C4291-100mg | Anhydrotetracycline (hydrochloride) [13803-65-1] Clinisciences

Background

Anhydrotetracycline (hydrochloride) (ATC) is a powerful effector for the tetracycline repressor (TetR) and reverse tetracycline repressor (revTetR) systems [1].

Tetracycline repressor (TetR) is an effector-regulated DNA-binding protein that binds tightly to its palindromic tetO operator DNA in the absence of effector, thereby blocking the transcription of any downstream genes. Binding of tetracycline (TC) or anhydrote-tracycline (ATC) to TetR causes the repressor to dissociate from the DNA and gene transcription can occur. Contrary to TetR, reverse tetracycline repressor (revTetR) mutant binds tetO only in the presence of ATC [2][3].

Anhydrotetracycline (hydrochloride) is a powerful effector for TetR and revTetR systems. Anhydrotetracycline (ATC) bound TetR with a 500-fold higher affinity and represented the most efficient inducer [2]. ATC bound the Tet repressor 35-fold more potent than Tet [4]. However, ATC acted as a corepressor in revTetR variant. In β-galactosidase (β-gal) assays, TetR inhibitedβ-gal expression to nearly 1%, while ~100% expression was accomplished in the presence of 0.4 μM ATC. RevTetR produced almost 100%β-gal activity in the absence of ATC, while the presence of 0.4 μM ATC resulted in a 5-fold decrease ofβ-gal activity [2].

References:
[1]. Gossen M, Bujard H. Anhydrotetracycline, a novel effector for tetracycline controlled gene expression systems in eukaryotic cells. Nucleic Acids Res. 1993 Sep 11;21(18):4411-2.
[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. 2004 Feb 4;32(2):842-7.
[3]. Resch M, Striegl H, Henssler EM, et al. A protein functional leap: how a single mutation reverses the function of the transcription regulator TetR. Nucleic Acids Res. 2008 Aug;36(13):4390-401.
[4]. Degenkolb J, Takahashi M, Ellestad GA, et al. Structural requirements of tetracycline-Tet repressor interaction: determination of equilibrium binding constants for tetracycline analogs with the Tet repressor. Antimicrob Agents Chemother. 1991 Aug;35(8):1591-5.

Chemical Properties

Storage	Store at -20°C
M.Wt	462.9
Cas No.	13803-65-1
Formula	C₂₂H₂₂N₂O₇·HCl
Solubility	≥12.5 mg/mL in H2O; ≥15.43 mg/mL in EtOH with gentle warming; ≥2.42 mg/mL in DMSO with ultrasonic
Chemical Name	4-(dimethylamino)-1,4S,4aS,5,12,12aS-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-monohydrochloride-2-naphthacenecarboxamide
SDF	Download SDF
Canonical 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
Shipping Condition	Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips	We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment:[1]
Cell lines	HeLa XI cells
Reaction Conditions	0 ~ 100 ng/ml anhydrotetracycline hydrochloride for 4 d incubation
Applications	Anhydrotetracycline was much more effective than tetracycline in inactivating transcriptional transactivator (tTA), and completely abolished tTA mediated luciferase activity at concentrations as low as 3 ng/ml. More importantly, the concentration at which the prolonged presence of anhydrotetracycline began to affect the growth rate of HeLa cells in culture (> 3 μg/ml) was more than thousand fold above the effective concentration. In addition, like tetracycline, anhydrotetracycline was well suited to attenuate gene expression at intermediate levels of induction. These properties together with the high functional stability of anhydrotetracycline in cell culture made anhydrotetracycline a most attractive alternative effector for tetracycline-controlled gene expression in higher eukaryotic systems.
Note	The technical data provided above is for reference only.
	References: 1. Gossen M, Bujard H. Anhydrotetracycline, a novel effector for tetracycline controlled gene expression systems in eukaryotic cells. Nucleic Acids Research, 1993, 21(18): 4411-4412.

Quality Control

Purity = 98.00%

Chemical structure

Anhydrotetracycline (hydrochloride) [13803-65-1]

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