Katayama Chemical Industries Co.

Mino, Japan

Katayama Chemical Industries Co.

Mino, Japan

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Li S.,Hunan University | Chen T.,Hunan University | Saga Y.,Katayama Chemical Industries Co. | Han L.-B.,Japan National Institute of Advanced Industrial Science and Technology
RSC Advances | Year: 2015

Chloroform-based Atherton-Todd-type reactions of alcohols and thiols with secondary phosphine oxides, generating phosphinothioates and phosphinates, respectively, are described. Various valuable phosphinothioates and phosphinates including those with functional groups are readily prepared under mild reaction conditions. This journal is © The Royal Society of Chemistry 2015.


Zhou Y.,Japan National Institute of Advanced Industrial Science and Technology | Wang G.,Japan National Institute of Advanced Industrial Science and Technology | Saga Y.,Katayama Chemical Industries Co. | Shen R.,Japan National Institute of Advanced Industrial Science and Technology | And 3 more authors.
Journal of Organic Chemistry | Year: 2010

A general and efficient method for the preparation of optically active Z1Z2P(O)Cl from the easily prepared optically active H-phosphinates and H-phosphine oxides was reported. H-Phosphinates and H-phosphine oxides react stereospecifically with CuCl2 to produce the corresponding optically active Z1Z2P(O)Cl with retention of configuration at the phosphorus center. Optically active Z1Z 2P(O)Cl reacts easily with a variety of nucleophiles to produce other chiral organophosphorus acid derivatives with inversion of configuration at phosphorus. © 2010 American Chemical Society.


Amano C.,Katayama Chemical Industries Co. | Minematsu H.,Katayama Chemical Industries Co. | Fujita K.,Senri Kinran University | Iwashita S.,Katayama Chemical Industries Co. | And 4 more authors.
PLoS ONE | Year: 2015

To explore a novel method using liposomes to suppress macrophages, we screened food constituents through cell culture assays. Curcumin was one of the strongest compounds exhibiting suppressive effects on macrophages. We subsequently tried various methods to prepare liposomal curcumin, and eventually succeeded in preparing liposomes with sufficient amounts of curcumin to suppress macrophages by incorporating a complex of curcumin and bovine serum albumin. The diameter of the resultant nanoparticles, the liposomes containing curcumin, ranged from 60 to 100 nm. Flow cytometric analyses revealed that after intraperitoneal administration of the liposomes containing curcumin into mice, these were incorporated mainly by macrophages positive for F4/80, CD36, and CD11b antigens. Peritoneal cells prepared from mice injected in vivo with the liposomes containing curcumin apparently decreased interleukin-6-producing activities. Major changes in body weight and survival rates in the mice were not observed after administrating the liposomes containing curcumin. These results indicate that the liposomes containing curcumin are safe and useful for the selective suppression of macrophages in vivo in mice. © 2015 Amano et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.


Li X.,Hunan University | Chen T.,Hunan University | Saga Y.,Katayama Chemical Industries Co. | Han L.-B.,Japan National Institute of Advanced Industrial Science and Technology
Dalton Transactions | Year: 2016

An efficient P-C bond-formation through iron-catalyzed cross coupling of P-H/C-O bonds is developed for the first time. This reaction proceeds efficiently to produce the corresponding valuable α-alkoxyphosphorus compounds under mild conditions with a wide generality. © The Royal Society of Chemistry 2016.


Wang X.-B.,Japan National Institute of Advanced Industrial Science and Technology | Saga Y.,Katayama Chemical Industries Co. | Shen R.,Japan National Institute of Advanced Industrial Science and Technology | Fujino H.,Katayama Chemical Industries Co. | And 2 more authors.
RSC Advances | Year: 2012

Trimethylphosphine efficiently catalyzed the dimerization reaction of vinylphosphorus compounds to selectively afford the linear non-branched tail-to-tail β,β-dimerization dimers via umpolung of the substrates. © The Royal Society of Chemistry 2012.


