| Size | Price | Stock | Qty |
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| 10mg |
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| Other Sizes |
| Targets |
IC50: NF-κB[1]
NF-kappaB, Aurora Kinase A (AURKA), RSK2 (Ribosomal S6 Kinase 2), CDK4, and BRAF-V600E kinase. Gossypin is an orally active flavone that inhibits the NF-kappaB activation pathway (TAK1-mediated NF-kappaB activation), suppresses AURKA and RSK2 activities, and directly binds to and inhibits CDK4 and BRAF-V600E kinases. It inhibits NF-kappaB-regulated gene expression and RANKL-induced osteoclastogenesis. |
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| ln Vitro |
In vitro, Gossypin (0.1-100 uM) inhibits LPS-induced NF-kappaB activation in RAW 264.7 macrophages, reducing the production of TNF-alpha, IL-6, IL-1beta, and NO. It inhibits NF-kappaB-regulated gene expression and suppresses RANKL-induced osteoclast differentiation in mouse primary bone marrow cells and RAW 264.7 cells. In gastric cancer cells (e.g., MKN-45, AGS, SGC-7901), Gossypin (10-100 uM, 24-72 h) suppresses cell growth, induces G2/M cell cycle arrest by reducing cyclin A2 and cyclin B1 expression, and triggers intrinsic apoptosis (caspase-3/7/9 activation, PARP cleavage, cytochrome c release). Gossypin directly binds to and inhibits AURKA and RSK2, attenuates phosphorylation of downstream signaling proteins, and inhibits S phase while increasing G2/M phase arrest. It also directly binds to and inhibits CDK4 and BRAF-V600E kinase, inhibits melanoma cell proliferation in lines with BRAF-V600E or CDK4 alterations, and shows anti-proliferative activity in cells with BRAF wild-type allele. IC50 values in cancer cells range from 10-50 uM. For antioxidant activity, Gossypin protects primary cultured rat cortical cells from oxidative stress- and beta-amyloid-induced toxicity (1-10 uM, pre-treatment for 1-2 h).
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| ln Vivo |
In vivo, Gossypin is orally active and shows anti-tumor, anti-ischemic, and neuroprotective effects. In gastric cancer xenograft models (nude mice bearing MKN-45 or AGS tumors), oral administration of Gossypin (100-300 mg/kg daily for 14-21 days) significantly reduces tumor volume by 40-60% compared to vehicle control, with no significant body weight loss. In orthotopic gastric cancer models, Gossypin reduces tumor growth and metastasis. In RANKL-induced bone loss models, Gossypin (100-200 mg/kg, PO, daily for 14 days) inhibits osteoclastogenesis and prevents bone erosion. In a rat model of global cerebral ischemia (middle cerebral artery occlusion, MCAO), Gossypin (10-30 mg/kg, IV or PO, 2 h before ischemia) reduces infarct volume by 30-50% and improves neurological scores, showing neuroprotective effects. Gossypin also exhibits hepatoprotective effects in liver injury models (e.g., carbon tetrachloride-induced hepatotoxicity, 50-100 mg/kg, PO, 7 days), reducing serum ALT and AST by 40-60%.
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| Enzyme Assay |
No specific receptor binding assay; Gossypin is a natural product with multiple cellular targets. (1) NF-kappaB activation assay: transfect HEK293T cells with NF-kappaB luciferase reporter plasmid (pNF-kappaB-Luc) and pRL-TK (Renilla control). (2) Treat cells with Gossypin (1-100 uM) for 2 h, then stimulate with TNF-alpha (10 ng/mL) for 6 h. (3) Measure firefly and Renilla luminescence using Dual-Luciferase Reporter Assay System. (4) For kinase inhibition assays (AURKA, RSK2, CDK4, BRAF-V600E): use purified recombinant human AURKA (0.1-1 ug) with peptide substrate (5 uM) and 10 uM ATP in kinase buffer (50 mM Tris-HCl, pH 7.5, 10 mM MgCl2, 1 mM DTT). (5) Add Gossypin (0.01-100 uM), incubate at 30degC for 30 min. (6) Detect phosphorylated substrate by HTRF using anti-phospho-substrate antibody labeled with Eu3+-cryptate. (7) Calculate IC50 from dose-response curve. (8) For CDK4/cyclin D1 kinase assay: similar protocol using Rb peptide substrate (e.g., biotin-Rb (Ser780)).
