CAS: 17575-22-3; (2R,3R,4S,6S)-6-(((2R,3S,4S,6S)-6-(((2R,3S,4S,6R)-6-(((3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-Dihydroxy-10,13-Dimethyl-17-(5-Oxo-2,5-Dihydrofuran-3-yl)Hexadecahydro-1H-Cyclopenta[a]Phenanthren-3-yl)Oxy)-4-Hydroxy-2-Methyltetrahydro-2H-Pyran-3-yl)Oxy)-4-Hy

该化合物是心脏甘蓝,是一种具有正非热带效应的化合物,意味着它增加了心脏萎缩的力力.它源自Digitalis lanata植物,通常被称为羊毛狐狸球.该化合物的特点是结构复杂,包括类固醇核和糖味,有助于其生物活动.Lanatoside C以其抑制纳+/K+ ATPase酶的能力而著称,导致细胞内钙含量增加,从而增加心脏萎缩.它通常用于治疗心脏衰竭和某些心律不齐,该化合物还因其治疗指数较低而引人注目,需要仔细监测剂量以避免毒性.在溶性方面,Lanatoside C一般在有机溶剂中溶解,但溶解性有限.其致癌性可能受到诸如病人年龄,肾功能和同时药物等因素的影响,使个人化治疗方法变得至关重要.

结构式图片

欧盟法规

ECHA物质ECHA物质C&L通报REACH预注册

上下游产品

毛花洋地黄苷a Lanatosid A 17575-20-1
毛花洋地黄苷b Lanatoside B 17575-21-2

合成工艺路线路线简述

    📜毛花洋地黄苷a,毛花洋地黄苷b 反应生成毛花苷c
    参考文献:Sterba,Jiri;Pitra,Josef
    标题:Sterba,Jiri;Pitra,Josef

    专利信息


    专利号:US-6015808-A
    优先权日:1993-08-20
    标 题 :Synthesis of pharmaceutical compositions with lactams and β-lactams/oxo thia azabicyclo compounds
    发明人:THIRUMALACHAR MANDAYAM JEERSAN; NARASIMHAN JR MANDAYAM JEERSAN
    摘要:Pharmaceutical compositions with heretofore unknown and enhanced physical, chemical, and biological properties are prepared by combining known biologically active parent compounds with oxo thia azabicyclo compounds, such as lactam and beta -lactam compounds, capable of rapidly transporting the parent compounds in undegraded form to their target sites of action. A process for combining the parent compound with beta -lactam compounds consists of dissolving the parent compound in a polar solvent, adding a beta -lactam compound, incubating the resulting mixture, followed by drying, and subjecting the remaining solid material to solvent washing or extraction to further purify the new pharmaceutical composition. The new pharmaceutical composition possesses the biological and therapeutic activity of the parent compound and the barrier penetrating characteristics of the beta -lactam compound, which results in improved pharmacodynamics, including bioavailability, and an improved chemotherapeutic index, such that lower amounts of the parent may be used to avoid the toxic effects of the parent compound. Some of the new pharmaceutical compounds provide for the first time parent compounds in an orally administerable form.

    专利号:US-6699676-B1
    优先权日:1999-06-03
    标题:Uses of ouabain and ouabain-like molecules in apoptosis related pathologies
    发明人:ORLOV SERGEI N; HAMET PAVEL; TREMBLAY JOHANNE
    权利人:CORP DU CT DE RECH DU CT HOSPI
    摘要:Longterm elevation of the intracellular Na + /K + ratio inhibits macromolecule synthesis and proliferation in the majority of cell types studied so far, including vascular smooth muscle cells (VSMC). We report here that inhibition of the Na + ,K + pump in VSMC by ouabain or 1 hour preincubation in K + -depleted medium attenuated apoptosis triggered by serum withdrawal, staurosporine or okadaic acid. In the absence of ouabain, both DNA degradation and caspase-3 activation in VSMC undergoing apoptosis were insensitive to modification of the extracellular Na + /K + ratio as well as to hyperosmotic cell shrinkage. In contrast, protection of VSMC from apoptosis by ouabain was abolished under equimolar substitution of Na + o with K + o , showing that the anti apoptotic action of Na + ,K + pump inhibition was caused by inversion of the intracellular Na + /K + ratio. Unlike VSMC, the same level of increment of the [Na + ] i /[K + ] i ratio caused by 2 hours preincubation of Jurkat cells with ouabain did not affect chromatin cleavage and caspase-3 activity triggered by treatment with Fas ligand, staurosporine or hyperosmotic shrinkage. Thus, our results show for the first time that similarly to cell proliferation, maintenance of a physiologically low intracellular Na + /K + ratio is required for progression of VSMC apoptosis.

    专利号:US-3963697-A
    优先权日:1974-08-29
    标题 :Labelled cardiotonic glycosides for use in radioimmunoassay
    发明人:COOMBES ROBERT F
    权利人:CURTIS NUCLEAR CORP
    摘要:Disclosed are radioactive cardiotonic glycosides and a process of making such glycosides, the compounds being useful for radioimmunoassay of body fluids for cardiotonic glycoside content. n The novel synthesis comprises reaction of a hydroxyl group of the sugar with a dicarboxylic acid derivative such as a diacid, diacid anhydride or a diacyl halide and thereafter reacting the free carboxylic group with a compound which will undergo electrophilic substitution reactions. A radioactive isotope, preferably 125 I, is reacted via electrophilic substitution with the compound to form the radioactive cardiotonic glycoside.

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Chao MW, Chen TH, Huang HL, Chang YW, HuangFu WC, Lee YC, Teng CM, Pan SL. Lanatoside C, a cardiac glycoside, acts through protein kinase Cδ to cause apoptosis of human hepatocellular carcinoma cells. Sci Rep. 2017 Apr 7;7:46134. doi: 10.1038/srep46134.
    2: Durmaz I, Guven EB, Ersahin T, Ozturk M, Calis I, Cetin-Atalay R. Liver cancer cells are sensitive to Lanatoside C induced cell death independent of their PTEN status. Phytomedicine. 2016 Jan 15;23(1):42-51. doi: 10.1016/j.phymed.2015.11.012. Epub 2015 Dec 12. doi: 10.1038/srep20154.
    4: Kang MA, Kim MS, Kim W, Um JH, Shin YJ, Song JY, Jeong JH. Lanatoside C suppressed colorectal cancer cell growth by inducing mitochondrial dysfunction and increased radiation sensitivity by impairing DNA damage repair. Oncotarget. 2016 Feb 2;7(5):6074-87. doi: 10.18632/oncotarget.6832.

    合成参考文献


    参考文献:10.1177/1087057116635503
    摘要:Voter AF, Manthei KA, Keck JL. A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. J Biomol Screen. 2016 Jul;21(6):626–33.
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