Referencia número: HY-13407

Gossypol

Name: Gossypol
Brand: MedChemExpress
SKU: HY-13407
Price: 40.00 USD
Availability: InStock
Rating: 5 (11 reviews)

(Synonyms: BL 193)

11 Cited Publications

Revisión del cliente

Based on 11 publication(s) in Google Scholar

Gossypol binds to Bcl-xL protein and Bcl-2 protein with K_is of 0.5-0.6 μM and 0.2-0.3 mM, respectively.

Para uso exclusivo en investigación. No vendemos a pacientes.

Pureza : 99.67%
No. CAS: 303-45-7
Fòrmula: C₃₀H₃₀O₈
Peso molecular:518.55

Almacenamiento:

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Gossypol Chemical Structure

No. CAS: 303-45-7

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Top Publications Citing

Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Actividad biológica
- Descripciòn
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
- Ensayo clínico
Chemical Information
Publications (11)
Solvente y solubilidad
- In Vitro
- In Vivo
Protocolo
Pureza y Documentación
Referencias
Help & FAQs
Classifications
Bioz

Actividad biológica

Descripciòn

Gossypol binds to Bcl-xL protein and Bcl-2 protein with K_is of 0.5-0.6 μM and 0.2-0.3 mM, respectively.

IC₅₀ & Target

^[1]

Bcl-xL

0.5-0.6 μM (Ki)

Bcl-2

0.2-0.3 mM (Ki)

Ver todos los productos específicos de isoformas Bcl-2 Family :

