一种稳定且口服生物可利用的恩格勒菌素类似物的合成。
Synthesis of a stable and orally bioavailable englerin analogue.
作者信息
Fash David M, Peer Cody J, Li Zhenwu, Talisman Ian J, Hayavi Sima, Sulzmaier Florian J, Ramos Joe W, Sourbier Carole, Neckers Leonard, Figg W Douglas, Beutler John A, Chain William J
机构信息
Department of Chemistry, University of Hawaii at Manoa, 2545 McCarthy Mall, Honolulu, HI 96822, United States.
Genitourinary Malignancies Branch, National Cancer Institute, Frederick, MD 21702, United States.
出版信息
Bioorg Med Chem Lett. 2016 Jun 1;26(11):2641-4. doi: 10.1016/j.bmcl.2016.04.016. Epub 2016 Apr 8.
Abstract
Synthesis of analogues of englerin A with a reduced propensity for hydrolysis of the glycolate moiety led to a compound which possessed the renal cancer cell selectivity of the parent and was orally bioavailable in mice.
摘要
合成了乙醇酸部分水解倾向降低的恩格勒菌素A类似物，得到了一种具有母体肾癌细胞选择性且在小鼠体内可口服生物利用的化合物。
相似文献
1
Synthesis of a stable and orally bioavailable englerin analogue.一种稳定且口服生物可利用的恩格勒菌素类似物的合成。
Bioorg Med Chem Lett. 2016 Jun 1;26(11):2641-4. doi: 10.1016/j.bmcl.2016.04.016. Epub 2016 Apr 8.
2
Chemical synthesis of the englerins.恩格勒菌素的化学合成。
Chem Asian J. 2012 Jan 2;7(1):22-35. doi: 10.1002/asia.201100780. Epub 2011 Dec 8.
3
Total synthesis and biological evaluation of (-)-englerin A and B: synthesis of analogues with improved activity profile.(-)-恩格勒菌素A和B的全合成及生物学评价：具有改善活性谱的类似物的合成
Angew Chem Int Ed Engl. 2011 Apr 18;50(17):3998-4002. doi: 10.1002/anie.201007790. Epub 2011 Mar 29.
4
Englerin A, a selective inhibitor of renal cancer cell growth, from Phyllanthus engleri.恩格勒因A，一种来自恩格勒叶下珠的肾癌细胞生长选择性抑制剂。
Org Lett. 2009 Jan 1;11(1):57-60. doi: 10.1021/ol802339w.
5
Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins.（-）-岩白菜素的全合成及截短岩白菜素的细胞毒性研究。
Chem Asian J. 2012 May;7(5):1052-60. doi: 10.1002/asia.201101021. Epub 2012 Mar 13.
6
Synthesis and Biological Evaluation of New (-)-Englerin Analogues.新型（-）-恩格勒菌素类似物的合成与生物学评价
ChemMedChem. 2016 May 6;11(9):1003-7. doi: 10.1002/cmdc.201600040. Epub 2016 Mar 23.
7
Total synthesis of englerin A.englerin A 的全合成。
J Am Chem Soc. 2010 Jun 16;132(23):8219-22. doi: 10.1021/ja102927n.
8
Chlorinated englerins with selective inhibition of renal cancer cell growth.具有选择性抑制肾癌细胞生长的氯化恩格尔菌素。
J Nat Prod. 2012 Mar 23;75(3):459-63. doi: 10.1021/np200905u. Epub 2012 Jan 26.
9
Englerin a selectively induces necrosis in human renal cancer cells.恩格勒因a选择性地诱导人肾癌细胞坏死。
PLoS One. 2012;7(10):e48032. doi: 10.1371/journal.pone.0048032. Epub 2012 Oct 22.
10
Chemical synthesis and biological evaluation of the englerin analogues.恩格勒菌素类似物的化学合成与生物学评价
ChemMedChem. 2011 Mar 7;6(3):420-3. doi: 10.1002/cmdc.201000544. Epub 2011 Jan 18.
引用本文的文献
1
The role of natural products versus miRNA in renal cell carcinoma: implications for disease mechanisms and diagnostic markers.天然产物与 miRNA 在肾细胞癌中的作用：对疾病机制和诊断标志物的启示。
Naunyn Schmiedebergs Arch Pharmacol. 2024 Sep;397(9):6417-6437. doi: 10.1007/s00210-024-03121-8. Epub 2024 May 1.
2
Biological Effects of Modifications of the Englerin A Glycolate.恩格勒菌素A乙醇酸修饰的生物学效应
ACS Med Chem Lett. 2022 Aug 22;13(9):1472-1476. doi: 10.1021/acsmedchemlett.2c00258. eCollection 2022 Sep 8.
3
Natural products targeting cancer cell dependency.针对癌细胞依赖性的天然产物。
J Antibiot (Tokyo). 2021 Oct;74(10):677-686. doi: 10.1038/s41429-021-00438-x. Epub 2021 Jun 23.
