13803-65-1

yellow to bright yellow powder

A Tetracycline derivative exhibiting no antibiotic activity, a useful effector of tetracycline-dependent gene expression in bacterial expression systems.

Anhydrotetracycline hydrochloride is a salt of a degradation product of tetracycline, formed by dehydration at the C6 position under acidic conditions to aromatise the B ring. Anhydrotetracycline is an important standard for monitoring tetracycline stability. Although the degradation is associated with a loss of antibiotic activity, anhydrotetracycline is considered biologically active and is thought responsible for aspects of tetracycline toxicity.

Anhydrotetracycline is a degradation product of tetracycline, formed by dehydration at the C6 position under acidic conditions to aromatise the B ring. Anhydrotetracycline is an important standard for monitoring tetracycline stability. Although the degradation is associated with a loss of antibiotic activity, anhydrotetracycline is considered biologically active and is thought responsible for aspects of tetracycline toxicity.

The tetracycline repressor (TetR) is a transcriptional regulator which normally binds tightly to its palindromic tetO operator DNA, blocking gene expression. 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. 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. Moreover, anhydrotetracycline poorly binds the 30S ribosomal subunit, compared to Tet, 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.

Tetracycline

[1] M GOSSEN  H B. Anhydrotetracycline, a novel effector for tetracycline controlled gene expression systems in eukaryotic cells.[J]. Nucleic Acids Research, 1993, 21 18: 4411-4412. DOI: 10.1093/nar/21.18.4411
[2] B RASMUSSEN. Molecular basis of tetracycline action: identification of analogs whose primary target is not the bacterial ribosome.[J]. Antimicrobial Agents and Chemotherapy, 1991, 35 11: 2306-2311. DOI: 10.1128/aac.35.11.2306