(R)-(-)-Gossypol
Based on 3 publication(s) in Google Scholar
(R)-(-)-Gossypol (AT-101) is the levorotatory isomer of a natural product Gossypol. AT-101 is determined to bind to Bcl-2, Mcl-1 and Bcl-xL proteins with Kis of 260±30 nM, 170±10 nM, and 480±40 nM, respectively.
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- Pureza : 99.79%
- No. CAS: 90141-22-3
- Fòrmula: C30H30O8
- Peso molecular:518.55
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Almacenamiento:
4°C, sealed storage, away from moisture and light
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
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Chemical Information
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Solvente y solubilidad
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Publications Citing Use of MedChemExpress (MCE) (R)-(-)-Gossypol
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Actividad biológica
Descripciòn
IC50 & Target
[2]|
Mcl-1 170 nM (Ki) |
Bcl-2 260 nM (Ki) |
Bcl-xL 480 nM (Ki) |
Autophagy |
In Vitro
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 IC50 of 2-5 μM and a less sensitive group with IC50 clusters around 10 μM[1]. (R)-(-)-Gossypol (AT-101) is determined to bind to Bcl-2, Mcl-1 and Bcl-xL proteins with Ki values of 260±30 nM, 170±10 nM, and 480±40 nM, respectively[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Ensayo clínico
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | 2011-05 | PHASE1 |
Chemical Information
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No. CAS 90141-22-3
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Appearance Solid
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Peso molecular 518.55
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Fòrmula C30H30O8
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Color Light yellow to yellow
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SMILES
OC1=C2C(C=O)=C(O)C(O)=C(C(C)C)C2=CC(C)=[C@]1[C@]3=C(C)C=C4C(C(C)C)=C(O)C(O)=C(C=O)C4=C3O
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Synonyms
AT-101; R-(-)-gossypol acetic acid
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
4°C, sealed storage, away from moisture and light
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
Publications (3)
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Journal Impact Factor
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Most Recent
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Nat Commun
2023 Jun 10;14(1):3445. PMID: 37301862 -
Cancer Lett
Synthetic lethality of combined AT-101 with idarubicin in acute myeloid leukemia via blockade of DNA repair and activation of intrinsic apoptotic pathway. [Abstract]2019 Oct 1:461:31-43. PMID: 31301319 -
Sci Rep
AT-101 inhibits the proliferation and invasion of tongue squamous carcinoma cells by targeting the miR-21-5p/FDX1 axis. [Abstract]2026 Feb 24;16(1):10361. PMID: 41735357
Solvente y solubilidad
In Vitro:
DMSO : 100 mg/mL (192.85 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pureza y Documentación
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Ficha de datos (280 KB)
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SDS (396 KB)
- English - EN (396 KB)
- Français - FR (396 KB)
- Deutsch - DE (396 KB)
- Norwegian - NO (396 KB)
- Español - ES (396 KB)
- Swedish - SV (396 KB)
- Italian - IT (396 KB)
- Korean - KR (396 KB)
- Portuguese - PT (396 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Oliver CL, et al. In vitro effects of the BH3 mimetic, (-)-Gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res. 2004 Nov 15;10(22):7757-63. [Content Brief]
[2]. Sun Y, et al. Apogossypolone, a nonpeptidic small molecule inhibitor targeting Bcl-2 family proteins, effectively inhibits growth of diffuse large cell lymphoma cells in vitro and in vivo. Cancer Biol Ther. 2008 Sep;7(9):1418-26. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 1.9285 mL | 9.6423 mL | 19.2845 mL | 48.2114 mL |
| 5 mM | 0.3857 mL | 1.9285 mL | 3.8569 mL | 9.6423 mL | |
| 10 mM | 0.1928 mL | 0.9642 mL | 1.9285 mL | 4.8211 mL | |
| 15 mM | 0.1286 mL | 0.6428 mL | 1.2856 mL | 3.2141 mL | |
| 20 mM | 0.0964 mL | 0.4821 mL | 0.9642 mL | 2.4106 mL | |
| 25 mM | 0.0771 mL | 0.3857 mL | 0.7714 mL | 1.9285 mL | |
| 30 mM | 0.0643 mL | 0.3214 mL | 0.6428 mL | 1.6070 mL | |
| 40 mM | 0.0482 mL | 0.2411 mL | 0.4821 mL | 1.2053 mL | |
| 50 mM | 0.0386 mL | 0.1928 mL | 0.3857 mL | 0.9642 mL | |
| 60 mM | 0.0321 mL | 0.1607 mL | 0.3214 mL | 0.8035 mL | |
| 80 mM | 0.0241 mL | 0.1205 mL | 0.2411 mL | 0.6026 mL | |
| 100 mM | 0.0193 mL | 0.0964 mL | 0.1928 mL | 0.4821 mL |
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