Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

• Sophie Letort,
• Sébastien Balieu,
• William Erb,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

• energy barrier for complex dissociation revealed the thermal stability conferred upon guest encapsulation within the CD molecules. NMR experiments allow the enantiomers discrimination in presence of a chiral additive to create visible diastereomeric species. 31P NMR spectroscopy in presence of CDs as

Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with β-cyclodextrin

• Daniel I. Hădărugă,
• Mustafa Ünlüsayin,
• Alexandra T. Gruia,
• Cristina Birău (Mitroi),
• Gerlinde Rusu and
• Nicoleta G. Hădărugă

Beilstein J. Org. Chem. 2016, 12, 179–191, doi:10.3762/bjoc.12.20

• -containing microcapsules [27][33] and spontaneous emulsification for obtaining nanoemulsions [20][31][32]. One nanoencapsulation method of fish oil components is the molecular encapsulation in cyclodextrins (CDs). The latter are natural or synthetically modified, cyclic oligosaccharides comprising 6, 7, and

• ratio. However, these values were higher for the kneading method. These results can be explained by the molecular encapsulation of FA glycerides by CDs, which theoretically implies a 3:1 molecular ratio (further studies are needed). A high content of fish oil remains nonencapsulated. It is washed with

• molecular encapsulation process. Thermogravimetric (TG) analysis TG analysis of β-CD/ASO complexes can furnish information on the behavior during heating. Both β-CD and its complexes release water (and possibly other solvents used in the complexation process) up to ≈140 °C, but mainly up to 100 °C. ASO

Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol

• Miriana Kfoury,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2016, 12, 29–42, doi:10.3762/bjoc.12.5

• . However, they suffer from poor aqueous solubility and pronounced flavoring ability that limit their application in food systems. These drawbacks could be surpassed by encapsulation in cyclodextrins (CDs). Applications of their inclusion complexes with CDs were reported without investigating the inclusion

• to a different binding stability with CDs. 2D ROESY NMR experiments were also performed to prove the encapsulation and illustrate the stable 3D conformation of the inclusion complexes. The structural investigation was accomplished with molecular modeling studies. Finally, the radical scavenging

• activity of carvacrol and thymol was evaluated by the ABTS radical scavenging assay. An improvement of this activity was observed upon encapsulation. Taken together, these results evidence that the encapsulation in CDs could be valuable for applications of carvacrol and thymol in food. Keywords

Recent advances in metathesis-derived polymers containing transition metals in the side chain

• Ileana Dragutan,
• Valerian Dragutan,
• Bogdan C. Simionescu,
• Albert Demonceau and
• Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

• used to prepare modified Pt electrodes with high stability and good qualitative sensing of ATP2− anions. It was supposed that the triethylene glycol domains in the block copolymers favor the amidoferrocene–ATP interactions by encapsulation. Astruc assumed that during the recognition process different H

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• evaluated and compared to those of the non-rotaxane counterpart 3. The influence of TM-βCD or TM-γCD encapsulation on the thermal stability, solubility in common organic solvents, film forming ability was also investigated. Polyrotaxane 3·TM-βCD exhibits a hypsochromic shift, while 3·TM-γCD displays a

• electrochemical band gap (ΔEg) of 3·TM-βCD polyrotaxane is smaller than that of 3·TM-γCD and 3, respectively. The lower ΔEg value for 3·TM-βCD suggests that the encapsulation has a greater effect on the reduction process, which affects the LUMO energy level value. Based on AFM analysis, 3·TM-βCD and 3·TM-γCD

• -threaded 3 counterpart, Scheme 1. Results and Discussion In continuation of our interest on the exploration of photophysical properties of PF copolymers by supramolecular encapsulation, we have performed the present study by using liphophylic CD derivatives, such as TM-βCD and TM-γCD instead native β- or

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• diffraction studies of the inclusion complexes between 2ME and the derivatised cyclodextrins heptakis(2,6-di-O-methyl)-β-CD (DIMEB) and heptakis(2,3,6-tri-O-methyl)-β-CD (TRIMEB) revealed for the first time the nature of the encapsulation of a bioactive steroid by representative CD host molecules. Inclusion

