Tetracycline is a broad spectrum polyketide antibiotic with clinical uses in treating bacterial infections such as Rocky Mountain spotted fever, typush fever, tick fevers, Q fever, and Brill-Zinsser disease and to treat upper respiratory infections and acne. It has been used in studies of multidrug resistance and potential side effects including acute pancreatitis.
Tetracyclines possess a wide range of antimicrobial activity against gram-positive and gram-negative bacteria. The bacterial ribosome is the site of action of tetracyclines. Access to the ribosomes of gram negative bacteria is obtained by passive diffusion through hydrophilic pores in the outer cell membrane and then by an energy-dependent active transport system that pumps all tetracyclines through the inner cytoplasmic membrane. This active transport system may require a periplasmic protein carrier. Tetracyclines bind specifically to 30S ribosomes and appear to inhibit protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. The inhibitory effects of the tetracyclines can be reversed by washing. This suggests that the reversibly bound antibiotic rather than the small portion of irreversibly bound drug is responsible for the antibacterial action.
Potency: ≥900 µg/mg
Product Type: Biochemicals
Biochemical Category: Antibiotics
Chemical Class: Antibiotics
Melting Point: 215 - 225°C
Extinction Coefficient (E1%): EMm (220nm) = 13 (free base in 0.1 M HCl); EmM (268nm) = 18.04 (free base in 0.1 M HCl); EmM (355nm) = 13.32 (free base in 0.1 M HCl)(Lit.)
Optical Rotation: -239 ° to -258 ° (c=0.01, 0.1 N HCl)
UV/Visible Absorbance: λ max (1N HCl) 219, 271, 357 ± 5 nm
Presentation: Yellow Powder
pH: 1.8 - 2.8 (1% aq soln)
pKa: (50% aq DMF): 8.3, 10.2 (Lit.)
Detection Method: FTIR
Moisture content: ≤2%
Solubility: Freely soluble in water or 0.1 N HCl (10 mg/mL - clear, bright yellow solution); soluble in methanol, ethanol. Insoluble in ether, hydrocarbons.
Storage & Handling: -20°C, protect from light