An antibiotic
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Negamycin (hydrochloride)

Item No. 37796

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-((3R,5R)-3,6-diamino-5-hydroxyhexanamido)-N-methylglycine, monohydrochloride
Synonyms
  • (+) Negamycin
Molecular Formula
C9H20N4O4 • HCl
Formula Weight
284.7
Purity
≥80%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO:Water (1:1): Slightly soluble
SMILES
NC[C@H](O)C[C@@H](N)CC(NN(C)CC(O)=O)=O.Cl
InChi Code
InChI=1S/C9H20N4O4.ClH/c1-13(5-9(16)17)12-8(15)3-6(11)2-7(14)4-10;/h6-7,14H,2-5,10-11H2,1H3,(H,12,15)(H,16,17);1H/t6-,7-;/m1./s1
InChi Key
NEDXOMDIXKPXQU-ZJLYAJKPSA-N
Origin
Bacterium/Streptomyces sp. M890-C2
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Negamycin is an antibiotic originally found in Streptomyces.1 It is active against various species of bacteria, including E. coli, S. typhosa, and K. pneumoniae, when used at concentrations ranging from 3.12 to 100 µg/ml. Negamycin (250 μM) stabilizes the interaction between tRNA and ribosomes and decreases the rate of mRNA translation.2 It also restores the auditory brainstem response to sound tones in a dystrophin-deficient mdx mouse model of Duchenne muscular dystrophy (DMD) when administered at a dose of 100 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamada, M., Takeuchi, T., Kondo, S., et al. A new antibiotic, negamycin. J. Antibiot. (Tokyo) 23(3), 170-171 (1970).

    2. Polikanov, Y.S., Szal, T., Jiang, F., et al. Negamycin interferes with decoding and translocation by simultaneous interaction with rRNA and tRNA. Mol. Cell 56(4), 541-550 (2014).

    3. Arakawa, M., Shiozuka, M., Nakayama, Y., et al. Negamycin restores dystrophin expression in skeletal and cardiac muscles of mdx mice. J. Biochem. 134(5), 751-758 (2003).