Cat. No.: HY-15464

(R)-(-)-Gossypol

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

3 Cited Publications

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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 K_is of 260±30 nM, 170±10 nM, and 480±40 nM, respectively.

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Pureté: 99.37%
CAS No.: 90141-22-3
Formule: C₃₀H₃₀O₈
Masse moléculaire:518.55

Stockage:

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)

(R)-(-)-Gossypol Chemical Structure

CAS No.: 90141-22-3

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Activité biologique
- Description
- IC₅₀ & Target
- In Vitro
- Essai clinique
Chemical Information
Publications (3)
Solvant et solubilité
- In Vitro
Protocole
Pureté et documentation
Références
Help & FAQs
Classifications
Bioz

Activité biologique

Description

IC₅₀ & Target^[2]

Mcl-1

170 nM (Ki)

Bcl-2

260 nM (Ki)

Bcl-xL

480 nM (Ki)

Autophagy

Voir tous les produits spécifiques à Isoform Bcl-2 Family :

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 K_i 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.

Essai clinique

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

CAS No. 90141-22-3
Appearance Solid
Masse moléculaire 518.55
Formule C₃₀H₃₀O₈
Color Light yellow to yellow
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
Synonyms

AT-101; R-(-)-gossypol acetic acid
Structure Classification
- Phenols
Initial Source
Livraison

Room temperature in continental US; may vary elsewhere.
Stockage

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

Nat Commun

Discovery of senolytics using machine learning. [Abstract]

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

Solvant et solubilité

In Vitro:

DMSO : ≥ 200 mg/mL (385.69 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

* "≥" means soluble, but saturation unknown.

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

1.9285 mL

9.6423 mL

19.2845 mL

5 mM

0.3857 mL

1.9285 mL

3.8569 mL

10 mM

0.1928 mL

0.9642 mL

1.9285 mL

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.

Calculateur de molarité

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

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Calculateur de dilution

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

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

Protocole

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 or (+)-Gossypol in a 6-day MTT cell survival assay^[1].

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

Pureté et documentation

Select Batch:

Pureté: 99.98%

Assay: 99.98%

ee.: 99.98%

Fiche technique (280 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Instruction de manipulation (2659 KB)

Références

[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]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

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

Keywords

(R)-(-)-Gossypol

3 Cited Publications

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(R)-(-)-Gossypol

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Publications Citing Use of MedChemExpress (MCE) (R)-(-)-Gossypol

Voir tous les produits spécifiques à Isoform Bcl-2 Family

Activité biologique

Chemical Information

Publications (3)

Solvant et solubilité

Protocole

Pureté et documentation

Références

Help & FAQs

Complete Stock Solution Preparation Table

(R)-(-)-Gossypol Related Classifications

HY-15464 Related Classifications