramon Isasi Department of Chemistry. University of Navarra. 31080 Pamplona, Spain 10.3762/bjoc.19.7 Abstract Cyclodextrins, cyclic oligosaccharides with a hydrophobic cavity that form inclusion complexes with nonpolar molecules, can be used to functionalize other
  • coronavirus vaccine chitosan–saponin coatings have been developed to study its immunogenic potential [32]. A complexation between saponin and cyclodextrins (native or derivative) is possible [33], and the resulting release kinetics is appropriate for the creation of new saponin-based drugs [34]. Their
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Published 24 Jan 2023

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

  • Alexios I. Vicatos,
  • Zakiena Hoossen and
  • Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

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  • ingredients (APIs) is necessary to render them bioavailable. This study addresses the poor solubility of two potent steroid hormones, 17β-estradiol (BES) and progesterone (PRO), via their complexation with two water-soluble native cyclodextrins (CDs) namely β-CD and γ-CD. The hydrated inclusion complexes β
  • pharmaceutical industry for many decades. However, the complexation of APIs with cyclodextrins (cyclic oligosaccharides) resulting in the formation of inclusion complexes, has proven to be a versatile technology for overcoming not only the poor aqueous solubility of APIs, but also unfavourable properties such as
  • , which is a distinct disadvantage for solid-state structural investigation and complex characterization by X-ray diffraction methods. Results and Discussion Complex screening The isolation of solid inclusion complexes of BES and PRO with the native cyclodextrins β-CD and γ-CD was successfully achieved by
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Published 22 Dec 2022

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

  • Konstantin Lebedinskiy,
  • Volodymyr Lobaz and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

Graphical Abstract
  • 1H NMR and NOESY NMR imply the dependence of molecular symmetry on the type of spacer. The ability of synthesized dimers to increase the solubility of tetracene in DMSO was evaluated and compared to native cyclodextrins and their methylated derivatives. The newly synthesized compounds expressed
  • better effectiveness than other tested supramolecular hosts. Keywords: cyclodextrin; dimer; methylation; solubilization; tetracene; Introduction Cyclodextrins (CDs) are cyclic oligomers of glucose that play an important role in supramolecular chemistry [1]. The structure of any CD contains a
  • and 10 times to get the absorbance of the solution into the linear range of the tetracene concentration/UV absorption calibration plot. ITC measurements The saturated solution of tetracene (0.71 mg/mL, 3.1 mM) was titrated at 298 K with the solutions of cyclodextrins: 13 (57 mg/mL; 50 mM), 16 (71 mg
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Published 25 Nov 2022

A study of the DIBAL-promoted selective debenzylation of α-cyclodextrin protected with two different benzyl groups

  • Naser-Abdul Yousefi,
  • Morten L. Zimmermann and
  • Mikael Bols

Beilstein J. Org. Chem. 2022, 18, 1553–1559, doi:10.3762/bjoc.18.165

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  • C134H137Cl8O30+, 2511.6706 (71.9%); found, 2511.69097. Structure of α-cyclodextrins 1–10. The reaction of perbenzylated α-cyclodextrin with iBu2AlH. Reaction conditions for the partial debenzylation of 7. The solvent was always toluene. 1H and 13C NMR (800/201 MHz, CDCl3) chemical shifts of diol 8. 1H and 13C
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Published 17 Nov 2022

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

  • Attila Palágyi,
  • Jindřich Jindřich,
  • Juraj Dian and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

Graphical Abstract
  • molecules and protect those agents from environmental degradation [1][2]. Cyclodextrins (CDs) serve as one of the simplest encapsulating systems. CDs are cyclic oligosaccharides composed of 1→4 linked α-ᴅ-glucopyranose units (6, 7, and 8 for the most common α-, β-, and γ-CD). CDs are well known for their
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Published 28 Sep 2022

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

  • Man-Ping Li,
  • Nan Yang and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

