| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Zika virus (ZIKV); Ebola virus (EBOV)
|
|---|---|
| ln Vitro |
Cephaeline, a desmethyl analog of emetine, exhibits a similar antiviral efficacy against both ZIKV and EBOV infections[2].
Cephaeline is an inductor of histone H3 acetylation and inhibitor of mucoepidermoid carcinoma cancer stem cells. A single administration of Cephaeline resulted in reduced viability of MEC cells along with the halt on tumor growth and cellular migration potential. Administration of Cephaeline resulted in chromatin histone acetylation as judged by the increased levels of H3K9ac and disruption of tumorspheres formation. Interestingly, ALDH levels were increased in UM-HMC-1 and UM-HMC-3A cell lines, while UM-HMC-2 showed a reduced enzymatic activity. Conclusion: Cephaeline has shown anti-cancer properties in all MEC cell lines tested by regulating tumor cells' viability, migration, proliferation, and disrupting the ability of cancer cells to generate tumorspheres[3]. |
| ln Vivo |
This study tested the protective efficacy of Emetine and cephaeline in an EBOV mouse model. Six to eight week-old, female BALB/c mice (n = 6 per group) were injected IP with 1000-times the mean lethal dose for 50% (LD50) of mouse-adapted Ebola virus (MA-EBOV). Before infection with MA-EBOV, mice were then treated either with emetine (1 mg/kg/day), cephaeline (5 mg/kg/day) or VC (in the control group) starting 3 h before viral innoculation via IP. After IP administration of MA-EBOV, mice continued treatment with emetine, cephaeline, or VC IP for 7 more days. The animals were monitored daily for survival. As expected, all of the control animals uniformly succumbed to EBOV infection with a mean time to death of 8.33 ± 1.03 d.p.i. In contrast, for 67%, or four out of six mice, survival was achieved in both treated groups (Fig. 4c and Supplementary Figure S5e-f). Similar to the effects of emetine and cephaeline treatment in ZIKV infection, the drugs effectively suppressed EBOV infection in vivo.[2]
This study investigates the anti-lung cancer activity and mechanisms of cephaeline in vivo. To investigate the antitumour effects of cephaeline in vivo, a subcutaneous tumor xenograft model was constructed. After 12 d of drug treatment, it was found that 5 and 10 mg/kg cephaeline conferred significant antitumour effects in vivo compared with the control group. Meanwhile, the ED50 was 3 mg/kg and minimum effective concentration (MEC) was 2.5 mg/kg measured in subcutaneous tumor xenograft model. However, 10 mg/kg cephaeline had the same anti-lung cancer effect in vivo as the ferroptosis inducer erastin (Figure 7(A–D)). Meanwhile, it was also found that there were no significant differences in body weight between the mice in the cephaeline, erastin and the control groups (Figure 7(E)). Moreover, to verify that cephaeline plays an anti-lung cancer role by inducing ferroptosis in vivo, we detected the key proteins of ferroptosis in different groups of tumor tissues by western blot, and the results were consistent with the in vitro findings (Figures 7(F) and and88).[4] |
| Enzyme Assay |
In vitro RNA polymerase assays[2]
An RNA polymerase assay kit was purchased from Profoldin. RNA synthesis assays were performed in 10 µL of reactions following the manufacturer’s instructions. After 23 ng of purified Zika NS5 was added into 384-well small-volume plate in 3 µL, serial dilutions of emetine were added into the wells in 3 µL. The mixtures were pre-incubated for 30 mins at room temperature. A master mix containing single-stranded polyribonucleotide, 10 µM of NTP mix, 20 mM Tris–HCl, pH 8.0, 1 mM DTT, and 8 mM MgCl2 was added into each well in 4 µL. The reactions were incubated at 37 °C for 1 h and then stopped by adding the fluorescence dye in 10 µL. The fluorescence intensities (Ex = 485 ± 5, Em = 535 ± 10 nm) were measured using a Tecan plate reader.
|
| Cell Assay |
The inhibition assay was performed as described previously48. In brief, Vero E6 cells were pre-treated with emetine or cephaeline (0–2.0 µM) or DMEM alone for 1 h at 37 °C, and infected with a MOI = 0.1 of GFP-expressing EBOV in the presence of emetine, cephaeline or DMEM alone for 1 h at 37 °C. Cells were then further incubated for 72 h in the presence of Emetine, Cephaeline or DMEM. At 72 h, the green fluorescent protein signal was quantified on a Biotek Synergy HTX plate reader. Infection was determined by comparing fluorescence readings of emetine or cephaeline-treated infected cells to DMEM-treated controls. The EC50 and EC90 values were calculated using a four-parameter logistic regression in Prism 5[2].
|
| Animal Protocol |
Evaluating the protective efficacy of emetine and cephaeline against MA-EBOV in mice[2]
Six to eight week-old BALB/C mice, female, were randomly assigned into groups (6 per group). All the mice were challenged with a dose of 1000 times the lethal dose (LD50) MA- EBOV via IP. Treatments with either emetine (1 mg/kg/day) or cephaeline (5 mg/kg/day) or PBS (same volume) for the control group were initiated at 3 h prior to challenge and continued for up to 6 d.p.i. All animals were monitored for signs of disease and weight change for 14 days post challenge, and survival for additional 14 days.
|
| References |
[1]. Determination of emetine and cephaeline in Ipecac roots by high- performance liquid chromatography. Journal of Chromatography A. 1982 Apr; 238( 2):525-529.
[2]. Emetine inhibits Zika and Ebola virus infections through two molecular mechanisms: inhibiting viral replication and decreasing viral entry. Cell Discov. 2018 Jun 5;4:31. [3]. Cephaeline is an inductor of histone H3 acetylation and inhibitor of mucoepidermoid carcinoma cancer stem cells. J Oral Pathol Med. 2022 Jul;51(6):553-562. [4]. Cephaeline promotes ferroptosis by targeting NRF2 to exert anti-lung cancer efficacy. Pharm Biol. 2024 Dec;62(1):195-206. |
| Additional Infomation |
See also: Cephaeline Dihydrochloride (annotation moved to).
|
| Molecular Formula |
C28H39CLN2O4
|
|---|---|
| Molecular Weight |
539.53
|
| Exact Mass |
538.236
|
| CAS # |
3738-70-3
|
| Related CAS # |
Cephaeline;483-17-0
|
| PubChem CID |
23616886
|
| Appearance |
Typically exists as solid at room temperature
|
| LogP |
6.511
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
35
|
| Complexity |
664
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
CC[C@@H]1[C@@H](C[C@@H]2C3=CC(=C(O)C=C3CCN2)OC)C[C@@H]2N(CCC3=CC(OC)=C(OC)C=C32)C1.Cl.Cl
|
| InChi Key |
NWYUGUJIBCMDEB-QJAXAJGISA-N
|
| InChi Code |
InChI=1S/C28H38N2O4.ClH/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23;/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3;1H/t17-,20-,23+,24-;/m0./s1
|
| Chemical Name |
(1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol;hydrochloride
|
| Synonyms |
CEPHAELINE HYDROCHLORIDE; 3738-70-3; Cephaeline (hydrochloride); NSC32944; NSC-32944; (-)-Cephaeline, dihydrochloride; CHEMBL1975597; SCHEMBL19742946;
|
| 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)
|
| 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
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 | 1.8535 mL | 9.2673 mL | 18.5347 mL | |
| 5 mM | 0.3707 mL | 1.8535 mL | 3.7069 mL | |
| 10 mM | 0.1853 mL | 0.9267 mL | 1.8535 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.
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