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| | ANHYDROTETRACYCLINE HYDROCHLORIDE Basic information |
| Product Name: | ANHYDROTETRACYCLINE HYDROCHLORIDE | | Synonyms: | ANHYDROTETRACYCLINE HYDROCHLORIDE;AnhydrotetracyclineHCl;Anhydrotetracycline hydrochloride, 'can be used as a secondary standard';2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-, monohydrochloride, (4S,4aS,12aS)-;5A,6-ANHYDROTETRACYCLINEHYDROCHLORIDE;Anhydrotetracycline hydrochloride,'can be used as secondary standard.';Anhydrotetracycline hydrochloride ,97%;(4S,4AS,12AS)-4-(DIMETHYLAMINO)-1,4,4A,5,12,12A-HEXAHYDRO-3,10,11,12A-TETRAHYDROXY-6-METHYL-1,12-DIOXO-2-NAPHTHACENECARBOXAMIDE MONOHYDROCHLORIDE | | CAS: | 13803-65-1 | | MF: | C22H23ClN2O7 | | MW: | 462.88 | | EINECS: | | | Product Categories: | Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 13803-65-1.mol |  |
| | ANHYDROTETRACYCLINE HYDROCHLORIDE Chemical Properties |
| Melting point | 223 °C | | RTECS | QI7860000 | | storage temp. | Refrigerator | | solubility | Soluble in ethanol, DMSO, or DMF | | form | Powder | | color | Yellow to bright yellow | | Sensitive | Moisture Sensitive | | BRN | 4228856 | | Stability: | Hygroscopic | | Major Application | clinical testing | | InChIKey | XBSQEFHDCDFNJU-WPJNXPDPSA-N | | SMILES | Cl[H].[H][C@@]12Cc3c(C)c4cccc(O)c4c(O)c3C(=O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C | | EPA Substance Registry System | 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-, hydrochloride (1:1), (4S,4aS,12aS)- (13803-65-1) |
| Hazard Codes | Xn | | Risk Statements | 63-36 | | Safety Statements | 36/37/39-26 | | WGK Germany | 3 | | HS Code | 29413020 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 4 Oral
Repr. 1B |
| Provider | Language |
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ACROS
| English |
| | ANHYDROTETRACYCLINE HYDROCHLORIDE Usage And Synthesis |
| Description | The tetracycline repressor (TetR) is a transcriptional regulator which normally binds tightly to its palindromic tetO operator DNA, blocking gene expression. Tet causes the repressor to dissociate from the DNA, allowing transcription to occur. A novel reverse TetR (revTetR) requires tetracycline as a co-repressor to bind tetO and block transcription. Anhydrotetracycline (hydrochloride) is a powerful effector in both the tetracycline repressor (TetR) and reverse TetR (revTetR) systems, binding the Tet repressor 35-fold more strongly than Tet. Moreover, anhydrotetracycline poorly binds the 30S ribosomal subunit, compared to Tet, so it does not act as a general inhibitor of translation and is a poor antibiotic. Perhaps related to this, the concentration of anhydrotetracycline that inhibits eukaryotic cell growth is more than a 1,000-fold above the dose that alters transcription through TetR. | | Chemical Properties | yellow to bright yellow powder | | Uses | A Tetracycline derivative exhibiting no antibiotic activity, a useful effector of tetracycline-dependent gene expression in bacterial expression systems. | | Uses | Anhydrotetracycline is a degradation product of tetracycline, formed by dehydration at the C6 position under acidic conditions to aromatise the B ring. Anhydrotetracycline is an important standard for monitoring tetracycline stability. Although the degradation is associated with a loss of antibiotic activity, anhydrotetracycline is considered biologically active and is thought responsible for aspects of tetracycline toxicity. | | Uses | Anhydrotetracycline hydrochloride is a salt of a degradation product of tetracycline, formed by dehydration at the C6 position under acidic conditions to aromatise the B ring. Anhydrotetracycline is an important standard for monitoring tetracycline stability. Although the degradation is associated with a loss of antibiotic activity, anhydrotetracycline is considered biologically active and is thought responsible for aspects of tetracycline toxicity. | | IC 50 | Tetracycline | | References | [1] M GOSSEN H B. Anhydrotetracycline, a novel effector for tetracycline controlled gene expression systems in eukaryotic cells.[J]. Nucleic Acids Research, 1993, 21 18: 4411-4412. DOI: 10.1093/nar/21.18.4411
[2] B RASMUSSEN. Molecular basis of tetracycline action: identification of analogs whose primary target is not the bacterial ribosome.[J]. Antimicrobial Agents and Chemotherapy, 1991, 35 11: 2306-2311. DOI: 10.1128/aac.35.11.2306 |
| | ANHYDROTETRACYCLINE HYDROCHLORIDE Preparation Products And Raw materials |
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