| Identification | Back Directory | [Name]
ANHYDROTETRACYCLINE HYDROCHLORIDE | [CAS]
13803-65-1 | [Synonyms]
AnhydrotetracyclineHCl
ANHYDROTETRACYCLINE HYDROCHLORIDE
5A,6-ANHYDROTETRACYCLINEHYDROCHLORIDE
Anhydrotetracycline hydrochloride ,97%
Anhydrotetracycline hydrochloride,'can be used as secondary standard.'
Anhydrotetracycline hydrochloride, 'can be used as a secondary standard'
(4S,4aS,12aS)-4-(DiMethylaMino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-Methyl-1,12-dioxo-2-naphthacenecarboxaMide Hydrochloride
(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
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)- | [Molecular Formula]
C22H23ClN2O7 | [MDL Number]
MFCD00151453 | [MOL File]
13803-65-1.mol | [Molecular Weight]
462.88 |
| Chemical Properties | Back Directory | [Appearance]
yellow to bright yellow powder | [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 Information | Back Directory | [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 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. | [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. | [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. | [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 |
| Safety Data | Back Directory | [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 |
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