Anhydrotetracycline Hydrochloride

Names

[ Name ]:
Anhydrotetracycline Hydrochloride

[Synonym ]:
(4S,4aS,12aS)-4-(DiMethylaMino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-Methyl-1,12-dioxo-2-naphthacenecarboxaMide Hydrochloride
(4S,4aS,12aS)-4-(Dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydro-2-tetracenecarboxamide hydrochloride (1:1)
Anhydrotetracycline hydrochloride,'can be used as secondary standard.'
(4S,4AS,12AS)-4-(DIMETHYLAMINO)-1,4,4A,5,12,12A-HEXAHYDRO-3,10,11,12A-TETRAHYDROXY-6-METHYL-1,12-DIOXO-2-NAPHTHACENECARBOXAMIDE MONOHYDROCHLORIDE
(4aS)-4c-Dimethylamino-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-(4ar,12ac)-1,4,4a,5,12,12a-hexahydro-naphthacen-2-carbonsaeure-amid,Hydrochlorid
Anhydrotetracycline hydrochloride,‘can be used as a secondary standard‘
5A,6-ANHYDROTETRACYCLINEHYDROCHLORIDE
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-, (4S,4aS,12aS)-, hydrochloride (1:1)
Anhydrotetracycline hydrochloride
2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-,monohydrochloride,(4S,4aS,12aS)
AnhydrotetracyclineHCl
Anhydrotetracycline hydrochloride,'can be used as a secondary standard'
(4aS)-4c-dimethylamino-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-(4ar,12ac)-1,4,4a,5,12,12a-hexahydro-naphthacene-2-carboxylic acid amide,hydrochloride
MFCD00151453

Biological Activity

[Description]:

Anhydrotetracycline hydrochloride, a tetracycline biosynthetic precursor, is a potent competitive broad-spectrum tetracycline destructase enzymes inhibitor. Anhydrotetracycline hydrochloride is an effector for tetracycline controlled gene expression systems in eukaryotic cells[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Anhydrotetracycline hydrochloride inhibits Tet(50) (IC50=210 μM),Tet(X) (IC50=41 μM), Tet(X)_3 (IC50=3 μM) degradations of tetracyclines. Anhydrotetracycline hydrochloride inhibits Tet(50) (IC50=210 μM),Tet(X) (IC50=75 μM), Tet(X)_3 (IC50=26 μM) degradations of chlortetracycline. Anhydrotetracycline hydrochloride inhibits Tet(50) (IC50=120 μM),Tet(X) (IC50=41 μM), Tet(X)_3 (IC50=7 μM) degradations of demeclocycline[1]. Anhydrotetracycline hydrochloride inhibits Tet(50) (IC50=210 μM),Tet(X) (IC50=41 μM), Tet(X)_3 (IC50=3 μM) degradations of tetracyclines. Anhydrotetracycline hydrochloride inhibits Tet(50) (IC50=210 μM),Tet(X) (IC50=75 μM), Tet(X)_3 (IC50=26 μM) degradations of chlortetracycline. Anhydrotetracycline hydrochloride inhibits Tet(50) (IC50=120 μM),Tet(X) (IC50=41 μM), Tet(X)_3 (IC50=7 μM) degradations of demeclocycline[1].

[References]

[1]. Jana L Markley, et al. Semisynthetic Analogues of Anhydrotetracycline as Inhibitors of Tetracycline Destructase Enzymes. ACS Infect Dis. 2019 Apr 12;5(4):618-633.

Chemical & Physical Properties

[ Boiling Point ]:
618.6ºC at 760 mmHg

[ Melting Point ]:
222.8ºC

[ Molecular Formula ]:
C₂₂H₂₃ClN₂O₇

[ Molecular Weight ]:
462.880

[ Flash Point ]:
327.9ºC

[ Exact Mass ]:
462.119385

[ PSA ]:
161.39000

[ LogP ]:
1.95810

[ Vapour Pressure ]:
3.66E-16mmHg at 25°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R63

[ Safety Phrases ]:
S36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
1702190000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 1702190000

Articles

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Bioorg. Med. Chem. Lett. 22 , 1709-11, (2012)

Over-expressions of miRNAs are being increasingly linked with many diseases including different types of cancer. In this study, the role of some known small molecular therapeutics has been investigate...

Tetracycline repressor allostery does not depend on divalent metal recognition.

Biochemistry 53(50) , 7990-8, (2014)

Genes that render bacteria resistant to tetracycline-derived antibiotics are tightly regulated by repressors of the TetR family. In their physiologically relevant, magnesium-complexed form, tetracycli...

Use of mCherry Red fluorescent protein for studies of protein localization and gene expression in Clostridium difficile.

Appl. Environ. Microbiol. 81(5) , 1652-60, (2015)

Fluorescent proteins are powerful reporters in biology, but most require O2 for chromophore maturation, making them inherently difficult to use in anaerobic bacteria. Clostridium difficile, a strict a...