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K1876

Sigma-Aldrich

Kanamycin disulfate salt from Streptomyces kanamyceticus

aminoglycoside antibiotic

Synonym(s):

Kanamycin Disulfate Salt, Kanamycin disulfate, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-2-deoxy-D-Streptamine sulfate (1:2) (salt), Kanamycin A, Kanamycin acid sulfate

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About This Item

CAS Number:
64013-70-3
MDL number:
MFCD00143916
UNSPSC Code:
51281654
PubChem Substance ID:
329817127
NACRES:
NA.76

biological source

Streptomyces kanamyceticus

Quality Level

200

form

powder

potency

~650 μg per mg

impurities

≤4% Kanamycin B

color

white to off-white

solubility

H2O: 10 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria
mycoplasma

Mode of action

protein synthesis | interferes

SMILES string

OS(O)(=O)=O.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/C18H36N4O11.2H2O4S/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;2*1-5(2,3)4/h4-18,23-29H,1-3,19-22H2;2*(H2,1,2,3,4)/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-;;/m1../s1

InChI key

OGTKIXVMLDAMNU-KNQICTBBSA-N

General description

Chemical structure: aminoglycoside

Application

Kanamycin sulfate is a broad spectrum minoglycoside-antibiotic It is used as an additive in culture media for the isolation of group D Streptococci on Kanamycin Esculin Azide Agar (Mossel et al.) or for selection of transformed plant cells containing the neomycin phosphotransferase (for kanamycin resistance); on a kanamycin-medium. Kanamycin has been used for electrophysiological recordings of outer hair cells and inner hair cells. It is used to inhibit shoot regeneration from Siberian Elmleaf explants. It is recommended for use in cell culture applications at 100 mg/mL.

Biochem/physiol Actions

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.

Caution

Solutions are stable at 37°C for approximately 5 days. Aqueous stock solutions can be stored at 2-8°C for long term storage.

Preparation Note

Kanamycin acid sulfate is prepared by solubilizing kanamycin sulfate in dilute sulfuric acid and drying. The sulfate content is approximately 25%.
Kanamycin sulfate is soluble in water at 10 mg/mL, yielding a clear solution. It is practically insoluble in alcohol, acetone, chloroform, ether and ethyl acetate. A 1% solution in water has a pH of 6.5 to 8.5. Sterile solutions can be prepared by a sterile filtration, through a .2μm filter.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360

Hazard Classifications

Repr. 1B

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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HortScience. Aminoglycoside Antibiotics Inhibit Shoot Regeneration from Siberian Elm Leaf Explants
James A. Kapaun et al .
Hortscience: a Publication of the American Society For Horticultural Science Hortscience, 34, 727-729 (1999)
Victoria Hsiao et al.
Molecular systems biology, 12(5), 869-869 (2016-05-20)
Engineered bacterial sensors have potential applications in human health monitoring, environmental chemical detection, and materials biosynthesis. While such bacterial devices have long been engineered to differentiate between combinations of inputs, their potential to process signal timing and duration has been
D.A.A. Mossel et al.
Archiv Fur Lebensmittelhygiene, 29, 121-121 (1978)
Michael G Leitner et al.
Molecular pharmacology, 79(1), 51-60 (2010-10-12)
Aminoglycoside antibiotics (AGs) are severely ototoxic. AGs cause degeneration of outer hair cells (OHCs), leading to profound and irreversible hearing loss. The underlying mechanisms are not fully understood. OHC survival critically depends on a specific K+ conductance (I(K,n)) mediated by
R.T. Fraley et al.
Miami Winter Symp., 20, 211-211 (1983)
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