Mahanine

CAS# 28360-49-8

Mahanine

Catalog No. BCN3176----Order now to get a substantial discount!

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Quality Control of Mahanine

Number of papers citing our products

Chemical structure

Mahanine

3D structure

Chemical Properties of Mahanine

Cas No. 28360-49-8 SDF Download SDF
PubChem ID 36689305 Appearance Powder
Formula C23H25NO2 M.Wt 347.5
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3R)-3,5-dimethyl-3-(4-methylpent-3-enyl)-11H-pyrano[3,2-a]carbazol-9-ol
SMILES CC1=C2C(=C3C(=C1)C4=C(N3)C=C(C=C4)O)C=CC(O2)(C)CCC=C(C)C
Standard InChIKey DWMBXHWBPZZCTN-HSZRJFAPSA-N
Standard InChI InChI=1S/C23H25NO2/c1-14(2)6-5-10-23(4)11-9-18-21-19(12-15(3)22(18)26-23)17-8-7-16(25)13-20(17)24-21/h6-9,11-13,24-25H,5,10H2,1-4H3/t23-/m1/s1
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 Mahanine

The leaves of Murraya koenigii

Biological Activity of Mahanine

Description1. Mahanine has a dose- and time-dependent anti-proliferative activity in acute lymphoid (MOLT-3) and chronic myeloid (K562) leukemic cell lines. 2. Mahanine has effects on the activation of the apoptotic pathway in human leukemia U937 cells, causes the mitochondrial membranes to lose their permeability, resulting in caspase-3 activation and apoptosis. 3. Mahanine can reverse an epigenetically silenced gene, RASSF1A in prostate cancer cells by inhibiting DNMT activity that in turn down-regulates a key cell cycle regulator, cyclin D1, is an encouraging therapeutic choice for advanced prostatic cancer. 4. Mahanine inhibited growth of PC3 and LNCaP prostate cancer cells in a dose and time-dependent manner, inhibits growth and induces apoptosis in both androgen-responsive, LNCaP and androgen-independent, PC3 cells by targeting cell survival pathway.
TargetsJAK | Src | STAT | ROS | Chk | CDK | Akt | PI3K | p53

Mahanine Dilution Calculator

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Mahanine Molarity Calculator

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Preparing Stock Solutions of Mahanine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8777 mL 14.3885 mL 28.777 mL 57.554 mL 71.9424 mL
5 mM 0.5755 mL 2.8777 mL 5.7554 mL 11.5108 mL 14.3885 mL
10 mM 0.2878 mL 1.4388 mL 2.8777 mL 5.7554 mL 7.1942 mL
50 mM 0.0576 mL 0.2878 mL 0.5755 mL 1.1511 mL 1.4388 mL
100 mM 0.0288 mL 0.1439 mL 0.2878 mL 0.5755 mL 0.7194 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 Mahanine

Improved chemosensitivity in cervical cancer to cisplatin: synergistic activity of mahanine through STAT3 inhibition.[Pubmed:24831030]

Cancer Lett. 2014 Aug 28;351(1):81-90.

Toxicity reduction of cisplatin is necessary for improved treatment of cancer. Here we have demonstrated the synergistic growth-inhibitory effect of cisplatin on cervical cancer cells in-combination with a nontoxic herbal carbazole alkaloid, Mahanine. Mahanine enhanced cisplatin-induced apoptosis and reduced its effective concentration approximately 5-8 folds. Mahanine inhibited JAK1 and Src and subsequently promoted proteasome-mediated degradation of STAT3. This event was further enhanced in-combination with cisplatin and subsequently inhibited cancer cell migration. Collectively, our results revealed that Mahanine may be a prospective agent to reduce the concentration of cisplatin in adjunct for the treatment of cancer and thereby decreasing its toxicity.

Mahanine, a novel mitochondrial complex-III inhibitor induces G0/G1 arrest through redox alteration-mediated DNA damage response and regresses glioblastoma multiforme.[Pubmed:25520856]

Am J Cancer Res. 2014 Nov 19;4(6):629-47. eCollection 2014.