• literature. Encapsulation of poorly soluble drug molecules by CDs with the aim of enhancing drug bioavailability has been practised for over four decades, the first demonstration of both in vivo and in vitro effects of complexation on drug release having been reported in the early 1970s [12][13]. Steroid

• hydrophilic terminals of the steroid molecule (namely the phenolic groups –O22–H on the A-ring and –O19–H on the D-ring). Each 2ME molecule is thus isolated from other 2ME molecules primarily by encapsulation within the DIMEB cavity, but also by hydrogen bonded water clusters that ‘cap’ the terminal rings

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• the drug encapsulation and release can be achieved. Experimental Materials Reagents and solvents were purchased from Sigma-Aldrich and used as received without further purification, unless noted otherwise. Millipore water with a resistivity of 18.2 MΩ cm at 25 °C was used in all the experiments. The

Life lessons

• Jonathan R. Nitschke

Beilstein J. Org. Chem. 2015, 11, 2350–2354, doi:10.3762/bjoc.11.256

• standards, and how to write one. We kept going in lab, seeking to generate new results of the kind that could underpin a successful UK grant proposal. The story of P4 encapsulation [10] garnered substantial positive attention, and an invited Nature Q&A piece on systems chemistry [11] probably helped, too

Synthesis and evaluation of the biostability and cell compatibility of novel conjugates of nucleobase, peptidic epitope, and saccharide

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum,
• Khalid Omar Al Footy,
• Khadija Omar Badahdah and
• Bing Xu

Beilstein J. Org. Chem. 2015, 11, 1352–1359, doi:10.3762/bjoc.11.145

• chromatography (HPLC) to purify the target conjugates. Gelation properties Supramolecular hydrogels [18][19][20][21][22][23][24] formed by self-assembly of small molecules in water, as demonstrated previously by us and other researchers, have numerous potential applications, such as encapsulation and delivery of

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• to chiral concave N-heterocyclic carbenes. Molecular encapsulation was achieved by using double RCM to generate insulated oligoynes 204. Here, the masked hexayne plays an important role to lock the flanking chains [158]. The synthesis of planer chiral cyclophanes is a difficult task owing to the

Regulation of integrin and growth factor signaling in biomaterials for osteodifferentiation

• Qiang Wei,
• Theresa L. M. Pohl,
• Anja Seckinger,
• Joachim P. Spatz and
• Elisabetta A. Cavalcanti-Adam

Beilstein J. Org. Chem. 2015, 11, 773–783, doi:10.3762/bjoc.11.87

• systems exist in both soluble and matrix-bound forms [82]. Therefore, growth factor delivery can be designed by both encapsulation and surface immobilization approaches (Figure 6). The proteins should be slowly released from the delivery systems in the former case. The latter immobilization systems have

• . For example, the immobilization or encapsulation methods, the concentration and ratio, and the distribution, i.e., spatial relationship should be optimized in biomaterials and cell therapeutics. Overall, engineering the local delivery of integrin ligands and growth factors provides powerful and

An unusually stable chlorophosphite: What makes BIFOP–Cl so robust against hydrolysis?

• Roberto Blanco Trillo,
• Jörg M. Neudörfl and
• Bernd Goldfuss

Beilstein J. Org. Chem. 2015, 11, 313–322, doi:10.3762/bjoc.11.36

• low reactivity of 1 to O- and C-nucleophiles is explained by the tight encapsulation of the P–Cl unit of the endo-fenchane moieties [15]. This unusual stability of the BIFOP–halides prompted the comparison of BIFOP–Cl (1) with its diphenyl ether derivative O–BIFOP–Cl (3). Despite similar encapsulation

• backbones provoke different reactivities due to tighter encapsulation of the P–Cl unit by the fenchane moieties in BIFOP–Cl (1) relative to O–BIFOP–Cl (3). Geometries bases on the X-ray structure of BIFOP–Cla and O–BIFOP–Cl. Computed relative energies (Erel, kcal/mol) for the reaction of 2, 4 or 8 with

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• uptake. Therefore the particle size should be in an optimum range which enables particles to diffuse and permeate through the biological membranes, but also should provide the maximum ability for encapsulation of drugs and sustained release. The influence of CD concentration, concentration of oil phase

