Physicochemical Properties
| Molecular Formula | C23H25NO2 |
| Molecular Weight | 347.45000 |
| Exact Mass | 347.189 |
| CAS # | 28360-49-8 |
| PubChem CID | 36689305 |
| Appearance | Light yellow to brown solid powder |
| LogP | 6.245 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 26 |
| Complexity | 581 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | CC1=CC2=C(C3=C1O[C@](C=C3)(C)CCC=C(C)C)NC4=C2C=CC(=C4)O |
| InChi Key | DWMBXHWBPZZCTN-HSZRJFAPSA-N |
| InChi Code | 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 |
| Chemical Name | (3R)-3,5-dimethyl-3-(4-methylpent-3-enyl)-11H-pyrano[3,2-a]carbazol-9-ol |
| 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) |
Biological Activity
| ln Vitro | AG83 promastigote cell viability decreased in a dose-dependent manner in response to mahanine (0-50 µM; 24 or 48 hours); the IC50 values were 16.7±1.7μM and 11.5±0.8μM, respectively. At 24 and 48 hours of treatment, Mahanine administration in resistant GE1 strains demonstrated dose-dependent cell killing with IC50 values of 40.3±2.2 µM and 29.1±1.3 µM, respectively [1]. Mahanine (5.0 and 10 µM; 24 h) increased G2/M phase cell accumulation in AG83 promastigotes, 39.0 ± 1.90%, respectively, compared to 41.0±2.10% and 35.3 ± 2.60%) in untreated promastigotes [1]. After reaching 1288 ± 56, mahanine (25 µM; 24 h) significantly raised intracellular ROS levels at 20 min (MFI of 889 ± 26) in comparison to basal levels in untreated promastigotes (604 ± 34) after one hour. FACS is used to evaluate H2DCFDA positivity [1]. |
| ln Vivo | In an established acute model, Mahani (oral gavage; 20 mg/kg/40 mg/kg; body weight/day; 5 days) led to an 89.1 ± 4.1% reduction in parasite burden at 20 mg/kg and a 96.2 ± 0.3% load reduction with 40 mg/kg to treat Leishmania infection [1]. |
| Animal Protocol |
Animal/Disease Models: virulent AG83 promastigote balb/c (Bagg ALBino) mouse [1] Doses: 20 mg/kg-40 mg/kg Route of Administration: po (oral gavage); 20 mg/kg/40 mg/kg; body weight/day; 5-day Experimental Results: Potential to clear parasite burden from the body. In vivo parasite load was almost completely diminished, and NO/iNOS/ROS/IL-12 and T cell proliferation were upregulated. |
| References |
[1]. Apoptotic effects of mahanine on human leukemic cells are mediated through crosstalk between Apo-1/Fas signaling and the Bid protein and via mitochondrial pathways. Biochem Pharmacol. 2010 Feb 1;79(3):361-72. [2]. Mahanine exerts in vitro and in vivo antileishmanial activity by modulation of redox homeostasis. Sci Rep. |
| Additional Infomation | Mahanine has been reported in Murraya euchrestifolia and Murraya koenigii with data available. |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8781 mL | 14.3906 mL | 28.7811 mL | |
| 5 mM | 0.5756 mL | 2.8781 mL | 5.7562 mL | |
| 10 mM | 0.2878 mL | 1.4391 mL | 2.8781 mL |