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マイタンシン

マイタンシン 化學(xué)構(gòu)造式
35846-53-8
CAS番號(hào).
35846-53-8
化學(xué)名:
マイタンシン
別名:
メイタンシン;マイタンシン;(1S,2R,3S,5S,16Z,18Z,20R,21S)-11-クロロ-21-ヒドロキシ-12,20-ジメトキシ-2,5,9,16-テトラメチル-8,23-ジオキソ-4,24-ジオキサ-9,22-ジアザテトラシクロ[19.3.1.110,14.03,5]ヘキサコサ-10(26),11,13,16,18-ペンタエン-6-イル (2S)-2-(N-メチルアセトアミド)プロパノアート
英語(yǔ)名:
Maytansine
英語(yǔ)別名:
NSC 153858;Maytansine;maitansine;Maitansina;Microtubule/Tubulin,tumor,mitotic,microtubule-targeted,arrest,Inhibitor,potent,subnanomolar,Maytansine,inhibit;(14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-Chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-acetyl-N-methyl-L-alaninate;(1S,2R,3S,5S,6R,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.11?,1?.03,?]hexacosa-10,12,14(26),16,18-pentaen-6-yl (2S)-2-(N-methylacetamido)propanoate
CBNumber:
CB8903295
化學(xué)式:
C34H46ClN3O10
分子量:
692.2
MOL File:
35846-53-8.mol
MSDS File:
SDS

マイタンシン 物理性質(zhì)

融點(diǎn) :
183.5-184℃
比旋光度 :
D26 -145° (c = 0.055 in chloroform)
沸點(diǎn) :
895.1±65.0 °C(Predicted)
比重(密度) :
1.1049 (rough estimate)
屈折率 :
1.6000 (estimate)
貯蔵溫度 :
Store at -20°C
溶解性:
DMF: 1 mg/ml; DMSO: 10 mg/ml; Ethanol: 2 mg/ml; PBS (pH 7.2): insol
外見(jiàn) :
A solid
酸解離定數(shù)(Pka):
9.82±0.70(Predicted)
光學(xué)活性 (optical activity):
-14526 (c 0.055, CHCl3)
安定性::
Light Sensitive
InChIKey:
WKPWGQKGSOKKOO-YHBUUTGONA-N
安全性情報(bào)
  • リスクと安全性に関する聲明
  • 危険有害性情報(bào)のコード(GHS)
毒性 LD50 in rats (mg/kg): 0.48 s.c. (Mugera, Ward)
絵表示(GHS) GHS hazard pictograms
注意喚起語(yǔ)
危険有害性情報(bào)
コード 危険有害性情報(bào) 危険有害性クラス 區(qū)分 注意喚起語(yǔ) シンボル P コード
H331 吸入すると有毒 急性毒性、吸入 3 危険 GHS hazard pictograms P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P262 眼、皮膚、衣類につけないこと。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時(shí)に、飲食または喫煙をしないこ と。
P271 屋外または換気の良い場(chǎng)所でのみ使用すること。
P280 保護(hù)手袋/保護(hù)衣/保護(hù)眼鏡/保護(hù)面を著用するこ と。
P301+P310 飲み込んだ場(chǎng)合:直ちに醫(yī)師に連絡(luò)すること。
P302+P352 皮膚に付著した場(chǎng)合:多量の水と石鹸で洗うこと。
P304+P340 吸入した場(chǎng)合:空気の新鮮な場(chǎng)所に移し、呼吸しやすい 姿勢(shì)で休息させること。
P311 醫(yī)師に連絡(luò)すること。
P321 特別な処置が必要である(このラベルの... を見(jiàn)よ)。
P330 口をすすぐこと。
P403+P233 換気の良い場(chǎng)所で保管すること。容器を密閉 しておくこと。
P405 施錠して保管すること。

