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841-67-8

中文名称 (-)-沙利度胺
英文名称 (-)-THALIDOMIDE
CAS 841-67-8
分子式 C13H10N2O4
分子量 258.23
MOL 文件 841-67-8.mol
更新日期 2024/08/06 14:59:37
841-67-8 结构式 841-67-8 结构式

基本信息

中文别名
S-沙利度胺
(-)-沙利度胺
英文别名
NSC 91730
(S)-(-)-THALIDOMIDE
6-dioxo-3-piperidyl)-n-(l-(-)-phthalimid
N-[(S)-2,6-Dioxopiperidine-3-yl]phthalimide
(-)-THALIDOMIDE >98% INHIBITOR OF ANGIOG EN
(-)-N-[(S)-2,6-Dioxo-3-piperidinyl]phthalimide
6-dioxo-3-piperidinyl)-3(2h)-dion(s)-1h-isoindole-2-(2
(3S)-3-(1,3-Dioxo-2H-isoindole-2-yl)piperidine-2,6-dione
2-[(3S)-2,6-Dioxo-3-piperidyl]-1H-isoindole-1,3(2H)-dione
S(-)-2-(2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE

物理化学性质

熔点269-271°C
沸点401.48°C (rough estimate)
密度1.2944 (rough estimate)
折射率1.5300 (estimate)
储存条件-20°C冷冻
溶解度DMSO: soluble
酸度系数(pKa)10.70±0.40(Predicted)
形态solid
颜色white
旋光性 (optical activity)[α]23/D 62.6°, c = 2 in DMF(lit.)

安全数据

危险性符号(GHS)GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
警示词危险
危险性描述H302-H360
危险品标志T
危险类别码61-22
安全说明53-36/37/39-45
危险品运输编号UN 2811 6.1/PG 2
WGK Germany3
RTECS号TI4925050

常见问题列表

生物活性
(S)-Thalidomide ((S)-(-)-Thalidomide) 是 Thalidomide 的 S-对映体。(S)-Thalidomide 具有免疫调节,抗炎,抗血管生成和促凋亡作用。(S)-Thalidomide 通过与 cereblon (CRBN) 结合诱导致畸作用。
靶点

Apoptosis

体外研究

(S)-Thalidomide treatment results in a reduction in cell viability in U266 cells with an IC 50 of 362 μM.
(S)-Thalidomide treatment increased apoptosis in a dose-dependent manner in U266 cells.
There are changes in the expression profile of genes involved in angiogenesis and apoptosis, but the changes are most dramatic in the apoptotic genes. In particular, the expression of I-κB kinase is decreased by two-fold, which is associated with a four-fold decrease in NF-κB expression. (S)-Thalidomide increases the Bax:Bcl-2 ratio, also increases I-kB protein levels, and decreases NF-kB activity. A dramatic decrease in Bcl-2 expression with (S)-Thalidomide suggests a possible enhancement of cytotoxic effect if combined with other cytotoxic agents.

Cell Viability Assay

Cell Line: U266 MM cells
Concentration: 0 µM, 10 µM, 100 µM, 150 µM, 200 µM, 1000 µM
Incubation Time: 3 days
Result: A reduction in cell viability was observed in U266 cells.

Apoptosis Analysis

Cell Line: U266 MM cells
Concentration: 100 µM, 150 µM, 200 µM, 1000 µM
Incubation Time: 3 days
Result: Increased apoptosis in U266 cells.
体内研究

Thalidomide does cause limb reduction defects in chick embryos as long as the embryos are directly exposed to the drug. The most useful techniques are implanting Thalidomide-soaked beads into the embryo immediately adjacent to the limb territory or soaking presumptive chick limb territories in Thalidomide and then grafting the explants to a host embryo celom. Thalidomide affects the chick limb grafted to a host embryo in a dose response fashion. Furthermore, (S)-Thalidomide is more teratogenic than (R)-Thalidomide.

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