CAS: 22144-77-0; Cytochalasin D

该化合物是一种自然产生的藻类,产自各种真菌,特别是原菌*Helminthosporium* ,以其抑制行为聚合的能力而著称,在包括细胞分解,运动力和形状维护在内的各种细胞过程中发挥着关键作用;该化合物展示了一种复杂的结构,其特点是内酯环和多种功能组,有助于其生物活动;作为强大的细胞骨骼干扰器,(-)-Cytochalasin D,已就其对细胞形态和运动的影响进行了广泛研究,使其成为细胞生物学研究的宝贵工具;在实验室环境中,该产品经常被用来调查细胞细胞细胞素的动态及其在各种生理和病理过程中的影响;此外,由于其生物特性,( --)-细胞素D在癌症研究和治疗发展方面可能应用,尽管其使用由于毒性有限,而且实验环境需要谨慎处理,但该产品的使用有限.

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(12),13,19-triene-1,17-dione(7S,13E,16S,18R,19E,21R)-21-Acetoxy-18-hydroxy-16,18-dimethyl-7-(2-trimethylsilylethoxymethoxy)-10-phenyl[11]cyt°Chalasa-6(12),13,19-triene-1,17-dione (5R)-1-benzoyl-5-benzylpyrrolidin-2-one (S)-1-Benzoyl-5-benzyl-3-((4E,8E,10E,12E)-(S)-4,6,12-trimethyl-tetradeca-4,8,10,12-tetraenoyl)-1,5-dihydro-pyrrol-2-one (5R)-1-Benzoyl-5-benzyl-3-[(4E,6S,8E,10E,12E)-4,6,12-trimethyl-1-oxotetradecatetra-4,8,10,12-enyl]pyrrolidin-2-one17,17O-Dihydr°Cyt°Chalasin D 12-hydroxy-zygosporin G 12-Mesyloxyzygosporin G 7-O-acetylcyt°Chalasin D

合成工艺路线路线简述

    📜(5R)-1-Benzoyl-5-Benzyl-3-[(4E,6S,8E,10E,12E)-4,6,12-Trimethyl-1-Oxotetradecatetra-4,8,10,12-Enyl]Pyrrolidin-2-One置于吡啶,2,6-二甲基吡啶,盐酸,4-二甲氨基吡啶,Sodium Hydroxide,Sodium Tetrahydroborate,四氧化锇,氯化亚砜,Cerium(III) Chloride,草酰氯,氢氟酸,四丁基氟化铵,水,双氧水,对甲苯磺酸,二甲基亚砜,三乙胺,N,N-二异丙基乙胺,间氯过氧苯甲酸,Lithium Hexamethyldisilazane体系中,用 四氢呋喃,吡啶,甲醇,正己烷,二氯甲烷,氯仿,水,乙腈,苯 用作溶剂,化学反应 53.83H,反应生成胞松弛素d
    参考文献:细胞松弛素d的全合成:细胞松弛素o的全合成和完整结构分配
    标题:细胞松弛素d的全合成:细胞松弛素o的全合成和完整结构分配
    摘要:据报道,细胞松弛素d 3的总合成过程中的关键步骤是分子内diels-Alder反应,该反应用于关闭11元环,同时在四个立体中心c(4),C(5)引入所需的立体化学.,C(8)和c(9).Diels-Alder反应的前体21是由醛13与二烯基膦酸酯14缩合制得三烯15,三烯15转化为酰基咪唑17后,用于酰化吡咯烷酮18.不稳定的吡咯烷酮21为然后通过苯硒化-氧化消除从吡咯烷酮生成,并通过在高稀释条件下在甲苯中加热而环化,得到大环三烯22(25-30%).研究了该三烯中双键的选择性官能化,其中环氧化对17,18-双键具有选择性,而使用四氧化在6,7-双键处选择性发生羟基化作用.为了完成细胞松弛素d 3的合成,通过保护和脱水将6,7-二醇26转化为环外烯烃30.使用四氧化进行进一步的羟基化反应,得到二醇31,通过保护,继之以苯硒化,将其转移至烯酮36中,N-脱苯甲酰化和氧化消除.在卢氏条件下还
    Doi:10.1039/a906412E

