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
  • [41] Synthesis and biological activities of jineol and its derivatives
    Cho, Soon-Chang
    Sultan, Md Zakir
    Moon, Surk-Sik
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (08): : 1587 - 1590
  • [42] Synthesis and biological activities of some indoline derivatives
    Rode, Milind A.
    Rindhe, Sahebrao S.
    Karale, Bhausaheb K.
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2009, 74 (12) : 1377 - 1387
  • [43] Synthesis, characterized and biological activities of chalcone derivatives
    Qiu, Xiaoyang
    Li, Suzhi
    Shi, Anran
    Yue, Qiaoli
    ADVANCED ENGINEERING MATERIALS II, PTS 1-3, 2012, 535-537 : 2540 - 2543
  • [44] Synthesis and biological activities of novel pyrazolomatrine derivatives
    Kong, Wenlong
    Bao, Yinhe
    Ma, Qianjun
    Xu, Hui
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2018, 28 (20) : 3338 - 3341
  • [45] Synthesis and biological activities of fluorinated chalcone derivatives
    Nakamura, C
    Kawasaki, N
    Miyataka, H
    Jayachandran, E
    Kim, IH
    Kirk, KL
    Taguchi, T
    Takeuchi, Y
    Hori, H
    Satoh, T
    BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (03) : 699 - 706
  • [46] Synthesis and biological activities of novel pyridazine derivatives
    S. G. Tiratsuyan
    A. A. Hovhannisyan
    A. V. Karapetyan
    T. A. Gomktsyan
    A. P. Yengoyan
    Russian Journal of Plant Physiology, 2016, 63 : 656 - 662
  • [47] Synthesis and biological activities of some benzimidazolone derivatives
    Karale, B. K.
    Rindhe, S. S.
    Rode, M. A.
    INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2015, 77 (02) : 230 - 236
  • [48] Synthesis of Chalcones Derivatives and Their Biological Activities: A Review
    Elkanzi, Nadia A. A.
    Hrichi, Hajer
    Alolayan, Ruba A.
    Derafa, Wassila
    Zahou, Fatin M.
    Bakr, Rania B.
    ACS OMEGA, 2022, 7 (32): : 27769 - 27786
  • [49] Synthesis and Biological Activities of Hydroxytyrosol Ester Derivatives
    Zang, Hao
    Xu, Qian
    Zhang, Luyun
    Xia, Guangqing
    Sun, Jiaming
    Zhu, Junyi
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2020, 42 (01): : 109 - 119
  • [50] Synthesis and Biological Activities of Novel Pyridazine Derivatives
    Tiratsuyan, S. G.
    Hovhannisyan, A. A.
    Karapetyan, A. V.
    Gomktsyan, T. A.
    Yengoyan, A. P.
    RUSSIAN JOURNAL OF PLANT PHYSIOLOGY, 2016, 63 (05) : 656 - 662