Synthesis and biological activities of lipid A-type pyrancarboxylic acid derivatives

被引:9
|
作者
Mochizuki, T
Iwano, Y
Shiozaki, M
Kurakata, S
Kanai, S
Nishijima, M
机构
[1] Sankyo Co Ltd, Exploratory Chem Res Labs, Shinagawa Ku, Tokyo 1408710, Japan
[2] ChemTech Lab Inc, Shinagawa Ku, Tokyo 1408710, Japan
[3] Sankyo Co Ltd, Biol Res Labs, Shinagawa Ku, Tokyo 1408710, Japan
[4] Natl Inst Infect Dis, Dept Biochem & Cell Biol, Shinjuku Ku, Tokyo 1628640, Japan
关键词
lipid A; pyrancarboxylic acid; LPS antagonist; TNF alpha production;
D O I
10.1016/S0008-6215(99)00326-2
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing part of the disaccharide instead of the phosphate group in lipid A, is described. One of the compounds thus synthesized, which has an acyl substitution pattern similar to that of Escherichia coli lipid A, showed lipopolysaccharide (LPS)-agonistic activity. The other, which contains four lipid chains in the molecule, exhibited strong LPS-antagonistic activity toward human monoblastic U937 cells. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:225 / 230
页数:6
相关论文
共 50 条
  • [31] Synthesis and biological activities of chaetocin and its derivatives
    Sodeoka, Mikiko
    Dodo, Kosuke
    Teng, Yuou
    Iuchi, Katsuya
    Hamashima, Yoshitaka
    Iwasa, Eriko
    Fujishiro, Shinya
    PURE AND APPLIED CHEMISTRY, 2012, 84 (06) : 1369 - 1378
  • [32] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF MITOMYCIN DERIVATIVES
    NAKANO, KI
    HETEROCYCLES, 1979, 13 : 373 - 387
  • [33] Synthesis and biological activities of novel thiocarbohydrazone derivatives
    Sun, Ya-Dong
    Xie, Zheng-Feng
    Liu, Fang-Ming
    Chen, Jia-Sheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (05) : 889 - 893
  • [34] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF PHOSPHONYLALKYLPURINE DERIVATIVES
    KIM, CU
    LUH, BY
    MISCO, PF
    BRONSON, JJ
    HITCHCOCK, MJM
    GHAZZOULI, I
    MARTIN, JC
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1989, 8 (5-6): : 927 - 931
  • [35] Synthesis and biological activities of some benzodiazepine derivatives
    Sharma, S., 1600, Journal of Chemical and Pharmaceutical Research, 3/668 Malviya Nagar, Jaipur, Rajasthan, India (05):
  • [36] Synthesis and biological activities of ferrocenyl derivatives of paclitaxel
    Plazuk, Damian
    Wieczorek, Anna
    Blauz, Andrzej
    Rychlik, Blazej
    MEDCHEMCOMM, 2012, 3 (04) : 498 - 501
  • [37] Synthesis, characterization and biological activities of acylthiourea derivatives
    Li Ying-Jun
    Zhang Zhi-Guang
    Jin Kun
    Peng Qin-Ji
    Ding Wan-Gang
    Liu Jun
    ACTA CHIMICA SINICA, 2007, 65 (09) : 834 - 840
  • [38] Practical Synthesis of Chalcone Derivatives and Their Biological Activities
    Jung, Jae-Chul
    Lee, Yongnam
    Min, Dongguk
    Jung, Mankil
    Oh, Seikwan
    MOLECULES, 2017, 22 (11):
  • [39] Synthesis of chloro pyrazolone derivatives and their biological activities
    Naik, C. G.
    Malik, G. M.
    ORIENTAL JOURNAL OF CHEMISTRY, 2010, 26 (01) : 211 - 214
  • [40] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF SYNEPHRINE DERIVATIVES
    EYA, BK
    FUKUTO, TR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 124 - PEST