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Methyl cyclodextrin

Danielle M Bailey, Mackenzie A Catron, Oleg Kovtun, Robert L Macdonald, Qi Zhang, Sandra J Rosenthal
Serotonin transporter (SERT) terminates serotonin signaling in the brain by enabling rapid clearance of the neurotransmitter. SERT dysfunction has been associated with a variety of psychiatric disorders, including depression, anxiety, and autism. Visualizing SERT behavior at the single molecule level in endogenous systems remains a challenge. In this study, we utilize quantum dot (QD) single particle tracking (SPT) to capture SERT dynamics in primary rat midbrain neurons. Membrane microenvironment, specifically membrane cholesterol, plays a key role in SERT regulation and has been found to affect SERT conformational state...
May 24, 2018: ACS Chemical Neuroscience
Lajos Szente, Ashutosh Singhal, Andras Domokos, Byeongwoon Song
Cyclodextrins (CDs) are cyclic oligosaccharides; the most common CDs contain six, seven, or eight glucose units called α-CDs, β-CDs, and γ-CDs, respectively. The use of CDs in biomedical research is increasing due to their ability to interact with membrane lipids as well as a wide variety of poorly water-soluble molecules. We assessed the impact of CD cavity size, occupancy, and substitutions on cytotoxicity and cholesterol homeostasis. The potency of CD-mediated cytotoxicity was in the order of β-CDs, α-CDs, and γ-CDs...
May 20, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Sandrine L Verstraeten, Marie Albert, Adrien Paquot, Giulio G Muccioli, Donatienne Tyteca, Marie-Paule Mingeot-Leclercq
Saponins exhibit several biological and pharmacological activities, such as antibacterial, anti-inflammatory and anticancer effects. Many studies attribute their activities to their interactions with cholesterol. In this study, we focus on the steroid saponin ginsenoside Rh2, one of the active principles of Panax ginseng root. Some evidence suggests that lipid rafts, defined as nanodomains enriched in cholesterol and sphingolipids, could be involved in the Rh2-induced apoptosis. However, the role of membrane lipids, especially cholesterol, in this process is still poorly understood...
May 18, 2018: Toxicology and Applied Pharmacology
Saharat Jantaratrirat, Chompunuch Boonarkart, Kanyarat Ruangrung, Ornpreya Suptawiwat, Prasert Auewarakul
Microparticles (MPs) are vesicles that are released by budding from plasma membrane of living cells. Recently, the role of MPs in antiviral activity has been proposed. We investigated quantity and anti-influenza activity of MPs from human alveolar epithelial cells A549, human bronchial epithelial cells BEAS-2B, human colon adenocarcinoma cells HT-29, and the human lung fibroblast cells MRC-5. MPs were found from all four cell lines. However, anti-influenza activity against an H1N1 influenza virus was found only from MPs of A549 and BEAS-2B...
May 21, 2018: Viral Immunology
Shuang Bai, Meili Hou, Xiaoxiao Shi, Jiucun Chen, Xiaoqian Ma, Yong-E Gao, Yajun Wang, Peng Xue, Yuejun Kang, Zhigang Xu
As one of the medical polymers approved by US Food and Drug Administration (FDA), poly(ethylene glycol) has low toxicity, high stability, good biocompatibility, unique physical and chemical properties. Cyclodextrin is an ideal candidate as a drug carrier due to its special structures and characteristics. These two materials were successfully assembled through chemosynthesis in combination with the hydrophilic poly(ethylene glycol) methyl ether methacrylate (OEGMA) chain and hydrophobic polymeric camptothecin (CPT) chain by atom transfer radical polymerization (ATRP)...
August 1, 2018: Carbohydrate Polymers
Elisa I León, Angeles Martín, Inés Pérez-Martín, Ernesto Suárez
The generation and fate of 2I-VII ,3I-VII ,6II-VII -icosa- O-methyl-β-cyclomaltoheptaos-6I - O-yl radical under reductive conditions is described. Two radical cascade reactions are involved: the main one is triggered by a 1,8-HAT of the hydrogen at 5VII C. The radical can reach the anomeric hydrogen at 1V C three sugar units ahead using a six-step sequence. The different hydrogen donor ability of the group 14 hydrides permits one to selectively stop the cascade at 5VII C, 2VI C, and 4VI C to obtain β-CD with a β-l-Ido p unit, acyclic hepta-, and hexa-saccharide structures, respectively...
May 16, 2018: Organic Letters
Ornin Srihakulung, Ryo Maezono, Pisanu Toochinda, Waree Kongprawechnon, Apichart Intarapanich, And Luckhana Lawtrakul
Molecular interactions of plumbagin inclusion complexes with β-cyclodextrin (BCD), dimethyl--cyclodextrin (MBCD), and hydroxypropyl-β-cyclodextrin (HPBCD) were investigated by semi-empirical, Parameterization Method 6 and 7 (PM6, and PM7) in the aqueous phase using polarizable continuum calculations. The results revealed two different binding modes of the plumbagin molecule inside the BCD cavity with a negative value of the complexation energy. In conformation-I, the hydroxyl phenolic group of plumbagin was placed in the BCD cavity near the narrow-side of the host molecule...
