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Indolmycin (CAS 21200-24-8)

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Alternate Names:
Antibiotic PA 155A
Application:
Indolmycin is an antibiotic that inhibits bacterial tryptophanyl-tRNA synthetase
CAS Number:
21200-24-8
Purity:
≥95%
Molecular Weight:
257.29
Molecular Formula:
C14H15N3O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Indolmycin is a natural product that functions as an inhibitor of bacterial protein synthesis. It specifically targets the bacterial enzyme tryptophanyl-tRNA synthetase, which is essential for the incorporation of tryptophan into proteins during translation. By binding to the active site of this enzyme, indolmycin disrupts the formation of aminoacyl-tRNA complexes, ultimately inhibiting protein synthesis in bacteria. This mechanism of action is for the bacteriostatic effect of indolmycin, as it prevents the production of essential proteins necessary for bacterial growth and survival. Additionally, indolmycin exhibits selectivity for bacterial tryptophanyl-tRNA synthetase over the human homolog, making it a promising candidate for the development of novel antibacterial agents. Overall, indolmycin′s ability to interfere with bacterial protein synthesis through its interaction with tryptophanyl-tRNA synthetase highlights its potential as useful for studying bacterial translation.


Indolmycin (CAS 21200-24-8) References

  1. Development of a stereoselective practical synthetic route to indolmycin, a candidate anti-H. pylori agent.  |  Hasuoka, A., et al. 2001. Chem Pharm Bull (Tokyo). 49: 1604-8. PMID: 11767081
  2. Indolmycin resistance of Streptomyces coelicolor A3(2) by induced expression of one of its two tryptophanyl-tRNA synthetases.  |  Kitabatake, M., et al. 2002. J Biol Chem. 277: 23882-7. PMID: 11970956
  3. Anti-staphylococcal activity of indolmycin, a potential topical agent for control of staphylococcal infections.  |  Hurdle, JG., et al. 2004. J Antimicrob Chemother. 54: 549-52. PMID: 15243028
  4. A novel tryptophanyl-tRNA synthetase gene confers high-level resistance to indolmycin.  |  Vecchione, JJ. and Sello, JK. 2009. Antimicrob Agents Chemother. 53: 3972-80. PMID: 19546369
  5. In vitro reconstitution of indolmycin biosynthesis reveals the molecular basis of oxazolinone assembly.  |  Du, YL., et al. 2015. Proc Natl Acad Sci U S A. 112: 2717-22. PMID: 25730866
  6. Production of the Bioactive Compounds Violacein and Indolmycin Is Conditional in a maeA Mutant of Pseudoalteromonas luteoviolacea S4054 Lacking the Malic Enzyme.  |  Thøgersen, MS., et al. 2016. Front Microbiol. 7: 1461. PMID: 27695447
  7. An engineered biosynthetic-synthetic platform for production of halogenated indolmycin antibiotics.  |  Hoffarth, ER., et al. 2021. Chem Sci. 12: 8817-8821. PMID: 34257882
  8. Investigate Natural Product Indolmycin and the Synthetically Improved Analogue Toward Antimycobacterial Agents.  |  Yang, Y., et al. 2022. ACS Chem Biol. 17: 39-53. PMID: 34908399
  9. Design, synthesis, and antibacterial activity of derivatives of Tryptophanyl-tRNA synthetase inhibitor indolmycin.  |  Sun, L., et al. 2022. Eur J Med Chem. 241: 114647. PMID: 35963132
  10. Interaction of indolmycin in the metabolism of tryptophan in rat liver.  |  Werner, RG. and Reuter, W. 1979. Arzneimittelforschung. 29: 59-63. PMID: 582120
  11. Indolmycin-mediated inhibition and stimulation of transcription at the trp promoter of Escherichia coli.  |  Bogosian, G., et al. 1983. J Bacteriol. 153: 1120-3. PMID: 6337120
  12. Indolmycin inhibits prokaryotic tryptophanyl-tRNA ligase.  |  Werner, RG., et al. 1976. Eur J Biochem. 68: 1-3. PMID: 786633
  13. Isolation and characterization of tryptophan transaminase and indolepyruvate C-methyltransferase. Enzymes involved in indolmycin biosynthesis in Streptomyces griseus.  |  Speedie, MK., et al. 1975. J Biol Chem. 250: 7819-25. PMID: 809439

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Indolmycin, 1 mg

sc-202183
1 mg
$373.00

when can this deliver to cambridge, MA by?

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Date published: 2020-03-04
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Rated 5 out of 5 by from Hurdle et alHurdle et al. (PubMed ID 15243028) found that Indolmycin showed bacteriostatic activity against staphylococcal infections like MSSA (methicillin-susceptible Staphylococcus aureus), MRSA (methicillin-resistant S. aureus) and VISA (vancomycin-intermediate S. aureus). -SCBT Publication Review
Date published: 2015-07-07
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Indolmycin is rated 5.0 out of 5 by 1.
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