Streptonigrin (CAS 3930-19-6)
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Alternate Names:
Streptonigrin is also known as Bruneomycin.
Application:
Streptonigrin is an aminoquinone antitumour antibiotic and phenylpyridylquinoline apoptosis inducer.
CAS Number:
3930-19-6
Purity:
≥95%
Molecular Weight:
506.46
Molecular Formula:
C25H22N4O8
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Streptonigrin is an aminoquinone antitumour antibiotic and phenylpyridylquinoline. The antineoplastic activity of Streptonigrin requires reductive activation by Xanthine-converting enzymes. Streptonigrin induces apoptosis by a mechanism involving NF-kB. Streptonigrin (10 μg/ml) inhibits DNA synthesis in and reduces survival of S. typhimurium bacteria. Streptonigrin is also known as Bruneomycin, Nigrin, SN, and (4R)-5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-2-pyridinecarboxylic acid.
Streptonigrin (CAS 3930-19-6) References
- Isolation of streptonigrin and its novel derivative from Micromonospora as inducing agents of p53-dependent cell apoptosis. | Wang, H., et al. 2002. J Nat Prod. 65: 721-4. PMID: 12027749
- Antitumor antibiotic streptonigrin and its derivatives as inhibitors of nitric oxide-dependent activation of soluble guanylyl cyclase. | Severina, IS., et al. 2004. Eur J Pharmacol. 483: 127-32. PMID: 14729099
- Streptonigrin inhibits β-Catenin/Tcf signaling and shows cytotoxicity in β-catenin-activated cells. | Park, S. and Chun, S. 2011. Biochim Biophys Acta. 1810: 1340-5. PMID: 21763403
- Streptonigrin induces delayed chromosomal instability involving interstitial telomeric sequences in Chinese hamster ovary cells. | Mencucci, MV., et al. 2012. Mutat Res. 747: 46-52. PMID: 22504371
- Characterization of streptonigrin biosynthesis reveals a cryptic carboxyl methylation and an unusual oxidative cleavage of a N-C bond. | Xu, F., et al. 2013. J Am Chem Soc. 135: 1739-48. PMID: 23301954
- The radiomimetic compound streptonigrin induces persistent telomere dysfunction in mammalian cells. | Paviolo, NS., et al. 2014. Mutat Res. 760: 16-23. PMID: 24406867
- Insights into the mechanism of streptonigrin-induced protein arginine deiminase inactivation. | Dreyton, CJ., et al. 2014. Bioorg Med Chem. 22: 1362-9. PMID: 24440480
- Identification of (2S,3S)-β-Methyltryptophan as the Real Biosynthetic Intermediate of Antitumor Agent Streptonigrin. | Kong, D., et al. 2016. Sci Rep. 6: 20273. PMID: 26847951
- Streptonigrin Inhibits SENP1 and Reduces the Protein Level of Hypoxia-Inducible Factor 1α (HIF1α) in Cells. | Ambaye, N., et al. 2018. Biochemistry. 57: 1807-1813. PMID: 29481054
- StnK2 catalysing a Pictet-Spengler reaction involved in the biosynthesis of the antitumor reagent streptonigrin. | Wang, X., et al. 2018. Org Biomol Chem. 16: 9124-9128. PMID: 30483694
- Protein Arginine Deiminases (PADs): Biochemistry and Chemical Biology of Protein Citrullination. | Mondal, S. and Thompson, PR. 2019. Acc Chem Res. 52: 818-832. PMID: 30844238
- Streptonigrin at low concentration promotes heterochromatin formation. | Loyola, AC., et al. 2020. Sci Rep. 10: 3478. PMID: 32103104
- A novel streptonigrin type alkaloid from the Streptomyces flocculus CGMCC 4.1223 mutant ΔstnA/Q2. | Wang, X., et al. 2022. Nat Prod Res. 36: 3337-3345. PMID: 33280413
- Streptonigrin-induced topoisomerase II sites exhibit base preferences in the middle of the enzyme stagger. | Leteurtre, F., et al. 1994. Biochem Biophys Res Commun. 203: 1259-67. PMID: 8093042
- The structure of streptonigrin semiquinone in solution. | Soedjak, H., et al. 1997. Biochim Biophys Acta. 1335: 73-90. PMID: 9133644
Inhibitor of:
Aminopeptidase P1, C15orf62, C1orf114, DGCR6L, LOC100039248, LOC100040996, Miner2, MLZE, MOBKL1A, Mpa2, MYLC2PL, NKHC1, NOL55, Oatp-Y, Olfr176, Olfr177, OR4C45, PADI2, PADI3, PADI6, PRAMEF19, RNA pol β, RNA pol σ 70, TGase1, TGase6, TGaseZ, Trimethyl Arg Asymmetric, and ZFP184.Activator of:
MRP-L38, MRP-S16, MRP-S18A, and RNA pol β′.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Streptonigrin, 1 mg | sc-500892 | 1 mg | $104.00 | |||
Streptonigrin, 5 mg | sc-500892A | 5 mg | $364.00 |