• ). Encapsulation of CPT in nanocapsules 3 fold increased the CPT transport compared with free CPT. Despite the fact that the particle size plays a critical role for the penetration through membranes, free CPT molecules showed a significantly lower permeability compared with CPT-loaded CD nanocapsules which is

• drug stability of CPT at this pH by reducing the rapid hydrolysis and probability of the occurrence of the carboxylate form. Hence encapsulation of CPT in nanocapsules results in an enhancement of the lactone form rate thereby improving the permeability. Moreover, CDs as absorption enhancers play also

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

• environment for encapsulation of a wide range of organic and inorganic molecules [2]. Therefore CDs and their derivatives are most often utilized in pharmaceutical industry for drug solubilization [3] and delivery [4]. Recently, we have published an article on the synthesis of a complete series of cationic

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• complex DMB·RSV·4.0H2O (a), ring and atomic nomenclature for the host molecule DMB (b), and structure and atomic numbering of the included RSV molecule (c). Space-filling model of the inclusion complex DMB·RSV·4.0H2O showing the encapsulation of part of the RSV molecule by the host DMB (left) and a

Release of β-galactosidase from poloxamine/α-cyclodextrin hydrogels

• César A. Estévez,
• José Ramón Isasi,
• Eneko Larrañeta and
• Itziar Vélaz

Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330

• physically cross-linked hydrogels have recently received attention as potential injectable and encapsulation materials. Poloxamers (Pluronics) are triblock copolymers comprised of polyethylene oxide (PEO) and polypropylene oxide (PPO) blocks. Poloxamines (Tetronics) are x-shaped copolymers comprised of four

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

• hydroxy groups on the narrow rim and C2 and C3 secondary groups on the wider rim, enables encapsulation of hydrophobic molecules inside their cavity. Since the 1950s, it has been demonstrated that CDs can form non-covalent-force complexes in water due to their unique spatial arrangement. In particular, β

A study on the inhibitory mechanism for cholesterol absorption by α-cyclodextrin administration

• Takahiro Furune,
• Naoko Ikuta,
• Yoshiyuki Ishida,
• Hinako Okamoto,
• Daisuke Nakata,
• Keiji Terao and
• Norihiro Sakamoto

Beilstein J. Org. Chem. 2014, 10, 2827–2835, doi:10.3762/bjoc.10.300

• various effects on stabilization of fatty acids, flavor retention and emulsion formation of triglycerides via the formation of an inclusion complex [4][6][7][8]. α-CD is not used only as an encapsulation agent but also as a water-soluble dietary fiber. Furthermore, it has been reported that α-CD intake

Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

• Daniel I. Hădărugă,
• Nicoleta G. Hădărugă,
• Corina I. Costescu,
• Ioan David and
• Alexandra T. Gruia

Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298

• , linalool or caryophyllene, with allergenic and skin sensitization properties [29]. The formation of these harmful oxi-derivatives is supported by the access of oxygen/air to the reaction site of the terpene molecule. This reaction could be significantly reduced by molecular encapsulation of the bioactive

• compounds. One of the most frequently used matrices for molecular encapsulation, protection against oxidation or other degradation processes, as well as controlled release of relatively small bioactive compounds, are cyclodextrins (CDs) [30][31][32][33][34][35]. These are cyclic oligosaccharides consisting

• ][42][43][44][45]. The main compounds from O. basilicum L. essential oil, linalool and methylchavicol, have been used as guests for bicomponent encapsulation in CDs [39][41][46][47]. Linalool was encapsulated in β-CD [41] and its derivative 2-hydroxypropyl-β-CD [39] with good results and the complex

Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes

• Bodee Nutho,
• Wasinee Khuntawee,
• Chompoonut Rungnim,
• Piamsook Pongsawasdi,
• Peter Wolschann,
• Alfred Karpfen,
• Nawee Kungwan and
• Thanyada Rungrotmongkol

Beilstein J. Org. Chem. 2014, 10, 2789–2799, doi:10.3762/bjoc.10.296

• to investigate the preferential binding mode and encapsulation of the flavonoid fisetin in the nano-pore of β-cyclodextrin (β-CD) at the molecular level using various theoretical approaches: molecular docking, molecular dynamics (MD) simulations and binding free energy calculations. The molecular

