| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| Other Sizes |
| Targets |
It is a benzylisoquinoline alkaloid isolated from the Coptidis Rhizoma-Euodiae Fructus couple [1].
DNA; enzymes; cancer cell targets. 8-Oxocoptisine is a natural protoberberine alkaloid with anticancer activity. The introduction of the 8-oxo functional group enhances its reactivity and may influence binding affinity to biological targets such as DNA or enzymes. The compound exhibits selective cytotoxicity against NCI-N87 gastric cancer cells. It also has anti-inflammatory, analgesic, cooling, antihypertensive, and anticancer properties. |
|---|---|
| ln Vitro |
8-Oxocoptisine (7) showed cytotoxic activity against human gastric carcinoma NCI-N87 cells with an IC50 value of 20.31 ± 3.08 μM. It exhibited poor activity against human colon adenocarcinoma Caco-2 cells (IC50 > 100 μM). Compared to compound 4 (13-carboxaldehyde-8-oxocoptisine), the absence of the aldehyde group at C-13 in 7 tended to enhance the cytotoxic activity against NCI-N87 cells [1].
Compared to Caco-2 (IC50>100 μM), 8-oxocoptisine exhibits no cytotoxicity against NCI-N87 (IC50=20.31 μM)[1]. 8-Oxocoptisine exhibits cytotoxicity against NCI-N87 gastric cancer cells with an IC₅₀ of 20.31 μM while showing no cytotoxicity against Caco-2 cells (IC₅₀ > 100 μM). The compound has anticancer activity and also exhibits anti-inflammatory, analgesic, cooling, antihypertensive, and anticancer properties. The introduction of the 8-oxo functional group enhances its reactivity and may influence binding affinity to biological targets. |
| ln Vivo |
In vivo studies of 8-oxocoptisine are limited. As a natural protoberberine alkaloid with anticancer, anti-inflammatory, analgesic, and antihypertensive activities, it has potential for evaluation in animal models of cancer, inflammation, pain, and hypertension. Its selective cytotoxicity against NCI-N87 cells suggests potential for gastric cancer research. Further in vivo studies are needed to characterize its pharmacokinetic and pharmacodynamic properties, as well as its efficacy and safety profile.
|
| Enzyme Assay |
Non-cell-based assays for 8-oxocoptisine include DNA binding studies using spectroscopic methods (UV-Vis, fluorescence) to assess intercalation or groove binding. Enzyme inhibition studies can be performed to assess effects on potential targets. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization and purity assessment.
|
| Cell Assay |
NCI-N87 human gastric carcinoma cells were cultured in RPMI 1640 medium supplemented with 10% fetal bovine serum, 100 U/mL penicillin, and 100 μg/mL streptomycin at 37°C in 5% CO2. Caco-2 human colon adenocarcinoma cells were cultured in DMEM medium with the same supplements. Cells were seeded into 96-well plates at a density of 1 × 10⁴ cells/well in 100 μL medium. After 24 hours of incubation, cells were treated with 8-oxocoptisine at various concentrations (0.25, 2.5, 10, 25, 50, and 100 μM) and incubated for 48 hours. Subsequently, 20 μL of MTT solution (5 mg/mL) was added to each well, and plates were incubated for another 4 hours. Then, 100 μL of dissolving solution (containing 10% sodium dodecyl sulfate, 5% isopropanol, and 0.1% HCl in water) was added to dissolve the formazan crystals. The optical density was measured at 540 nm using a microplate reader. The vehicle (DMSO) content in the medium never exceeded 1% (v/v), and vehicle control showed no inhibitory effect on cell viability. IC50 values were calculated using Sigmoidal fit. Vinorelbine was used as a positive control drug (IC50 = 12.19 ± 4.33 μM against NCI-N87 cells) [1].
