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K0879 Sigma-Aldrich

Kanamycin sulfate Streptomyces kanamyceticus

powder, γ-irradiated

Synonym: Kanamycin A, Kanamycin sulfate from Streptomyces kanamyceticus, Kanamycin sulfate salt

  • CAS Number 25389-94-0

  • Empirical Formula (Hill Notation) C18H36N4O11 · H2O4S

  • Molecular Weight 582.58

  •  EC Number 246-933-9

  •  MDL number MFCD00070253

  •  PubChem Substance ID 57654313

  •  NACRES NA.85

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Properties

Related Categories Aminoglycosides, Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Application,
Quality Level   200
biological source   Streptomyces kanamyceticus
grade   for molecular biology
sterility   γ-irradiated
form   powder
potency   ≥700 μg per mg
color   white to off-white
pH range   6.5 - 8.5 (1% solution)
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
  mycoplasma
storage temp.   2-8°C
suitability   nonselective for Escherichia coli
  nonselective for coliforms
SMILES string   OS(O)(=O)=O.NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChI   1S/C18H36N4O11.H2O4S/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17;1-5(2,3)4/h4-18,23-29H,1-3,19-22H2;(H2,1,2,3,4)/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-;/m1./s1
InChI key   OOYGSFOGFJDDHP-KMCOLRRFSA-N

Description

General description

Chemical structure: aminoglycoside

Kanamycin, A from Streptomyces kanamyceticus is a polycationic aminoglycoside and a broad-spectrum antibiotic. Structurally, it comprises hydroxyl and amino functional groups.

Application

Kanamycin sulfate Streptomyces kanamyceticus has been used as an antibiotic component in Murashige and Skoog medium for the selection of tobacco tissue culture explants. It has also been used as an antibiotic in Luria broth for culturing Escherichia coli K-12 strain MG1655 cells for secretion assay and E. coli TV1061 cells for immobilization studies.

Biochem/physiol Actions

Kanamycin′s hydroxyl and amino functional groups are crucial for its membrane action functionality. However, it also exhibits toxicity towards mammalian cells. It prevents contamination in cell culture as well as a selective agent for bacteria with kanamycin resistance.

Mode of Action: The product acts by binding to the 70S ribosomal subunit, inhibiting translocation and eliciting miscoding.

Mode of Resistance:Aminoglycoside-modifying enzymes (including acetyltransferase, phosphotransferase, nucleotidyltransferase) can alter this antibiotic, preventing its interaction with ribosomes.

Antimicrobial spectrum: Kanamycin sulfate is effective against gram-negative and gram-postiive bacteria, and mycoplasma.

Principle

Kanamycin binds to the 30S ribosomal subunit and inhibits protein synthesis, leading to cell death.

Preparation Note

Prepare stock solution directly in the vial with sterile water to a final concentration of 10mg/mL. Stock solution should be stored at 2-8°C.

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
NZ3225030

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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