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T9823 Sigma-Aldrich

Tetracycline hydrochloride

Biotechnology Performance Certified, suitable for cell culture, ≥95%

  • CAS Number 64-75-5

  • Empirical Formula (Hill Notation) C22H24N2O8 · HCl

  • Molecular Weight 480.90

  •  Beilstein/REAXYS Number 3844873

  •  EC Number 200-593-8

  •  MDL number MFCD00078142

  •  PubChem Substance ID 24900607

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Properties

grade   Biotechnology Performance Certified
InChI Key   XMEVHPAGJVLHIG-FMZCEJRJSA-N
assay   ≥95%
application(s)   cell culture | mammalian: suitable
impurities   endotoxin, tested
mp   220-223 °C (lit.)
solubility   H2O: soluble 50 mg/mL
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
storage temp.   −20°C

Description

General description

Chemical structure: tetracycline

Application

Tetracycline is a broad spectrum polyketide antibiotic. It is used clinically to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever and Brill-Zinsser disease. It is used to treat upper respiratory infections and acne. It is used to study multidrug resistance as well as potential side effects such as acute pancreatitis. It has been used in target and resistance based mechanistic studies of novel antibiotics.

Biochem/physiol Actions

Tetracycline inhibits bacterial protein synthesis elongation at the level of aminoacyl-tRNA binding to the 30S ribosome. Tetracycline passively diffuses through porin channels in the bacterial cell membrane. It also binds to the bacterial 50S ribosomal subunit which may alter the cytoplasmic membrane, causing intracellular components to leak from bacterial cells. Mode of resistance is loss of cell wall permeability.

Mode of Action: Tetracycline passively diffuses through proin channels in the cell membrane, binding to 30S ribosomes and inhibits protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. It also binds to the bacterial 50S ribosomal subunit, altering the membrane and causing intracellular components to leak from bacterial cells. The inhibitory effects can be reversed by washing, suggesting that it is the reversibly bound antibiotic, and not the irreversibly bound drug, that is responsible for antibacterial action.

Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.

Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
2
RTECS 
QI9100000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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