The Electron transport chain (ETC) is responsible for oxidative phosphorylation-mediated mitochondrial respiration. Here we wanted to address the Mahanine-induced targeted pathways in glioblastoma multiforme (GBM) in the context of G0/G1 phase arrest and redox alteration. We have demonstrated Mahanine, as a novel mitochondrial complex-III inhibitor which induced G0/G1 phase arrest in GBM. This event was preceded by accumulation of intracellular ROS by the inhibition of mitochondrial ETC. The accumulated ROS induced DNA damage response (DDR), that mediated Chk1/Chk2 upregulation and activation which were essential factors for the G0/G1 arrest. NAC-mediated scavenging of ROS generation reduced the propensity of G0/G1 phase arrest in GBM cells by Mahanine. Knockdown of Chk1/Chk2 also affected the cell cycle inhibitory potential of Mahanine. During G0/G1 arrest, other hallmark proteins like, cyclin D1/cyclin D3, CDK4/CDK6 and CDC25A were also downregulated. The G0/G1 phase restriction property of Mahanine was also established in in vivo mice model. Mahanine-induced complex-III inhibition triggered enhanced ROS in hypoxia responsible for higher G0/G1 arrest. Furthermore, we demonstrated that Mahanine-treated G0/G1 arrested cells were less potent to form xenograft tumor in vivo. Additionally, they exhibited reduced ability to migrate and form intracellular tube-like structures. Moreover, they became susceptible to differentiate and astrocyte-like cells were generated from the epithelial lineage. Taken together, our results established that complex-III of ETC is one of the possible potential targets of Mahanine. This nontoxic chemotherapeutic molecule enhanced ROS production, induced cell cycle arrest and thereafter regressed GBM without effecting normal astrocytes.

Mahanine, a DNA minor groove binding agent exerts cellular cytotoxicity with involvement of C-7-OH and -NH functional groups.[Pubmed:23829449]

J Med Chem. 2013 Jul 25;56(14):5709-21.

Mahanine, a carbazole alkaloid is a potent anticancer molecule. To recognize the structure-activity correlation, Mahanine was chemically modified. Antiproliferative activity of these derivatives was determined in 19 cancer cell lines from 7 different origins. Mahanine showed enhanced apoptosis compared to dehydroxy-Mahanine-treated cells, indicating significant contribution of the C-7-OH group. O-Methylated-Mahanine and N-methylated dehydroxy-Mahanine-treated cells exhibited apoptosis only at higher concentrations, suggesting additional contribution of 9-NH group. Using biophysical techniques, we demonstrated that Mahanine interacts with DNA through strong association with phosphate backbone compared to other derivatives but is unable to induce any conformational change in DNA, hence suggesting the possibility of being a minor groove binder. This was corroborated by molecular modeling and isothermal titration calorimetry studies. Taken together, the results of the current study represent the first evidence of involvement of C-7-OH and 9-NH group of Mahanine for its cytotoxicity and its minor groove binding ability with DNA.

Mahanine restores RASSF1A expression by down-regulating DNMT1 and DNMT3B in prostate cancer cells.[Pubmed:24001151]

Mol Cancer. 2013 Aug 30;12(1):99.

BACKGROUND: Hypermethylation of the promoter of the tumor suppressor gene RASSF1A silences its expression and has been found to be associated with advanced grade prostatic tumors. The DNA methyltransferase (DNMT) family of enzymes are known to be involved in the epigenetic silencing of gene expression, including RASSF1A, and are often overexpressed in prostate cancer. The present study demonstrates how Mahanine, a plant-derived carbazole alkaloid, restores RASSF1A expression by down-regulating specific members of the DNMT family of proteins in prostate cancer cells. RESULTS: Using methylation-specific PCR we establish that Mahanine restores the expression of RASSF1A by inducing the demethylation of its promoter in prostate cancer cells. Furthermore, we show that Mahanine treatment induces the degradation of DNMT1 and DNMT3B, but not DNMT3A, via the ubiquitin-proteasome pathway; an effect which is rescued in the presence of a proteasome inhibitor, MG132. The inactivation of Akt by wortmannin, a PI3K inhibitor, results in a similar down-regulation in the levels DNMT1 and DNMT3B. Mahanine treatment results in a decline in phospho-Akt levels and a disruption in the interaction of Akt with DNMT1 and DNMT3B. Conversely, the exogenous expression of constitutively active Akt inhibits the ability of Mahanine to down-regulate these DNMTs, suggesting that the degradation of DNMT1 and DNMT3B by Mahanine occurs via Akt inactivation. CONCLUSIONS: Taken together, we show that Mahanine treatment induces the proteasomal degradation of DNMT1 and DNMT3B via the inactivation of Akt, which facilitates the demethylation of the RASSF1A promoter and restores its expression in prostate cancer cells. Therefore, Mahanine could be a potential therapeutic agent for advanced prostate cancer in men when RASSF1A expression is silenced.

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