Antitumor Activity, Mitogenicity, and Lethal Toxicity of Chemically Synthesized Monosaccharide Analogs of Lipid A

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概要

• 論文の詳細を見る

• Antitumor activity of three derivatives of chemically synthesized diacyloxyacylglucosamine-4-phosphate (acyl-GlcN-4P) linked 3-deoxy-D-manno-2-octulosonic acid (KDO) and 12 derivatives of acyl-GlcN-4P or acyloxyacylglucosamine-6-phosphate (acyl-GlcN-6P) with chiral acyloxyacyl groups at the C-2 and C-3 positions was examined. Ehrlich carcinoma cells (1×10^4) were inoculated i.p. into ddY mice on day 0,and these compounds (100μg/d/mouse) were administered i.p. on days -5,-2,+1,+3,and +5. Although the antitumor activity of the acyl-GlcN-4P linked KDO was weaker than that of the natural lipopolysaccharide, groups of mice administered A-301 with di-3-hexadecanoyloxy-tetradecanoyl [(R)C_<14>-O-C_<16>] at C-2,-3,and A-303 with di-3-tetradecanoyloxytetradecanoyl [(R)C_<14>-O-C_<14>] showed longer mean survival times than the control group. However, KDO-attachment appeared not to enhance the antitumor activity of acyl-GlcN-4P. The group of mice administered acyl-GlcN-4P (A-145) or acyl-GlcN-6P (A-144 and A-146), which have an acyloxyacyl group at C-2,-3,showed prolonged survival times when compared to the control group, but the differences were not significant. On the other hand, when compound A-107 with [(S)C_<14>-O-C_<14>] at the C-2 position and 6-phosphate was administered to 5 mice, 3 mice survived for 25d. Furthermore, mitogenicity for splenocytes of C57BL/6 mice and lethal toxicity in C57BL/6 mice sensitized with D-galactosamine were observed with the acyl-GlcN-4P or-6P derivatives with (R) or (S) isomers of fatty acid. The findings suggest that these activities do not correlate with stereoisomer of fatty acids and the position of phosphate group.

• 公益社団法人日本薬学会の論文

著者

• MASUZAWA Toshiyuki

  Department of Microbiology and COE Program in the 21st Century, University of Shizuoka School of Pha

• YANAGIHARA Yasutake

  Department of Microbiology, School of Pharmaceutical Sciences, University of Shizuoka

• Yanagihara Y

  Univ. Shizuoka Shizuoka Jpn

• ITOH Hajime

  Department of Chemistry, Faculty of Science, Okayama University

• Itoh H

  Fuji Chemical Industries Toyama Jpn

• SHIMIZU Tadayori

  Department of Microviology, School of Pharmaceutical Sciences, University of Shizuoka

• Masuzawa T

  Univ. Shizuoka Shizuoka Jpn

• Masuzawa Toshiyuki

  Department Of Microbiology And Coe Program In The 21st Century University Of Shizuoka School Of Phar

• NAKAMOTO Shinichi

  Department of Microbiology, and Department of Medicinal Chemistry. School of Pharmaceutical Sciences

• ACHIWA Kazuo

  Department of Microbiology, and Department of Medicinal Chemistry. School of Pharmaceutical Sciences

• SHIMIZU Tadayori

  University of Shizuoka, School of Pharmaceutical Sciences

• Shimizu Tadayori

  University Of Shizuoka School Of Pharmaceutical Sciences

• Nakamoto Shinichi

  Department Of Microbiology And Department Of Medicinal Chemistry. School Of Pharmaceutical Sciences

• Yanagihara Yasutake

  Department Of Medical Microbiology College Of Public Health University Of The Philippines

• Itoh Hajime

  Department Of Aerospace Engineering National Defense Academy

• Shimizu Takao

  Department Of Veterinary Medicine Faculty Of Agriculture Tokyo University Of Agriculture And Technol

• Masuzawa Toshiyuki

  Shizuoka Inst. Environment And Hygiene Shizuoka

• SHIMIZU Tadayori

  Department of Microbiology, Jichi Medical School

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