Epianhydrotetracycline (hydrochloride)
(Synonyms: 4-差向脱水四环素) 目录号 : GC45447
A degradation product of tetracycline
Cas No.:4465-65-0
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Epianhydrotetracycline (EATC) is a degradation product of the antibiotic tetracycline .1 EATC is active against Pseudomonas, Agrobacterium, Moraxella, Bacillus, and E. coli (MIC50s = 0.75-16 mg/L).
References
1. Halling-S•rensen, B., Sengel•v, G., and Tj•rnelund, J. Toxicity of tetracyclines and tetracycline degradation products to environmentally relevant bacteria, including selected tetracycline-resistant bacteria. Arch. Environ. Contam. Toxicol. 42(3), 263-271 (2002).
| Cas No. | 4465-65-0 | SDF | |
| 别名 | 4-差向脱水四环素 | ||
| Canonical SMILES | O=C([C@@](C(C(C(N)=O)=C(O)[C@@H]1N(C)C)=O)(O)[C@@]1([H])C2)C3=C2C(C)=C4C(C(O)=CC=C4)=C3O.Cl | ||
| 分子式 | C22H22N2O7.HCl | 分子量 | 462.9 |
| 溶解度 | DMF: 10 mg/ml,DMSO: 20 mg/ml,Ethanol: 2 mg/ml,PBS (pH 7.2): 0.25 mg/ml | 储存条件 | Store at -20°C |
| 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.1603 mL | 10.8015 mL | 21.6029 mL |
| 5 mM | 0.4321 mL | 2.1603 mL | 4.3206 mL |
| 10 mM | 0.216 mL | 1.0801 mL | 2.1603 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。
Development and validation of an HPLC method for tetracycline-related USP monographs
Biomed Chromatogr 2014 Sep;28(9):1278-83.PMID:24619929DOI:10.1002/bmc.3161.
A novel reversed-phase HPLC method was developed and validated for the assay of tetracycline hydrochloride and the limit of 4-epianhydrotetracycline hydrochloride impurity in tetracycline hydrochloride commercial bulk and pharmaceutical products. The method employed L1 (3 µm, 150 × 4.6 mm) columns, a mobile phase of 0.1% phosphoric acid and acetonitrile at a flow rate of 1.0 mL/min, and detection at 280 nm. The separation was performed in HPLC gradient mode. Forced degradation studies showed that tetracycline eluted as a spectrally pure peak and was well resolved from its degradation products. The fast degradation of tetracycline hydrochloride and 4-epianhydrotetracycline hydrochloride in solution was retarded by controlling the autosampler temperature at 4 °C and using 0.1% H3 PO4 as diluent. The robustness of the method was tested starting with the maximum variations allowed in the US Pharmacopeia (USP) general chapter Chromatography <621>. The method was linear over the range 80-120% of the assay concentration (0.1 mg/mL) for tetracycline hydrochloride and 50-150% of the acceptance criteria specified in the individual USP monographs for 4-epianhydrotetracycline hydrochloride. The limit of quantification for 4-epianhydrotetracycline hydrochloride was 0.1 µg/mL, 20 times lower than the acceptance criteria. The method was specific, precise, accurate and robust.
Temperature-dependent terahertz vibrational spectra of tetracycline and its degradation products
Spectrochim Acta A Mol Biomol Spectrosc 2019 Nov 5;222:117179.PMID:31202030DOI:10.1016/j.saa.2019.117179.
Terahertz (THz) spectroscopy has emerged as an attractive technique for qualitative and quantitative detection. Analysis of these chemicals in the THz range under various temperatures can yield detailed information on molecular vibrational modes, which is of utmost importance for effective detection. Here we report the use of THz time-domain spectroscopy (THz-TDS) to measure tetracyclines hydrochloride (TCH) and its degradation products including epitetracycline hydrochloride (ETCH), anhydrotetracycline hydrochloride (ATCH), and Epianhydrotetracycline hydrochloride (EATCH) over the temperature range of 4.5-300 K for the first time. The results showed that these four tetracyclines exhibited numerous distinct spectral features in frequency-dependent absorption spectra, which demonstrated the qualitative capacity of THz-TDS. Through density functional theory (DFT) calculations and analysis of temperature-dependent absorption spectra, the origin of the observed terahertz absorption peaks of these four tetracyclines were well interpreted. This study could lay the foundation for high-performance analysis of biological and chemical molecules by THz spectroscopy, which is essential for sensing application.
