(-)-沙利度胺

(-)-沙利度胺

中文名称(-)-沙利度胺
中文同义词S-沙利度胺;(-)-沙利度胺;S)-(-)-THALIDOMIDE[干冰运输];化合物 T12644L
英文名称(-)-THALIDOMIDE
英文同义词6-dioxo-3-piperidinyl)-3(2h)-dion(s)-1h-isoindole-2-(2;6-dioxo-3-piperidyl)-n-(l-(-)-phthalimid;(S)-2-(2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3-(2H)-DIONE;S(-)-2-(2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE;(S)-(-)-THALIDOMIDE;(-)-THALIDOMIDE >98% INHIBITOR OF ANGIOG EN;(-)-N-[(S)-2,6-Dioxo-3-piperidinyl]phthalimide;(3S)-3-(1,3-Dioxo-2H-isoindole-2-yl)piperidine-2,6-dione
CAS号841-67-8
分子式C13H10N2O4
分子量258.23
EINECS号635-910-2
相关类别Pharmaceuticals;Chiral Reagents;Intermediates & Fine Chemicals
Mol文件841-67-8.mol
结构式(-)-沙利度胺 结构式

(-)-沙利度胺 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 Freezer
溶解度可溶于DMSO
酸度系数(pKa)10.70±0.40(Predicted)
形态固体
颜色白色
旋光性 (optical activity)[α]23/D 62.6°, c = 2 in DMF(lit.)

(-)-沙利度胺 用途与合成方法

(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。

Apoptosis

(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.

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.

安全信息

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

MSDS信息

提供商 语言
英文
更新日期产品编号产品名称CAS号包装价格
2024/01/25HY-14658A(S)-Thalidomide5 mg700元
2024/01/25HY-14658A(S)-Thalidomide10 mg1100元

(-)-沙利度胺 上下游产品信息

下游产品
"(-)-沙利度胺"相关产品信息
沙利度胺 (S)-3-氨基哌啶-2-酮盐酸盐 (S)-3-氨基哌啶 3-氨基哌啶,98% (-)-沙利度胺 3-氨基哌啶-2-酮
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