Cephaeline
(Synonyms: 吐根酚碱; (-)-Cephaeline; NSC 32944 free base) 目录号 : GC43228
An alkaloid with diverse biological activities
Cas No.:483-17-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cephaeline is an alkaloid originally isolated from C. ipecacuanha with diverse biological activities. It inhibits the cytochrome P450 (CYP) isoforms CYP2D6 and CYP3A4 in vitro (Kis = 54 and 355 μM, respectively). Cephaeline reduces Zika virus (ZIKV) NS1 protein expression in HEK293 cells (IC50 = 26.4 nM) and reduces viral titer in ZIKV-infected SNB-19 cells (IC50 = 3.11 nM). In vivo, cephaeline (2 mg/kg, i.p.) reduces serum viral load in ZIKV-infected Ifnar1-/- mice. It induces emesis in ferrets when administered at a dose of 0.5 mg/kg, an effect that is prevented by the serotonin (5-HT) receptor subtype 5-HT3 antagonist ondansetron. Cephaeline (1 mg/kg) also increases output of respiratory tract fluid in rabbits.
| Cas No. | 483-17-0 | SDF | |
| 别名 | 吐根酚碱; (-)-Cephaeline; NSC 32944 free base | ||
| Canonical SMILES | CC[C@H]1CN2CCC(C=C(C(OC)=C3)OC)=C3[C@]2([H])C[C@@H]1C[C@@]4(C5=CC(OC)=C(C=C5CCN4)O)[H] | ||
| 分子式 | C28H38N2O4 | 分子量 | 466.6 |
| 溶解度 | Acetonitrile: slightly soluble,Chloroform: slightly soluble,Ethanol: slightly soluble,Methanol: slightly soluble | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.1432 mL | 10.7158 mL | 21.4316 mL |
| 5 mM | 0.4286 mL | 2.1432 mL | 4.2863 mL |
| 10 mM | 0.2143 mL | 1.0716 mL | 2.1432 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
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.PMID:PMC9013730DOI:10.1111/jop.13252.
Aim: To evaluate the potential use of Cephaeline as a therapeutic strategy to manage mucoepidermoid carcinomas (MEC) of the salivary glands. Material and methods: UM-HMC-1, UM-HMC-2, and UM-HMC-3A MEC cell lines were used to establish the effects of Cephaeline over tumor viability determined by MTT assay. In vitro wound healing scratch assays were performed to address cellular migration while immunofluorescence staining for histone H3 lysine 9 (H3k9ac) was used to identify the acetylation status of tumor cells upon Cephaeline administration. The presence of cancer stem cells was evaluated by the identification of ALDH enzymatic activity by flow cytometry and through functional assays using in vitro tumorsphere formation. Results: 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.
Biotransformation of the ipecac alkaloids Cephaeline and emetine from ipecac syrup in rats
Eur J Drug Metab Pharmacokinet 2002 Jan-Mar;27(1):29-35.PMID:11996324DOI:10.1007/BF03190402.
The metabolism of Cephaeline and emetine, which are the primary active components of ipecac syrup, were investigated in rats. Cephaeline-6'-O-glucuronide was found to be a biliary metabolite of Cephaeline. Cephaeline (6'-O-demethylemetine) and 9-O-demethylemetine were observed to be enzyme-hydrolyzed biliary metabolites of emetine. Cephaeline was conjugated to glucuronide, while emetine was demethylated to Cephaeline and 9-0-demethylemetine, and may be conjugated to glucuronides afterwards. Urine, feces and bile were collected from rats within 48 hours following the administration of ipecac syrup containing tritium (3H)--labeled Cephaeline or emetine. Metabolites were separated and quantified by thin layer chromatography (TLC) or high-performance liquid chromatography (HPLC). Biliary and urinary excretion rates of 3H-cephaeline were 57.5% and 16.5% of the dose, respectively. Cephaeline-6'-O-glucuronide was comprised 79.5% of biliary radioactivity and 84.3% of urinary radioactivity. Unchanged Cephaeline was detected in 42.4% of the dose in feces. Biliary excretion rate of 3H-emetine was 6.9% of the dose. Emetine, Cephaeline and 9-0-demethylemetine comprised 5.8%, 43.2% and 13.6% in hydrolyzed bile, respectively. There were no emetine-derived metabolites in urine or feces. The occurrence of unchanged emetine was 6.8% and 19.7% of the dose in urine and feces, respectively.
Metabolism of ipecac alkaloids Cephaeline and emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities
Biol Pharm Bull 2001 Jun;24(6):678-82.PMID:11411558DOI:10.1248/bpb.24.678.
