Regulator of TetR and revTetR transcriptional repressors
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Diastereomer(s)
27954Epianhydrotetracycline (hydrochloride)
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Anhydrotetracycline (hydrochloride)

Item No. 10009542

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(dimethylamino)-1,4S,4aS,5,12,12aS-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide, monohydrochloride
CAS Number
13803-65-1
Molecular Formula
C22H22N2O7 • HCl
Formula Weight
462.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mlDMSO: 20 mg/mlEthanol: 2 mg/mlPBS (pH 7.2): 0.25 mg/ml
λmax
224, 272, 428 nm
SMILES
OC1=CC=CC2=C(C)C(C[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C3=O)([H])[C@]3(O)C4=O)=C4C(O)=C21.Cl
InChi Code
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;/h4-6,11,16,25-27,31H,7H2,1-3H3,(H2,23,30);1H/t11-,16-,22-;/m0./s1
InChi Key
XBSQEFHDCDFNJU-WPJNXPDPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    Product Description

    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.1,2 Moreover, anhydrotetracycline poorly binds the 30S ribosomal subunit, compared to Tet,3 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gossen, M., and Bujard, H. Anhydrotetracycline, a novel effector for tetracycline controlled gene expression systems in eukaryotic cells. Nucleic Acids Res. 21(18), 4411-4412 (1993).

    2. Degenkolb, J., Takahashi, M., Ellestad, G.A., et al. Structural requirements of tetracycline-Tet repressor interaction: Determination of equilibrium binding constants for tetracycline analogs with the Tet repressor. Antimicrob. Agents Chemother. 35(8), 1591-1595 (1991).

    3. Rasmussen, B., Noller, H.F., Daubresse, G., et al. Molecular basis of tetracycline action: Identification of analogs whose primary target is not the bacterial ribosome. Antimicrob. Agents Chemother. 35(11), 2306-2311 (1991).