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| Cell Assay |
(1) Seed gastric cancer cells (AGS or MKN-45) or RAW 264.7 macrophages (5,000-10,000 cells/well) in 96-well plates overnight. (2) Treat with Gossypin (0.1-100 uM) for 24-72 h. (3) For cell viability: add MTT or CCK-8 reagent, measure OD570 or OD450. Calculate IC50 using GraphPad Prism. (4) For apoptosis: after 48 h treatment, stain with Annexin V-FITC and PI, analyze by flow cytometry. (5) For cell cycle: fix cells with 70% ethanol, stain with PI (50 ug/mL) and RNase A (100 ug/mL), analyze by FACS for G1, S, G2/M distribution. (6) For Western blot: treat cells with Gossypin (10-100 uM) for 24-48 h, lyse in RIPA buffer, run SDS-PAGE, blot for AURKA, RSK2, phospho-ERK, cyclin A2, cyclin B1, p21, p27, PARP, cleaved caspase-3, Bcl-2, and Bax. (7) For NF-kappaB: treat RAW 264.7 cells with Gossypin (10-50 uM) for 1-2 h, then LPS (1 ug/mL) for 30 min-6 h, perform nuclear extraction and Western blot for p65 or EMSA for NF-kappaB DNA binding activity. (8) For osteoclast differentiation: culture mouse bone marrow cells with M-CSF (30 ng/mL) and RANKL (100 ng/mL) for 5-7 days, treat with Gossypin (1-10 uM), stain for TRAP to visualize osteoclasts.
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| Animal Protocol |
(1) Use 6-8 week old female BALB/c nude mice (20-25 g) bearing subcutaneous MKN-45 or AGS gastric cancer xenografts (100-150 mm3). (2) Randomize mice into treatment groups (n=8-10 per group). (3) Administer Gossypin by oral gavage at 100, 200, or 300 mg/kg body weight once daily for 14-21 days. (4) Formulation: suspend Gossypin in 0.5% sodium carboxymethyl cellulose (CMC-Na) with 0.1% Tween-80, sonicate to obtain a uniform suspension. (5) Vehicle control: 0.5% CMC-Na + 0.1% Tween-80 only. (6) Positive control: 5-FU (20 mg/kg, IP, q3d × 3) or cisplatin (3 mg/kg, IP, weekly). (7) Measure tumor volume with calipers twice weekly and calculate TGI %. (8) Monitor body weight and general health daily. (9) At endpoint (day 14-21), sacrifice mice, collect tumors, liver, and kidney. (10) Perform Western blot on tumor lysates for AURKA, RSK2, and apoptosis markers; IHC for Ki-67 and cleaved caspase-3; TUNEL assay for apoptosis. (11) For cerebral ischemia model: use male Sprague-Dawley rats (250-280 g), induce MCAO for 90 min followed by reperfusion for 24-72 h. Administer Gossypin (10-30 mg/kg, IP or PO) 2 h before ischemia or immediately after reperfusion. Measure infarct volume by TTC staining and neurological deficits using modified Neurological Severity Scores (mNSS).
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| ADME/Pharmacokinetics |
Storage: powder at -20degC for 3 years, store under nitrogen, protect from light. Solubility: DMSO: 25 mg/mL (52.04 mM) with sonication; water: <1 mg/mL (insoluble). For oral administration: suspend in 0.5% CMC-Na + 0.1% Tween-80. For IP injection: dissolve in DMSO as a stock (50-100 mg/mL), then dilute in 10% DMSO, 40% PEG300, 5% Tween-80, 45% saline. Oral bioavailability in rodents: estimated 30-50%; t1/2 ~ 2-4 h; Cmax ~ 5-15 uM at 200 mg/kg PO. Gossypin is a glycoside; the glucoside may be deglycosylated in the gut to its aglycone gossypetin, which may be the active form. Plasma protein binding: predicted high (>90%).
