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Methyl cyclodextrin

Martina Cugovčan, Jasna Jablan, Jasmina Lovrić, Dominik Cinčić, Nives Galić, Mario Jug
Mechanochemical activation using several different co-grinding additives was applied as a green chemistry approach to improve physiochemical and biopharmaceutical properties of praziquantel (PZQ). Liquid assisted grinding with an equimolar amount of citric acid (CA), malic acid (MA), salicylic acid (SA) and tartaric acid (TA) gained in cocrystal formation, which all showed pH-dependent solubility and dissolution rate. However, the most soluble cocrystal of PZQ with MA was chemically unstable, as seen during the stability testing...
January 10, 2017: Journal of Pharmaceutical and Biomedical Analysis
Huichen Guo, Mei Huang, Quan Yuan, Yanquan Wei, Yuan Gao, Lejiao Mao, Lingjun Gu, Yong Wah Tan, Yanxin Zhong, Dingxiang Liu, Shiqi Sun
Lipid raft is an important element for the cellular entry of some viruses, including coronavirus infectious bronchitis virus (IBV). However, the exact role of lipid rafts in the cellular membrane during the entry of IBV into host cells is still unknown. In this study, we biochemically fractionated IBV-infected cells via sucrose density gradient centrifugation after depleting plasma membrane cholesterol with methyl-β-cyclodextrin or Mevastatin. Our results demonstrated that unlike IBV non-structural proteins, IBV structural proteins co-localized with lipid raft marker caveolin-1...
2017: PloS One
Hiroko Ohtsuka, Tomohiro Iguchi, Moyuru Hayashi, Mizuho Kaneda, Kazuko Iida, Motoyuki Shimonaka, Takahiko Hara, Morio Arai, Yuichi Koike, Naomasa Yamamoto, Kohji Kasahara
Stromal cell-derived factor-1α (SDF-1α)-induced platelet aggregation is mediated through its G protein-coupled receptor CXCR4 and phosphatidylinositol 3 kinase (PI3K). Here, we demonstrate that SDF-1α induces phosphorylation of Akt at Thr308 and Ser473 in human platelets. SDF-1α-induced platelet aggregation and Akt phosphorylation are inhibited by pretreatment with the CXCR4 antagonist AMD3100 or the PI3K inhibitor LY294002. SDF-1α also induces the phosphorylation of PDK1 at Ser241 (an upstream activator of Akt), GSK3β at Ser9 (a downstream substrate of Akt), and myosin light chain at Ser19 (a downstream element of the Akt signaling pathway)...
2017: PloS One
Z I Krutetskaya, L S Milenina, A A Naumova, S N Butov, V G Antonov, A D Nozdrachev
Using Fura-2AM microfluorimetry, we have shown for the first time that methyl-β-cyclodextrin, inducing cholesterol extraction from membranes and raft disruption, significantly inhibits glutoxim- and molixan-induced Ca(2+)-responses in rat peritoneal macrophages. The results suggest that intact rafts are necessary for signaling cascade induced by glutoxim or molixan and leading to intracellular Ca(2+) concentration increase in macrophages.
November 2016: Doklady. Biochemistry and Biophysics
Anil Badana, Madhuri Chintala, Gayathri Varikuti, Nagaseshu Pudi, Seema Kumari, Vijaya Rachel Kappala, Rama Rao Malla
PURPOSE: Lipid rafts are cholesterol enriched microdomains that colocalize signaling pathways involved in cell proliferation, metastasis, and angiogenesis. We examined the effect of methyl-β-cyclodextrin (MβCD)-mediated cholesterol extraction on the proliferation, adhesion, invasion, and angiogenesis of triple negative breast cancer (TNBC) cells. METHODS: We measured cholesterol and estimated cell toxicity. Detergent resistant membrane (DRM) and non-DRM fractions were separated using the OptiPrep gradient method...
December 2016: Journal of Breast Cancer
Teruhiko Matsubara, Ryohei Otani, Miki Yamashita, Haruka Maeno, Hanae Nodono, Toshinori Sato
Glycosphingolipids are major components of the membrane raft, and several kinds of viruses and bacterial toxins are known to bind to glycosphingolipids in the membrane raft. Since the viral genes and pathogenic proteins that are taken into cells are directly delivered to their target organelles, caveolae/raft-mediated endocytosis represents a promising pathway for specific delivery. In the present study, we demonstrated the ability of an artificial pentadecapeptide, which binds to ganglioside GM3, to deliver protein into cells by caveolae/raft-mediated endocytosis...
January 4, 2017: Biomacromolecules
Juu-Chin Lu, Yu-Ting Chiang, Yu-Chun Lin, Yu-Tzu Chang, Chia-Yun Lu, Tzu-Yu Chen, Chia-Shan Yeh
The adipocyte is unique in its capacity to store lipids. In addition to triglycerides, the adipocyte stores a significant amount of cholesterol. Moreover, obese adipocytes are characterized by a redistribution of cholesterol with depleted cholesterol in the plasma membrane, suggesting that cholesterol perturbation may play a role in adipocyte dysfunction. We used methyl-β-cyclodextrin (MβCD), a molecule with high affinity for cholesterol, to rapidly deplete cholesterol level in differentiated 3T3-L1 adipocytes...