Cellular Effect

Cell Line	Type	Value	Description	References
B16-F10	IC₅₀	5.56 μg/mL Compound: (R)-Gossypol	Antiproliferative activity against mouse B16/F10 cells after 48 hrs by MTT assay Antiproliferative activity against mouse B16/F10 cells after 48 hrs by MTT assay	[PMID: 22739087]
Cancer cell lines	GI₅₀	2.85 μM Compound: (+/-)-Gossypol	Cytotoxicity against human non-small cell lung cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human non-small cell lung cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
Cancer cell lines	GI₅₀	2.97 μM Compound: (+/-)-Gossypol	Cytotoxicity against human CNS cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human CNS cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
Cancer cell lines	GI₅₀	3.16 μM Compound: (+/-)-Gossypol	Cytotoxicity against human renal cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human renal cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
Cancer cell lines	GI₅₀	3.19 μM Compound: (+/-)-Gossypol	Cytotoxicity against human colon cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human colon cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
Cancer cell lines	GI₅₀	3.5 μM Compound: (+/-)-Gossypol	Cytotoxicity against human ovarian cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human ovarian cancer cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
HEK293	IC₅₀	11.04 μM Compound: AT-101	Cytotoxicity against human HEK293 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human HEK293 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 27353532]
HeLa	IC₅₀	0.08 μg/mL Compound: 18	Cytotoxicity against human HeLa cells by SRB assay Cytotoxicity against human HeLa cells by SRB assay	[PMID: 18553924]
HepG2	IC₅₀	10.16 μg/mL Compound: (R)-Gossypol	Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay	[PMID: 22739087]
HL-60	IC₅₀	6.6 μM Compound: AT-101	Cytotoxicity against human HL60 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human HL60 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 27353532]
HT-29	IC₅₀	>5 μg/mL Compound: 18	Cytotoxicity against human HT29 cells by SRB assay Cytotoxicity against human HT29 cells by SRB assay	[PMID: 18553924]
K562	IC₅₀	4.55 μM Compound: (R)-Gossypol	Antiproliferative activity against human K562 cells after 48 hrs by MTT assay Antiproliferative activity against human K562 cells after 48 hrs by MTT assay	[PMID: 25818766]
K562	IC₅₀	7.31 μM Compound: Gossypol	Antiproliferative activity against human K562 cells by MTT assay Antiproliferative activity against human K562 cells by MTT assay	[PMID: 26421995]
K562	IC₅₀	5.91 μM Compound: Gossypol	Antiproliferative activity against human K562 cells after 48 hrs by MTT assay Antiproliferative activity against human K562 cells after 48 hrs by MTT assay	[PMID: 26620718]
K562	IC₅₀	5.6 μM Compound: Gossypol	Antiproliferative activity against human K562 cells measured after 48 hrs by MTT assay Antiproliferative activity against human K562 cells measured after 48 hrs by MTT assay	[PMID: 27810438]
K562	IC₅₀	8.28 μM Compound: (-)-(R)-Gossypol	Antiproliferative activity against human K562 cells after 48 hrs by MTT assay Antiproliferative activity against human K562 cells after 48 hrs by MTT assay	[PMID: 28233676]
KB	IC₅₀	0.04 μg/mL Compound: 18	Cytotoxicity against human KB cells by SRB assay Cytotoxicity against human KB cells by SRB assay	[PMID: 18553924]
Leukemia cell	GI₅₀	2.47 μM Compound: (+/-)-Gossypol	Cytotoxicity against human leukemia cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human leukemia cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
MCF7S	IC₅₀	13.2 μM Compound: Gossypol	Inhibitory concentration in MCF-7 cells Inhibitory concentration in MCF-7 cells	[PMID: 13678404]
MDA-MB-231	IC₅₀	1.9 μM Compound: 1	Growth inhibition of human MDA-MB-231 cells after 4 days by WST-based assay Growth inhibition of human MDA-MB-231 cells after 4 days by WST-based assay	[PMID: 17552510]
MDA-MB-231	IC₅₀	3.7 μM Compound: 2, R-(-)-gossypol	Growth inhibition of human MDA-MB-231 2LMP cells after 4 days by WST-8 based assay Growth inhibition of human MDA-MB-231 2LMP cells after 4 days by WST-8 based assay	[PMID: 18237106]
MDA-MB-231	IC₅₀	9.21 μM Compound: (R)-Gossypol	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay	[PMID: 25818766]
MDA-MB-231	IC₅₀	4.8 μM Compound: Gossypol	Antiproliferative activity against human MDA-MB-231 cells by MTT assay Antiproliferative activity against human MDA-MB-231 cells by MTT assay	[PMID: 26421995]
MDA-MB-231	IC₅₀	9.42 μM Compound: Gossypol	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay	[PMID: 26620718]
MDA-MB-231	IC₅₀	9.23 μM Compound: Gossypol	Antiproliferative activity against human MDA-MB-231 cells measured after 48 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells measured after 48 hrs by MTT assay	[PMID: 27810438]
MDA-MB-231	IC₅₀	8.54 μM Compound: (-)-(R)-Gossypol	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay	[PMID: 28233676]
MDCK	CC₅₀	3.53 μM Compound: Gossypol	Cytotoxicity against MDCK cells by MTT assay Cytotoxicity against MDCK cells by MTT assay	[PMID: 22226654]
MDCK	IC₅₀	2.14 μM Compound: Gossypol, (-)/(+)-Gossypol	Antiviral activity against H5N1 subtype infected in MDCK cells Antiviral activity against H5N1 subtype infected in MDCK cells	[PMID: 23538114]
Melanoma cell	GI₅₀	3.22 μM Compound: (+/-)-Gossypol	Cytotoxicity against human melanoma cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human melanoma cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 27994761]
NCI-H1299	EC₅₀	6 μM Compound: 1, Gossypol	Cytotoxicity against human H1299 cells assessed as cell viability after 72 hrs by ATP-LITE assay Cytotoxicity against human H1299 cells assessed as cell viability after 72 hrs by ATP-LITE assay	[PMID: 19555126]
NCI-H460	EC₅₀	3 μM Compound: 1, Gossypol	Cytotoxicity against human H460 cells assessed as cell viability after 72 hrs by ATP-LITE assay Cytotoxicity against human H460 cells assessed as cell viability after 72 hrs by ATP-LITE assay	[PMID: 19555126]
PC-3	IC₅₀	2.5 μM Compound: 2, R-(-)-gossypol	Growth inhibition of human PC3 cells after 4 days by WST-8 based assay Growth inhibition of human PC3 cells after 4 days by WST-8 based assay	[PMID: 18237106]
PC-3	IC₅₀	6.71 μg/mL Compound: (R)-Gossypol	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	[PMID: 22739087]
PC-3	IC₅₀	6.26 μM Compound: (R)-Gossypol	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	[PMID: 25818766]
PC-3	IC₅₀	5.61 μM Compound: Gossypol	Antiproliferative activity against human PC3 cells by MTT assay Antiproliferative activity against human PC3 cells by MTT assay	[PMID: 26421995]
PC-3	IC₅₀	5.78 μM Compound: Gossypol	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	[PMID: 26620718]
PC-3	IC₅₀	7.54 μM Compound: Gossypol	Antiproliferative activity against human PC3 cells measured after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells measured after 48 hrs by MTT assay	[PMID: 27810438]
PC-3	IC₅₀	8.58 μM Compound: (-)-(R)-Gossypol	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	[PMID: 28233676]
TZM	CC₅₀	9.76 μM Compound: Gossypol	Cytotoxicity in human TZM-bl cells by MTT assay Cytotoxicity in human TZM-bl cells by MTT assay	[PMID: 22226654]
ZR-75-1	IC₅₀	8.4 μM Compound: Gossypol	Inhibitory concentration in ZR-75-1 cells Inhibitory concentration in ZR-75-1 cells	[PMID: 13678404]

