AnhydrotetracyclineHydrochloride , 98% , 13803-65-1

Synonym(s):
(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 NO.：13803-65-1

Empirical Formula: C22H23ClN2O7

Molecular Weight: 462.88

MDL number: MFCD00151453

PRODUCT 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)

Description and Uses

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.

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.

Safety

• Symbol(GHS): GHS07,GHS08
• Signal word: Warning
• Hazard statements: H319-H361
• Precautionary statements: P201-P202-P264b-P280i-P305+P351+P338-P308+P313-P403-P501c
• PPE: Eyeshields, Gloves, type N95 (US)
• 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