4-Epianhydrotetracycline hydrochloride
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| Category | Bioactive by-products |
| Catalog number | BBF-04533 |
| CAS | 4465-65-0 |
| Molecular Weight | 462.88 |
| Molecular Formula | C22H22N2O7.HCl |
| Purity | >95% by HPLC |
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Description
A secondary degradation product formed by epimerisation of tetracycline and dehydration at the C6 position to aromatise the B ring. It is an important standard for monitoring tetracycline stability. It is considered to be biologically active and responsible for the toxicity of tetracycline. It is active against Pseudomonas, Agrobacterium, Moraxella, Bacillus and E. coli.
Specification
| Related CAS | 7518-17-4 (free base) |
| Synonyms | 4-Epianhydrotetracycline HCl; (4R,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide Hydrochloride; 4-Epi-anhydrotetracycline hydrochloride; EATC hydrochloride |
| Storage | Store at -20°C |
| IUPAC Name | (4R,4aS,12aR)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-4a,5-dihydro-4H-tetracene-2-carboxamide;hydrochloride |
| Canonical SMILES | CC1=C2C=CC=C(C2=C(C3=C1CC4C(C(=O)C(=C(C4(C3=O)O)O)C(=O)N)N(C)C)O)O.Cl |
| InChI | InChI=1S/C22H22N2O7.ClH/c1-8-9-5-4-6-12(25)13(9)17(26)14-10(8)7-11-16(24(2)3)18(27)15(21(23)30)20(29)22(11,31)19(14)28;/h4-6,11,16,25-26,29,31H,7H2,1-3H3,(H2,23,30);1H/t11-,16+,22-;/m0./s1 |
| InChI Key | SPFAOPCHYIJPHJ-MOMXNFOMSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Orange Solid |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 618.6°C at 760 mmHg |
| Melting Point | >180°C (dec.) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO, Water |
Reference Reading
1.Conditional silencing of topoisomerase I gene of Mycobacterium tuberculosis validates its essentiality for cell survival.
Ahmed W1, Menon S, Godbole AA, Karthik PV, Nagaraja V. FEMS Microbiol Lett. 2014 Apr;353(2):116-23. doi: 10.1111/1574-6968.12412. Epub 2014 Apr 3.
Topoisomerases are an important class of enzymes for regulating the DNA transaction processes. Mycobacterium tuberculosis (Mtb) is one of the most formidable pathogens also posing serious challenges for therapeutic interventions. The organism contains only one type IA topoisomerase (Rv3646c), offering an opportunity to test its potential as a candidate drug target. To validate the essentiality of M. tuberculosis topoisomerase I (TopoI(Mt) ) for bacterial growth and survival, we have generated a conditionally regulated strain of topoI in Mtb. The conditional knockdown mutant exhibited delayed growth on agar plate. In liquid culture, the growth was drastically impaired when TopoI expression was suppressed. Additionally, novobiocin and isoniazid showed enhanced inhibitory potential against the conditional mutant. Analysis of the nucleoid revealed its altered architecture upon TopoI depletion. These studies establish the essentiality of TopoI for the M.
2.Conditional gene expression in Chlamydia trachomatis using the tet system.
Wickstrum J1, Sammons LR, Restivo KN, Hefty PS. PLoS One. 2013 Oct 7;8(10):e76743. doi: 10.1371/journal.pone.0076743. eCollection 2013.
Chlamydia trachomatis is maintained through a complex bi-phasic developmental cycle that incorporates numerous processes that are poorly understood. This is reflective of the previous paucity of genetic tools available. The recent advent of a method for transforming Chlamydia has enabled the development of essential molecular tools to better study these medically important bacteria. Critical for the study of Chlamydia biology and pathogenesis, is a system for tightly controlled inducible gene expression. To accomplish this, a new shuttle vector was generated with gene expression controlled by the Tetracycline repressor and anhydryotetracycline. Evaluation of GFP expression by this system demonstrated tightly controlled gene regulation with rapid protein expression upon induction and restoration of transcription repression following inducer removal. Additionally, induction of expression could be detected relatively early during the developmental cycle and concomitant with conversion into the metabolically active form of Chlamydia.
3.Programmable bacteria detect and record an environmental signal in the mammalian gut.
Kotula JW1, Kerns SJ, Shaket LA, Siraj L, Collins JJ, Way JC, Silver PA. Proc Natl Acad Sci U S A. 2014 Apr 1;111(13):4838-43. doi: 10.1073/pnas.1321321111. Epub 2014 Mar 17.
The mammalian gut is a dynamic community of symbiotic microbes that interact with the host to impact health, disease, and metabolism. We constructed engineered bacteria that survive in the mammalian gut and sense, remember, and report on their experiences. Based on previous genetic memory systems, we constructed a two-part system with a "trigger element" in which the lambda Cro gene is transcribed from a tetracycline-inducible promoter, and a "memory element" derived from the cI/Cro region of phage lambda. The memory element has an extremely stable cI state and a Cro state that is stable for many cell divisions. When Escherichia coli bearing the memory system are administered to mice treated with anhydrotetracycline, the recovered bacteria all have switched to the Cro state, whereas those administered to untreated mice remain in the cI state. The trigger and memory elements were transferred from E. coli K12 to a newly isolated murine E. coli strain; the stability and switching properties of the memory element were essentially identical in vitro and during passage through mice, but the engineered murine E.
4.Investigation of relationships between removals of tetracycline and degradation products and physicochemical parameters in municipal wastewater treatment plant.
Topal M1, Uslu Şenel G2, Öbek E3, Arslan Topal EI2. J Environ Manage. 2016 May 15;173:1-9. doi: 10.1016/j.jenvman.2016.02.046. Epub 2016 Mar 4.
Determination of the effect of physicochemical parameters on the removal of tetracycline (TC) and degradation products is important because of the importance of the removal of antibiotics in Wastewater Treatment Plant (WWTP). Therefore, the purpose of this study was to investigate the relationships between removals of TC and degradation products and physicochemical parameters in Municipal Wastewater Treatment Plant (MWWTP). For this aim, (i) the removals of physicochemical parameters in a MWWTP located in Elazığ city (Turkey) were determined (ii) the removals of TC and degradation products in MWWTP were determined (iii) the relationships between removals of TC and degradation products and physicochemical parameters were investigated. TC, 4-epitetracycline (ETC), 4-epianhydrotetracycline (EATC), anhydrotetracycline (ATC), and physicochemical parameters (pH, temperature, electrical conductivity (EC), suspended solids (SS), BOD5, COD, total organic carbon (TOC), NH4(+)-N, NO2(-)-N, NO3(-)-N and O-PO4(-3)) were determined.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
