(R)-(-)-棉子酚_化工百科

中文名	(-)-棉子素
英文名	(-)-Gossypol
别名	左旋醋酸棉酚 (-)-棉子素 (R)-(-)-棉子酚
英文别名	CS-619 (-)-Gossypol (R)-Gossypol (R)-(-)-Gossypol GOSSYPOL 90141-22-3 DL-gossypol acetic acid R-(-)-gossypol acetic acid (R)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde
CAS	90141-22-3
化学式	C30H30O8
分子量	518.55
密度	1.403
熔点	166-167℃
沸点	707.9±55.0 °C(Predicted)
比旋光度	D28 -386 to -390° (c = 0.5 g/100 g soln in CHCl3)
溶解度	DMSO: 可溶15mg/mL，澄清
酸度系数	7.15±0.50(Predicted)
存储条件	-20°C
稳定性	从提供的购买之日起稳定2年。DMSO或乙醇中的溶液可以在-20 °C下储存长达1个月。
外观	粉末
颜色	white to light brown
体外研究	The natural racemic Gossypol has two enantiomers, namely the (R)-(-)-Gossypol (AT-101) and (+)-Gossypol enantiomers. (R)-(-)-Gossypol (AT-101) and (+)-Gossypol binds to Bcl-2 or Bcl-xL with similar binding affinities, AT-101 is more potent than (+)-Gossypol in inhibition of cell growth and induction of apoptosis, possibly due to the influence of serum in the cell culture experiments. The racemic form and each of the enantiomers of Gossypol are tested against UM-SCC-6 and UM-SCC-14A in 6-day MTT assays. AT-101 exhibits greater growth inhibition relative to (±)-Gossypol than (+)-Gossypol in both cell lines tested (P<0.001). An intermediate growth inhibitory effect is observed with (±)-Gossypol but this effect is only observed at the higher dose of Gossypol (10 μM, P<0.0001). (R)-(-)-Gossypol (AT-101) binds to the BH3-binding groove of Bcl-xL and Bcl-2 proteins with fairly high affinity, has potent activity against head and neck squamous cell carcinomas (HNSCC) cell lines in vitro. Furthermore, it induces apoptosis with high efficiency in HNSCC tumor cells that express functional p53 and that also kills tumor cells with mutant p53 by a different mechanism. AT-101 doses required to inhibit the growth of human fibroblast cell lines by 50% were 2- to 10-fold higher than for HNSCC cell lines. To inhibit human oral keratinocyte growth by 50%, (R)-(-)-Gossypol (AT-101) concentrations are 2-to 3-fold higher than for HNSCC cell lines. (R)-(-)-Gossypol (AT-101) causes dose-dependent inhibition of cell growth in ten UM-SCC cell lines over a range from 0.5 to 10 μM in a 6-day MTT assay. The relative sensitivity of the cell lines vary from a very sensitive group with an IC 50 of 2-5 μM and a less sensitive group with IC 50 clusters around 10 μM. (R)-(-)-Gossypol (AT-101) is determined to bind to Bcl-2, Mcl-1 and Bcl-xL proteins with K i values of 260±30 nM, 170±10 nM, and 480±40 nM, respectively.
WGK Germany	3

(R)-(-)-棉子酚 - 简介

(-)-棉子素是一种天然产物，属于二萜类化合物。它是一种白色固体，具有独特的结构和特殊的生物活性。

棉子素具有多种用途。其次，棉子素还可以用作植物生长调节剂，可以促进植物的生长和抵抗病虫害。棉子素还被用于有机合成反应中作为催化剂和不对称催化剂。

制取棉子素的方法主要有天然提取和化学合成两种。在天然提取中，棉子素从植物中提取得到，然后通过纯化和结晶等步骤得到纯品。在化学合成中，可以通过有机合成反应来合成棉子素。

安全信息：不正确使用或接触(-)-棉子素可能对人体产生一定的危害。它可能对眼睛、皮肤和呼吸系统造成刺激和损伤。在使用或处理该化合物时，应采取必要的防护措施，如佩戴护目镜、手套和口罩。应避免将其吞服或长时间接触皮肤，以防止不良反应发生。如果意外接触或误食了该化合物，应立即寻求医疗咨询。

最后更新：2024-04-09 20:52:54