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Purity: ≥98%
Xanthatin is natural product of the sesquiterpenoid class. Xanthatin, a novel potent inhibitor of VEGFR2 signaling, inhibits angiogenesis and tumor growth in breast cancer cells. Xanthatin, a novel potent inhibitor of VEGFR2 signaling, inhibits angiogenesis and tumor growth in breast cancer cells. Xanthatin induces cell cycle arrest at G2/M checkpoint and apoptosis via disrupting NF-κB pathway in A549 non-small-cell lung cancer cells.
Targets |
Natural sesquiterpene lactone; antibacterial, anticancer and antifungal
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ln Vitro |
Xanthatin is a naturally occurring sesquiterpene lactone,with significant antitumor activity against a variety of cancer cells; it exhibits significant antitumor effects through cell cycle arrest and apoptosis induction in A549 cells, these effects are associated with intrinsic apoptosis pathway and disrupted NF-κB signaling, suggests that it may have therapeutic potential against human non-small-cell lung cancer.[1]
Xanthatin has bactericidal and fungicidal activity against Colletotrichum gloesporoides, Trichothecium roseum, Bacillus cereus and Staphylococcus aureus.[2] Xanthatin and the crude extracts of Xanthium strumarium have cytotoxic activity.[3] (−)-Xanthatin is a highly effective inhibitor of MDA-MB-231 cell growth, inducing caspase-independent cell death, and that these effects were independent of FTase inhibition; GADD45γ was selectively induced by (−)-xanthatin and that GADD45γ-primed JNK and p38 signaling pathways are, at least in part, involved in mediating the growth inhibition and potential anticancer activities of this agent; GADD45γ is becoming increasingly recognized for its tumor suppressor function, suggests that the novel possibility that (−)-xanthatin may have therapeutic value as a selective inducer of GADD45γ in human cancer cells, in particular in FTI-resistant aggressive breast cancers.[4] Xanthatin induces G2/M cell cycle arrest and apoptosis in human gastric carcinoma MKN-45 cells, it may have therapeutic potential against human gastric carcinoma.[5] Xanthatin is a novel potent inhibitor of VEGFR2 signaling, can inhibit angiogenesis and tumor growth in breast cancer cells.[6] |
Cell Assay |
Xanthatin, a natural sesquiterpene lactone, has significant antitumor activity against a variety of cancer cells, yet little is known about its anticancer mechanism. In this study, we demonstrated that xanthatin had obvious dose-/time-dependent cytotoxicity against the human non-small-cell lung cancer (NSCLC) cell line A549. Flow cytometry analysis showed xanthatin induced cell cycle arrest at G2/M phase. Xanthatin also had pro-apoptotic effects on A549 cells as evidenced by Hoechst 33258 staining and annexin V-FITC staining. Mechanistic data revealed that xanthatin downregulated Chk1, Chk2, and phosphorylation of CDC2, which contributed to the cell cycle arrest. Xathatin also increased total p53 protein levels, decreased Bcl-2/Bax ratio and expression of the downstream factors procaspase-9 and procaspase-3, which triggered the intrinsic apoptosis pathway. Furthermore, xanthatin blocked phosphorylation of NF-κB (p65) and IκBa, which might also contribute to its pro-apoptotic effects on A549 cells. Xanthatin also inhibited TNFa induced NF-κB (p65) translocation. We conclude that xanthatin displays significant antitumor effects through cell cycle arrest and apoptosis induction in A549 cells. These effects were associated with intrinsic apoptosis pathway and disrupted NF-κB signaling. These results suggested that xanthatin may have therapeutic potential against NSCLC.[1]
exo-Methylene lactone group-containing compounds, such as (--)-xanthatin, are present in a large variety of biologically active natural products, including extracts of Xanthium strumarium (Cocklebur). These substances are reported to possess diverse functional activities, exhibiting anti-inflammatory, antimalarial, and anticancer potential. In this study, we synthesized six structurally related xanthanolides containing exo-methylene lactone moieties, including (--)-xanthatin and (+)-8-epi-xanthatin, and examined the effects of these chemically defined substances on the highly aggressive and farnesyltransferase inhibitor (FTI)-resistant MDA-MB-231 cancer cell line. The results obtained demonstrate that (--)-xanthatin was a highly effective inhibitor of MDA-MB-231 cell growth, inducing caspase-independent cell death, and that these effects were independent of FTase inhibition. Further, our results show that among the GADD45 isoforms, GADD45γ was selectively induced by (--)-xanthatin and that GADD45γ-primed JNK and p38 signaling pathways are, at least in part, involved in mediating the growth inhibition and potential anticancer activities of this agent. Given that GADD45γ is becoming increasingly recognized for its tumor suppressor function, the results presented here suggest the novel possibility that (--)-xanthatin may have therapeutic value as a selective inducer of GADD45γ in human cancer cells, in particular in FTI-resistant aggressive breast cancers.[4] |
References |
[1]. Molecules, 2012, 17(4):3736-50.
[2]. Lett Appl Microbiol, 1994, 18(4):206-8. [3]. Planta Med, 1994, 60(5):473-4. [4]. Chem Res Toxicol, 2011, 24(6):855-65. [5]. Planta Med, 2012, 78(9):890-5. [6]. Int J Clin Exp Pathol, 2015, 8(9):10355-64. |
Additional Infomation |
Xanthatin is a sesquiterpene lactone.
Xanthatin has been reported in Xanthium pungens, Dittrichia graveolens, and other organisms with data available. |
Molecular Formula |
C15H18O3
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Molecular Weight |
246.3016
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Exact Mass |
246.125
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CAS # |
26791-73-1
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PubChem CID |
5281511
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Appearance |
Typically exists as solid at room temperature
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Density |
1.1±0.1 g/cm3
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Boiling Point |
444.3±45.0 °C at 760 mmHg
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Melting Point |
114.5-115°
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Flash Point |
199.1±28.8 °C
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Vapour Pressure |
0.0±1.1 mmHg at 25°C
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Index of Refraction |
1.528
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LogP |
1.58
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Hydrogen Bond Donor Count |
0
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Hydrogen Bond Acceptor Count |
3
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Rotatable Bond Count |
2
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Heavy Atom Count |
18
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Complexity |
456
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Defined Atom Stereocenter Count |
3
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SMILES |
O1C(C(=C([H])[H])[C@@]2([H])C([H])([H])C([H])=C(/C(/[H])=C(\[H])/C(C([H])([H])[H])=O)[C@@]([H])(C([H])([H])[H])C([H])([H])[C@]12[H])=O
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InChi Key |
RBRPTFMVULVGIC-ZTIIIDENSA-N
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InChi Code |
InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14-/m0/s1
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Chemical Name |
(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
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Synonyms |
Xanthatin; Xanthatin; 26791-73-1; (-)-Xanthatin; (3aR,7S,8aS)-7-Methyl-3-methylene-6-((E)-3-oxobut-1-en-1-yl)-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one; (3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one; CHEBI:10058; 298X1N12LS; CHEMBL404466;
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 4.0601 mL | 20.3004 mL | 40.6009 mL | |
5 mM | 0.8120 mL | 4.0601 mL | 8.1202 mL | |
10 mM | 0.4060 mL | 2.0300 mL | 4.0601 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.