May 15, 2018: Scientia Pharmaceutica
Nehman Makdissy, Katia Haddad, Jeanne D'arc AlBacha, Diana Chaker, Bassel Ismail, Albert Azar, Ghada Oreibi, David Ayoub, Ibrahim Achkar, Didier Quilliot, Ziad Fajloun
BACKGROUND: The subcellular distribution of prorenin receptor and adaptor protein ATP6AP2 may affect neurogenesis. In this study, we hypothesized that ATP6AP2 expression and subcellular relocalization from caveolae/lipid raft microdomains (CLR-Ms) to intracellular sites may correlate with neuronal differentiation (Neu-Dif) of adipose-derived mesenchymal stem cells (ADSCs). METHODS: Human ADSCs isolated from 24 healthy donors and 24 patients with neurological disorders (ND) were cultured and induced for Neu-Dif...
May 11, 2018: Stem Cell Research & Therapy
Ling Chen, Xueping Dang, Youhong Ai, Huaixia Chen
An acryloyl β-cyclodextrin-silica hybrid monolithic column for pipette tip solid-phase extraction and high-performance liquid chromatography determination of methyl parathion and fenthion have been prepared through a sol-gel polymerization method. The synthesis conditions, including the volume of cross-linker and the ratio of inorganic solution to organic solution, were optimized. The prepared monolithic column was characterized by thermogravimetric analysis, scanning electron microscopy and Fourier transform infrared spectroscopy...
May 7, 2018: Journal of Separation Science
Yumeng Zhang, Lin Chen, Yuanqi Lv, Shuangxi Wang, Zhiyao Suo, Xingguang Cheng, Xinglian Xu, Guanghong Zhou, Zhixi Li, Xianchao Feng
High levels of polyphenols can interact with myofibrillar proteins (MPs), causing damage to a MP emulsion gel. In this study, β-cyclodextrins were used to reduce covalent and non-covalent interaction between epigallocatechin-3-gallate (EGCG) and MPs under oxidative stress. The loss of both thiol and free amine groups and the unfolding of MPs caused by EGCG (80 μM/g protein) were significantly prevented by β-cyclodextrins, and the structural stability and solubility were improved. MP emulsion gel treated with EGCG (80 μM/g protein) had the highest cooking loss (68...
June 2018: Food Research International
Anna Maria Piras, Angela Fabiano, Federica Chiellini, Ylenia Zambito
Purpose: The present study aimed to compare a novel cyclodextrin-polymer-drug complex in solution with a dispersed supramolecular nanosize system, made of the same complex, for ability to carry dexamethasone (DEX) across excised rat intestine. Results: Methyl-β-cyclodextrin-quaternary ammonium chitosan conjugate (QA-Ch-MCD) was obtained by covalent grafting through a 10-atom spacer. The conjugate was characterized by 1 H-NMR, resulting in 24.4% w/w of MCD content...
2018: International Journal of Nanomedicine
Sophia Malli, Christian Bories, Gilles Ponchel, Philippe M Loiseau, Kawthar Bouchemal
Metronidazole (MTZ) is a 5-nitroimidazole drug used for the treatment of Trichomonas vaginalis parasitic infection. Aqueous formulations containing MTZ are restricted because apparent solubility in water of this drug is low. In this context, two methylated-β-cyclodextrins (CRYSMEB and RAMEB) were used as a tool to increase apparent solubility of MTZ in water. CRYSMEB was limited by its own solubility in water (15% w/w, 12.59 mM), while RAMEB at a concentration of 40% w/w (300.44 mM) allowed a maximal increase of apparent solubility of MTZ (3...
April 27, 2018: Experimental Parasitology
Agnieszka Partyka, Maciej Strojecki, Wojciech Niżański
This study was designed to test if treating chicken sperm with i) the cyclodextrins 2-hydroxypropyl-β-cyclodextrin (HBCD) and methyl-β-cyclodextrin (MBCD) alone improve fresh, liquid-stored and cryopreserved semen quality, or ii) cholesterol-loaded cyclodextrins (CLCs): 2-hydroxypropyl-β-cyclodextrin loaded with cholesterol (HCLC) and methyl-β-cyclodextrin loaded with cholesterol (MCLC) enhance chicken semen quality for application to assisted reproductive technologies. Three consecutive experiments were performed with different concentrations of additives: Exp...
April 21, 2018: Animal Reproduction Science
Natthapol Issaraseriruk, Yongsak Sritana-Anant, Aroonsiri Shitangkoon
Chiral resolutions of trifluoroacetyl-derivatized 1-phenylalkylamines with different type and position of substituent were investigated by capillary gas chromatography by using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin diluted in OV-1701 as a chiral stationary phase. The influence of column temperature on retention and enantioselectivity was examined. All enantiomers of meta-substituted analytes as well as fluoro-substituted analytes could be resolved. Temperature had a favorable influence on enantioselectivity for small amines with substituents at the ortho-position...
