Schizophyllan

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Seiji Shinkai - One of the best experts on this subject based on the ideXlab platform.

Kazuo Sakurai - One of the best experts on this subject based on the ideXlab platform.

Kazuya Koumoto - One of the best experts on this subject based on the ideXlab platform.

  • in situ monitoring of polysaccharide polynucleotide interaction using a Schizophyllan immobilized qcm device
    Sensors and Actuators B-chemical, 2005
    Co-Authors: Do-hyeon Yang, Kazuya Koumoto, Kazuo Sakurai, Ah-hyun Bae, Seung-woo Lee, Seiji Shinkai
    Abstract:

    Abstract Schizophyllan belongs to the β-(1 → 3)- d -glucan family and is well known as a triple helix polysaccharide. It is already known that the single chain of Schizophyllan (s-SPG) can specifically form a complex with particular polynucleotides. As an application of this recognition capability, a novel Schizophyllan derivative connected with a disulfide bond through a long methylene spacer was synthesized, and its interaction with polynucleotides was directly monitored with a self-assembled monolayer on QCM. The gold-coated QCM electrode was covered in ca. 60% as a monolayer of s-SPG. The QCM resonator showed sensitive mass increases for poly(C) and poly(U) in the presence of K+ ion, which are consistent with our previous results. The present results indicate that the Schizophyllan-immobilized QCM resonator can be a new sensing device for biomolecules.

  • In situ monitoring of polysaccharide–polynucleotide interaction using a Schizophyllan-immobilized QCM device
    Sensors and Actuators B: Chemical, 2005
    Co-Authors: Do-hyeon Yang, Kazuya Koumoto, Kazuo Sakurai, Ah-hyun Bae, Seung-woo Lee, Seiji Shinkai
    Abstract:

    Abstract Schizophyllan belongs to the β-(1 → 3)- d -glucan family and is well known as a triple helix polysaccharide. It is already known that the single chain of Schizophyllan (s-SPG) can specifically form a complex with particular polynucleotides. As an application of this recognition capability, a novel Schizophyllan derivative connected with a disulfide bond through a long methylene spacer was synthesized, and its interaction with polynucleotides was directly monitored with a self-assembled monolayer on QCM. The gold-coated QCM electrode was covered in ca. 60% as a monolayer of s-SPG. The QCM resonator showed sensitive mass increases for poly(C) and poly(U) in the presence of K+ ion, which are consistent with our previous results. The present results indicate that the Schizophyllan-immobilized QCM resonator can be a new sensing device for biomolecules.

  • Poly( N -substituted-acrylamide)-branched Schizophyllans Are Useful for Selective Recovery of Homopolynucleotides through Convenient and Quick Precipitation Procedures
    Polymer Journal, 2005
    Co-Authors: Takahiro Matsumoto, Munenori Numata, Teruaki Hasegawa, Mariko Umeda, Kazuya Koumoto, Kazuo Sakurai, Seiji Shinkai
    Abstract:

    Schizophyllans carrying poly(N-substituted-acrylamide)-branches were synthesized from native Schizophyllan through Ce(IV)-initiated radical homo- or co-polymerization of N-iso-propyl- and N-sec-butyl-acrylamide. A series of structural analyses including elemental analysis, gel permeation chromatography, 1H NMR, and enzymatic degradation using β-1,3-glucanase revealed that Schizophyllans (150 kDa) bearing long poly(N-substituted-acrylamide)-branches (ca. 290 kDa) are obtained. These SPG-conjugates form macromolecular complexes with certain homopolynucleotides such as poly(C), poly(dA), and poly(A) and then efficiently co-precipitate them on heating. For example, Schizophyllan carrying poly(N-iso-propylacrylamide)-branches can selectively recover poly(C) from a mixture of poly(C) and poly(U) by simple heating (36 °C) followed by centrifugation. HPLC analysis of the recovered polynucleotide revealed the high poly(C)-selectivity (poly(C):poly(U) = 95:5). Similarly, Schizophyllan carrying more hydrophobic poly(N-iso-propylacrylamide-co-N-sec-butylacrylamide)-branches precipitates at lower temperature (ca. 20 °C) and is applicable to isolation of poly(A) that forms less stable macromolecular complexes with SPG and SPG-derivatives (the dissociation temperatures are around 30 °C).

