DL-gossypol acetic acid
(-)-Gossypol
CAS: 90141-22-3
Molecular Formula: C30H30O8
DL-gossypol acetic acid - Names and Identifiers
| Name | (-)-Gossypol |
| Synonyms | 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 |
DL-gossypol acetic acid - Physico-chemical Properties
| Molecular Formula | C30H30O8 |
| Molar Mass | 518.55 |
| Density | 1.403 |
| Melting Point | 166-167℃ |
| Boling Point | 707.9±55.0 °C(Predicted) |
| Specific Rotation(α) | D28 -386 to -390° (c = 0.5 g/100 g soln in CHCl3) |
| Solubility | DMSO: soluble15mg/mL, clear |
| Appearance | powder |
| Color | white to light brown |
| pKa | 7.15±0.50(Predicted) |
| Storage Condition | -20°C |
| Stability | 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. |
| In vitro study | 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. |
DL-gossypol acetic acid - Risk and Safety
| WGK Germany | 3 |
DL-gossypol acetic acid - Reference Information
| properties | at room temperature,(-)-cotton seed is easily soluble in organic solvents such as ethanol, acetone, chloroform, etc., and is also soluble in grease, but not soluble in water. Most of the organic solvents are highly toxic to humans and are not suitable as drug carriers, making it difficult to make injection preparations. (-)-Cotton seed is also hardly soluble in water. |
| action | (-)-the spermatocidal effect of cottonseed has been well known and can be used as a male birth control drug. At present, gymnosin acetate oral preparations are on the market as male contraceptives or used to treat gynecological diseases, including endometriosis, menorrhagia or disorders. The cottonseed acetate is added to the sustained-release material to form a sustained-release preparation to avoid the phenomenon of "peak and valley" and to solve the phenomenon of "peak and valley.? |
| biological activity | (R)-(-)-Gossypol (AT-101) is the left-handed isomer of natural product Gossypol. (R)-(-)-Gossypol (AT-101) binds to Bcl-2,Mcl-1 and Bcl-xL proteins with Ki values of 260±30 nM,170±10 nM and 480±40 nM, respectively. |
| target | Bcl-2 260 nM (Ki) Bcl-xL 480 nM (Ki) Mcl-1 170 nM (Ki) Autophagy |
| in vitro study | 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 series 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 (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 μ m, P<0.0001). (R)-(-)-Gossypol (AT-101) binds to the BH3-binding grove of Bcl-xL and Bcl-2 proteins with fair 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 tumour cells that express functional p53 and that also kills tumour cells with mutant p53 by a different mechanism. AT-101 dos required to inhibit the growth of human fibroblast cells lines by 50% were 2-to 10-fold higher than for HNSCC cells 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) causesdose-dependent inhibition of cell growth in ten UM-SCC cell lines over a range from 0.5 to 10 μ m in a 6-day mtsay. the relative sensitivity of the cell lines from a very sensitive group with an IC 50 of 2-5 μ m. And a less sensitive group with IC 50 clusters around 10 μ m. (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. |
Last Update：2024-04-09 20:52:54
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Product Name: AT-101 Visit Supplier Webpage Request for quotation
CAS: 90141-22-3
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
CAS: 90141-22-3
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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