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Nishi-Tokyo-shi, Japan

Shigehiro T.,Okayama University | Shigehiro T.,Japan Society for the Promotion of Science | Zhai W.,Okayama University | Vaidyanath A.,Okayama University | And 10 more authors.
Journal of Microencapsulation | Year: 2016

Docetaxel comprises one of the most effective anti-cancer drugs despite of serious side effects. Liposomes encapsulation is practically feasible to deliver the drug. However, due to the significant hydrophobicity, docetaxel will be integrated into the lipid bilayer resulting in poor encapsulation capacity. Here, we evaluated a remote loading strategy using a solubility gradient made between the two solvents for 7-glucosyloxyacetyldocetaxel, which has enhanced water solubility of docetaxel with a coupled glucose moiety. Therefore, 7-glucosyloxyacetyldocetaxel was more effectively encapsulated into liposomes with 71.0% of encapsulation efficiency than docetaxel. While 7-glucosyloxyacetyldocetaxel exhibited 90.9% of tubulin stabilisation activity of docetaxel, 7-glucosyloxyacetyldocetaxel encapsulated in liposomes significantly inhibited the growth of tumour in vivo with side effects less than unencapsulated drug. Collectively, the encapsulation of 7-glucosyloxyacetyldocetaxel into liposomes by remote loading under the solubility gradient is considered to be a promising application to prepare practical drug delivery system. © 2016 Taylor & Francis Source


Wu Y.,University of Tokyo | Enomoto-Rogers Y.,University of Tokyo | Masaki H.,Ensuiko Sugar Refining Co. | Iwata T.,University of Tokyo
ACS Sustainable Chemistry and Engineering | Year: 2016

d-Glucaric acid (GA), an aldaric acid isolated from various vegetables and fruits, is an important biobased building block. Glucaric acid acetate (GAA), which is acyclic, was synthesized in an acetic anhydride/sulfuric acid mixture. GAA was converted to glucaric acid chloride acetate (GACA) and then polymerized with various diols and diamines in dimethylacetamide solution or by interfacial polymerization in water and chloroform solutions. The polyesters and polyamides were amphiphilic and soluble in water and common organic solvents. The weight-average molecular weights of the polyesters were (0.4-0.7) × 103 those of the polyamides obtained by solution and interfacial polymerizations were (5.9-8.0) × 103 and (14.5-20.8) × 103, respectively. Differential scanning calorimetry showed that the polyamides were thermoplastic and melted at ca. 140 °C, indicating crystallinity; the melting points increased with increasing number of diamine alkyl carbons. Novel biobased crystalline amphiphilic polymers were synthesized from GA. © 2016 American Chemical Society. Source


Shigehiro T.,Okayama University | Kasai T.,Okayama University | Murakami M.,Okayama University | Sekhar S.C.,Okayama University | And 10 more authors.
PLoS ONE | Year: 2014

Although the encapsulation of paclitaxel into liposomes has been extensively studied, its significant hydrophobic and uncharged character has generated substantial difficulties concerning its efficient encapsulation into the inner water core of liposomes. We found that a more hydrophilic paclitaxel molecule, 7-glucosyloxyacetylpaclitaxel, retained tubulin polymerization stabilization activity. The hydrophilic nature of 7-glucosyloxyacetylpaclitaxel allowed its efficient encapsulation into the inner water core of liposomes, which was successfully accomplished using a remote loading method with a solubility gradient between 40% ethylene glycol and Cremophor EL/ethanol in PBS. Trastuzumab was then conjugated onto the surface of liposomes as immunoliposomes to selectively target human epidermal growth factor receptor-2 (HER2)-overexpressing cancer cells. In vitro cytotoxicity assays revealed that the immunoliposomes enhanced the toxicity of 7-glucosyloxyacetylpaclitaxel in HER2-overexpressing cancer cells and showed more rapid suppression of cell growth. The immunoliposomes strongly inhibited the tumor growth of HT-29 cells xenografted in nude mice. Notably, mice survived when treated with the immunoliposomes formulation, even when administered at a lethal dose of 7-glucosyloxyacetylpaclitaxel in vivo. This data successfully demonstrates immunoliposomes as a promising candidate for the efficient delivery of paclitaxel glycoside. Source


Patent
Ensuiko Sugar Refining Co. and Osaka Municipal Technical Research Institute | Date: 2013-06-03

The present invention provides a D-glucaric acid-producing bacterium and a method for producing D-glucaric acid. The present invention is characterized in that D-glucaric acid or a salt thereof is produced from one or more saccharides selected from the group consisting of D-glucose, D-gluconic acid and D-glucuronic acid with catalytic action of a specific alcohol dehydrogenase PQQ-ADH (1) and a specific aldehyde dehydrogenase PQQ-ALDH (2), and that D-glucaric acid or a salt thereof is produced by using a microorganism having the PQQ-ADH (1) and the PQQ-ALDH (2) or a processed product thereof in the presence of the one or more saccharides. The present invention can provide a microorganism having improved productivity of D-glucaric acid to be used for production of D-glucaric acid and a method for efficiently producing D-glucaric acid.


Patent
Ensuiko Sugar Refining Co. and Okayama University | Date: 2013-03-22

In order to reduce the side effects of paclitaxel derivatives having excellent anti-cancer effects, an attempt was made to produce a liposome encapsulating paclitaxel derivatives such as paclitaxel monoglycosides and docetaxel monoglycosides. However, the introduction efficiency of paclitaxel derivatives, etc., into a liposome was poor, and this technique was not developed to a practical level. The present invention provides a method for producing a liposome encapsulating a paclitaxel monoglycoside and/or a docetaxel monoglycoside, and having an antibody specifically recognizing a cancer cell, the method comprising a step of bringing a liposome encapsulating a polyoxyethylene ester derivative, a lower alcohol, and a buffer or water into contact with a solution in which a paclitaxel monoglycoside and/or a docetaxel monoglycoside is dissolved in an alkylene glycol-containing buffer or water.

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