Streptonigrin

Streptonigrin (Bruneomycin) is an orally active antibiotic and pan-PAD inhibitor, inhibiting PAD1, PAD2, PAD3 and PAD4 with IC50 of 48.3 μM, 26.1 μM, 0.43 μM and 2.5 μM, respectively. Streptonigrin inhibits SENP1 (IC50 of 0.518 μM) and reduces HIF1α. Streptonigrin increases p53 and Apoptosis. Streptonigrin shows antiviral activity against Rauscher murine leukemia virus. Streptonigrin has immunosuppressive effects. Streptonigrin has antitumor activity against osteosarcoma[1][2][3][4][5][6][7][8][9][10].

Product Specifications

CAS Number

[3930-19-6]

Product Name Alternative

Bruneomycin

UNSPSC

12352005

Hazard Statement

H300

Target

Antibiotic; Apoptosis; E1/E2/E3 Enzyme; HIF/HIF Prolyl-Hydroxylase; MDM-2/p53; Protein Arginine Deiminase

Type

Natural Products

Related Pathways

Anti-infection; Apoptosis; Epigenetics; Metabolic Enzyme/Protease

Applications

COVID-19-immunoregulation

Field of Research

Cancer; Infection; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/Streptonigrin.html

Purity

99.20

Solubility

10 mM in DMSO

Smiles

O=C(C1=NC(C2=NC3=C(C(C(OC)=C(N)C3=O)=O)C=C2)=C(N)C(C4=CC=C(OC)C(OC)=C4O)=C1C)O

Molecular Formula

C25H22N4O8

Molecular Weight

506.46

Precautions

H300

References & Citations

[1]Dreyton CJ, et al. Insights into the mechanism of Streptonigrin-induced protein arginine deiminase inactivation. Bioorg Med Chem. 2014 Feb 15;22 (4) :1362-9.|[2]Park S, et al. Streptonigrin inhibits β-Catenin/Tcf signaling and shows cytotoxicity in β-catenin-activated cells. Biochim Biophys Acta. 2011 Dec;1810 (12) :1340-5.|[3]Piatakova NV, et al. Soluble guanylate cyclase in the molecular mechanism underlying the therapeutic action of drugs]. Biomed Khim. 2012 Jan-Feb;58 (1) :32-42. Russian.|[4]Ambaye N, et al. Streptonigrin Inhibits SENP1 and Reduces the Protein Level of Hypoxia-Inducible Factor 1α (HIF1α) in Cells. Biochemistry. 2018 Mar 20;57 (11) :1807-1813.|[5]Loyola AC, et al. Streptonigrin at low concentration promotes heterochromatin formation. Sci Rep. 2020 Feb 26;10 (1) :3478.|[6]Yamashita Y, et al. Induction of mammalian DNA topoisomerase II dependent DNA cleavage by antitumor antibiotic streptonigrin. Cancer Res. 1990 Sep 15;50 (18) :5841-4.|[7]McBride TJ, et al. The activity of streptonigrin against the Rauscher murine leukemia virus in vivo. Cancer Res. 1966 Apr;26 (4) :727-32.|[8]Suzuki H, et al. Immunosuppressive activity of streptonigrin in vitro and in vivo. Biosci Biotechnol Biochem. 1996 May;60 (5) :789-93.|[9]Kang JH, et al. Inhibition of Transglutaminase 2 but Not of MDM2 Has a Significant Therapeutic Effect on Renal Cell Carcinoma. Cells. 2020 Jun 16;9 (6) :1475.|[10]Long GV, et al. Interaction of the antitumour antibiotic streptonigrin with DNA and oligonucleotides. Anticancer Drug Des. 1997 Sep;12 (6) :453-72.