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Chemical Structure
Chemical Structure
Chemical Structure

Gentamicin sulfate (USP Grade) [1405-41-0]

Research Use Only
AG-CN2-0066
AdipoGen Life Sciences
Estimated PurityMixture of gentamicin C1, C1a and C2.
Product group Chemicals
Molecular Weight575.6
Price on request
Packing Size
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Gentamicin sulfate (USP Grade) [1405-41-0]
  • Delivery Days Customer
    10
  • Certification
    Research Use Only
  • Estimated Purity
    Mixture of gentamicin C1, C1a and C2.
  • Hazard Information
    Danger,Non-hazardous
  • Molecular Formula
    C21H43N5O7 . H2SO4 (unspecified)
  • Molecular Weight
    575.6
  • Scientific Description
    Aminoglycoside antibiotic. Protein synthesis inhibitor. Causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site. Antibacterial against Gram-negative aerobic bacteria, Gram-positive bacteria and mycoplasmas. Used as a selection agent (gentamicin-resistance gene) in molecular biology applications. Broad-spectrum cell culture antibiotic that is nontoxic to viruses and mammalian cells at antibacterial and antimycoplasmal concentrations. Due to its extended stability and slow development of bacterial resistance, it is a useful antibiotic in long-term virus und tissue culture studies. Bactericidal effects are exerted by the binding to the outer membrane, causing disruption of the membrane. This increases the permeability of the cell envelope, leakage of cell contents, and leading to apoptosis and proteolysis (cell death). Causes also cell death by generation of free radicals, phospholipidosis, extracellular calcium-sensing receptor stimulation and energetic catastrophe. - Chemical. CAS: 1405-41-0. Formula: C21H43N5O7 . H2SO4 (unspecified). MW: 575.6. Isolated from Micromonospora sp. Aminoglycoside antibiotic. Protein synthesis inhibitor. Causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site. Antibacterial against Gram-negative aerobic bacteria, Gram-positive bacteria and mycoplasmas. Used as a selection agent (gentamicin-resistance gene) in molecular biology applications. Broad-spectrum cell culture antibiotic that is nontoxic to viruses and mammalian cells at antibacterial and antimycoplasmal concentrations. Due to its extended stability and slow development of bacterial resistance, it is a useful antibiotic in long-term virus und tissue culture studies. Bactericidal effects are exerted by the binding to the outer membrane, causing disruption of the membrane. This increases the permeability of the cell envelope, leakage of cell contents, and leading to apoptosis and proteolysis (cell death). Causes also cell death by generation of free radicals, phospholipidosis, extracellular calcium-sensing receptor stimulation and energetic catastrophe.
  • SMILES
    CCN.CC(C)N.CNC(C)C.OS(O)(=O)=O.CN[C@H]1[C@@H](O)C(OC2[C@H](N)CC(N)[C@H](OC3O[C@H]([*])CC[C@H]3N)[C@H]2O)OCC1(C)O
  • Storage Instruction
    2°C to 8°C
  • UNSPSC
    12352200

References

  • Gentamicin: antibacterial activity, clinical pharmacology and clinical applications: M. Finland; Med. Times 97, 161 (1969) (Review)
  • Aminoglycoside uptake and mode of action--with special reference to streptomycin and gentamicin. I. Antagonists and mutants: R.E. Hancock; J. Antimicrob. Chemother. 8, 249 (1981) (Review)
  • Aminoglycoside uptake and mode of action-with special reference to streptomycin and gentamicin. II. Effects of aminoglycosides on cells: E. Hancock; J. Antimicrob. Chemother. 8, 429 (1981) (Review)
  • Gentamicin interaction with Pseudomonas aeruginosa cell envelope: N.L. Martin & T.J. Beveridge; Antimicrob. Agents Chemother. 29, 1079 (1986)
  • Surface action of gentamicin on Pseudomonas aeruginosa: J. Kadurugamuwa, et al.; J. Bacteriol. 175, 5798 (1993)
  • Leupeptin and E-64, inhibitors of cysteine proteinases, prevent gentamicin-induced lysosomal phospholipidosis in cultured rat fibroblasts: J.P. Montenez, et al.; Toxicol. Lett. 73, 201 (1994)
  • Gentamicin as gene therapy: F.C. Luft; J. Mol. Med. (Berl) 80, 543 (2002) (Review)
  • An integrative overview on the mechanisms underlying the renal tubular cytotoxicity of gentamicin: Y. Quiros, et al.; Toxicol. Sci. 119, 245 (2011) (Review)