Determination of tetracycline hydrochloride in presence of anhydrotetracycline by differential pulse polarography
J Pharm Sci 1988 Jan;77(1):78-80.PMID:3346827DOI:10.1002/jps.2600770115.
A differential pulse polarographic method is described for the determination of the antibiotic tetracycline HCl in the presence of its degradation product anhydrotetracycline. The method utilizes the large difference in their differential pulse polarograms at a peak potential of -1.39 V in 0.1 M phosphate buffer as the base electrolyte (pH 6.8). The assay was evaluated using synthetic mixtures and applied to the analysis of commercial tetracycline HCl samples. The results obtained with this method are in close agreement with those from the spectrophotometric absorbance ratio method.
[Embryotoxicity and the immunodepressive action of tetracycline and its epi- and anhydro- derivatives]
Antibiotiki 1976 Nov;21(11):1018-22.PMID:1035488doi
The toxic effect of tetracycline and its epi- and anhydro-derivatives on growing chick embryos and the spleen cells of immunized mice was studied. High acute toxicity of 4-epianhydrotetracycline with respect to the chick embryos was found. Its LD50 was 4.8 times lower than toxicity of tetracycline hydrochloride. The characteristics of the acute toxicity was confirmed by the data on the embryo survival by the time of hatching. The same survival rate, i. e. 12 per cent was observed with the use of tetracycline and 4-epianhydrotetracycline in doses of 1000 and 100gamma per embryo respectively. Comparative investigation of the effect of tetracycline and anhydrotetracycline on the spleen cells revealed high toxicity of anhydrotetracycline which induced the same decrease in the number of the antibody-producing cells as tetracycline when used in doses 40 to 100 times lower than those of tetracycline. High toxicity of the anhydro-derivatives of tetracycline was also observed with respect to their teratogenic effect. Extremely pronounced anomalies in the embryo development were observed after exposure to 500gamma of 4-epianhydrotetracycline.
Toxic effects of tetracycline and its degradation products on freshwater green algae
Ecotoxicol Environ Saf 2019 Jun 15;174:43-47.PMID:30818259DOI:10.1016/j.ecoenv.2019.02.063.
Tetracycline antibiotics are the most widely used antibiotics in the world and the most common veterinary drugs and feed additives used in livestock, poultry and aquaculture operations. Because antibiotics cannot be completely removed by currently existing sewage treatment facilities, these materials enter the environment directly via sewage treatment plant discharge, where they degrade. Accordingly, the metabolism and the ecological toxicity of tetracycline degradation products are worthy of attention. Herein, we investigated the effects of tetracycline and its degradation products (anhydrotetracycline and epitetracycline hydrochloride) on the growth, cell structure and algal cell oxidative stress of common Chlorella vulgaris. The results showed that the 96h-EC50 values of tetracycline (TC), anhydrotetracycline (ATC) and epitetracycline (ETC) on algal cells were 7.73, 5.96 and 8.42 mg/L, respectively. Moreover, the permeability of algal cells exposed to high concentrations of these three drugs was significantly enhanced. In addition, there were structural changes in the cells such as plasmolysis and starch granule deposition appeared, the thylakoid lamellae in the chloroplasts became blurred and deformed, and the vacuoles became larger. Exposure to higher concentrations (>5 mg/L) of TC and its degradation products ATC and ETC significantly upregulated the activity of ROS, as well as the antioxidants SOD and CAT. The levels of the lipid peroxidation product MDA also showed the same trend. Finally, ATC had the strongest toxicity toward algal cells, followed by TC and then ETC.