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MilliporeSigma

K0879

Sigma-Aldrich

Canamicina sulfate from Streptomyces kanamyceticus

powder, γ-irradiated

Sinónimos:

Canamicina A, Canamicina sulfate salt

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About This Item

Fórmula empírica (notación de Hill):
C18H36N4O11 · H2O4S
Número de CAS:
Peso molecular:
582.58
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces kanamyceticus

grade

for molecular biology

sterility

γ-irradiated

form

powder

potency

≥700 μg per mg

color

white to off-white

pH

6.5-8.5(1% solution)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycoplasma

mode of action

protein synthesis | interferes

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

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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.
Modo de acción: El producto actúa uniéndose a la subunidad ribosómica 70S, inhibiendo la translocación y provocando una codificación errónea.

Modo de resistencia: las enzimas modificadoras de los aminoglucósidos (como la acetiltransferasa, la fosfotransferasa y la nucleotidiltransferasa) pueden alterar este antibiótico y evitar su interacción con los ribosomas.

Espectro antimicrobiano: El sulfato de canamicina es eficaz contra las bacterias gramnegativas y grampositivas, y contra los micoplasmas.

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.

pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)


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Kevin M Krause et al.
Cold Spring Harbor perspectives in medicine, 6(6) (2016-06-03)
Aminoglycosides are natural or semisynthetic antibiotics derived from actinomycetes. They were among the first antibiotics to be introduced for routine clinical use and several examples have been approved for use in humans. They found widespread use as first-line agents in
Shoot Regenerative Capacity Assays in Arabidopsis and Tobacco
Tian-QiZ and Jia-Wei W
Bio-protocol, 6(5) (2016)
Torsten John et al.
Biochimica et biophysica acta. Biomembranes, 1859(11), 2242-2252 (2017-08-30)
Biological membranes are natural barriers to the transport of molecules and drugs within human bodies. Many antibacterial agents need to cross these membranes to reach their target and elicit specific effects. Kanamycin A belongs to the family of aminoglycoside antibiotics
Tim Axelrod et al.
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Antimicrobial agents and chemotherapy, 58(8), 4795-4803 (2014-06-11)
Highly pathogenic avian influenza A (H5N1) viruses cause severe and often fatal disease in humans. We evaluated the efficacy of repeated intravenous dosing of the neuraminidase inhibitor peramivir against highly pathogenic avian influenza virus A/Vietnam/UT3040/2004 (H5N1) infection in cynomolgus macaques.

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