In this study, we identified the metabolites and the CYP forms that are specifically involved in emetine O-demethylation in human liver microsomes, and cleared the inhibitory potential of Cephaeline and emetine on the activity of the major drug-metabolizing CYP enzymes. Incubation of emetine with human liver microsomes yielded three metabolites identified by using HPLC by comparison of the retention time with the authentic sample of Cephaeline, 9-O-demethylemetine and 10-O-demethylemetine. CYP3A4 and CYP2D6 were able to metabolize emetine to Cephaeline and 9-O-demethylemetine, and CYP3A4 also participated in metabolizing emetine to 10-O-demethylemetine. Cephaeline and emetine inhibited probe substrates metabolism. IC50 for Cephaeline against CYP2D6 and CYP3A4 were 121 and 1000 microM, respectively. For the emetine, CYP2D6 and CYP3A4 were 80 and 480 microM, respectively. Inhibition constants (Ki) for both compounds on the CYP2D6 and CYP3A4 activities were determined by graphic analysis of Dixon plots at various concentrations. The obtained Ki values of Cephaeline for CYP2D6 and CYP3A4 were 54 and 355 microM, respectively, and the values of emetine were 43 and 232 microM, respectively. We concluded that these in vitro inhibitions of Cephaeline and emetine would hardly increase plasma concentrations of co-administered drugs in clinical therapy.
Absorption, distribution and excretion of 3H-labeled cephaeline- and emetine-spiked ipecac syrup in rats
Eur J Drug Metab Pharmacokinet 2002 Jan-Mar;27(1):17-27.PMID:11996323DOI:10.1007/BF03190401.
The maximum plasma radioactivity levels of tritium (3H)-labeled Cephaeline, (24.3, 28.7 and 40.6 ng eq./mL) were reached at 2.00-3.33 hours following oral dosing of ipecac syrup. The maximum plasma radioactivity levels of 3H-emetine (2.71, 6.47 and 9.62 ng eq./mL) were reached at 1.08-2.33 hours following ipecac syrup administration. The Cmax values of 3H-cephaeline were followed by a biexponential decrease with half-lives t 1/2(lambda z) of 3.45-9.40 hours. On the other hand, the t 1/2 (lambda z)of 3H-emetine were 65.4-163 hours, which revealed a biexponential decrease. The radioactivity of both tritium-labeled compounds was distrbuted maximally in most tissues at 24 hours. For 3H-cephaeline, the maximum radioactivity levels in tissues were approximately 100-150 times greater than in plasma. For 3H-emetine, the radioactivity levels in tissues were approximately 1000-3000 times greater than in plasma. Tissue radioactivity levels decreased at a substantially slower rate than that observed in plasma. Tissue radioactivity of 3H-emetine decreased more slowly than that of 3H-cephaeline. For 3H-cephaeline, the cumulative biliary excretion of radioactivity was 57.5% at 48 hours. The cumulative urinary and fecal excretion of radioactivity in these rats was 16.5% and 29.1%, respectively, of the dose at 48 hours following dosing. For 3H-emetine, the cumulative biliary excretion of radioactivity was 12.5% at 48 hours. The cumulative urinary and fecal excretion of radioactivity was 9.4% and 34.1%, respectively, of the administered dose at 48 hours. The radioactivity level of 3H-emetine remaining in the carcasses at 48 hours was equivalent to approximately 50% of the dose. A portion of each tritium-labeled compound was subjected to entero-hepatic circulation. Thus, the absorption rate of 3H-cephaeline and 3H-emetine was estimated to be approximately 70% on the basis of the data obtained from excretion studies. There was no difference in the absorption process between these two compounds. However, the difference was admitted in the biliary clearance, which is the main excretion route of both compounds. Delayed excretion of 3H-emetine may be primarily due to its resorption as related to entero-hepatic circulation and tissue retention. This study has determined the absorption, distribution and excretion of 3H-cephaeline and 3H-emetine in rats.
The simultaneous assay of emetine and Cephaeline in ipecacuanha and its preparations by spectrofluorimetry
J Pharm Biomed Anal 1984;2(3-4):441-8.PMID:16867724DOI:10.1016/0731-7085(84)80047-3.
A rapid assay is described for the simultaneous determination of emetine and Cephaeline in ipecacuanha and its preparations, based upon the different fluorescence intensities of the alkaloids at pH 1 and pH 12. The assay involves the measurement of fluorescence at 317 nm of dilutions of the sample in 0.1 M hydrochloric acid (pH 1) and 0.01 M sodium hydroxide (pH 12) with an excitation wavelength of 283 nm. Concentrations of the individual alkaloids are calculated using two simultaneous equations derived from the experimentally determined coefficients of fluorescence of solutions (1 mug/ml) of emetine and Cephaeline at pH 1 and pH 12. The procedure, which has been shown to be accurate, precise and sensitive, requires only 1 ml of a liquid sample and less than 0.5 g of powdered root. There was reasonable agreement between the total concentrations of alkaloids in tinctures and liquid extracts of ipecacuanha determined by the spectrofluorimetric method and by the titrimetric procedure of the British Pharmacopoeia. The fluorimetric procedure gave higher levels of alkaloids in the powdered root than did the B.P. method; this difference is explained by incomplete extraction of the alkaloids in the B.P. procedure for powdered ipecacuanha root.