Sulfated glycofuranans as inhibitors of melanoma lung metastasis

Kamitakahara, Hiroshi; Nishigaki, Fusako; Mikawa, Yuji; Hori, Michiko; Tsujihata, Shigetomo; Fujii, Takashi; Nakatsubo, Fumiaki

doi:10.1007/bf00771368

Cited by 4 publications

(6 citation statements)

References 17 publications

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“…[8] Thus, a variety of unconventional properties can be expected especially concerning the biological activity as already found for sulfated polysaccharides, e.g., curdlan-and shizophyllan sulfuric acid half esters, which are among the most promising drugs with anti-HIV and cancerostatic activities. [9][10][11] Experimental Part…”

Section: Introductionmentioning

confidence: 99%

Click Chemistry with Polysaccharides

Liebert

Hänsch

Heinze

2006

Macromol. Rapid Commun.

201

132

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Summary: The copper‐catalyzed Huisgen reaction as a typical example of click chemistry was realized with the polysaccharide cellulose for the first time. The generality, selectivity, and the efficiency of click chemistry perfectly fit the requirements of polysaccharide modification, which is demonstrated by the introduction of triazole‐spacer bound functional groups, i.e., carboxylic ester, thiophene, and aniline moieties. Azide moieties introduced into cellulose via the tosyl derivative were simply transferred with ethynyl compounds under Cu(I) catalysis and mild and easily applicable conditions. Hydrolytically stable cellulose derivatives soluble in organic solvents, e.g., DMSO or DMF with DS up to 0.9 are obtained. The triazole substituted cellulose derivatives were characterized by elemental analysis, FTIR, 1H NMR, and 13C NMR spectroscopies and show no impurities or substructures resulting from side reactions.6‐Azido‐6‐deoxy cellulose.image6‐Azido‐6‐deoxy cellulose.

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Section: Introductionmentioning

confidence: 99%

Click Chemistry with Polysaccharides

Liebert

Hänsch

Heinze

2006

Macromol. Rapid Commun.

201

132

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“…Cellulose has broad potential to designing more advanced polymeric materials such as liquid crystalline polymers (Harkness and Gray 1990), welldefined multilayered assemblies (Shaub et al 1993), selective membranes (Hoenich and Stamp 2000), sensor matrixes (Tiller et al 1999), recognition devices (Kubota et al 2001), organic-inorganic complex materials (Hanemann and Ballauff 1997), bioactive and biocompatible materials (Kamitakahara et al 2002) because of its specific structure; strictly linear (1 fi 4)-b-glucan structure and three reactive hydroxyl groups per anhydro glucose unit . One of the interesting attempts is to introduce hydrophobic side chains onto cellulose to yield an amphiphilic polymer that may possibly form a stable monolayer at the air/water interface (Kawaguchi et al 1985).…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of 6-O-(4-stearyloxytrityl)Cellulose acetate Langmuir–Blodgett Films

et al. 2005

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Multilayer films of 2,3-di-O-acetyl-6-O-(4-stearyloxytrityl)cellulose (ASTC) were prepared and investigated. The fairly high surface pressure (p)-area (A) isotherms (36-47 mN/m) suggest that the balky and hydrophobic trityl group contribute to form a condensed monolayer. The cellulose derivative formed a homogeneous monolayer at 10 mN/m. The monolayer on the water surface was transferred successfully at 10 mN/m onto various substrates by modifying the preparation methods, to form Z-type multilayer films. The ultraviolet-visible (UV-Vis) absorbance was independent of the number of layers, indicating that each layer is made of definite number of anhydroglucose unit (AGU). The monolayer thickness determined from atomic force microscope (AFM) and ellipsometry was calculated to be about 1.9 nm, suggesting that the long alkyl chain in the film has a so-called hairy-rod type structure. This is the first paper about the Z-type LB film prepared from cellulose derivatives having long mono-alkyl chain only at 6-O-position.

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“…Cellulose is the most abundant biopolymer and is important as a biodegradable and renewable organic material. Functionalized cellulose has several attractive material properties, such as gelation properties, liquid‐crystalline properties, chiral recognition ability, anticoagulant and metastasis inhibition activities, and antitumor activity 14–18. Wegner and coworkers19, 20 reported the preparation of LB films of trimethylsilylcellulose and the in situ conversion of the thin films on substrates to films of pure cellulose.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of redox cellulose Langmuir–Blodgett films containing a ferrocene derivative

Ifuku

Tsujii

Kamitakahara

et al. 2005

J. Polym. Sci. A Polym. Chem.

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The 3-ferrocenoylpropanoyl group, one of the redox species, was introduced at C-2 and/or C-3 positions of 6-O-(4-stearyloxytrityl)cellulose. The spreading behavior of the cellulose derivatives on the water surface and the properties of Langmuir-Blodgett (LB) films were investigated. The surface pressure-area isotherm of the cellulose monolayer was changed by the subphase temperature. Uniform monolayers of 6-O-(4-stearyloxytrityl)cellulose 3-ferrocene propionate (STCFc) could be deposited successively onto several substrates by the horizontal lifting method at 10 mN m À1 , and this produced X-type LB films. The successive uniform depositions of STCFc were confirmed by ultraviolet-visible absorption spectra. X-ray diffraction measurements indicated that the thickness of the STCFc molecules in the LB films was 1.99 nm. Fourier transform infrared spectroscopy measurements supported the idea that hydrocarbon chains in the LB films were highly ordered (trans-zigzag) and oriented considerably perpendicular to the surface of the substrate. Moreover, the C¼ ¼O group of the ferrocenoyl groups was perpendicular to the surface of the substrate, and the ferrocene group was occupied in the water phase. Cyclic voltammograms for the STCFc monolayer on a gold electrode exhibited surface waves. The interfacial electron-transfer process between the redox site incorporated into the cellulose LB monolayer and the electrode surface was fast enough at a scanning rate lower than 100 mV s À1 . V V C 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 5023-5031, 2005

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Sulfated glycofuranans as inhibitors of melanoma lung metastasis

Cited by 4 publications

References 17 publications

Click Chemistry with Polysaccharides

Click Chemistry with Polysaccharides

Preparation and Characterization of 6-O-(4-stearyloxytrityl)Cellulose acetate Langmuir–Blodgett Films

Preparation and characterization of redox cellulose Langmuir–Blodgett films containing a ferrocene derivative

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