1. Apoptosis Autophagy
  2. Bcl-2 Family Autophagy
  3. (R)-(-)-Gossypol acetic acid

(R)-(-)-Gossypol acetic acid  (Synonyms: AT-101 (acetic acid); (-)-Gossypol acetic acid; (R)-Gossypol acetic acid)

Cat. No.: HY-15464A Purity: 98.93%
COA Handling Instructions

(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.

For research use only. We do not sell to patients.

(R)-(-)-Gossypol acetic acid Chemical Structure

(R)-(-)-Gossypol acetic acid Chemical Structure

CAS No. : 866541-93-7

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5 mg USD 93 In-stock
10 mg USD 145 In-stock
50 mg USD 528 In-stock
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Customer Review

Based on 2 publication(s) in Google Scholar

Other Forms of (R)-(-)-Gossypol acetic acid:

Top Publications Citing Use of Products

2 Publications Citing Use of MCE (R)-(-)-Gossypol acetic acid

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  • Biological Activity

  • Protocol

  • Purity & Documentation

  • References

  • Customer Review

Description

(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.

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
Molecular Weight

578.61

Formula

C32H34O10

CAS No.
Appearance

Solid

Color

Light yellow to brown

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

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

-20°C, protect from light, stored under nitrogen

*The compound is unstable in solutions, freshly prepared is recommended.

Solvent & Solubility
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)

Preparing
Stock Solutions
Concentration Solvent Mass 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
View the 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.

  • Molarity Calculator

  • Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass
=
Concentration
×
Volume
×
Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

×
Volume (start)

V1

=
Concentration (final)

C2

×
Volume (final)

V2

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.

  • Protocol 1

    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.
  • Protocol 2

    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:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO +
+
%
Tween-80 +
%
Saline
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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).
Calculation results:
Working solution concentration: 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.

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
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.
Purity & Documentation

Purity: 98.93%

References
Cell Assay
[1]

Two representative UM-SCC cell lines, UM-SCC-6 and UM-SCC-14A, are continuously exposed to 0 (vehicle control), 5 or 10 μM (±)-Gossypol, (R)-(-)-Gossypol (AT-101) or (+)-Gossypol in a 6-day MTT cell survival assay[1].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

References

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
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
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(R)-(-)-Gossypol acetic acid Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Product Name:
(R)-(-)-Gossypol acetic acid
Cat. No.:
HY-15464A
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