マイタンシン 価格

メーカー 製品番號(hào) 製品説明 CAS番號(hào) 包裝 価格 更新時(shí)間 購(gòu)入

マイタンシン 化學(xué)特性,用途語(yǔ),生産方法

効能

抗悪性腫瘍薬, 微小管重合阻害薬

説明

This novel ansa macrolide alkaloid occurs in a number of May tan us species. The structure given has been elucidated from chemical and spectroscopic data. In low doses (25-50 mcg/kg), maytansine prolonged the survival of mice bearing vincristine-sensitive P388 leukemia but not those bearing vincristine-resistant tumour lines. In vitro, it suppressed the growth of U21 0, LSl78Y and P388 leukemia cells with ED50 of 2 X 10-9 , 1.5 X 10-9 and 6 X 10-10M respectively and elevated the mitotic index in L 121 0 cells. From labelling studies it was shown that the alkaloid inhibited DNA formation by P388 cells to a greater extent than RNA and protein synthesis. Maytensine did not inhibit RNA polymerase from Escherichia coli at levels as high as 1 X 10-4M.

使用

Antineoplastic.

定義

ChEBI: An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumo r cell lines.

生物學(xué)の機(jī)能

Maytansine is a potent microtubule-targeted compound that inhibits proliferation of cells at mitosis. Antibody-maytansinoid conjugates consisting of maytansinoids (DM1 and DM4) attached to tumor-specific antibodies have shown promising clinical results The microtubule-targeting maytansinoids accumulate in cells and induce mitotic arrest at 250- to 1000-fold lower concentrations than those required for their association with tubulin or microtubules.

毒性學(xué)

Maytansine, an ansa macrolide isolated from African plants of the genera Maytenus and Putterlickia was first described almost two decades ago. It had been reported to be active against several forms of cancer, but a later phase II evaluation suggested no major role for this drug in tumor treatment. Although the toxic side effects were moderate, the antitumor activity was also not impressive.
Maytansine binds to tubulin rapidly and reversibly. Competitive inhibition of binding between maytansine and the vinca alkaloids has been observed, suggesting that maytansine must occupy at least one of vinblastine's binding sites on the tubulin molecule. The number of the maytansine binding sites is not known. Assembly of MT is inhibited at maytansine concentrations below 1μM. This suggests a substoichiometric poisoning mechanism as in the cases of colchicine, vinblastine and podophyllotoxin, but the details are not known. In contrast to many other MT-interacting toxins,maytansine does not promote the formation of aberrant tubulin polymers, even at millimolar concentrations. In fact, low concentrations of maytansine even inhibit vinblastine-induced formation of aberrant polymers.

參考文獻(xiàn)

Walpert-Defillipes et al., Biochem. Pharmacol., 24, 751 (1975)

參考文獻(xiàn)

S.M. Kupchan, et al., J. Org. Chem., 42, 2349 (1977), DOI: 10.1021/jo00434a001.

マイタンシン 上流と下流の製品情報(bào)

原材料

準(zhǔn)備製品


マイタンシン 生産企業(yè)

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35846-53-8(マイタンシン)キーワード:


  • 35846-53-8
  • maitansine
  • Maytansine
  • NSC 153858
  • (14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-Chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-acetyl-N-methyl-L-alaninate
  • Maitansina
  • Microtubule/Tubulin,tumor,mitotic,microtubule-targeted,arrest,Inhibitor,potent,subnanomolar,Maytansine,inhibit
  • (1S,2R,3S,5S,6R,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.11?,1?.03,?]hexacosa-10,12,14(26),16,18-pentaen-6-yl (2S)-2-(N-methylacetamido)propanoate
  • メイタンシン
  • マイタンシン
  • (1S,2R,3S,5S,16Z,18Z,20R,21S)-11-クロロ-21-ヒドロキシ-12,20-ジメトキシ-2,5,9,16-テトラメチル-8,23-ジオキソ-4,24-ジオキサ-9,22-ジアザテトラシクロ[19.3.1.110,14.03,5]ヘキサコサ-10(26),11,13,16,18-ペンタエン-6-イル (2S)-2-(N-メチルアセトアミド)プロパノアート
  • 抗腫瘍薬
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