Anhydrotetracycline (hydrochloride)

Cayman Chemical Item Number 10009542

(CAS 13803-65-1)

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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 tetracycline repressor (TetR) and reverse TetR (revTetR) systems, binding the Tet repressor 35-fold more strongly than Tet.1,4 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

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. Kamionka, A., Bogdanska-Urbaniak, J., Scholz, O., et al. Two mutations in the tetracycline repressor change the inducer anhydrotetracycline to a corepressor. Nucleic Acids Res 32(2) 842-847 (2004).

3. Resch, M., Striegl, H., Henssler, E.M., et al. A protein functional leap: How a single mutation reverses the function of the transcription regulator TetR. Nucleic Acids Res 36(13) 4390-4401 (2008).

4. 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).

5. 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).

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
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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
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​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
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XBSQEFHDCDFNJU-WPJNXPDPSA-N

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Background Reading

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).

Kamionka, A., Bogdanska-Urbaniak, J., Scholz, O., et al. Two mutations in the tetracycline repressor change the inducer anhydrotetracycline to a corepressor. Nucleic Acids Res 32(2) 842-847 (2004).

Resch, M., Striegl, H., Henssler, E.M., et al. A protein functional leap: How a single mutation reverses the function of the transcription regulator TetR. Nucleic Acids Res 36(13) 4390-4401 (2008).

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).

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).

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Size Price Quantity Subtotal
10 mg $25.00 $0.00
25 mg $53.00 $0.00
50 mg $88.00 $0.00
100 mg $138.00 $0.00
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