Graphical Abstract
  • (CXs), cyclodextrins (CDs), cucurbiturils (CBs), and pillararenes, are of particular interest because they can act as vehicles for anticancer drugs by either self-assembling into nanocarriers [14][15][16] or forming host–guest complexes with anticancer drugs [17][18][19][20]. Tribenzotriquinacene (TBTQ
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Published 12 May 2022

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

  • Hao Guo,
  • Yu-Fei Ao,
  • De-Xian Wang and
  • Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

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  • ][10][11][12][13][14]. Among which, macrocyclic compounds have attracted extensive attentions due to their enzyme-mimicking cavity and preorganized binding sites [4][6][15][16]. Various macrocyclic compounds including the privileged scaffolds like cyclodextrins [17][18][19], calixarenes [20][21][22][23
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Published 02 May 2022

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

  • Tommaso Lorenzetto,
  • Fabrizio Fabris and
  • Alessandro Scarso

Beilstein J. Org. Chem. 2022, 18, 337–349, doi:10.3762/bjoc.18.38

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  • structures endowed with catalytic features are full covalent units (e.g., cyclodextrins, cucurbiturils, pillararenes and other derivatives) whose synthesis can be sometimes time consuming. Alternatively, supramolecular catalysts can be obtained through self-assembling units [18][19], metal-ligand components
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Published 28 Mar 2022

Site-selective reactions mediated by molecular containers

  • Rui Wang and
  • Yang Yu

Beilstein J. Org. Chem. 2022, 18, 309–324, doi:10.3762/bjoc.18.35

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  • environment inside the container. The containers include supramolecular structures self-assembled through metal/ligand interactions or hydrogen bonding and open-ended covalent structures such as cyclodextrins and cavitands. Challenges and prospects for the future are also provided. Keywords: confinement
  • mimicking the recognition and catalysis behavior of enzymes with designed and synthesized molecular containers such as cyclodextrins, cucurbiturils, calixarenes, and resorcinarenes, chemists try to tackle problems of traditional synthetic chemistry, including increase in reactivity, induction of selectivity
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Published 14 Mar 2022

Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions

  • Qingkai Zeng,
  • Qiumeng Long,
  • Jihong Lu,
  • Li Wang,
  • Yuting You,
  • Xiaoting Yuan,
  • Qianjun Zhang,
  • Qingmei Ge,
  • Hang Cong and
  • Mao Liu

Beilstein J. Org. Chem. 2021, 17, 2840–2847, doi:10.3762/bjoc.17.195

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  • Macrocycles with converging binding sites and functional groups hold a key position in supramolecular chemistry, which has been repeatedly confirmed by classic macrocyclic molecules, such as crown ethers, cyclodextrins, calixarenes, cucurbiturils and their homologues [1]. For the past decades, numerous
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Published 06 Dec 2021

Progress and challenges in the synthesis of sequence controlled polysaccharides

  • Giulio Fittolani,
  • Theodore Tyrikos-Ergas,
  • Denisa Vargová,
  • Manishkumar A. Chaube and
  • Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

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  •  6C) [182]. To avoid the chemical formation of this challenging bond, natural compounds containing 1,2-cis linkages could be exploited. α-, β- and γ-cyclodextrins offered a good starting material to prepare stereoselectively a 6-O-methylated α(1–4)-glucopolysaccharides consisting of 6–20 monomer units
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Published 05 Aug 2021

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

  • Minzan Zuo,
  • Krishnasamy Velmurugan,
  • Kaiya Wang,
  • Xueqi Tian and
  • Xiao-Yu Hu

Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

Graphical Abstract
  • with various macrocyclic hosts as well as on the role of macrocyclic-hosts-assisted hybrid materials in energy transfer. To keep the clarity of this review, the macrocycles are categorized into the most commonly used supramolecular hosts, including crown ethers, cyclodextrins, cucurbiturils
  • supramolecular hosts (Figure 1); crown ethers (CEs), cyclodextrins (CDs), cucurbiturils (CBs), calixarenes (CAs), and pillararenes (PAs) for various photocatalytic reactions. However, biomolecules and other supramolecular-host-related photocatalytic reactions are not included in this minireview. Generally, a
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Published 18 Jan 2021

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

  • Jonas Becher,
  • Daria V. Berdnikova,
  • Heiko Ihmels and
  • Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

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  • , cyclodextrins or micelles [55][56][57][58]. Presumably the radiationless deactivation of the excited state by conformational changes, that leads to the low emission intensity in aqueous solution, is suppressed in the sterically restricted binding site. Therefore, it can be deduced that the increased emission of
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Published 18 Nov 2020

Particle size effect in the mechanically assisted synthesis of β-cyclodextrin mesitylene sulfonate

  • Stéphane Menuel,
  • Sébastien Saitzek,
  • Eric Monflier and
  • Frédéric Hapiot

Beilstein J. Org. Chem. 2020, 16, 2598–2606, doi:10.3762/bjoc.16.211

Graphical Abstract
  • considerable attention as it may be unique in features to selectively direct the reaction pathway. In the continuation of our work on the synthesis of modified cyclodextrins (CDs) via mechanochemical activation, we sought to discriminate the contribution of supramolecular effects and grinding during the course
  • purification steps. We especially focused our attention on the utilization of cyclodextrins (CDs), which are cyclic α-ᴅ-glucopyranoside-based saccharides. CDs feature the advantage of adjustable cavity sizes and a broad synthetic diversity. The most commonly used CDs are α-CD, β-CD, and γ-CD, that consist of 6
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Published 22 Oct 2020

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

  • Si-Yuan Liu,
  • Xin-Rui Wang,
  • Man-Ping Li,
  • Wen-Rong Xu and
  • Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

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  • C60 and C70 [1][2][3][4][5]. It is generally accepted that good complexation of fullerenes requires host molecules with bowl or basket-like shapes, such as calixarenes [6], corannulenes [7][8][9][10], cyclodextrins [11][12][13], cyclotriveratrylenes [14][15][16], and similar macrocycles [17][18][19
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Published 14 Oct 2020

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

  • Alberto Rubin Pedrazzo,
  • Fabrizio Caldera,
  • Marco Zanetti,
  • Silvia Lucia Appleton,
  • Nilesh Kumar Dhakar and
  • Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

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  • crosslinked polymers made up of cyclodextrins. The reactive hydroxy groups of CDs allow them to act as multifunctional monomers capable of crosslinking to bi- or multifunctional chemicals. The most common NS synthetic pathway consists in dissolving the chosen CD and an appropriate crosslinker in organic polar
  • . Polysaccharides and, among them, starch derivatives such as cyclodextrins (CD), have recently emerged as they are safe, of low cost and biodegradable. Cyclodextrin nanosponges (CD-NS) are crosslinked cyclodextrin polymers characterized by a nanosized three-dimensional network. The reactive hydroxy groups of CDs
  • instance, dye-modified cyclodextrins and CD derivatives have found wide use for the preparation of chemical sensors [24][25]. As CDs and consequently CD nanosponges can be easily coupled with fluorophores, they could find applications in the pharmacological area, for example, as biological markers, in
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Published 29 Jun 2020

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

  • Margareta Sohora,
  • Leo Mandić and
  • Nikola Basarić

Beilstein J. Org. Chem. 2020, 16, 1296–1304, doi:10.3762/bjoc.16.110

Graphical Abstract
  • initiated by phthalimides in organic synthesis [14][15]. Furthermore, H-abstractions were investigated in inclusion complexes, in the cavity of β-cyclodextrins (β-CD) [16]. We found out that H-abstraction reactions were about ten times more efficient in the β-CD complexes than in the isotropic solution, and
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Published 12 Jun 2020
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