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

• reported that depletion of cholesterol by methyl-β-cyclodextrin could inhibit EGFR signals, induce apoptosis, and suppress tumor growth in colon tumor-induced mice [57]. Shimolina et al. evaluated membrane fluidity in CT26 and HeLa Kyoto cells treated with cisplatin in a monolayer conventional cell culture

• anticancer medicines [68][69][70]. It was reported that cholesterol content is related to metastasis and tumor growth in oral squamous cell carcinoma, and cholesterol depletion using methyl-β-cyclodextrin caused an increase in the expression of stem cell markers in cancer cell lines [71]. According to a

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• complexation mode of the inclusion complexes involving 4-thiothymidine (S4TdR, a known photosensitizer) and five CDs, namely 2-hydroxypropyl-α-cyclodextrin (2-HP-α-CD), 2-hydroxypropyl-β-cyclodextrin (2-HP-β-CD), 2-hydroxypropyl-γ-cyclodextrin (2-HP-γ-CD), heptakis-(2,6-di-O-methyl)-β-cyclodextrin (DIMEB CD

• ) and heptakis-(2,3,6-tri-O-methyl)-β-cyclodextrin (TRIMEB CD) were investigated by different spectroscopic techniques (UV–vis, FTIR–ATR, 1H NMR) and cyclic voltammetry analysis (CV). This work is necessary for a prospective research on the photoreactivity of S4TdR in aqueous environment and in the

Polydisperse methyl β-cyclodextrin–epichlorohydrin polymers: variable contact time ¹³C CP-MAS solid-state NMR characterization

• Isabelle Mallard,
• Davy Baudelet,
• Franca Castiglione,
• Monica Ferro,
• Walter Panzeri,
• Enzio Ragg and
• Andrea Mele

Beilstein J. Org. Chem. 2015, 11, 2785–2794, doi:10.3762/bjoc.11.299

Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin

• Waratchada Sangpheak,
• Jintawee Kicuntod,
• Roswitha Schuster,
• Thanyada Rungrotmongkol,
• Peter Wolschann,
• Nawee Kungwan,
• Helmut Viernstein,
• Monika Mueller and
• Piamsook Pongsawasdi

Beilstein J. Org. Chem. 2015, 11, 2763–2773, doi:10.3762/bjoc.11.297

• improve physical properties and biological activities of the two flavanones hesperetin and naringenin by complexation with β-cyclodextrin (β-CD) and its methylated derivatives (2,6-di-O-methyl-β-cyclodextrin, DM-β-CD and randomly methylated-β-CD, RAMEB). The free energies of inclusion complexes between

• )-glycosidic bonds. It contains a highly hydrophobic central cavity and the hydrophilic outer surface. The 2,6-di-O-methyl-β-cyclodextrin (DM-β-CD), a commercially available β-CD derivative, is obtained by methylation of the hydroxy groups at C2 and C6 of all glucose units, thus having the degree of

Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels

• Shintaro Kawano,
• Toshiyuki Kida,
• Mitsuru Akashi,
• Hirofumi Sato,
• Motohiro Shizuma and
• Daisuke Ono

Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257

• -active property. Results: CD nanogels were prepared by crosslinking heptakis(2,6-di-O-methyl)-β-cyclodextrin with phenyl diisocyanate and subsequent immersion of the resulting polymer in water. A dynamic light scattering study shows that primary CD nanogels with 30–50 nm diameter assemble into larger CD

• new building blocks for microcapsules with porous surfaces and stimuli-responsive nanocarriers in storage and/or release systems. Experimental Materials Heptakis(2,6-di-O-methyl)-β-cyclodextrin (DM-β-CD) was purchased from Nacalai Tesque, Inc. (Japan). DM-β-CD was vacuum dried at 80 °C overnight prior

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

• /bjoc.10.325 Abstract The mono-6-deoxy-6-azides of 2,6-di-O-methyl-β-cyclodextrin (DIMEB) and randomly methylated-β-cyclodextrin (RAMEB) were conjugated to propargylated hydroxyethyl starch (HES) by Cu+-catalysed [2 + 3] cycloaddition. The resulting water soluble polymers showed lower critical solution