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    专利信息


    专利号:US-9662347-B2
    优先权日:2010-05-11
    标题 :Method for inhibiting the induction of cell death by inhibiting the synthesis or secretion of age-albumin in cells of the mononuclear phagocyte system
    发明人:LEE BONG HEE; BYUN KYUNG HEE
    权利人:LEE BONG HEE; BYUN KYUNG HEE; GACHON UNIV OF INDUSTRY-ACADEMIC COOP FOUND
    摘要:The present invention relates to a method for inhibiting the induction of cell death by inhibiting the synthesis or secretion of AGE-albumin in cells of the mononuclear phagocyte system, to an AGE-albumin synthesis inhibitor, and to a pharmaceutical composition comprising the AGE-albumin synthesis inhibitor for preventing or treating degenerative disease and autoimmune disease. The AGE-albumin of the present invention is synthesized and secreted in human microglia or human macrophages in an Alzheimer's model, stroke model, Parkinson's disease model and rheumatoid arthritis model. The AGE-albumin synthesis and secretion are caused by oxidative stress. The expression of RAGE increases in first-order human neurons or cartilage cells to which AGE-albumin is administered, whereupon a MAPK signaling pathway is activated and the expression of Bax increases to induce an increase in calcium in mitochondria, thus finally inducing cell death. Therefore, the AGE-albumin synthesis inhibitor of the present invention can be valuably used in the diagnosis or treatment of degenerative diseases or autoimmune diseases such as Alzheimer's disease, strokes, Parkinson's disease, amyotrophic lateral sclerosis, rheumatoid arthritis, diabetic retinopathy, AIDS, aging, pulmonary fibrosis, spinal cord injuries, etc.

    专利号:US-2008317875-A1
    优先权日:2006-07-10
    标题 :Inhibitor of PI3 kinase-dependent inflammatory cytokine synthesis and method for inhibiting the same
    发明人:KOYASU SHIGEO; OHTANI MASASHI; SASAKAW CHIHIRO; YOSHIDA SEI
    权利人:KOYASU SHIGEO; OHTANI MASASHI; SASAKAW CHIHIRO; YOSHIDA SEI
    摘要:The present invention provides a novel inhibitor for inhibiting synthesis of a PI3 kinase-dependent inflammatory cytokine in vivo in a vertebrate and a method for inhibiting the same. More particularly, the present invention provides a suppressor for suppressing a cell-mediated immune response and a method for suppressing the same, as well as an activator for activating a humoral immune response and a method for activating the same. In the present invention, by administering Li ion to a living body to inhibit synthesis of an inflammatory cytokine, a cell-mediated immune responses can be suppressed, and immune-mediated inflammatory disorders (IMIDs) can be treated.

    专利号:US-2024239805-A1
    优先权日:2022-12-16
    标 题:Aza-yang cyclization-buchner aromatic ring expansion: collective synthesis of cycloheptatriene-containing azetidine lactones
    发明人:SINGH MANVENDRA PAL; BOSKOVIC ZARKO; GASKINS BRYCE
    权利人:UNIV KANSAS
    摘要:The present disclosure is directed to a compound of Formula I, Formula II, Formula III, Formula IV, or Formula Vor a pharmaceutically acceptable salt and/or solvate thereof.

    专利号:US-2006134779-A1
    优先权日:2004-03-10
    标题:Modulation of cell intrinsic strain to control cell modulus, matrix synthesis, secretion, organization, material properties and remodeling of tissue engineered constructs
    发明人:BANES ALBERT J; QI JIE
    权利人:BANES ALBERT J; QI JIE
    摘要:The present invention provides methods for manipulating the intrinsic strain of cells by treating tissue engineered constructs or native tissue with compounds which affect the intrinsic strain setpoint of the cells in order to modulate matrix synthesis, secretion, organization and/or remodeling so that the tissues withstand in vivo mechanical forces and have the structural characteristics of host tissue which has been permanently altered by injury, atrophy or disease. The compounds include binding site peptides, ATP, UTP and related analogues, IL-1β, TGF-α, cytochalasin D, hyaluronic acid, nocodazole and others. Also provided are methods for applying a mechanical external strain to the tissues, as well as methods for modulating the expression of cytoskeletal genes that transcribe cytoskeletal proteins which regulate a cell's intrinsic strain setpoint.