Minematsu H.,Katayama Chemical Industries Co. | Otani T.,Katayama Chemical Industries Co. | Oohashi T.,Okayama University of Science | Hirai M.,Katayama Chemical Industries Co. | And 3 more authors.
Journal of Electron Microscopy | Year: 2011

Active targeting of the liposome is an attractive strategy for drug delivery and in vivo bio-imaging. We previously reported the specific accumulation of Sialyl Lewis X (SLX) liposome to inflamed tissue in arthritic model mice or tumor-bearing mice. SLX-liposome encapsulation with fluorescent substances allows for the visualization of these liposomes by the time-dependent transvascular accumulation of fluorescent signals in the histological sections. In the present study, we developed a new SLX-liposome encapsulated with colloidal gold for transmission electron microscopic observation. We herein describe the characterization of the colloidal gold-loaded SLX-liposomes and demonstrate its specific targeting to the endothelial cells of tumor blood vessels in tumor-bearing mice. © The Author 2010. Published by Oxford University Press [on behalf of Japanese Society of Microscopy]. All rights reserved.


The present invention provides a method of producing a liposome encapsulating an ammine platinum complex. The method includes A) providing a water-soluble ammine platinum complex, platinum complex raw materials or the combination thereof; B) providing a liposome, liposome raw materials or the combination; and C) preparing a mixture of the water-soluble ammine platinum complex, platinum complex raw materials or the combination thereof and the liposome, liposome raw materials or the combination thereof and subjecting it to a liposome-forming/maintaining condition, wherein the salt of the platinum complex forms when the liposome is in a water-soluble form.


Patent
Katayama Chemical Industries Co. and Gifu University | Date: 2010-12-01

The present invention provides a glycolipid-containing liposome. In such a glycolipid-containing liposome, the glycolipid includes a plant ceramide portion and a sugar chain portion. The present invention also provides a method of producing a glycolipid-containing liposome. This method includes the following steps of: A) providing a glycolipid in which the glycolipid includes a plant ceramide portion and a sugar chain portion; and B) mixing the provided glycolipid with a liposome raw material and subjecting the mixture to conditions in which a liposome is formed.


PubMed | Senri Kinran University and Katayama Chemical Industries Co.
Type: Journal Article | Journal: PloS one | Year: 2015

To explore a novel method using liposomes to suppress macrophages, we screened food constituents through cell culture assays. Curcumin was one of the strongest compounds exhibiting suppressive effects on macrophages. We subsequently tried various methods to prepare liposomal curcumin, and eventually succeeded in preparing liposomes with sufficient amounts of curcumin to suppress macrophages by incorporating a complex of curcumin and bovine serum albumin. The diameter of the resultant nanoparticles, the liposomes containing curcumin, ranged from 60 to 100 nm. Flow cytometric analyses revealed that after intraperitoneal administration of the liposomes containing curcumin into mice, these were incorporated mainly by macrophages positive for F4/80, CD36, and CD11b antigens. Peritoneal cells prepared from mice injected in vivo with the liposomes containing curcumin apparently decreased interleukin-6-producing activities. Major changes in body weight and survival rates in the mice were not observed after administrating the liposomes containing curcumin. These results indicate that the liposomes containing curcumin are safe and useful for the selective suppression of macrophages in vivo in mice.


PubMed | Osaka University, Teikyo University, Osaka Prefecture University and Katayama Chemical Industries Co.
Type: | Journal: Journal of controlled release : official journal of the Controlled Release Society | Year: 2015

We designed functional liposomes with target specificity, temperature-triggered drug release, and near-infrared fluorescence imaging. We prepared the liposomes by triple functionalization of stable pegylated liposomes with thermosensitive poly[2-(2-ethoxy)ethoxyethyl vinyl ether] chains (lower critical solution temperature around 38 C) with conjugation of antibody trastuzumab (Herceptin, HER), which targets human epidermal growth factor 2, and with incorporation of indocyanine green for near-infrared fluorescence imaging. The liposomes retained DOX in the interior below physiological temperature but released DOX immediately at temperatures higher than 40 C. The liposomes exhibited excellent ability for association and internalization to target cells overexpressing Her-2, such as SK-OV3 and SB-BR3 cells, and killed these cells when heated at 45 C for 5 min. When administered intravenously to mice bearing SK-OV3 tumor, the liposomes having HER accumulated in the tumor more efficiently than the liposomes without HER. They stayed there more than 48 h, as judged with near-infrared fluorescence imaging. Furthermore, when the tumor sites of the mice being administered with the DOX-loaded liposomes were heated mildly at 44C for 10 min at 7h after administration, tumor growth was suppressed strongly thereafter. Treatment with the HER-conjugated liposomes produced more efficient tumor-suppressive effects. Results demonstrate that the synergy of target-specific association, temperature-triggered drug release, and imaging is important for efficient tumor chemotherapy.

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