(-)-棉子素
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- CAS号:
- 90141-22-3
- 英文名:
- (-)-Gossypol
- 英文别名:
- R-(-)-gossypol acetic acid;CS-619;C:C&B61;(R)-Gossypol;(-)-Gossypol;AT 101, >=98%;GOSSYPOL，AT101;(R)-(-)-Gossypol;GOSSYPOL 90141-22-3;(-)-Gossypol USP/EP/BP
- 中文名:
- (-)-棉子素
- 中文别名:
- 左旋醋酸棉酚;(-)-棉子素;(R)-(-)-棉子酚;AT 101,BCL-2 AND MCL-1抑制剂(BH3-MIMETIC)
- CBNumber:
- CB91437592
- 分子式:
- C30H30O8
- 分子量:
- 518.55
- MOL File:
- 90141-22-3.mol
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(-)-棉子素化学性质
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熔点:
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166-167℃
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比旋光度:
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D28 -386 to -390° (c = 0.5 g/100 g soln in CHCl3)
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沸点:
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707.9±55.0 °C(Predicted)
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密度:
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1.403
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储存条件:
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-20°C
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溶解度:
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DMSO: soluble15mg/mL, clear
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酸度系数(pKa):
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7.15±0.50(Predicted)
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形态:
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powder
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颜色:
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white to light brown
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旋光度 (Optical Rotation):
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[α]/D -350 to -365°, c = 0.3 (CDCl3)
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稳定性:
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Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
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InChI:
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1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
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InChIKey:
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QBKSWRVVCFFDOT-UHFFFAOYSA-N
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(-)-棉子素性质、用途与生产工艺
常温下，(-)-棉子素易溶于乙醇、丙酮、三氯甲烷等有机溶剂，亦溶于油脂，但不溶于水。其中大部分有机溶剂对人体毒性较大，不适于作为药物载体，很难制成注射制剂。(-)-棉子素也难溶于水。
(-)-棉子素的杀精作用已为人们所熟知，可以作为男性节育药使用。目前已有醋酸棉子素口服制剂上市，作为男用避孕药或用于治疗妇科疾病，包括子宫内膜异位症、月经过多或失调等。将醋酸棉子素加入缓释材料形成缓释制剂，避免出现“峰谷”现象，用于解决“峰谷”现象。?
(R)-(-)-Gossypol (AT-101) 是天然产物 Gossypol 的左旋异构体。(R)-(-)-Gossypol (AT-101) 结合到 Bcl-2，Mcl-1 和 Bcl-xL 蛋白，Ki 值分别为 260±30 nM，170±10 nM 和 480±40 nM。
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Bcl-2
260 nM (Ki)
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Bcl-xL
480 nM (Ki)
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Mcl-1
170 nM (Ki)
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Autophagy
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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.
(-)-棉子素
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下游产品
| 更新日期 | 产品编号 | 产品名称 | CAS编号 | 包装 | 价格 |
|---|
| 2026/06/05 | HY-15464 | (-)-棉子素
(R)-(-)-Gossypol | 90141-22-3 | 5 mg | 2300元 |
| 2026/06/05 | HY-15464 | (-)-棉子素
(R)-(-)-Gossypol | 90141-22-3 | 10 mM * 1 mL in DMSO | 2624元 |
90141-22-3, (-)-棉子素 相关搜索:
异氰酸叔丁酯 异腈基乙酸甲酯 双水杨酰胺乙基钴 乙酰丙酮银 1,1,3,3-四甲基丁基异氰 对甲基苯磺酰甲基异腈 三乙酰丙酮铝 异氰基乙酸乙酯 乙酰丙酮酸铜 乙酰丙酮钴水合物 三(2,2,6,6-四甲基-3,5-庚二酸)铕 乙二胺氯化铂 苯硒酚 2,2,6,6-四甲基-3,5-庚烷二酸镝 异腈基正丁烷 乙酰丙酮铬盐 三乙酰丙酮铁 苄异腈
- Inhibitors
- 信号转导通路激酶抑制剂
- 抑制剂
- 对照品
- 细胞信号通路抑制剂
- 小分子抑制剂，天然产物
- 细胞凋亡
- AT 101,BCL-2 AND MCL-1抑制剂(BH3-MIMETIC)
- (R)-(-)-棉子酚
- 左旋醋酸棉酚
- (-)-棉子素
- 90141-22-3
- R-(-)-gossypol acetic acid
- (R)-(-)-Gossypol (AT-101)
- AT 101, Bcl-2 and Mcl-1 inhibitor (BH3-mimetic)
- GOSSYPOL，AT101
- (-)-Gossypol USP/EP/BP
- (-)-Gossypol
- [2,2'-Binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)-
- C:C&B61
- (R)-(-)-GOSSYPOL;R-(-)-GOSSYPOL ACETIC ACID
- CS-619
- GOSSYPOL 90141-22-3
- (R)-Gossypol
- (R)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde
- (R)-(-)-Gossypol
- DL-gossypol acetic acid
- AT 101, >=98%