    专利号:US-2007077653-A1
    优先权日:2003-09-04
    标 题:Modulation of cell intrinsic strain to control matrix synthesis, secretion, organization and remodeling
    发明人:BANES ALBERT J; QI JIE
    权利人:MEDTRAIN TECHNOLOGIES LLC
    摘要:The present invention provides methods for manipulating the intrinsic strain of cells by treating tissue engineered constructs or native tissue with compounds which affect the intrinsic strain setpoint of the cells in order to modulate matrix synthesis, secretion, organization and/or remodeling so that the tissues withstand in vivo mechanical forces and have the structural characteristics of host tissue which has been permanently altered by injury, atrophy or disease. The compounds include binding site peptides, ATP, UTP and related analogues, IL-1&bgr; TGF-&agr; cytochalasin D, hyaluronic acid, nocodazole and others. Also provided are methods for applying a mechanical external strain to the tissues, as well as methods for modulating the expression of cytoskeletal genes that transcribe cytoskeletal proteins which regulate a cell's intrinsic strain setpoint.

    专利号:US-6200808-B1
    优先权日:1995-03-29
    标 题 :Induction of embryogenesis from plant microspores
    发明人:SIMMONDS DAINA H; NEWCOMB WILLIAM; ZHAO JIPING; GERVAIS CARMEN
    权利人:UNITED KINGDOM GOVERNMENT
    摘要:Embryogenesis from plant microspores is routinely induced with a 16-24 h temperature treatment of 32.5° C. Continuous culture at 25° C. results in pollen development. However, microspore treatment with anti-cytoskeletal agents, or protein synthesis inhibitors, at the non-inductive temperature of 25° C., can induce embryogenesis, thus demonstrating that heat shock is not required for embryogenic induction. Furthermore, when anti-microtubule agents (e.g. colchicine) are used, embryo induction and chromosome doubling occur simultaneously, thus generating doubled haploids, whereas heat induction generates haploids. Thus, the use of microtubule inhibitors will provide a simple one-step process to simultaneously induce embryogenesis and chromosome doubling for the production of fertile plants, thus providing minimal manipulation which will be very advantageous for genetic studies and plant breeding programs. As noted, heat shock induces haploids. A low level of chromosome doubling can be obtained by adding colchicine to microspore cultures during the heat treatment. However, the use of trifluralin with the heat treatment, to generate doubled haploid plants results in an improved recovery of fertile doubled haploid plants than previously shown in the prior art.

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    主要参考文献


    1: Erdoes G, Reid C, Koster A. The Dark Side of FIBTEM: Cytochalasin D. J Cardiothorac Vasc Anesth. 2020 Jun;34(6):1474-1475. doi: 10.1053/j.jvca.2020.01.029. Epub 2020 Jan 22. 20(1):79-88. doi: 10.2174/1566524019666191007104816. 19(7):2234-2255. doi: 10.7150/ijbs.77166.
    4: Huang FY, Li YN, Mei WL, Dai HF, Zhou P, Tan GH. Cytochalasin D, a tropical fungal metabolite, inhibits CT26 tumor growth and angiogenesis. Asian Pac J Trop Med. 2012 Mar;5(3):169-74. doi: 10.1016/S1995-7645(12)60019-4. 14(12):1109-13. doi: 10.3109/02713689508995817. 3(2):151-5. doi: 10.1080/10286020108041383. 424(1):52-7. doi: 10.1016/j.bbrc.2012.06.063. Epub 2012 Jun 20. 529 Pt 2(Pt 2):405-11. doi: 10.1111/j.1469-7793.2000.00405.x.
    9: Leatherwood WH, Bortner BA, Draeger RW, Dahners LE, Rubin J, Weinhold PS. Evaluation of zoledronate, cytochalasin-D, and desferrioxamine on osseointegration in an intra-medullary femoral implant model. J Musculoskelet Neuronal Interact. 2020 Mar 3;20(1):121-127.

    合成参考文献


    参考文献:10.1021/jm00348a011
    摘要:Patwardhan BH, Flashner M, Miller CA, Tanenbaum SW. Structure-activity correlations of cytochalasins. Novel halogenated and related cytochalasin C and D derivatives. J Med Chem. 1982 Jun;25(6):663–6. doi: 10.1021/jm00348a011.
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