  • Cholesterol-appended β-(1→3)-D-glucan Schizophyllan for antisense oligonucleotides delivery to enhance the cellular uptake
    Bulletin of the Chemical Society of Japan, 2005
    Co-Authors: Kazuya Koumoto, Seiji Shinkai, Masami Mizu, Takahisa Anada, Takeshi Nagasaki, Kazuo Sakurai
    Abstract:

    Schizophyllan is a natural β-(1→3)-D-glucan existing as a triple helix in water and as a single chain in dimethyl sulfoxide (DMSO), respectively. As we already reported, when a homo-polynucleotide is added to a Schizophyllan solution, the single chain of Schizophyllan forms a complex with the polynucleotide. One of the potential applications of this novel complex is an antisense-oligonucleotide (AS ODN) carrier. The present paper describes a modification technique that enables us to introduce a cholesterol group only to the side chain of Schizophyllan. We prepared four cholesterol-appended Schizophyllans with different modification levels. Using these compounds, we made complexes and carried out an in vitro antisense assay, administrating a phosphorothioate AS ODN to the several cell lines to depress their c-myb mRNA. When we used 2.2-2.3 mol % modified Schizophyllan as the carrier, the antisense effect was most enhanced among others. The addition of;6-cyclodextrin improved the complexation ability as well as the up-take for highly modified samples. Furthermore, the cytotoxicity for these modified Schizophyllan samples was negligibly as small as the natural (unmodified) Schizophyllan. The present work has thus clarified that Schizophyllan can act as a new potential candidate for AS ODN carriers.

  • PEG-appended β-(1→3)-D-glucan Schizophyllan to deliver antisense-oligonucleotides with avoiding lysosomal degradation
    Biomaterials, 2005
    Co-Authors: Ryouji Karinaga, Seiji Shinkai, Masami Mizu, Kazuya Koumoto, Takahisa Anada, Kazuo Sakurai
    Abstract:

    Schizophyllan is a natural beta-(1-->3)-d-glucan existing as a triple helix in water and as a single chain in dimethylsulfoxide (DMSO). As we already reported, when a homo-polynucleotide [e.g., poly(dA) or poly(C)] is added to the Schizophyllan/DMSO solution and subsequently DMSO is exchanged for water, the single chain of Schizophyllan forms a complex with the polynucleotide. One of the potential applications for this novel complex is an antisense-oligonucleotide (AS ODN) carrier. The present paper describes a modification technique that enabled us to introduce PEG only to the side chain of Schizophyllan. This technique consisted of periodate oxidation of the glucose side chain and subsequent reaction between methoxypolyethylene glycol amine and the formyl terminate, followed by reduction with NaBH4. Subsequently, we made a complex from PEG-appended Schizophyllan and an AS ODN sequence, and carried out an in vitro antisense assay, administrating the AS ODN complex to depress A375 c-myb mRNA of A375 melanoma cell lines. The PEG-SPG/AS ODN complex showed more enhanced antisnese effect than naked AS ODN dose, i.e., the same level as that of RGD-appended SPG. Here, the RGD system has been shown one on the most effective AS ODN carrier (Science 261 (1993) 1004-1012). When we added nigericin to the assay system, the antisense effect was not affected in the PEG-SPG system, on the other hand, it was almost eliminated in the RGD system. Nigericin is well known to interrupt transport from endosome to lysosome. Therefore, the difference between the PEG and RGD complexes indicates that, in the PEG system, AS ODN was able to escape from lysosomal degradation. The present work has thus proposed a new strategy to delivery AS ODN using Schizophyllan as a new carrier.

Kazuto Yoshiba - One of the best experts on this subject based on the ideXlab platform.