In Vitro

Gossypol, a natural product isolated from cottonseeds and roots that has been studied as an anticancer agent. The racemic form of Gossypol [(±)-Gossypol] is tested in several clinical trials and is well tolerated. The racemic form Gossypol ((±)-Gossypol) binds to Bcl-xL protein with a K_i of 0.5 to 0.6 μM. (±)-Gossypol also potently binds to Bcl-2 protein with a K_i value of 0.2-0.3 mM. The natural racemic Gossypol has two enantiomers, namely the (-)-Gossypol and (+)-Gossypol enantiomers. 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. (-)-Gossypol 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)^[1].

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

In Vivo

Note:
Please do not refer to only one article to determine the experimental conditions. It is recommended to determine the optimal experimental conditions (animal strain, age, dosage, frequency and cycle, detection time and indicators, etc.) through preliminary experiments before the formal experiment.

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 A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

No. CAS 303-45-7
Appearance Solid
Peso molecular 518.55
Fòrmula C₃₀H₃₀O₈
Color Light yellow to yellow
SMILES

O=CC1=C(O)C(O)=C(C(C)C)C2=CC(C)=C(C3=C(C)C=C4C(C(C)C)=C(O)C(O)=C(C=O)C4=C3O)C(O)=C12
Synonyms

BL 193
Structure Classification
- Phenols
- Polyphenols
Initial Source
Envío

Room temperature in continental US; may vary elsewhere.
Almacenamiento

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Publications (11)

All Cell Imaging/StainingRT-PCRWB

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Journal Impact Factor

Nat Commun

Discovery of senolytics using machine learning. [Abstract]

2023 Jun 10;14(1):3445. PMID: 37301862
Clin Transl Med

Functional inhibition of lactate dehydrogenase suppresses pancreatic adenocarcinoma progression. [Abstract]

2021 Jun;11(6):e467. PMID: 34185423
Cell Rep

Carvedilol sensitizes chemotherapy by targeting STING to boost anti-tumor immunity. [Abstract]

2025 Apr 16;44(5):115572. PMID: 40249703
Cancer Gene Ther

C1orf35 contributes to high anabolic metabolism by simultaneously promoting aerobic glycolysis and oxidative phosphorylation in multiple myeloma cells. [Abstract]

2026 Jan 31. PMID: 41620562
Toxicol Sci

Gossypol acetic acid affects locomotor activity by inducing mitophagy-related ferroptosis and apoptosis in zebrafish. [Abstract]

2025 Oct 24:kfaf149. PMID: 41134649
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

Natural small molecule compounds targeting Wnt signaling pathway inhibit HPV infection. [Abstract]

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

Gossypol 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.

Gossypol 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.

Gossypol 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.

Gossypol 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.

Gossypol 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.
Transbound Emerg Dis

Gossypol Affects Viral Replication by Inhibiting Pseudorabies Virus Adsorption. [Abstract]

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
Patent

US20220162561A1.

Solvente y solubilidad

In Vitro:

DMSO : 33.33 mg/mL (64.28 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

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 (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Calculadora de molaridad

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

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Calculadora de dilución

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

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

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: ≥ 2.08 mg/mL (4.01 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 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.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
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

Protocolo

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, (-)-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.

Pureza y Documentación

Select Batch:

Pureza: 99.98%

Assay: 99.98%

ee.: 99.98%

Ficha de datos (278 KB)
SDS (418 KB)
- English - EN (418 KB)
- Français - FR (418 KB)
- Deutsch - DE (418 KB)
- Norwegian - NO (418 KB)
- Español - ES (418 KB)
- Swedish - SV (418 KB)
- Italian - IT (418 KB)
- Korean - KR (418 KB)
- Portuguese - PT (418 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)
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]

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

Bioz

Keywords

Gossypol

11 Cited Publications

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Gossypol

Publications Citing Use of MedChemExpress (MCE) Gossypol

Ver todos los productos específicos de isoformas Bcl-2 Family