2016: PloS One
LaVana Greene, Brianda Elzey, Mariah Franklin, Sayo O Fakayode
The negative health impact of polycyclic aromatic hydrocarbons (PAHs) and differences in pharmacological activity of enantiomers of chiral molecules in humans highlights the need for analysis of PAHs and their chiral analogue molecules in humans. Herein, the first use of cyclodextrin guest-host inclusion complexation, fluorescence spectrophotometry, and chemometric approach to PAH (anthracene) and chiral-PAH analogue derivatives (1-(9-anthryl)-2,2,2-triflouroethanol (TFE)) analyses are reported. The binding constants (Kb), stoichiometry (n), and thermodynamic properties (Gibbs free energy (ΔG), enthalpy (ΔH), and entropy (ΔS)) of anthracene and enantiomers of TFE-methyl-β-cyclodextrin (Me-β-CD) guest-host complexes were also determined...
December 5, 2016: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Leo-Paul Tisserant, Aziz Aziz, Nathalie Jullian, Philippe Jeandet, Christophe Clément, Eric Courot, Michèle Boitel-Conti
Stilbenes are defense molecules produced by grapevine in response to stresses including various elicitors and signal molecules. Together with their prominent role in planta, stilbenes have been the center of much attention in recent decades due to their pharmaceutical properties. With the aim of setting up a cost-effective and high purity production of resveratrol derivatives, hairy root lines were established from Vitis vinifera cv Pinot Noir 40024 to study the organ-specific production of various stilbenes...
December 10, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Young-Jun Shim, Yoo-Keung Tae, Byeong-Ho Kang, Jin-Sung Park, Sol-Yi Jeon, Bon-Hong Min
Clusterin is a secretory glycoprotein that is up-regulated in areas of inflammation and under increased levels of oxidative stress. Previously, we demonstrated that clusterin activates NF-κB, and up-regulates the expression of MMP-9 and TNF-α. In this research, we extend our previous findings by reporting that such clusterin-induced macrophage response is mediated via TLR4 signaling. Specifically, we found that TNF-α induced by clusterin was significantly abrogated by pretreatment of TLR4-signaling inhibitors and anti-TLR4 neutralizing antibody...
January 22, 2017: Biochemical and Biophysical Research Communications
Margarita Valero, Franca Castiglione, Andrea Mele, Marcelo A da Silva, Isabelle Grillo, Gustavo González-Gaitano, Cécile A Dreiss
Polymeric micelles, in particular PEO-PPO-based Pluronic, have emerged as promising drug carriers, while cyclodextrins (CD), cyclic oligosaccharides with an apolar cavity, have long been used for their capacity to form inclusion complexes with drugs. Dimethylated β-cyclodextrin (DIMEB) has the capacity to fully breakup F127 Pluronic micelles, while this effect is substantially hindered if drugs are loaded within the micellar aggregates. Four drugs were studied at physiological temperature: lidocaine (LD), pentobarbital sodium salt (PB), sodium naproxen (NP), and sodium salicylate (SAL); higher temperatures shift the equilibrium toward higher drug partitioning and lower drug/CD binding compared to 25 °C ( Valero, M...
December 13, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
Keisuke Ikeda, Minoru Nakano
Here, we report an experimental approach for determining the change in the free energy and the enthalpy that accompanies the mixing of the anionic phosphatidylglycerol and the zwitterionic phosphatidylcholine. The enthalpy change originates in the thermal changes of disrupting lipid bilayer vesicles titrated into a surfactant micelle solution and is monitored using isothermal titration calorimetry. The difference in the solubilization enthalpies between pure and mixed lipid vesicles yields the lipid mixing enthalpy...
December 13, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
É De Vuyst, A Mound, C Lambert de Rouvroit, Y Poumay
Most crucial role of epidermis is to maintain efficient barrier between the organism and its environment. This barrier is however perturbed in inflammatory skin conditions like atopic dermatitis (AD), one common chronic disease. This review depicts characteristics of a model intending to reproduce epidermal features of AD in vitro. Firstly, methyl-β-cyclodextrin (MβCD) during reconstruction of epidermis was used to deplete cholesterol from plasma membrane because this condition reproduces characteristics of AD at transcriptomic level in monolayer cultures...
October 2016: Current Research in Translational Medicine
Taichi Sugiura, Keisuke Ikeda, Minoru Nakano
Methyl-β-cyclodextrin (MβCD) can transfer phospholipids between vesicles, and its transfer ability has been utilized for the preparation of asymmetric vesicle and lipid incorporation into culture cells. Nevertheless, a detailed kinetic analysis of the MβCD-mediated phospholipid transfer has not yet been carried out. We performed real-time monitoring of intervesicular lipid transfer by means of the fluorescence of pyrene-labeled phospholipids. Intermolecular excimer formation of the pyrene-labeled lipids in a membrane strongly depends on the local concentration of the fluorophore and decreases when the pyrene-labeled lipids are transferred from donor (fluorophore-containing) vesicles to acceptor (fluorophore-free) vesicles...
