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

• pressure autoclave. [CD]tot is the starting concentration of cyclodextrin. [CD·CO2]/[CD]tot is the calculated ratio of bound CO2 in solution using a Kg of 0.18 bar−1. Kd for binding of 7 and Ka for binding CO2 for cyclodextrin derivatives in citrate-phosphate buffer at pH 3. Crystal data and structure

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

• different formulations were compared in terms of similarity (f2) and difference (f1) factors, and the results revealed that the release profiles of nanoparticles, which we obtained using the same formulation parameters with structurally similar amphiphilic cyclodextrin derivatives, showed similar release

• also have increased. The 6-O-capro-β-CD and poly-β-CD-C6 derivatives used in the study are cyclodextrin derivatives with the same core structure. Heptakis(6-O-hexanoyl)-β-CD (6-O-capro-β-CD) is a primary face-modified amphiphilic CD derivative with a 6C fatty acid chain attached via an ester bond to

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

• ), Dunkerque, France 10.3762/bjoc.18.140 Abstract A simple method for the preparation of β-cyclodextrin derivatives containing covalently bonded aldehydes via an imine bond was developed and used to prepare a series of derivatives from 6I-amino-6I-deoxy-β-cyclodextrin and the following volatile aldehydes

• time evolutions of integral of the imine group proton signal at 8.30 ppm in the acquired 1H NMR spectrum of the compound 3d for various pH. Funding The authors thank Erasmus + mobility program for the financial support of AP traineeship that resulted into the bachelor thesis: Palágyi, A. Cyclodextrin

• derivatives containing covalently bound volatile substances and studies of their release. Bachelor Thesis, Charles University, Czech Republic 2018.

New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

• Iveta Chena Tichá,
• Simona Hybelbauerová and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2019, 15, 830–839, doi:10.3762/bjoc.15.80

Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives

• Iveta Tichá,
• Gábor Benkovics,
• Milo Malanga and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2018, 14, 2829–2837, doi:10.3762/bjoc.14.261

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• investigated. Cyclodextrins have been already reported to change the transformation efficiency of different E. coli strains, although not in a standardized manner. Different cyclodextrin derivatives can cause from a 10-fold decrement up to a four-fold increment in the number of transformants compared to

• antibiotics. The fact that these cyclodextrin derivatives might be loaded with an antibiotic allows speculating that a possible antibiotic–CD complex could target the pathogen and in the meanwhile to bind and sequester extracellular DNA, inhibiting its role in vivo. Finally, a particular mention is deserved

Superstructures with cyclodextrins: Chemistry and applications IV

• Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

• ]. The group of Ravoo also conjugated arylazopyrazoles to amphiphilic cyclodextrin derivatives that form vesicles triggered by light [17]. A star-shaped polycationic CD derivative with many breakable, intrinsic, disulfide linkages forms nanoparticles with messenger RNA and drugs and is particularly

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• chromatography; L-lactide; MALDI; mass spectrometry; NMR; Introduction Cyclodextrin derivatives are increasingly important and their variety is dictated by the wide range of applications in which these compounds are employed with preponderance in the pharmaceutical field [1][2]. The employed strategies for the

• in the cyclodextrin’s modification. The presented combination of analytical methods can help in further studies to optimize the reaction conditions in order to achieve a modification of all CD molecules. Further characterization studies will aim for the quantitative measurement of cyclodextrin

• derivatives and PLA homopolymers in the reaction mixture. Experimental Materials L-lactide (L-LA) (Sigma-Aldrich) was recrystallized twice from ethyl acetate, dried under vacuum and sublimated before use; α-, β- and γ-cyclodextrins (CDs) (Cyclolab, Hungary) were dried over P2O5 under vacuum at 80 °C for 72

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• investigations were then performed with the monosubstituted cyclodextrin derivatives 4 and 5 (Figure 7). In the case of compound 5, no activity was observed. In contrast, scavenger 4, bearing only the α-nucleophile through a three-carbon atom linker showed a similar efficiency than 2. Therefore, it can be

• hydrolytic activity. The relative abilities of IBA and compounds 1–4 (0.25 mM) to accelerate the methyl paraoxon (0.5 mM) hydrolysis were then measured by determining the pseudo-first-order rate constants during the initial course of the process (Table 1). Under the conditions, the cyclodextrin derivatives 1

• derivatives. Therefore, the design of new scavengers will require further structural studies on the inclusion complexes and affinity measurements with carefully selected analogs of organophosphates. Conclusion New β-cyclodextrin derivatives were synthesized and their efficiency to degrade the organophosphorus

