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Anhydrotetracycline (hydrochloride)

Cayman Chemical Item Number 10009542

(CAS 13803-65-1)

Anhydrotetracycline (hydrochloride) (CAS 13803-65-1)

See more	Molecular Biology (20) Gene Regulation (203)

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

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%
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard 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

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).

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).

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).

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Size	Price	Quantity	Subtotal
10 mg	$19.00		$0.00
25 mg	$45.00		$0.00
50 mg	$86.00		$0.00
100 mg	$152.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-05-25. Prices are subject to change without notice.

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