  • Cooperative Order-Disorder Transition of Carboxylated Schizophyllan in Water-Dimethylsulfoxide Mixtures.
    The journal of physical chemistry. B, 2018
    Co-Authors: Kazuto Yoshiba, Toshiaki Dobashi, Ann-sissel Teialeret Ulset, Bjørn E. Christensen
    Abstract:

    Carboxylated Schizophyllan (“sclerox”) is a chemically modified polysaccharide obtained by partial periodate oxidation and subsequent chlorite oxidation of Schizophyllan, a water-soluble neutral polysaccharide having a β-1,3-linked glucan backbone and a β-1,6-linked d-glucose residue side chain at every third residue of the main chain. The triple helix of Schizophyllan in water has a cooperative order–disorder transition associated with the side chains. The transition is strongly affected by the presence (mole fraction) of dimethylsulfoxide (DMSO). In the present study, the solvent effects on the order–disorder transition of sclerox with different degrees of carboxylation (DS) in water–DMSO mixtures were investigated with differential scanning calorimetry and optical rotation. The transition temperature (Tr) and transition enthalpy (ΔHr) strongly depended on the mole fraction of DMSO (xD). Data were further analyzed with the statistical theory for the linear cooperative transition, taking into account the...

  • Effects of carboxylation of the side chains on the order-disorder transition in aqueous solution of Schizophyllan, a triple helical polysaccharide
    Carbohydrate polymers, 2017
    Co-Authors: Kazuto Yoshiba, Toshiaki Dobashi, Bjørn E. Christensen, Satoka Okamoto, Hiroyuki Oku, Takahiro Sato
    Abstract:

    Abstract Schizophyllan and scleroglucan are water-soluble polysaccharides having repeating units consisting of three β-1,3-linked glucose residues in the main chain and a single β-1,6-linked glucose residue as the side chain. This polysaccharide dissolves as a triple helix in an aqueous solution and shows a cooperative order-disorder transition between the side chain and solvent molecules while retaining the triple helical conformation. Periodate and subsequent chlorite oxidations selectively modify the side chain glucose to provide the corresponding dicarboxylate units. Optical rotation measurements and differential scanning calorimetry were performed on carboxylated Schizophyllan/scleroglucan (‘sclerox’) samples to investigate the effects of the degree of carboxylation on the order-disorder transition in deuterium oxide with 0.1 M NaCl. The transition curves for the sclerox samples are strongly dependent on the degree of carboxylation. The modified side chains cannot take the ordered structure, resulting in a reduction of the transition enthalpy. The transition temperature for carboxylated Schizophyllan becomes lowered and the transition curve broadens with increasing the degree of carboxylation. The permanent disordered units are included in a trimer by the carboxylation to inhibit a long sequence of the ordered units.

  • Conformation of carboxylated Schizophyllan in aqueous solution
    Carbohydrate polymers, 2015
    Co-Authors: Kazuto Yoshiba, Takahiro Sato, Ann-sissel Teialeret Ulset, Takaaki Osumi, Bjørn E. Christensen
    Abstract:

    Carboxylated Schizophyllan (sclerox) samples of different degrees of oxidation were molecularly characterized by size exclusion chromatography equipped with a multi-angle light scattering detector (SEC-MALS) in 0.10 M aqueous NaCl solution. The molar mass distribution obtained by SEC-MALS shows that sclerox of low degree of oxidation is dissolved mainly as the trimer, whereas the trimer and single chain coexist in solution of sclerox of high degree of oxidation. The trimer of sclerox is much more flexible than the fully ordered triple helix of the parent Schizophyllan and easily dissociates into single chains upon heating.

  • Water Structures of Differing Order and Mobility in Aqueous Solutions of Schizophyllan, a Triple-Helical Polysaccharide as Revealed by Dielectric Dispersion Measurements
    Biomacromolecules, 2004
    Co-Authors: Kazuto Yoshiba, Akio Teramoto, Naotake Nakamura, Yuji Miyazaki, Michio Sorai, Toshiyuki Shikata, Yoshihito Hayashi, Nobuhiro Miura
    Abstract:

    Dielectric dispersion measurements were made on aqueous solutions of a triple-helical polysaccharide Schizophyllan over a wide concentration range 10−50 wt % at −45 to +30 °C. In the solution state...