Cell-based assays for 8-oxocoptisine use various cancer cell lines to assess cytotoxicity. NCI-N87 gastric cancer cells and Caco-2 cells are treated with the compound at various concentrations, and cell viability is measured using MTT or SRB assays. Apoptosis is evaluated by flow cytometry using Annexin V/PI staining. The compound’s effects on cell cycle progression and signaling pathways can be assessed. Cytotoxicity is assessed using standard cell viability assays. |
| Animal Protocol |
In vivo studies of 8-oxocoptisine are limited. Based on its biological activities, potential animal models include: tumor xenograft models for anticancer evaluation; carrageenan-induced paw edema models for anti-inflammatory evaluation; pain models for analgesic evaluation; and hypertension models for antihypertensive evaluation. Standard protocols for these models involve administration of the compound followed by measurement of relevant endpoints.
|
| ADME/Pharmacokinetics |
8-Oxocoptisine has a molecular formula of C₁₉H₁₃NO₅ and a molecular weight of approximately 335.31 g/mol. It is a natural protoberberine alkaloid found in Coptis chinensis and other sources. Purity is >98%. The compound should be stored under recommended conditions. It is intended for research use only.
|
| Toxicity/Toxicokinetics |
Specific toxicity data for 8-oxocoptisine are limited. The compound exhibits selective cytotoxicity against NCI-N87 gastric cancer cells (IC₅₀ = 20.31 μM) while showing no cytotoxicity against Caco-2 cells (IC₅₀ > 100 μM), suggesting some selectivity for cancer cells. Standard laboratory safety practices should be followed when handling this compound.
|
| References | |
| Additional Infomation |
8-Oxocoptisine is a known benzylisoquinoline alkaloid isolated from the Coptidis Rhizoma-Euodiae Fructus couple (Zuojin formula, ratio 6:1 w/w). Its structure was identified by comparison of spectral data with reported and authentic standard data. It was obtained as a yellow precipitate from the n-BuOH fraction of the ethanolic extract. The compound has a molecular formula of C₁₉H₁₃NO₆. The 1H NMR spectrum of 7 showed two methylenedioxy groups, a -CH₂-CH₂-N- group, two isolated aromatic protons, and a pair of ortho-coupled aromatic protons [1].
According to reports, 8-oxocorydin has been found in plants of the genus Corydalis ternata, Corydalis yanhusuo, and other organisms with available data. 8-Oxocoptisine (8-Oxycoptisine) is a natural protoberberine alkaloid found in Coptis chinensis and other plant sources. It exhibits anticancer activity with cytotoxicity against NCI-N87 gastric cancer cells (IC₅₀ = 20.31 μM) while showing no cytotoxicity against Caco-2 cells (IC₅₀ > 100 μM). The compound also has anti-inflammatory, analgesic, cooling, antihypertensive, and anticancer properties. The 8-oxo functional group enhances its reactivity and may influence binding affinity to biological targets. It is for research use only. |
| Molecular Formula |
C19H13NO5
|
|---|---|
| Molecular Weight |
335.31
|
| Exact Mass |
335.079
|
| CAS # |
19716-61-1
|
| PubChem CID |
5245667
|
| Appearance |
Light yellow to yellow solid
|
| Density |
1.6±0.0 g/cm3
|
| Boiling Point |
617.5±0.0 °C at 760 mmHg
|
| Flash Point |
327.3±0.0 °C
|
| Vapour Pressure |
0.0±0.0 mmHg at 25°C
|
| Index of Refraction |
1.768
|
| LogP |
4.65
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
25
|
| Complexity |
621
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O1C([H])([H])OC2=C1C([H])=C1C(=C2[H])C([H])([H])C([H])([H])N2C(C3C4=C(C([H])=C([H])C=3C([H])=C21)OC([H])([H])O4)=O
|
| InChi Key |
UCAFJBSQKXVPDX-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C19H13NO5/c21-19-17-11(1-2-14-18(17)25-9-22-14)5-13-12-7-16-15(23-8-24-16)6-10(12)3-4-20(13)19/h1-2,5-7H,3-4,8-9H2
|
| Chemical Name |
5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(24),2,4(8),9,15(23),16(20),21-heptaen-14-one
|
| Synonyms |
8-Oxocoptisine; 5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(24),2,4(8),9,15(23),16(20),21-heptaen-14-one; DTXSID901317158; 5,7,17,19-tetraoxa-13-azahexacyclo(11.11.0.02,10.04,8.015,23.016,20)tetracosa-1(24),2,4(8),9,15(23),16(20),21-heptaen-14-one;
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO: 2.08 mg/mL (6.20 mM)
|
|---|---|
| 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 | 2.9823 mL | 14.9116 mL | 29.8231 mL | |
| 5 mM | 0.5965 mL | 2.9823 mL | 5.9646 mL | |
| 10 mM | 0.2982 mL | 1.4912 mL | 2.9823 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
