Katayama Chemical Industries Co.

Mino, Japan

Katayama Chemical Industries Co.

Mino, Japan
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Guo H.,Japan National Institute of Advanced Industrial Science and Technology | Yoshimura A.,Japan National Institute of Advanced Industrial Science and Technology | Chen T.,Japan National Institute of Advanced Industrial Science and Technology | Saga Y.,Katayama Chemical Industries Co. | Han L.-B.,Japan National Institute of Advanced Industrial Science and Technology
Green Chemistry | Year: 2017

An air-induced double addition of diphenyl phosphine oxide to various alkynes is reported. This reaction can proceed efficiently under metal- and solvent-free conditions, and is a clean and practically useful method for the preparation of the valuable 1,2-bisphosphorylethanes. © The Royal Society of Chemistry 2017.


Koyama T.,National Health Research Institute | Shimura M.,National Health Research Institute | Minemoto Y.,National Health Research Institute | Nohara S.,Meito Sangyo Co. | And 10 more authors.
Journal of Controlled Release | Year: 2012

Active targeting by monoclonal antibodies (mAbs) combined with nanosize superparamagnetic iron oxide (SPIO) is a promising technology for magnetic resonance imaging (MRI) diagnosis. However, the clinical applicability of this technology has not been investigated using appropriate controls. It is important to evaluate the targeting technology using widely used clinical 1.5-Tesla MRI in addition to the high-Tesla experimental MRI. In this study, we measured mAb-conjugated dextran-coated SPIO nanoparticles (CMDM) in vivo using clinical 1.5-Tesla MRI. MRI of tumor-bearing mice was performed using a simple comparison between positive and negative tumors derived from the same genetic background in each mouse. The system provided significant tumor-targeting specificity of the target tumor. To the best of our knowledge, this is the first report on the specific detection of target tumors by mAb-conjugated SPIO using clinical 1.5-Tesla MRI. Our observations provide clues for reliable active targeting using mAb-conjugated SPIO in clinical applications. © 2012 Elsevier B.V. All rights reserved.


Yuba E.,Osaka Prefecture University | Nakajima Y.,Osaka Prefecture University | Tsukamoto K.,Osaka Prefecture University | Iwashita S.,Katayama Chemical Industries Co. | And 3 more authors.
Journal of Controlled Release | Year: 2012

In an earlier study, we developed a new type of gene vector using poly(amidoamine) (PAMAM) dendron-bearing lipids and reported that their transfection activity was affected by their structures, such as dendron generation and alkyl chain length. In this study, for improvement of their performance as gene vectors, we examined the effect of unsaturated chains of the dendron-bearing lipids using DL-G1-2C 18, which consists of PAMAM G1 dendron moiety and two octadecyl chains, and achieved the most efficient transfection activity among the dendron-bearing lipids having saturated alkyl chains, and DL-G1-2C 18-U2, which consists of the same dendron-moiety and two octadecenyl chains. DL-G1-2C 18-U2 showed a higher ability to form lipoplexes with plasmid DNA than DL-G1-2C 18. The DL-G1-2C 18-U2 lipoplexes exhibited much smaller particle sizes than the DL-G1-2C 18. In addition, the DL-G1-2C 18-U2 lipoplexes exhibited more efficient transfection of HeLa cells than DL-G1-2C 18 did. Results demonstrate the importance of unsaturated chains for the production of the dendron-bearing lipids having excellent gene transfection performance. Without the help of additional fusogenic lipids such as dioleoylphosphatidylethanolamine, DL-G1-2C 18-U2 lipoplexes achieved the highly efficient transfection of the cells without marked cellular toxicity, in the presence of serum. Therefore, DL-G1-2C 18-U2 might be promising as a potent gene vector. © 2012 Elsevier B.V. All rights reserved.


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.


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.

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