  • Chiral Interactions in Polymer Liquid Crystals Reflecting Polymer Conformations: Triple-Helical Polysaccharide Schizophyllan and Poly(γ-benzyll-glutamate)
    Macromolecules, 2003
    Co-Authors: Kazuto Yoshiba, And Akio Teramoto, Naotake Nakamura, Takahiro Sato
    Abstract:

    Cholesteric pitch P was measured on D2O solutions of a triple-helical polysaccharide Schizophyllan as functions of temperature and concentration. The value of P varied with concentration and temperature and showed different concentration dependencies at lower and higher temperatures, with a sudden decrease in P in between. This is due to the order−disorder transition in Schizophyllan solutions around 17 °C in D2O. These data were analyzed by a statistical theory taking into account chiral repulsive and attractive interactions proposed by Sato et al. A subtle imbalance between the attractive and repulsive interactions gave rise to a large change in P. For the Schizophyllan solutions, the attractive interaction changed according to the transition, while the change of the repulsive one was less remarkable. Similar analyses were performed on poly(γ-benzyl l-glutamate) data, elucidating the roles of the two interactions in determining the cholesteric structure.

Masami Mizu - One of the best experts on this subject based on the ideXlab platform.

  • Cholesterol-appended β-(1→3)-D-glucan Schizophyllan for antisense oligonucleotides delivery to enhance the cellular uptake
    Bulletin of the Chemical Society of Japan, 2005
    Co-Authors: Kazuya Koumoto, Seiji Shinkai, Masami Mizu, Takahisa Anada, Takeshi Nagasaki, Kazuo Sakurai
    Abstract:

    Schizophyllan is a natural β-(1→3)-D-glucan existing as a triple helix in water and as a single chain in dimethyl sulfoxide (DMSO), respectively. As we already reported, when a homo-polynucleotide is added to a Schizophyllan solution, the single chain of Schizophyllan forms a complex with the polynucleotide. One of the potential applications of this novel complex is an antisense-oligonucleotide (AS ODN) carrier. The present paper describes a modification technique that enables us to introduce a cholesterol group only to the side chain of Schizophyllan. We prepared four cholesterol-appended Schizophyllans with different modification levels. Using these compounds, we made complexes and carried out an in vitro antisense assay, administrating a phosphorothioate AS ODN to the several cell lines to depress their c-myb mRNA. When we used 2.2-2.3 mol % modified Schizophyllan as the carrier, the antisense effect was most enhanced among others. The addition of;6-cyclodextrin improved the complexation ability as well as the up-take for highly modified samples. Furthermore, the cytotoxicity for these modified Schizophyllan samples was negligibly as small as the natural (unmodified) Schizophyllan. The present work has thus clarified that Schizophyllan can act as a new potential candidate for AS ODN carriers.

  • PEG-appended β-(1→3)-D-glucan Schizophyllan to deliver antisense-oligonucleotides with avoiding lysosomal degradation
    Biomaterials, 2005
    Co-Authors: Ryouji Karinaga, Seiji Shinkai, Masami Mizu, Kazuya Koumoto, Takahisa Anada, Kazuo Sakurai
    Abstract:

    Schizophyllan is a natural beta-(1-->3)-d-glucan existing as a triple helix in water and as a single chain in dimethylsulfoxide (DMSO). As we already reported, when a homo-polynucleotide [e.g., poly(dA) or poly(C)] is added to the Schizophyllan/DMSO solution and subsequently DMSO is exchanged for water, the single chain of Schizophyllan forms a complex with the polynucleotide. One of the potential applications for this novel complex is an antisense-oligonucleotide (AS ODN) carrier. The present paper describes a modification technique that enabled us to introduce PEG only to the side chain of Schizophyllan. This technique consisted of periodate oxidation of the glucose side chain and subsequent reaction between methoxypolyethylene glycol amine and the formyl terminate, followed by reduction with NaBH4. Subsequently, we made a complex from PEG-appended Schizophyllan and an AS ODN sequence, and carried out an in vitro antisense assay, administrating the AS ODN complex to depress A375 c-myb mRNA of A375 melanoma cell lines. The PEG-SPG/AS ODN complex showed more enhanced antisnese effect than naked AS ODN dose, i.e., the same level as that of RGD-appended SPG. Here, the RGD system has been shown one on the most effective AS ODN carrier (Science 261 (1993) 1004-1012). When we added nigericin to the assay system, the antisense effect was not affected in the PEG-SPG system, on the other hand, it was almost eliminated in the RGD system. Nigericin is well known to interrupt transport from endosome to lysosome. Therefore, the difference between the PEG and RGD complexes indicates that, in the PEG system, AS ODN was able to escape from lysosomal degradation. The present work has thus proposed a new strategy to delivery AS ODN using Schizophyllan as a new carrier.

