(7S)-1,2,3,10-テトラメトキシ-7α-(メチルアミノ)-5,6-ジヒドロベンゾ[a]ヘプタレン-9(7H)-オン 化学特性,用途語,生産方法
説明
Colcemid is a colchicine derivative that inhibits tubulin polymerization as potently as colchicine (IC
50 = 2.1 and 2.4 μM, respectively) but is less toxic. At very low (nanomolar) concentrations, colcemid suppresses microtubule dynamicity and inhibits cell migration, while at micromolar levels it blocks microtubule assembly, arresting cells in metaphase. Mitotic block by colcemid is used to synchronize cells and for karyotyping in cytogenetic studies. Prolonged exposure to colcemid can activate p53, leading to apoptosis.
化学的特性
Faintly Yellow Crystalline Powder
使用
An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway.
定義
ChEBI: A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than
olchicine and is used as an antineoplastic.
一般的な説明
Colcemid is also known as demecolcine. Its generic name is
N-methyl-
N-deacetyl-colchicine. Colcemid depolymerizes microtubules and blocks mitosis at metaphase.
安全性プロファイル
Poison by ingestion,
intraperitoneal, parenteral, intravenous, and
intramuscular routes. Human systemic
effects by ingestion: (skin and appendages)
hair effects. Human mutation data reported.
An experimental teratogen. Experimental
reproductive effects. When heated to
decomposition it emits toxic fumes of NOx.
純化方法
Colcemide is purified by chromatography on silica and eluting with CHCl3/MeOH (9:1), and by recrystallisation from EtOAc/Et2O to form yellow prisms. UV in EtOH has max 243nm ( 30,200) and 350nm ( 16,3000). [Synthesis, IR, NMR, MS: Capraro & Brossi Helv Chim Acta 62 965 1979, Beilstein 8 IV 3319.]
(7S)-1,2,3,10-テトラメトキシ-7α-(メチルアミノ)-5,6-ジヒドロベンゾ[a]ヘプタレン-9(7H)-オン 上流と下流の製品情報
原材料
準備製品