新型咖啡酸衍生物的合成及其对脂多糖诱导的RAW 264.7巨噬细胞中一氧化氮生成的影响
Synthesis and effects of new caffeic acid derivatives on nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages.
作者信息
Zhang Jie, Xu Liu-Xin, Xu Xu-Sheng, Li Bo-Wei, Wang Rui, Fu Jian-Jun
机构信息
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology Shanghai 200237, China.
出版信息
Int J Clin Exp Med. 2014 Apr 15;7(4):1022-7. eCollection 2014.
Abstract
In this study, 20 new derivatives of caffeic acid esters were synthesized and their inhibitory activities against the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages were determined. Compounds 3l, 3r, 3s and 3t were found to decrease nitrite levels in a dose-dependent manner in LPS-induced cells and showed potent inhibitory activities against the NO production in RAW264.7 macrophages with IC50 values of 7.4, 5.9, 3.3 and 2.2 μM, respectively. They could be selected as compromising compounds for the later pharmacological study.
摘要
在本研究中，合成了20种新的咖啡酸酯衍生物，并测定了它们对脂多糖（LPS）诱导的RAW264.7巨噬细胞中一氧化氮（NO）产生的抑制活性。发现化合物3l、3r、3s和3t能以剂量依赖的方式降低LPS诱导细胞中的亚硝酸盐水平，并对RAW264.7巨噬细胞中NO的产生表现出强大的抑制活性，IC50值分别为7.4、5.9、3.3和2.2 μM。它们可被选为后续药理学研究的潜在化合物。
相似文献
1
Synthesis and effects of new caffeic acid derivatives on nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages.新型咖啡酸衍生物的合成及其对脂多糖诱导的RAW 264.7巨噬细胞中一氧化氮生成的影响
Int J Clin Exp Med. 2014 Apr 15;7(4):1022-7. eCollection 2014.
2
Caffeic acid derivatives: in vitro and in vivo anti-inflammatory properties.咖啡酸衍生物：体外和体内抗炎特性
Free Radic Res. 2004 Nov;38(11):1241-53. doi: 10.1080/10715760400016139.
3
Caffeic acid phenethyl ester protects mice from lethal endotoxin shock and inhibits lipopolysaccharide-induced cyclooxygenase-2 and inducible nitric oxide synthase expression in RAW 264.7 macrophages via the p38/ERK and NF-kappaB pathways.咖啡酸苯乙酯通过p38/ERK和NF-κB途径保护小鼠免受致死性内毒素休克，并抑制脂多糖诱导的RAW 264.7巨噬细胞中环氧合酶-2和诱导型一氧化氮合酶的表达。
Int J Biochem Cell Biol. 2008;40(11):2572-82. doi: 10.1016/j.biocel.2008.05.005. Epub 2008 May 15.
4
Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.咖啡酸类似物烷基侧链对RAW264.7巨噬细胞中脂多糖诱导的一氧化氮生成的抑制作用。
Bioorg Med Chem. 2008 Aug 15;16(16):7795-803. doi: 10.1016/j.bmc.2008.07.006. Epub 2008 Jul 8.
5
Synthesis of New Tricyclic and Tetracyclic Fused Coumarin Sulfonate Derivatives and Their Inhibitory Effects on LPS-Induced Nitric Oxide and PGE Productions in RAW 264.7 Macrophages: Part 2.新型三环和四环稠合香豆素磺酸盐衍生物的合成及其对RAW 264.7巨噬细胞中脂多糖诱导的一氧化氮和前列腺素E生成的抑制作用：第2部分。
Arch Pharm (Weinheim). 2016 Nov;349(11):853-863. doi: 10.1002/ardp.201600243. Epub 2016 Oct 24.
6
Novel -caffeate hydrazide derivatives: synthesis, inhibition of nitric oxide (NO) production and molecular docking studies.新型 - 咖啡酰肼衍生物的合成、一氧化氮（NO）生成抑制作用及分子对接研究。
Nat Prod Res. 2024 Nov;38(22):3964-3971. doi: 10.1080/14786419.2023.2272020. Epub 2023 Oct 19.
7
Inhibition of Nitric Oxide Production in LPS-Stimulated RAW 264.7 Macrophages and 15-LOX Activity by Anthraquinones from Pentas schimperi.来自辛氏五星花的蒽醌对脂多糖刺激的RAW 264.7巨噬细胞中一氧化氮生成及15-脂氧合酶活性的抑制作用
Planta Med. 2016 Sep;82(14):1246-51. doi: 10.1055/s-0042-104417. Epub 2016 Apr 19.
8
Synthesis of New Triarylpyrazole Derivatives Possessing Terminal Sulfonamide Moiety and Their Inhibitory Effects on PGE₂ and Nitric Oxide Productions in Lipopolysaccharide-Induced RAW 264.7 Macrophages.新型三芳基吡唑衍生物的合成及其对脂多糖诱导的 RAW 264.7 巨噬细胞中 PGE₂和一氧化氮生成的抑制作用。
Molecules. 2018 Oct 7;23(10):2556. doi: 10.3390/molecules23102556.
