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Epitetracycline (hydrochloride)

(Synonyms: 差向四环素) 目录号 : GC43620

An epimer of tetracycline

Epitetracycline (hydrochloride) Chemical Structure

Cas No.:23313-80-6

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10mg
¥793.00
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25mg
¥1,650.00
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50mg
¥2,919.00
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100mg
¥3,871.00
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产品描述

Epitetracycline is an epimer of the antibiotic tetracycline . Epimers of tetracycline form without catalysis and are considered degradation products. Epitetracycline has decreased activity as an antibiotic or a Tet repressor effector but may have stronger toxic effects in animals.

Chemical Properties

Cas No. 23313-80-6 SDF
别名 差向四环素
Canonical SMILES O=C1C2=C(O)C=CC=C2[C@](O)(C)[C@]3([H])C1=C(O)[C@@](C(C(C(N)=O)=C(O)[C@@H]4N(C)C)=O)(O)[C@@]4([H])C3.Cl
分子式 C22H24N2O8•HCl 分子量 480.9
溶解度 DMF: 1.4 mg/ml,DMSO: 1 mg/ml,PBS (pH 7.2): 3.3 mg/ml 储存条件 Store at -20°C
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溶解性数据

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1 mM 2.0794 mL 10.3972 mL 20.7943 mL
5 mM 0.4159 mL 2.0794 mL 4.1589 mL
10 mM 0.2079 mL 1.0397 mL 2.0794 mL
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Research Update

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.

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.

Response of captive skunks to microencapsulated tetracycline

J Wildl Dis 2010 Jul;46(3):1024-8.PMID:20688717DOI:10.7589/0090-3558-46.3.1024.

A captive striped skunk (Mephitis mephitis) study was conducted between February and June 2004 at the United States Department of Agriculture, Animal and Plant Health Inspection Service, Wildlife Services National Wildlife Research Center, Fort Collins, Colorado, USA. The main objective was to determine the percentage of adult striped skunks that were marked after consuming placebo oral rabies vaccine (ORV) baits containing 100 mg of an experimental microencapsulated (coated microparticle) tetracycline hydrochloride biomarker. Biomarkers were identified in the canine teeth and mandibles of five of five skunks that consumed an ORV bait. A second objective was to determine if the microencapsulated tetracycline was resistant to photochemical conversion from tetracycline to Epitetracycline. After 15 days of exposure, conversion from tetracycline to Epitetracycline concentration in the microencapsulated product (mean 1.9% conversion, SD=1.24) was significantly less (P=0.006) than the pure-grade tetracycline powder (mean 7.5% conversion, SD=1.37). Results support the use of microencapsulated tetracycline hydrochloride as a biomarker in circumstances where the use of conventional powdered tetracycline hydrochloride is not feasible due to ORV bait design constraints.

High-performance liquid chromatographic analysis of oxytetracycline in chinook salmon following administration of medicated feed

J Chromatogr 1991 Dec 27;588(1-2):181-6.PMID:1818082DOI:10.1016/0021-9673(91)85021-7.

A high-performance liquid chromatographic assay was developed to detect oxytetracycline (OTC) in chinook salmon muscle tissue. A solid-phase extraction protocol was used to recover OTC and the internal standard, Epitetracycline hydrochloride, from the salmon tissue samples. OTC was analyzed using a mobile phase of methanol-0.02 M phosphate buffer, pH 2.25 (60:190), an ultraviolet detection wavelength of 365 nm and 250 mm x 4.6 mm I.D. Ultrasphere ODS column. A linear calibration curve (r2 = 0.999) of OTC in salmon muscle tissue from 0.05 to 3.0 ppm was obtained. Using a signal-to-noise ratio of 5:1, the OTC detection limit was 0.5 ppm in salmon muscle tissue. OTC recovery (74.4%) and intra-assay variability (2.3%) were optimized for salmon muscle tissue. An in vivo feeding study was performed by administrating OTC-medicated feed for a period of 10 days, followed by a 42-day sampling period. The half-life for the elimination of OTC in chinook salmon muscle tissue was found to be 5.4 days.

How to evaluate the separation efficiency of CZE methods?

Pharmeur Bio Sci Notes 2011 Jun;2011(1):81-8.PMID:21619858doi

In trying to estimate the separation efficiency of Capillary Electrophoresis (CE) methods, the resolution (RS), the number of theoretical plates (N) and the peak-to-valley ratio (p/v) are often used assessment criteria. This study demonstrates that these criteria are not as suitable to describe the separation efficiency in case of Capillary Zone Electrophoresis (CZE) methods as they are for Liquid Chromatography (LC) methods. The investigations were performed by means of a validated CZE method for the evaluation of tetracyclines and their related substances. Four impurities of tetracycline hydrochloride are described in the European Pharmacopoeia. Three were found in the sample used for our investigations, i.e. epi-tetracycline formed by keto-enol-tautomerism, anhydrotetracyclin and epi-anhydrotetracyline. It could be shown that higher values of these assessment criteria like RS do not necessarily represent better separation. Thus, a discussion on the usefulness of separation selectivity and efficiency as assessment criteria for capillary electrophoresis as well as on the introduction of additional parameters is needed.