• -azido-heptakis(2,6-di-O-methyl)-β-cyclodextrin (1a): 3.0 g (2.59 mmol) mono-(6-deoxy-6-azido)-β-CD was dissolved in 150 mL DMF/DMSO 1:1 (v/v) under N2 and a mixture of 26 g (168 mmol) BaO and 26 g Ba(OH)2 (153 mmol) was added in small portions within 10 min under stirring. The mixture was cooled to 0 °C

Modification of physical properties of poly(L-lactic acid) by addition of methyl-β-cyclodextrin

• Toshiyuki Suzuki,
• Ayaka Ei,
• Yoshihisa Takada,
• Hiroki Uehara,
• Takeshi Yamanobe and
• Keiko Takahashi

Beilstein J. Org. Chem. 2014, 10, 2997–3006, doi:10.3762/bjoc.10.318

• PLLA and enhanced the drawability. Keywords: crystallinity; DSC; methyl-β-cyclodextrin; poly(L-lactic acid); Raman spectroscopy; Introduction Poly(L-lactic acid) (PLLA) has attracted attention because it is a biodegradable polymer derived from carbon-neutral resources. However, its melting point (Tm

• interactions, a modified CD may improve the mechanical properties of PLLA. Methyl-β-cyclodextrin (MeCD) is soluble in chloroform, as is PLLA, and the affinity of MeCD for PLLA may be sufficient to improve the mechanical properties of PLLA. In order to analyze the interchain interactions of polymers, it is

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

• Dyanne L. Cruickshank,
• Natalia M. Rougier,
• Raquel V. Vico,
• Susan A. Bourne,
• Elba I. Buján,
• Mino R. Caira and
• Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117, doi:10.3762/bjoc.9.14

• )phosphorothioate] and the host compound heptakis(2,6-di-O-methyl)-β-cyclodextrin (DIMEB) was prepared and its structure elucidated by single-crystal X-ray diffraction. This revealed two independent host molecules in the asymmetric unit. In one of these, the cavity is occupied by two disordered guest components

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

• Robert Hilgraf,
• Nicole Zimmermann,
• Lutz Lehmann,
• Armin Tröger and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1256–1264, doi:10.3762/bjoc.8.141

• mixture of OV1701 and heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin as an enantioselective stationary phase. Figure 3 shows the structures and retention times of all eight stereoisomers of trans-fused iridomyrmecins on both capillary column systems. Despite the small differences in

• Y and Z to show the same mass spectra and retention times as the two early eluting racemates of the synthetic iridomyrmecins, i.e., B/B' and A/A', respectively (Figure 3). Enantioselective gas chromatography on heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin showed that A and A

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

• Nicole Zimmermann,
• Robert Hilgraf,
• Lutz Lehmann,
• Daniel Ibarra and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1246–1255, doi:10.3762/bjoc.8.140

• 1:1-mixture of OV1701 and heptakis-(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin as an optically active stationary phase. Figure 3 shows the corresponding retention times of all eight stereoisomers that were obtained with the two used capillary column systems. Coupled GC/MS using FFAP

Free radical homopolymerization of a vinylferrocene/cyclodextrin complex in water

• Helmut Ritter,
• Beate E. Mondrzik,
• Matthias Rehahn and
• Markus Gallei

Beilstein J. Org. Chem. 2010, 6, No. 60, doi:10.3762/bjoc.6.60

• insoluble in water. Complexation of 1 with methyl-β-cyclodextrin 2 results in clearly water-soluble structures due to incorporation of the ferrocene moiety into the cyclodextrin cavity. After free radical polymerization of the water-soluble complexed monomer, corresponding to polyvinylferrocene (PVFc), the

• homopolymerization of vinylferrocene 1 as a guest in the host methyl-β-cyclodextrin (methyl-β-CD) 2. The stability of the resulting complexed polymers in water is also reported. Results and Discussion Vinylferrocene 1 was added to an aqueous solution of methyl-β-CD 2 and the complex obtained was subjected to radical

• cyclodextrin ring. Experimental Part Materials and Instrumentation Methyl-β-cyclodextrin was obtained from Wacker-Chemie GmbH, Burghausen, Germany, and used after drying overnight with a vacuum oil pump over P4O10. Dimethyl-d6 sulfoxide (99.9 atom % D) was obtained from Euriso-Top SA, France. 2,2-Azobis[2-(2