• other oxygen atoms. In complex I, more water molecules can be accessible to solvate the O3 and O3' atoms located at the wider rim of cyclodextrin by 0.7/0.9 and 0.5/0.4 molecules relative to those of complex II/III, respectively. By the well-formed encapsulation of fisetin in the hydrophobic cavity of β

Anomalous diffusion of Ibuprofen in cyclodextrin nanosponge hydrogels: an HRMAS NMR study

• Monica Ferro,
• Franca Castiglione,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2014, 10, 2715–2723, doi:10.3762/bjoc.10.286

• ) giving two different products (Scheme 1). Drug loading and NMR samples preparation The encapsulation of IP in CDNSEDTA 1:4 and CDNSEDTA 1:8 for the preparation of the loaded gels for HRMAS NMR analysis was done in three steps: (1) A 0.27 M stock solution of Ibuprofen sodium salt was prepared by

Linear-g-hyperbranched and cyclodextrin-based amphiphilic block copolymer as a multifunctional nanocarrier

• Yamei Zhao,
• Wei Tian,
• Guang Yang and
• Xiaodong Fan

Beilstein J. Org. Chem. 2014, 10, 2696–2703, doi:10.3762/bjoc.10.284

• Technology, School of Science, Northwestern Polytechnical University, Xi’an, 710072, P. R. China 10.3762/bjoc.10.284 Abstract In this paper, a novel, multifunctional polymer nanocarrier was designed to provide adequate volume for high drug loading, to afford a multiregion encapsulation ability, and to

• time, is very important and necessary for DDS [20]. On the other hand, some new functionalities for ABC micelles could be developed and expanded. For example, multiregion encapsulation ability, where various drugs can be encapsulated simultaneously in the core and shell layers of ABC micelles, could be

• (Scheme 1D) and simultaneously perform three functionalities including high loading, multiregion encapsulation, and controlled release (Scheme 1E). As prepared ABC, consisting of two hydrophobic poly[2-hydroxyethyl methacrylate] (PHEMA) blocks and one hydrophilic poly(N,N-dimethylaminoethyl methacrylate

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• hosts are probably the cyclodextrins (CDs). CDs can form water-soluble complexes with numerous hydrophobic compounds. They have been widespread used in medicine, drug delivery and are of interest for the biocides encapsulation. Indeed, this enables the development of more or less complex systems that

• release antimicrobial agents with time. In this paper, the general features of CDs and their applications in the field of biocides have been reviewed. As the key point is the formation of biocide–CD inclusion complexes, this review deals with this in depth and the advantages of biocide encapsulation are

• : cyclodextrin; biocide; encapsulation; host–guest chemistry; pathogen; textile; Introduction Since the first reference to cyclodextrins (CDs) in 1891 by Villiers, CD has been of great interest to researchers [1]. Cyclodextrins are composed of several α-D-glucopyranose units linked 1→4 and arranged in a conical

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

• Chrysie Aggelidou,
• Theodossis A. Theodossiou,
• Antonio Ricardo Gonçalves,
• Mariza Lampropoulou and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 2414–2420, doi:10.3762/bjoc.10.251

• hydrophobic cavity [7]. The cyclodextrins (CDs) are a notable family of semi-natural carbohydrate molecules approved as pharmaceutical excipients that improve the solubility and bioavailability of drugs through molecular encapsulation. We demonstrated [6] the conjugate’s (PpIX-CD) bimodal action of

• amino groups is expected to play a major role in the interaction with the anionic parts of phospholipids, rather than the β-CD cavity and its encapsulation ability of hydrophobic membrane components. Conclusion The present work demonstrates the synthesis and characterization of the bimodal conjugate

Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

• Miriana Kfoury,
• David Landy,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

• limited water solubility, stability and poor bioavailability [8][9]. Thus, their encapsulation may enhance their apparent solubility without losing their structural integrity and bioactivity. During the past years, cyclodextrins (CDs) have been widely used as encapsulating agents to enhance the solubility