December 27, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
Leo-Paul Tisserant, Jane Hubert, Michelle Lequart, Nicolas Borie, Nicolas Maurin, Serge Pilard, Philippe Jeandet, Aziz Aziz, Jean-Hugues Renault, Jean-Marc Nuzillard, Christophe Clément, Michèle Boitel-Conti, Eric Courot
Resveratrol and related oligostilbenes are defense molecules produced by grapevine in response to stresses including various elicitors or signal molecules. Together with their prominent role in planta, these compounds have been the center of much attention in recent decades due to their pharmacological properties. The cost-effective production of resveratrol derivatives such as viniferins or more structurally complex stilbene oligomers remains a challenging task. In this study, the chemical diversity of stilbenes produced by Vitis vinifera Pinot Noir hairy roots was investigated after elicitation for 4 days with a mixture of methyl jasmonate (100 μM) and cyclodextrins (50 mM)...
November 23, 2016: Journal of Natural Products
Reine-Solange Sauer, Heike Lydia Rittner, Norbert Roewer, Tamás Sohajda, Sergey Shityakov, Alexander Brack, Jens-Albert Broscheit
BACKGROUND: Inhibitors of cyclooxygenase, which block the formation of prostaglandin (PG) E2, are the standard treatment of inflammatory pain. These drugs, however, have serious gastrointestinal, renal, and cardiovascular side effects that limit their clinical use. Cyclodextrins are neutral glucose oligomers that form a hydrophilic outer and a hydrophobic interior cavity used to carry hydrophilic substances. Methyl-β-cyclodextrins are used currently in several drugs as enhancers and also to deliver PGs...
December 8, 2016: Anesthesia and Analgesia
Kazunori Kadota, Arisa Senda, Hideaki Tagishi, John Oluwasogo Ayorinde, Yuichi Tozuka
This work aims to identify a suitable formulation for the pulmonary delivery of combinations of inhalational drugs using highly branched cyclic dextrin (HBCD) macromolecules. We compared the effectiveness between powders prepared from HBCD with those prepared from five alternative excipients (lactose, maltose, sucrose, β-cyclodextrin and methyl β-cyclodextrin) in the pulmonary delivery of a single-dosage form of two anti-tuberculosis drugs (isoniazid and rifampicin). Fine particles of untreated active pharmaceutical ingredients (APIs) and combination products using excipients were prepared by spray drying...
November 29, 2016: International Journal of Pharmaceutics
Adrián Matencio, Mario J Bermejo-Gimeno, Francisco García-Carmona, José Manuel López-Nicolás
INTRODUCTION: Several authors have reported on the different bioactivities of methyl jasmonate (MeJA) stereoisomers. However, no simple, precise and cheap method for separating and identifying them using reversed-phase high performance liquid chromatography (RP-HPLC) has been developed. OBJECTIVE: (1) To create a simple, precise and cheap method for separating and identifying the four stereoisomers present in commercial racemic mixtures of MeJA and (2) to identify the four stereoisomers using molecular docking techniques and coinjection...
December 2, 2016: Phytochemical Analysis: PCA
T Iglesias, A López de Cerain, J M Irache, N Martín-Arbella, M Wilcox, J Pearson, A Azqueta
The main concerns with drugs designed for oral administration are their inactivation or degradation in the harsh conditions of the gastrointestinal tract, their poor solubility through the gastrointestinal mucus gel layer, the poor intestinal epithelium permeability that limits their absorption, and their toxicity. In this context, poly(anhydride) nanoparticles are capable of protecting the drug from the harsh environment, reduce the drug's toxicity and, by virtue of surface modification, to enhance or reduce their mucus permeability and the bioadhesion to specific target cells...
November 28, 2016: International Journal of Pharmaceutics
Ayat Allah Al-Massaedh, Ute Pyell
With the aim to improve the understanding of morphology and efficiency properties, we investigate in this series the impact of the complex formation constant of the hydrophobic monomer with respect to statistically methylated-β-cyclodextrin (Me-β-CD) on the electrochromatographic properties of highly crosslinked amphiphilic mixed-mode acrylamide-based monolithic stationary phases. Based on our previous work on amphiphilic mixed-mode monolithic stationary phases for capillary electrochromatography (CEC) using N-(1-adamantyl)acrylamide (Ad-AAm) as hydrophobic monomer that forms an extremely strong water-soluble inclusion complex with Me-β-CD, we now selected N-tert-butylacrylamide (NTBA) as hydrophobic monomer forming an inclusion complex with Me-β-CD with a much lower value of the formation constant...
December 16, 2016: Journal of Chromatography. A
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