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2,3,9,10-Tetrahydroxyberberine

CAS# 162854-37-7

2,3,9,10-Tetrahydroxyberberine

2D Structure

Catalog No. BCN3550----Order now to get a substantial discount!

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Quality Control of 2,3,9,10-Tetrahydroxyberberine

3D structure

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2,3,9,10-Tetrahydroxyberberine

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Chemical Properties of 2,3,9,10-Tetrahydroxyberberine

Cas No. 162854-37-7 SDF Download SDF
PubChem ID 443768 Appearance Powder
Formula C17H14NO4 M.Wt 296.3
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2,3,9,10-tetrol
SMILES C1C[N+]2=C(C=C3C=CC(=C(C3=C2)O)O)C4=CC(=C(C=C41)O)O
Standard InChIKey DAHMYCXNJSCLGA-UHFFFAOYSA-O
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 2,3,9,10-Tetrahydroxyberberine

The rhizomes of Coptis chinensis Franch.

Biological Activity of 2,3,9,10-Tetrahydroxyberberine

Description2,3,9,10-Tetrahydroxyberberine chloride shows antioxidant activity.
In vitro

Antioxidant Effect of Berberine and its Phenolic Derivatives Against Human Fibrosarcoma Cells.[Reference: WebLink]

Asian Pacific journal of cancer prevention: APJCP, 2015, 16(13):5371-5376.


METHODS AND RESULTS:
Berberine (B1), isolated from stems of Coscinium fenestratum (Goetgh.) Colebr, was used as a principle structure to synthesize three phenolic derivatives: berberrubine (B2) with a single phenolic group, berberrubine chloride (B3) as a chloride counter ion derivative, and 2,3,9,10-Tetrahydroxyberberine chloride (B4) with four phenolic groups, to investigate their direct and indirect antioxidant activities. For DPPH assay, compounds B4, B3, and B2 showed good direct antioxidant activity (IC50 values=10.7±1.76, 55.2±2.24, and 87.4±6.65 μM, respectively) whereas the IC50 value of berberine was higher than 500 μM. Moreover, compound B4 exhibited a better DPPH scavenging activity than BHT as a standard antioxidant (IC50=72.7±7.22 μM) due to the ortho position of hydroxyl groups and its capacity to undergo intramolecular hydrogen bonding.
CONCLUSIONS:
For cytotoxicity assay against human fibrosarcoma cells (HT1080) using MTT reagent, the sequence of IC50 value at 7-day treatment stated that B1.

2,3,9,10-Tetrahydroxyberberine Dilution Calculator

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2,3,9,10-Tetrahydroxyberberine Molarity Calculator

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Preparing Stock Solutions of 2,3,9,10-Tetrahydroxyberberine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.375 mL 16.8748 mL 33.7496 mL 67.4992 mL 84.3739 mL
5 mM 0.675 mL 3.375 mL 6.7499 mL 13.4998 mL 16.8748 mL
10 mM 0.3375 mL 1.6875 mL 3.375 mL 6.7499 mL 8.4374 mL
50 mM 0.0675 mL 0.3375 mL 0.675 mL 1.35 mL 1.6875 mL
100 mM 0.0337 mL 0.1687 mL 0.3375 mL 0.675 mL 0.8437 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 2,3,9,10-Tetrahydroxyberberine

Oxygen Vacancy Promoted Heterogeneous Fenton-like Degradation of Ofloxacin at pH 3.2-9.0 by Cu Substituted Magnetic Fe3O4@FeOOH Nanocomposite.[Pubmed:28934546]

Environ Sci Technol. 2017 Nov 7;51(21):12699-12706.

To develop an ultraefficient and reusable heterogeneous Fenton-like catalyst at a wide working pH range is a great challenge for its application in practical water treatment. We report an oxygen vacancy promoted heterogeneous Fenton-like reaction mechanism and an unprecedented ofloxacin (OFX) degradation efficiency of Cu doped Fe3O4@FeOOH magnetic nanocomposite. Without the aid of external energy, OFX was always completely removed within 30 min at pH 3.2-9.0. Compared with Fe3O4@FeOOH, the pseudo-first-order reaction constant was enhanced by 10 times due to Cu substitution (9.04/h vs 0.94/h). Based on the X-ray photoelectron spectroscopy (XPS), Raman analysis, and the investigation of H2O2 decomposition, (*)OH generation, pH effect on OFX removal and H2O2 utilization efficiency, the new formed oxygen vacancy from in situ Fe substitution by Cu rather than promoted Fe(3+)/Fe(2+) cycle was responsible for the ultraefficiency of Cu doped Fe3O4@FeOOH at neutral and even alkaline pHs. Moreover, the catalyst had an excellent long-term stability and could be easily recovered by magnetic separation, which would not cause secondary pollution to treated water.

Cytotoxicity and mode of action of a naturally occurring naphthoquinone, 2-acetyl-7-methoxynaphtho[2,3-b]furan-4,9-quinone towards multi-factorial drug-resistant cancer cells.[Pubmed:28887921]

Phytomedicine. 2017 Sep 15;33:62-68.