4
Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition.恩格勒因A的桥头修饰降低TRPC4活性和静脉毒性，但不影响细胞生长抑制作用。
ACS Med Chem Lett. 2020 Aug 3;11(9):1711-1716. doi: 10.1021/acsmedchemlett.0c00186. eCollection 2020 Sep 10.
5
Remarkable Progress with Small-Molecule Modulation of TRPC1/4/5 Channels: Implications for Understanding the Channels in Health and Disease.TRPC1/4/5通道小分子调控取得显著进展：对理解健康与疾病中的这些通道的意义
Cells. 2018 Jun 1;7(6):52. doi: 10.3390/cells7060052.
6
The Role of Compounds Derived from Natural Supplement as Anticancer Agents in Renal Cell Carcinoma: A Review.天然补充剂衍生化合物在肾细胞癌中的抗癌作用：综述。
Int J Mol Sci. 2017 Dec 31;19(1):107. doi: 10.3390/ijms19010107.
7
Englerins: A Comprehensive Review.恩格勒菌素：全面综述。
J Nat Prod. 2017 Mar 24;80(3):771-781. doi: 10.1021/acs.jnatprod.6b01167. Epub 2017 Feb 7.
8
(-)-Englerin A-evoked Cytotoxicity Is Mediated by Na+ Influx and Counteracted by Na+/K+-ATPase.（-）-恩格勒菌素A诱导的细胞毒性由钠离子内流介导，并被钠钾ATP酶抵消。
J Biol Chem. 2017 Jan 13;292(2):723-731. doi: 10.1074/jbc.M116.755678. Epub 2016 Nov 14.
本文引用的文献
1
Synthesis and Biological Evaluation of New (-)-Englerin Analogues.新型（-）-恩格勒菌素类似物的合成与生物学评价
ChemMedChem. 2016 May 6;11(9):1003-7. doi: 10.1002/cmdc.201600040. Epub 2016 Mar 23.
2
Englerin A Inhibits EWS-FLI1 DNA Binding in Ewing Sarcoma Cells.恩格勒菌素A抑制尤因肉瘤细胞中EWS-FLI1与DNA的结合。
J Biol Chem. 2016 May 6;291(19):10058-66. doi: 10.1074/jbc.M115.701375. Epub 2016 Mar 9.
3
Tonantzitlolone cytotoxicity toward renal cancer cells is PKCθ- and HSF1-dependent.托南齐特洛龙对肾癌细胞的细胞毒性依赖于蛋白激酶Cθ（PKCθ）和热休克因子1（HSF1）。
Oncotarget. 2015 Oct 6;6(30):29963-74. doi: 10.18632/oncotarget.4676.
4
Trends in Metastatic Kidney Cancer Survival From the Cytokine to the Targeted Therapy Era.从细胞因子时代到靶向治疗时代转移性肾癌的生存趋势
Urology. 2015 Aug;86(2):262-8. doi: 10.1016/j.urology.2015.05.008. Epub 2015 Jul 18.
5
Englerin A Agonizes the TRPC4/C5 Cation Channels to Inhibit Tumor Cell Line Proliferation.恩格勒因A作用于TRPC4/C5阳离子通道以抑制肿瘤细胞系增殖。
PLoS One. 2015 Jun 22;10(6):e0127498. doi: 10.1371/journal.pone.0127498. eCollection 2015.
6
Renal effects of molecular targeted therapies in oncology: a review by the Cancer and the Kidney International Network (C-KIN).肿瘤分子靶向治疗的肾脏效应：癌症与肾脏国际网络（C-KIN）的综述。
Ann Oncol. 2015 Aug;26(8):1677-84. doi: 10.1093/annonc/mdv136. Epub 2015 Mar 3.
7
(-)-Englerin A is a potent and selective activator of TRPC4 and TRPC5 calcium channels.（-）-恩格勒林A是瞬时受体电位阳离子通道亚家族C成员4（TRPC4）和瞬时受体电位阳离子通道亚家族C成员5（TRPC5）钙通道的强效选择性激活剂。
Angew Chem Int Ed Engl. 2015 Mar 16;54(12):3787-91. doi: 10.1002/anie.201411511. Epub 2015 Feb 23.
8
The past, present, and future of cancer incidence in the United States: 1975 through 2020.美国癌症发病率的过去、现在和未来：1975年至2020年
Cancer. 2015 Jun 1;121(11):1827-37. doi: 10.1002/cncr.29258. Epub 2015 Feb 3.
9
Renal cancer-selective Englerin A induces multiple mechanisms of cell death and autophagy.肾癌选择性恩格勒因A诱导多种细胞死亡和自噬机制。
J Exp Clin Cancer Res. 2013 Aug 20;32(1):57. doi: 10.1186/1756-9966-32-57.
10
A short enantioselective total synthesis of (-)-englerin A.（-）-恩格勒菌素A的短路线对映选择性全合成。
Angew Chem Int Ed Engl. 2013 May 10;52(20):5390-2. doi: 10.1002/anie.201301247. Epub 2013 Apr 15.
Zotero 插件