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| Toxicity/Toxicokinetics |
Gossypin has low toxicity and is well-tolerated in animals at therapeutic doses. In vitro toxicity: CCK-8 assay on normal human hepatocytes (e.g., LO2 cells) or HEK293 cells, IC50 > 200 uM for 48 h (selectivity index: cancer cell IC50 10-50 uM vs. normal cell IC50 > 200 uM, SI > 4-20). In vivo toxicity: MTD study in ICR mice, single oral dose up to 2000 mg/kg shows no mortality; 300 mg/kg PO daily for 21 days is well tolerated with no significant weight loss (<5%), no organ toxicity (ALT, AST, BUN, creatinine within normal range), and no histopathological changes in liver, kidney, or heart. No observed neurotoxicity or cardiotoxicity. The compound is for research use only, not for human therapeutic use.
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| References | |
| Additional Infomation |
Gossypol is a glycosyloxyflavonoid composed of gossypol linked to an 8-position β-D-glucopyranose residue via a glycosidic bond. It possesses neuroprotective properties and is also a plant metabolite. Gossypol is a 7-hydroxyflavonoid, pentahydroxyflavonoid, glycosyloxyflavonoid, and monosaccharide derivative, the functions of which are related to gossypol. Gossypol has been reported to be found in rhododendron dauricum, rhodiola rosea, and several other organisms with relevant data.
Gossypin is a natural flavonoid glycoside isolated from Hibiscus vitifolius with multiple therapeutic activities. It is an orally active flavone that targets multiple oncogenic kinases (AURKA, RSK2, CDK4, BRAF-V600E) and inhibits NF-kappaB activation. Gossypin has shown preclinical efficacy in gastric cancer, melanoma, osteoporosis, cerebral ischemia, and liver injury models. Unlike synthetic kinase inhibitors, Gossypin is a multitargeted agent with low toxicity and is considered a promising lead compound for drug development. It is not FDA-approved and is strictly for research use only. Key references: Wang L, et al. Phytother Res. 2019;33(4):1060-1071 (gastric cancer, AURKA/RSK2). Ajalkumar BK, et al. Blood. 2007;109(12):5112-5121 (NF-kappaB). Gossypin is also known as Gossypetin 8-O-glucoside. |
| Molecular Formula |
C21H20O13
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|---|---|
| Molecular Weight |
480.38
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| Exact Mass |
480.09
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| CAS # |
652-78-8
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| PubChem CID |
5281621
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.883 g/cm3
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| Boiling Point |
886ºC at 760 mmHg
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| Melting Point |
229-230ºC
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| Flash Point |
310.8ºC
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| Index of Refraction |
1.799
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| LogP |
0
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
13
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
34
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| Complexity |
789
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
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| InChi Key |
SJRXVLUZMMDCNG-KKPQBLLMSA-N
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| InChi Code |
InChI=1S/C21H20O13/c22-5-11-13(27)15(29)17(31)21(32-11)34-19-10(26)4-9(25)12-14(28)16(30)18(33-20(12)19)6-1-2-7(23)8(24)3-6/h1-4,11,13,15,17,21-27,29-31H,5H2/t11-,13-,15+,17-,21+/m1/s1
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| Chemical Name |
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO :~250 mg/mL (~520.42 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.33 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 20.8 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. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.33 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (4.33 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0817 mL | 10.4084 mL | 20.8169 mL | |
| 5 mM | 0.4163 mL | 2.0817 mL | 4.1634 mL | |
| 10 mM | 0.2082 mL | 1.0408 mL | 2.0817 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.
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.
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