INTRODUCTION: Malignacies are still a major public concern worldwide and despite the intensive search of new chemotherapeutic agents, treatment still remains a challenging issue. The present study was designed to evaluate the cytotoxicity of 2-acetyl-7-methoxynaphtho[2,3-b]furan-4,9-quinone (AMNQ) isolated from the bark of Milletia versicolor towards a panel of drug-sensitive and multidrug-resistant (MDR) cancer cell lines. METHODS: The resazurin reduction assay was used to evaluate the cytotoxicity of AMNQ against 9 drug-sensitive and multidrug-resistant (MDR) cancer cell lines. Cell cycle, mitochondrial membrane potential (MMP) and levels of reactive oxygen species were all analyzed by flow cytometry. RESULTS: Following resazurin assay, the naphthoquinone AMNQ displayed IC50 values ranging from 0.79microM (against HepG2 hepatocarcinoma cells) to 3.26microM (against MDA-MB231/BCRP breast cancer cells) on 9 tested cancer cell lines, whilst doxorubicin showed IC50 values ranging from 0.40microM (against CCRF-CEM leukemia cells) to 91.37microM (against CEM/ADR5000 leukemia cells). IC50 values below 1microM were recorded with AMNQ towards CCRF-CEM cells (0.57microM), U87MG.DeltaEGFR gliobastoma multiforme cells (0.96microM cells) and HepG2 cells (0.76microM). Compared to its corresponding sensitive cell lines U87MG, sensitivity was observed in epidermal growth factor receptor-transfected U87MG.DeltaEGFR cells to AMNQ. MMP was found to be the main mode of action of induction of apoptosis by AMNQ. CONCLUSIONS: The results of this work demonstrate the cytotoxicity of AMNQ towards various types of cancer cell lines, including MDR phenotypes. AMNQ is a potential antiproliferative natural compound that deserves more investigations to develop novel cytotoxic drugs against sensitive and MDR cancers.

Crystal structure and DFT study of (E)-N-[2-(1H-indol-3-yl)eth-yl]-1-(anthracen-9-yl)methanimine.[Pubmed:28932467]

Acta Crystallogr E Crystallogr Commun. 2017 Aug 11;73(Pt 9):1329-1332.

The title compound, C25H20N2, (I), was synthesized from the condensation reaction of anthracene-9-carbaldehyde and tryptamine in dry ethanol. The indole ring system (r.m.s. deviation = 0.016 A) makes a dihedral angle of 63.56 (8) degrees with the anthracene ring (r.m.s. deviation = 0.023 A). There is a short intra-molecular C-Hcdots, three dots, centeredN inter-action present, and a C-Hcdots, three dots, centeredpi inter-action involving the two ring systems. In the crystal, the indole H atom forms an inter-molecular N-Hcdots, three dots, centeredpi inter-action, linking mol-ecules to form chains along the b-axis direction. There are also C-Hcdots, three dots, centeredpi inter-actions present, involving the central and terminal rings of the anthracene unit, linking the chains to form an overall two-dimensional layered structure, with the layers parallel to the bc plane. The density functional theory (DFT) optimized structure, at the B3LYP/6-311 G(d,p) level, is compared with the experimentally determined mol-ecular structure in the solid state.

After 9 Years of 3-Column Osteotomies, Are We Doing Better? Performance Curve Analysis of 573 Surgeries With 2-Year Follow-up.[Pubmed:28973410]

Neurosurgery. 2018 Jul 1;83(1):69-75.

BACKGROUND: In spinal deformity treatment, the increased utilization of 3-column (3CO) osteotomies reflects greater comfort and better training among surgeons. This study aims to evaluate the longitudinal performance and adverse events (complications or revisions) for a multicenter group following a decade of 3CO. OBJECTIVE: To investigate if performance of 3CO surgeries improves with years of practice. METHODS: Patients who underwent 3CO for spinal deformity with intra/postoperative and revision data collected up to 2 yr were included. Patients were chronologically divided into 4 even groups. Demographics, baseline deformity/correction, and surgical metrics were compared using Student t-test. Postoperative and revision rates were compared using Chi-square analysis. RESULTS: Five hundred seventy-three patients were stratified into: G1 (n = 143, 2004-2008), G2 (n = 142, 2008-2009), G3 (n = 144, 2009-2010), G4 (n = 144 2010-2013). The most recent patients were more disabled by Oswestry disability index (G4 = 49.2 vs G1 = 38.3, P = .001), and received a larger osteotomy resection (G4 = 26 degrees vs G1 = 20 degrees , P = .011) than the earliest group. There was a decrease in revision rate (45%, 35%, 33%, 30%, P = .039), notably in revisions for pseudarthrosis (16.7% G1 vs 6.9% G4, P = .007). Major complication rates also decreased (57%, 50%, 46%, 39%, P = .023) as did excessive blood loss (>4 L, 27.2 vs 16.7%, P = .023) and bladder/bowel deficit (4.2% vs 0.7% P = .002). Successful outcomes (no complications or revision) significantly increased (P = .001). CONCLUSION: Over 9 yr, 3COs are being performed on an increasingly disabled population while gaining a greater correction at the osteotomy site. Revisions and complication rate decreased while success rate improved during the 2-yr follow-up period.

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