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Protein Synthesis Inhibitor with Antimicrobial Activity Negamycin (hydrochloride)

Date:April 14 2022Web Page No:95026

Negamycin is a natural product derived from Streptomyces that exhibits anti-bacterial activity against gram-positive and gram-negative bacteria including multidrug-resistant Pseudomonas aeruginosa.1-4) Its mechanism of action also inhibits bacterial protein synthesis. It is also attracting attention as a lead compound for the treatment of intractable diseases such as muscular dystrophy.


Negamycin-Structure

Specification

CAS#Not applicable*
Parent CAS#33404-78-3 (salt free form)
Molecular FormulaC9H20N4O4 HCl
Molecular Weight284.741
SourceStreptomyces sp. M890-C2
Purity>80% (qNMR)
SolubilitySoluble in DMSO, H2O. Insoluble in Hexane

*This product is supplied as the HCl salt form which a CAS number has not been given. CAS# 33404-78-3 is the salt free form of negamycin.

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Application Notes

  • Negamycin shows excellent therapeutic efficacy against in vivo mouse models of bacterial infection:1)
    - Pseudomonas aeruginosa (ED50: 4.4 mg/kg/sc)
    - Klebsiella pneumoniae (ED50: 5.0 mg/kg/sc)
    - Salmonella typhi (ED50: 2.5 mg/kg/sc)
    The LD50 value of negamycin to mice by intravenous injection is 400-500 mg/kg.
  • Negamycin restores dystrophin expression in skeletal and cardiac muscles of the mdx mouse, an animal model of Duchenne muscular dystrophy(DMD).5)
  • Negamycin crosses the bacterial cytoplasmic membrane by multiple routes.6)

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References

  1. Hamada, M., et al., J. Antibiot., 23 (3), 170~171 (1970). [PMID:5453311]
  2. Mizuno, S., et al., J. Antibiot., 23 (12), 581~588 (1970). [PMID:4950815]
  3. Mizuno, S., et al., J. Antibiot., 23 (12), 589~594 (1970). [PMID:4950816]
  4. Olivier, N.B., et al., Proc. Natl. Acad. Sci. USA, 111 (46), 16274~16279 (2014). [PMID:25368144]
  5. Arakawa, M., et al., J. Biochem., 134 (5), 751~758 (2003). [PMID:14688241]
  6. Hörömpöli, D,, et al., Antimicrob. Agents Chemother., 65 (4), e00986-20 (2021). [PMID:33468467]
  7. Kondo, S., et al., J. Antibiot., 29 (2), 208~211 (1976). [PMID:945259]
  8. Uehara, Y., et al., J. Antibiot., 29 (9), 937~946 (1976). [PMID:791912]
  9. McKinney, D.C., et al., ACS Med. Chem. Lett., 6 (8), 930~935 (2015). [PMID:26288696]
  10. Tagichi, A., et al., ACS Med. Chem. Lett., 3 (2), 118~122 (2012). [PMID:24900441]
  11. Hamada, K., et al., ACS Med. Chem. Lett., 10 (10), 1450~1456 (2019). [PMID:31620232]

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[Date : June 20 2024 00:07]

Detail Product Name Product Code Supplier Size Price
Negamycin (Hydrochloride),Antibacterial (Gram-Positive & Negative),Bacterial Protein Synthesis Inhibitor
DatasheetThis may not be the latest data sheet.
14662 IMCInstitute of Microbial Chemistry 5 mg $500

Description
Storage -20°C CAS 33404-78-3 (salt free form)
Link

Bioactive Compounds

[Date : June 20 2024 00:07]

Negamycin (Hydrochloride),Antibacterial (Gram-Positive & Negative),Bacterial Protein Synthesis Inhibitor


  • Product Code: 14662
  • Supplier: IMC
  • Size: 5mg
  • Price: $500

Description
Storage -20°C CAS 33404-78-3 (salt free form)
Link

Bioactive Compounds

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CONTACT

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