Gossypol Acetate

Alias: Pogosin, AT101; BL-193; AT-101; (±)-Gossypol-acetic acid; BL19;AT 101; 3BL 193 (acetic acid); Gossypol acetate; Gossypol acetic acid; Acetic acid Gossypol.
Cat No.:V0871 Purity: ≥98%
Gossypol Acetate (Pogosin, AT101; BL-193; AT-101)is a naturally occuring polyphenolic aldehyde with potential anticancer activity.
Gossypol Acetate Chemical Structure CAS No.: 12542-36-8
Product category: Dehydrogenase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
250mg
Other Sizes

Other Forms of Gossypol Acetate:

  • Gossypol
  • AT101
  • (S)-Gossypol acetic acid
  • (R)-(-)-Gossypol
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Gossypol Acetate (Pogosin, AT101; BL-193; AT-101) is a naturally occuring polyphenolic aldehyde with potential anticancer activity. It inhibit Bcl-xL and Bcl-2 proteins with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively. It also acts as an inhibitor for various dehydrogenase enzymes. Gossypol, a known antispermatogenic agent from the cotton plant genus Gossypium, was found to inhibit yellow perch sperm motility in vitro and lactate dehydrogenase activity in spermatozoa when used in a dose-dependent manner. Gossypol has been approved to have antiproliferative and apoptosis-inducing effects on some kinds of cancer cell lines in vitro.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
One natural substance that has been investigated as an anticancer agent is gingsypol, which is extracted from cottonseeds and roots. Tested in multiple clinical trials, the racemic version of Gossypol [(±)-Gossypol] is well tolerated. -Gossypol) has a Ki of 0.5 to 0.6 μM when binding to the Bcl-xL protein. Additionally, (±)-Gossypol binds to Bcl-2 protein potently, with a Ki value of 0.2-0.3 mM. The (-)-Gossypol and (+)-Gossypol enantiomers are the two enantiomers of the natural racemic Gossypol. In 6-day MTT tests, the racemic form and all enantiomers of Gossypol are evaluated against UM-SCC-6 and UM-SCC-14A. shows higher growth inhibition in comparison to (+)-Gossypol compared to (±)-Gossypol in both evaluated cell lines (P<0.001). With (±)-Gossypol, an intermediate growth inhibitory impact is seen, however this effect is only noticeable at the higher dose (10 μM, P<0.0001)[1].
ln Vivo
Gossypol acetate is able to inhibit tumor growth in Wus1-bearing mice, but the survival of mice is not prolonged, and tumor grows rapidly after short inhibition. Gossypol has now been found to have inhibitory effects on proliferation or to induce apoptosis in ovarian cancer, endometrial cancer, adrenal cortical tumor, thyroid cancer, lung cancer, colon carcinoma, leukemia, pancreatic cancer, melanoma and lymphoma. In addition, gossypol can increase the sensitivity of drug-resistant tumor cells to chemotherapy and radiotherapy. Some clinical trials showed gossypol is well-tolerated, and partial responses are observed in some patients.
Animal Protocol
N/A
Wus1-bearing mice
References
[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
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C32H34O10
Molecular Weight
578.61
CAS #
12542-36-8
Related CAS #
Gossypol;303-45-7;(R)-(-)-Gossypol acetic acid;866541-93-7;(S)-Gossypol (acetic acid);1189561-66-7;(R)-(-)-Gossypol;90141-22-3
SMILES
OC1=C(C2=C(O)C(C(C=O)=C(O)C(O)=C3C(C)C)=C3C=C2C)C(C)=CC4=C(C(C)C)C(O)=C(O)C(C=O)=C41.O=C(O)C
Synonyms
Pogosin, AT101; BL-193; AT-101; (±)-Gossypol-acetic acid; BL19;AT 101; 3BL 193 (acetic acid); Gossypol acetate; Gossypol acetic acid; Acetic acid Gossypol.
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (172.8 mM)
Water:<1 mg/mL
Ethanol: 21 mg/mL (36.4 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7283 mL 8.6414 mL 17.2828 mL
5 mM 0.3457 mL 1.7283 mL 3.4566 mL
10 mM 0.1728 mL 0.8641 mL 1.7283 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Gossypol Acetate

    DNA content analysis of U266 cells after incubation with gossypol acetate. (A-D) Results of flow cytometry for U266 cells after induction with DMSO, 5, 10, 25 μM of gossypol acetate for 48 h.Oncol Rep.2013 Aug;30(2):731-8.
  • Gossypol Acetate

    Caspase-3 fluorometric activity assay on Wus1 and U266 cell exposure to 25 μmol/l gossypol acetate for 0, 6, 12, 18 and 24 h.Oncol Rep.2013 Aug;30(2):731-8.
  • Gossypol Acetate

    Bcl-2 expression of Wus1 after treating with 25 μmol/l gossypol acetate for 24 h. Purple, BCL-2 expression in untreated Wus1 cells; red, BCL-2 expression in Wus1 cells treated with gossypol acetate; orange, IgG homotype control in untreated Wus1 cells; yellow, IgG homotype control in Wus1 cells treated with gossypol acetate.Oncol Rep.2013 Aug;30(2):731-8.
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