(R)-(-)-Gossypol acetic acid
Based on 7 publication(s) in Google Scholar
(R)-(-)-Gossypol acetic acid (AT-101 (acetic acid)) 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.
Nur für Forschungszwecke. Wir verkaufen nicht an Patienten.
- Reinheit : 98.93%
- CAS. Nr.: 866541-93-7
- Formel: C32H34O10
- Molecular Weight:578.61
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Speicherung:
-20°C, protect from light, stored under nitrogen
* The compound is unstable in solutions, freshly prepared is recommended.
To place orders, for customer services and technical support, please contact: MedChemExpress USA
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Biologische Aktivität
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Chemical Information
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Publications Citing Use of MedChemExpress (MCE) (R)-(-)-Gossypol acetic acid
More- Nat Commun. 2023 Jun 10;14(1):3445. [Abstract]
- Cancer Lett. 2019 Oct 1:461:31-43. [Abstract]
- Sci Rep. 2026 Feb 24;16(1):10361. [Abstract]
- Microb Pathog. 2024 Nov:196:106960. [Abstract]
- Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]
- Transbound Emerg Dis. 2023 Nov 11:2023:9073566. [Abstract]
- Anticancer Res. 2026 May;46(5):2317-2327. [Abstract]
Customer Validation & Images
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Cell Imaging/Staining
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Cell Imaging/Staining
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RT-PCR
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Cell Imaging/Staining
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WB
Biologische Aktivität
Beschreibung
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 acetic acid (AT-101 (acetic acid)) 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. (R)-(-)-Gossypol (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. (R)-(-)-Gossypol (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. .
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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CAS. Nr. 866541-93-7
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Appearance Solid
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Molecular Weight 578.61
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Formel C32H34O10
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Color Light yellow to brown
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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.CC(O)=O
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Synonyms
AT-101 (acetic acid); (-)-Gossypol acetic acid; (R)-Gossypol acetic acid
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Versand
Room temperature in continental US; may vary elsewhere.
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Speicherung
-20°C, protect from light, stored under nitrogen
* The compound is unstable in solutions, freshly prepared is recommended.
Publications (7)
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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 -
Microb Pathog
2024 Nov:196:106960. PMID: 39313132 -
Food Chem Toxicol
Melatonin protects porcine oocytes from gossypol-induced meiosis defects via regulation of SIRT1-mediated mitophagy. [Abstract]2025 Jan:195:115122. PMID: 39571718
(R)-(-)-Gossypol acetic acid purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]
Representative images of cumulus expansion in Gossypol (0, 10, 20, 40 μM) -exposed oocytes after 44 h culture in vitro maturation.
(R)-(-)-Gossypol acetic acid purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]
(A) Illustrative images of ROS staining of Gossypol (0, 10, 20, 40 μM)-exposed oocytes. (B) Fluorescence intensity of ROS in control and gossypol treatment groups.
(R)-(-)-Gossypol acetic acid purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]
Expression of oxidative stress-related genes (CAT, GSH-Px, SOD1, and SOD2) in control and Gossypol (0, 10, 20, 40 μM) treatment groups in porcine oocytes.
(R)-(-)-Gossypol acetic acid purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]
Illustrative images of mitochondrial membrane potential (MMP) in Gossypol (0, 10, 20, 40 μM) -exposed oocytes.
(R)-(-)-Gossypol acetic acid purchased from MedChemExpress. Usage Cited in: Food Chem Toxicol. 2025 Jan:195:115122. [Abstract]
Expression of PINK1/Parkin-mediated mitophagy related proteins (PINK1, Parkin and P62) of Gossypol (20 μM)-exposed oocytes treated with melatonin. Statistical analysis of the expressions of PINK1/Parkin-mediated mitophagy related proteins in control, gossypol treatment and gossypol-melatonin co-treatment groups.
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Transbound Emerg Dis
2023 Nov 11:2023:9073566. PMID: 40303819 -
Anticancer Res
Gossypol Inhibits GLI3-dependent SHH Signaling to Selectively Target SPOP-deficient Breast Cancer Cells. [Abstract]2026 May;46(5):2317-2327. PMID: 42049345
Lösungsmittel & Löslichkeit
In Vitro:
DMSO : 16.67 mg/mL (28.81 mM; ultrasonic and warming and heat to 60°C; 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. The compound is unstable in solutions, freshly prepared is recommended.
Please refer to the solubility information to select the appropriate solvent. The compound is unstable in solutions, freshly prepared is recommended.
Konzentration (Stammlösung) × Volumen (Stammlösung) = Konzentration (Ziellösung) × Volumen (Ziellösung)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 1.25 mg/mL (2.16 mM); Clear solution
This protocol yields a clear solution of ≥ 1.25 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (12.5 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: 1.25 mg/mL (2.16 mM); Suspended solution; Need ultrasonic
This protocol yields a suspended solution of 1.25 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (12.5 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * The compound is unstable in solutions, freshly prepared is recommended.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Reinheit & Dokumentation
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Data Sheet (282 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
Verweise
[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. The compound is unstable in solutions, freshly prepared is recommended.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
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| DMSO | 1 mM | 1.7283 mL | 8.6414 mL | 17.2828 mL | 43.2070 mL |
| 5 mM | 0.3457 mL | 1.7283 mL | 3.4566 mL | 8.6414 mL | |
| 10 mM | 0.1728 mL | 0.8641 mL | 1.7283 mL | 4.3207 mL | |
| 15 mM | 0.1152 mL | 0.5761 mL | 1.1522 mL | 2.8805 mL | |
| 20 mM | 0.0864 mL | 0.4321 mL | 0.8641 mL | 2.1603 mL | |
| 25 mM | 0.0691 mL | 0.3457 mL | 0.6913 mL | 1.7283 mL |
(R)-(-)-Gossypol acetic acid Related Classifications
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