  • Removal of the side-chain glucose groups from Schizophyllan improves the thermal stability of the polycytidylic acid complexes under the physiological conditions.
    Biopolymers, 2004
    Co-Authors: Kazuya Koumoto, Ryouji Karinaga, Masami Mizu, Kazuo Sakurai, Takahisa Anada, Toyoki Kunitake, Seiji Shinkai
    Abstract:

    Thermal stabilization of the complex between polycytidylic acid [poly(C)] and the modified Schizophyllan (SPG) whose hydrophilic side-chain glucose groups are selectively removed utilizing mild Smith-degradation has been investigated. With the decrease in the side-chain glucose groups of Schizophyllan, the complex with poly(C) can be considerably stabilized compared with unmodified SPG; for example, the Tm value after the removal of the side-chain glucose groups from 33.3 (unmodified) to 1.0 is enhanced by 14°C. In addition, the thermal stabilization effect is even operative under the physiological conditions ([NaCl] = 0.15 mol dm−3). This effect is exerted owing to the construction of the hydrophobic atmosphere around the complex. Although Schizophyllan lost the side-chain glucose groups, it still kept the protection effect of the bound poly(C) chain against RNaseA-mediated hydrolysis as observed for unmodified Schizophyllan. The assessment of the cytotoxicity for A375:human malignant melanoma, and HL60:human promyelocytic leukemia revealed that the modified Schizophyllan scarcely increases the cytotoxicity. These results indicate that the present modification for Schizophyllan is of great significance in a viewpoint to develop the practical gene carriers operative even under the physiological conditions. © 2004 Wiley Periodicals, Inc. Biopolymers, 2004

  • Schizophyllans carrying oligosaccharide appendages as potential candidates for cell-targeted antisense carrier
    Organic & biomolecular chemistry, 2004
    Co-Authors: Teruaki Hasegawa, Munenori Numata, Tomohisa Fujisawa, Takahiro Matsumoto, Mariko Umeda, Ryouji Karinaga, Masami Mizu, Kazuya Koumoto, Taro Kimura, Shiro Okumura
    Abstract:

    Schizophyllans carrying β-lactoside and α-mannoside appendages were prepared from native Schizophyllan through NaIO4 oxidation followed by reductive amination using aminoethyl-β-lactoside and α-mannoside, respectively. The resulting Schizophyllans form stable macromolecular complexes with polynucleotides, such as poly(C) and poly(dA). Specific affinity between these macromolecular complexes and saccharide-binding proteins was demonstrated by surface plasmon resonance and agarose gel staining assays. β-Lactoside-appended Schizophyllan enhanced an antisense activity in hepatocytes which express lactoside-binding proteins on their cell surfaces.

  • Lactose-appended Schizophyllan is a potential candidate as a hepatocyte-targeted antisense carrier.
    Chemical communications (Cambridge England), 2004
    Co-Authors: Teruaki Hasegawa, Munenori Numata, Takahiro Matsumoto, Mariko Umeda, Masami Mizu, Kazuya Koumoto, Kazuo Sakurai, Seiji Shinkai
    Abstract:

    A Schizophyllan (β-1,3-glucan) derivative carrying lactose-appendages prepared by reductive amination can form stable macromolecular complexes with polynucleotides, shows excellent affinity with a lactose-binding lectin, and effectively mediates gene transfection into hepatocytes.

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