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Anhydrotetracycline (hydrochloride)
Cayman Chemical Item Number 10009542
Description The tetracycline repressor (TetR) is a transcriptional regulator which normally binds tightly to its palindromic tetO operator DNA, blocking gene expression.1↗ 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.2↗,3↗ Anhydrotetracycline (hydrochloride) is a powerful effector in both the TetR and revTetR systems, binding the TetR 35-fold more strongly than Tet.4↗,1↗ Moreover, anhydrotetracycline poorly binds the 30S ribosomal subunit, compared to Tet,5↗ 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.1↗
Formal Name 4-(dimethylamino)-1,4S,4aS,5,12,12aS-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-monohydrochloride-2-naphthacenecarboxamide
CAS Number 13803-65-1
Molecular Formula C22H22N2O7 · HCl
Formula Weight 462.9
Formulation A crystalline solid
Purity ≥98%
λmax 224, 272, 428 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES CN(C)[C@@H]1C(=C(C(=O)N)C(=O)[C@]2(O)[C@H]1Cc1c(C)c3cccc(O)c3c(O)c1C2=O)OCl
InCHI Code 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;/h4-6,11,16,25-27,31H,7H2,1-3H3,(H2,23,30);1H/t11-,16-,22-;/m0./s1
InCHI Key XBSQEFHDCDFNJU-WPJNXPDPSA-N |