April 25, 2018: Chirality
Kei Nishida, Atsushi Tamura, Nobuhiko Yui
In prior research, it has been demonstrated that methylated β-cyclodextrins-threaded acid-labile polyrotaxanes (Me-PRXs) exhibit a lower critical solution temperature (LCST) and form coacervate droplets above their LCST. In this study, the encapsulation of proteins in coacervate droplets and the pH-responsive release of proteins, through the acid-induced dissociation of the Me-PRX, were investigated. The coacervate droplets encapsulate various proteins, such as bovine serum albumin (BSA), lysozyme, and β-galactosidase, at pH 7...
April 24, 2018: Biomacromolecules
Olena Yakymenko, Ida Schoultz, Elisabeth Gullberg, Magnus Ström, Sven Almer, Conny Wallon, Arthur Wang, Åsa V Keita, Barry J Campbell, Derek M McKay, Johan D Söderholm
OBJECTIVE: Infliximab is important in the therapeutic arsenal of Crohn's disease (CD). However, its effect on mucosal barrier function is not fully understood. Adherent-invasive Escherichia coli (AIEC) are important in CD pathophysiology, but the transmucosal uptake routes are partly unknown. We investigated effects of infliximab on uptake of colon-specific AIEC HM427 across CD colonic mucosa. MATERIALS AND METHODS: Endoscopic biopsies from non-inflamed colon of seven patients with CD, before and after two infliximab infusions, and eight non-inflammation controls, were mounted in Ussing chambers...
April 24, 2018: Scandinavian Journal of Gastroenterology
Anh Khoa Nguyen, Thi Hiep Nguyen, Bui Quoc Bao, Long Giang Bach, Dai Hai Nguyen
Porous nanosilica (PNS) has been regarded as a promising candidate for controlled delivery of anticancer drugs. Unmodified PNS-based nanocarriers, however, showed a burst release of encapsulated drugs, which may limit their clinical uses. In this report, PNS was surface conjugated with adamantylamine (ADA) via disulfide bridges (-SS-), PNS-SS-ADA, which was further modified with cyclodextrin-poly(ethylene glycol) methyl ether conjugate (CD-mPEG) to form a core@shell structure PNS-SS-ADA@CD-mPEG for redox triggered delivery of doxorubicin (DOX), DOX/PNS-SS-ADA@CD-mPEG...
2018: International Journal of Biomaterials
Carolyn Vargas, Christian Schönbeck, Ina Heimann, Sandro Keller
Cyclodextrin (CD) complexation is a convenient method to sequester surfactants in a controllable way, for example, during membrane-protein reconstitution. Interestingly, the equilibrium stability of CD/surfactant inclusion complexes increases with the length of the nonpolar surfactant chain even beyond the point where all hydrophobic contacts within the canonical CD cavity are saturated. To rationalize this observation, we have dissected the inclusion complexation equilibria of a structurally well-defined CD, that is, heptakis(2,6-di-O methyl)-CD (DIMEB), and a homologous series of surfactants, namely, n alkyl-N,N dimethyl-3 ammonio-1 propanesulfonates (SB3 x) with chain lengths ranging from x = 8 to 14...
April 23, 2018: Langmuir: the ACS Journal of Surfaces and Colloids
Hiroaki Kitagishi, Daiki Shimoji, Takehiro Ohta, Ryo Kamiya, Yasuhiro Kudo, Akira Onoda, Takashi Hayashi, Jean Weiss, Jennifer A Wytko, Koji Kano
In mitochondria, cytochrome c oxidase (C c O) catalyses the reduction of oxygen (O2 ) to water by using a heme/copper hetero-binuclear active site. Here we report a highly efficient supramolecular approach for the construction of a water-soluble biomimetic model for the active site of C c O. A tridentate copper(ii) complex was fixed onto 5,10,15,20-tetrakis(4-sulfonatophenyl)porphinatoiron(iii) (FeIII TPPS) through supramolecular complexation between FeIII TPPS and a per- O -methylated β-cyclodextrin dimer linked by a (2,2':6',2''-terpyridyl)copper(ii) complex (CuII TerpyCD2 )...
February 21, 2018: Chemical Science
Nicolas Chuard, Amalia I Poblador-Bahamonde, Lili Zong, Eline Bartolami, Jana Hildebrandt, Wolfgang Weigand, Naomi Sakai, Stefan Matile
The emerging power of thiol-mediated uptake with strained disulfides called for a move from sulfur to selenium. We report that according to results with fluorescent model substrates, cellular uptake with 1,2-diselenolanes exceeds uptake with 1,2-dithiolanes and epidithiodiketopiperazines with regard to efficiency as well as intracellular localization. The diselenide analog of lipoic acid performs best. This 1,2-diselenolane delivers fluorophores efficiently to the cytosol of HeLa Kyoto cells, without detectable endosomal capture as with 1,2-dithiolanes or dominant escape into the nucleus as with epidithiodiketopiperazines...
February 21, 2018: Chemical Science
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