9
Inhibitory effect of carbazolequinone derivatives on lipopolysaccharide and interferon-γ-induced nitric oxide production in mouse macrophage RAW264.7 cells.咔唑醌衍生物对脂多糖和干扰素-γ诱导的小鼠巨噬细胞 RAW264.7 细胞一氧化氮产生的抑制作用。
J Pharm Pharmacol. 2013 Aug;65(8):1204-13. doi: 10.1111/jphp.12087. Epub 2013 Jun 7.
10
Inhibition of lipopolysaccharide-induced nitric oxide production by flavonoids in RAW264.7 macrophages involves heme oxygenase-1.黄酮类化合物对RAW264.7巨噬细胞中脂多糖诱导的一氧化氮生成的抑制作用涉及血红素加氧酶-1。
Biochem Pharmacol. 2003 Nov 1;66(9):1821-32. doi: 10.1016/s0006-2952(03)00422-2.
引用本文的文献
1
Tailored Functionalization of Natural Phenols to Improve Biological Activity.定制天然酚类化合物的功能化以提高生物活性。
Biomolecules. 2021 Sep 7;11(9):1325. doi: 10.3390/biom11091325.
2
Multifaceted effect of caffeic acid against Streptococcus mutans infection: microbicidal and immunomodulatory agent in macrophages.没食子酸对变形链球菌感染的多效性作用：巨噬细胞中的杀菌和免疫调节因子。
Arch Microbiol. 2021 Aug;203(6):2979-2987. doi: 10.1007/s00203-021-02290-x. Epub 2021 Mar 26.
3
Cardiovascular Effects of Caffeic Acid and Its Derivatives: A Comprehensive Review.咖啡酸及其衍生物的心血管效应：综述
Front Physiol. 2020 Nov 27;11:595516. doi: 10.3389/fphys.2020.595516. eCollection 2020.
4
Caffeates and Caffeamides: Synthetic Methodologies and Their Antioxidant Properties.咖啡酸酯和咖啡酰胺：合成方法及其抗氧化性能。
Int J Med Chem. 2019 Nov 11;2019:2592609. doi: 10.1155/2019/2592609. eCollection 2019.
5
The Hydroalcoholic Extract Obtained from L. Leaves Attenuates Oxidative Stress and Improves Survival in Lipopolysaccharide-Treated Macrophages.从 L. 叶中获得的水醇提取物可减轻氧化应激并提高脂多糖处理的巨噬细胞的存活率。
J Immunol Res. 2017;2017:2078794. doi: 10.1155/2017/2078794. Epub 2017 Sep 20.
本文引用的文献
1
Effect of Adlay ( Coix lachryma-jobi L. var. ma-yuen Stapf) Testa and its phenolic components on Cu2+-treated low-density lipoprotein (LDL) oxidation and lipopolysaccharide (LPS)-induced inflammation in RAW 264.7 macrophages.薏苡仁 testa 及其酚类成分对 Cu2+ 处理的低密度脂蛋白（LDL）氧化和脂多糖（LPS）诱导的 RAW 264.7 巨噬细胞炎症的影响。
J Agric Food Chem. 2009 Mar 25;57(6):2259-66. doi: 10.1021/jf803255p.
2
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.反式咖啡酸类似物的合成及其对HIV-1整合酶和癌细胞系的生物活性。
Bioorg Med Chem Lett. 2008 Dec 15;18(24):6553-7. doi: 10.1016/j.bmcl.2008.10.046. Epub 2008 Oct 15.
3
Evaluation of caffeic acid amide analogues as anti-platelet aggregation and anti-oxidative agents.
Bioorg Med Chem. 2005 Mar 1;13(5):1791-7. doi: 10.1016/j.bmc.2004.11.055.
4
Anti-inflammatory effect of caffeic acid methyl ester and its mode of action through the inhibition of prostaglandin E2, nitric oxide and tumor necrosis factor-alpha production.咖啡酸甲酯的抗炎作用及其通过抑制前列腺素E2、一氧化氮和肿瘤坏死因子-α产生的作用方式。
Biochem Pharmacol. 2004 Dec 15;68(12):2327-36. doi: 10.1016/j.bcp.2004.08.002.
5
iNOS-mediated nitric oxide production and its regulation.诱导型一氧化氮合酶介导的一氧化氮生成及其调控。
Life Sci. 2004 Jun 25;75(6):639-53. doi: 10.1016/j.lfs.2003.10.042.
6
Recent progress in pharmacological research of propolis.蜂胶药理学研究的最新进展。
Phytother Res. 2001 Nov;15(7):561-71. doi: 10.1002/ptr.1029.
7
Caffeic acid, chlorogenic acid, and dihydrocaffeic acid metabolism: glutathione conjugate formation.咖啡酸、绿原酸和二氢咖啡酸代谢：谷胱甘肽共轭物的形成。
Drug Metab Dispos. 2001 Nov;29(11):1432-9.
8
Nitric oxide and the immune response.一氧化氮与免疫反应。
Nat Immunol. 2001 Oct;2(10):907-16. doi: 10.1038/ni1001-907.
9
Inducible nitric oxide synthase in human diseases.人类疾病中的诱导型一氧化氮合酶
Clin Exp Immunol. 1998 Aug;113(2):147-56. doi: 10.1046/j.1365-2249.1998.00648.x.
10
Natural products in drug discovery and development.药物研发中的天然产物。
J Nat Prod. 1997 Jan;60(1):52-60. doi: 10.1021/np9604893.
Zotero 插件