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

• Tamás Zoltán Agócs,
• István Puskás,
• Erzsébet Varga,
• Mónika Molnár and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286

• behavior and stability of nanoTiO2 in cyclodextrin solutions. On the other hand, we used various monomer and polymer cyclodextrin derivatives, and assessed the options for nanoTiO2 stabilization in the presence of various salts and tap water on the basis of turbidity tests. The physical stability of

• nanoTiO2 dispersions is diminished in the presence of the salts found in tap water (and occurring also in surface waters and ground water) and they are precipitated immediately. This colloidal instability can be improved by cyclodextrin derivatives. Based on the results of our studies we have selected

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• exquisitely shaped hydrophobic pocket/active site. Ronald Breslow was asking similar questions and addressing it with cyclodextrin derivatives as enzyme mimics, but as I neared the end of my Ph.D. degree I confess I knew nothing of this facet of supramolecular chemistry. In 1991, as lab work started to be

Optimized methods for preparation of 6^I-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives

• Eva Bednářová,
• Simona Hybelbauerová and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2016, 12, 349–352, doi:10.3762/bjoc.12.38

• Prague, Hlavova 8, 128 43, Prague 2, Czech Republic 10.3762/bjoc.12.38 Abstract A general high-yielding method for the preparation of monosubstituted β-cyclodextrin derivatives which have attached a thiol group in position 6 is described. The thiol group is attached through linkers of different lengths

• during the syntheses of thiol-group-containing cyclodextrin derivatives and presented reproducible methods for their elimination. The main problem – formation of the corresponding disulfides by air oxidation – could be suppressed substantially by using an inert atmosphere and performing work-up under

Supramolecular structures based on regioisomers of cinnamyl-α-cyclodextrins – new media for capillary separation techniques

• Gabor Benkovics,
• Ondrej Hodek,
• Martina Havlikova,
• Zuzana Bosakova,
• Pavel Coufal,
• Milo Malanga,
• Eva Fenyvesi,
• Andras Darcsi,
• Szabolcs Beni and
• Jindrich Jindrich

Beilstein J. Org. Chem. 2016, 12, 97–109, doi:10.3762/bjoc.12.11

• that the position of the cinnamyl group plays an important role in the intermolecular complex formation. Keywords: capillary electrophoresis; cyclodextrin derivatives; mono-cinnamyl; regioisomers; supramolecular structures; Introduction Supramolecular polymers (SP) are aggregates of monomer units

• reached higher values due to lower viscosity of the BGE. Subsequently differences between electrophoretic mobilities with and without Cin-α-CDs in BGE decreased because of smaller size of Cin-α-CDs aggregates. The studied α-cyclodextrin derivatives offer a potential for employing them in capillary

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

• Martin Popr,
• Sergey K. Filippov,
• Nikolai Matushkin,
• Juraj Dian and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

Conjugates of methylated cyclodextrin derivatives and hydroxyethyl starch (HES): Synthesis, cytotoxicity and inclusion of anaesthetic actives

• Lisa Markenstein,
• Antje Appelt-Menzel,
• Marco Metzger and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 3087–3096, doi:10.3762/bjoc.10.325

Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers

• Milo Malanga,
• Mihály Bálint,
• István Puskás,
• Kata Tuza,
• Tamás Sohajda,
• László Jicsinszky,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3007–3018, doi:10.3762/bjoc.10.319

• Milo Malanga Mihaly Balint Istvan Puskas Kata Tuza Tamas Sohajda Laszlo Jicsinszky Lajos Szente Eva Fenyvesi CycloLab Cyclodextrin Research and Development Laboratory Ltd, Illatos 7, Budapest, H-1097 Hungary 10.3762/bjoc.10.319 Abstract The fluorescent tagging of cyclodextrin derivatives enlarges

• either by branching the proper cyclodextrin derivatives (pre-branching modification) or by derivatization of the cyclodextrin polymers (post-branching modification). Several examples of both modification types of these macromolecules with additional groups are reported in the literature [5] and an update

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

• Lisa F. Becker,
• Dennis H. Schwarz and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

• the β-cyclodextrin derivatives exhibit very high binding potentials towards the anaesthetic drugs sevoflurane and halothane. Since the resulting inclusion compounds are highly soluble in water at temperatures ≤37 °C they are good candidates for new aqueous dosage forms which would avoid inhalation

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• live cell monitoring [23]. The kinetic curve of cell survival rates obtained using real-time xCELLigence impedance analysis is shown in Figure 3. Both cyclodextrin derivatives induced a gradual decline in the cell survival rate over a 20 hour exposure period, suggesting that CDs may cause some corneal

• components are considered suitable for ocular use from an irritation study point of view. Ion-sensitive ophthalmic gel Because both cyclodextrin derivatives were shown to be safe, non-irritant and able to form complexes with fluconazole (with similar stability properties), both substances were considered as

• multiple comparison test. Phase solubility diagrams for fluconazole obtained with β-cyclodextrin derivatives at 25 °C in water (mean ± SD, n = 6). The dotted lines indicate the necessary CD concentration required to solubilize 10 mg/mL of fluconazole. Solubility of fluconazole in aqueous solutions

Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer

• Florian Hamon,
• Claire Blaszkiewicz,
• Marie Buchotte,
• Estelle Banaszak-Léonard,
• Hervé Bricout,
• Sébastien Tilloy,
• Eric Monflier,
• Christine Cézard,
• Laurent Bouteiller,
• Christophe Len and
• Florence Djedaini-Pilard

Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304

• ]. As an exception, Vargas et al. [29] described the synthesis of 1,2,3-triazole-linked azobenzene-cyclodextrin derivatives producing rather good yields but the photoisomerization and inclusion complex properties were not investigated. Here, we report an efficient preparation of a new bis-β-CD with

Synthesis of modified cyclic and acyclic dextrins and comparison of their complexation ability

• Kata Tuza,
• László Jicsinszky,
• Tamás Sohajda,
• István Puskás and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 2836–2843, doi:10.3762/bjoc.10.301

• insight into the complexation should reveal the differences in the structures of the associates that will support the observed tendencies in interaction behavior. The synthesis and investigations of further derivatives are in progress. Experimental Materials: Cyclodextrin derivatives, peracetylated

• applied for the native compounds. The guest candidates were chlorpheniramine, histidine, ibuprofen, camphoric acid, and chrysanthemic acid. Most of the guest compounds were racemates in order to detect enantiorecognition ability if there is any. In most cases the maltooligomers and the cyclodextrin

• derivatives behaved similarly, although the enantiorecognition properties frequently differed. For example, the enantiomers of chrysanthemic acid were only recognized by HP-β-CD whereas the only host resulting in a partial chiral separation of chlorpheniramine enantiomers was HP-G6 (Figure 2, fifth and first

Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene

• Ludmilla Lumholdt,
• Sophie Fourmentin,
• Thorbjørn T. Nielsen and
• Kim L. Larsen

Beilstein J. Org. Chem. 2014, 10, 2743–2750, doi:10.3762/bjoc.10.290

• organic compounds are known to form stable inclusion complexes with cyclodextrins. Six different amphiphilic cyclodextrin derivatives were synthesised in order to elucidate whether or not the uptake abilities of the coating depend on the structure of the derivative. Headspace gas chromatography was used

A green approach to the synthesis of novel phytosphingolipidyl β-cyclodextrin designed to interact with membranes

• Yong Miao,
• Florence Djedaïni-Pilard and
• Véronique Bonnet

Beilstein J. Org. Chem. 2014, 10, 2654–2657, doi:10.3762/bjoc.10.278

• (yield = 80%, see Scheme 1). Indeed, COMU is an efficient peptide coupling reagent and can be used in the synthesis of cyclodextrin derivatives. Insertion of fatty acid chain In previous work, the synthesis of the reaction of permethylated 6-amino-6-deoxy-β-cyclodextrin and vinyl ester catalyzed by

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• with β-cyclodextrin derivatives. Since 4-alkylphenyl moieties are good guests for ß-cyclodextrin [37][38], we were encouraged to use 4-tert-butylphenol as well as 4-tert-octylphenol and modify them with mercapto groups. By doing so, well-defined PDEAAm end-group labeled polymers can be obtained by

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

• Sophie Fourmentin,
• Anca Ciobanu,
• David Landy and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1185–1191, doi:10.3762/bjoc.9.133

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• mixtures are described in the literature [4], and dimers [5], trimers [6], and polymers have also been obtained [7]. A different approach is to synthesise cross-linked cyclodextrin-based polymers so as to prepare insoluble multifunctional cyclodextrin derivatives [8][9][10]. These polymers can be obtained

• molecules is widely used in the pharmaceutical field as a strategy to increase the aqueous solubility and, consequently, bioavailability of lipophilic drugs. For hydrophilic or moderately polar drugs this approach is less effective, and consequently cyclodextrin derivatives have been investigated