Referencia número: HY-124586

Streptonigrin

(Synonyms: Bruneomycin)

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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.

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Pureza: 99.9%
No. CAS: 3930-19-6
Fòrmula: C₂₅H₂₂N₄O₈
Peso molecular:506.46

Almacenamiento:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

Streptonigrin Chemical Structure

No. CAS: 3930-19-6

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Actividad biológica
- Descripciòn
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
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Actividad biológica

Descripciòn

IC₅₀ & Target^[4]

HIF-1α

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Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	0.33 μg/mL Compound: Streptonigrin	In vitro cytotoxic activity against A 549 (non-small cell lung) using SRB (sulforhodamine B) assay In vitro cytotoxic activity against A 549 (non-small cell lung) using SRB (sulforhodamine B) assay	[PMID: 10328288]
A549	IC₅₀	0.33 μg/mL Compound: 1	Cytotoxicity against Homo sapiens (human) A549 cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) A549 cells after 72 hr by MTT assay	10.1007/s00044-004-0032-8
B16	IC₅₀	0.48 μg/mL Compound: 1a	Cytotoxicity against mouse melanoma cell culture(B-16) Cytotoxicity against mouse melanoma cell culture(B-16)	[PMID: 3656364]
CAKI-1	IC₅₀	0.4 nM Compound: 1	Cytotoxicity against CD30 deficient and CD70 expressing human Caki1 cells after 96 hrs by resazurin conversion assay Cytotoxicity against CD30 deficient and CD70 expressing human Caki1 cells after 96 hrs by resazurin conversion assay	[PMID: 19386499]
CCRF-CEM	IC₅₀	0.00017 μg/mL Compound: 1a	Cytotoxicity against human lymphoblastic leukemia cell culture (CCRF-CEM) Cytotoxicity against human lymphoblastic leukemia cell culture (CCRF-CEM)	[PMID: 3656364]
CCRF-CEM	IC₅₀	0.17 ng/mL Compound: 1a	Cytotoxicity against human lymphoblastic leukemia cell culture (CCRF-CEM) Cytotoxicity against human lymphoblastic leukemia cell culture (CCRF-CEM)	[PMID: 3656364]
Epidermoid carcinoma cell line	IC₅₀	0.0025 μg/mL Compound: 1a	Cytotoxicity against human epidermoid carcinoma of the nasopharynx (9KB) Cytotoxicity against human epidermoid carcinoma of the nasopharynx (9KB)	[PMID: 3656364]
HCT-15	IC₅₀	0.02 μg/mL Compound: Streptonigrin	In vitro cytotoxic activity against HCT-15 (colon) using SRB (sulforhodamine B) assay In vitro cytotoxic activity against HCT-15 (colon) using SRB (sulforhodamine B) assay	[PMID: 10328288]
HCT-15	IC₅₀	0.02 μg/mL Compound: 1	Cytotoxicity against Homo sapiens (human) HCT15 cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) HCT15 cells after 72 hr by MTT assay	10.1007/s00044-004-0032-8
KARPAS-299	IC₅₀	0.4 nM Compound: 1	Cytotoxicity against CD30 expressing and CD70 deficient human KARPAS299 cells after 96 hrs by resazurin conversion assay Cytotoxicity against CD30 expressing and CD70 deficient human KARPAS299 cells after 96 hrs by resazurin conversion assay	[PMID: 19386499]
L1210	IC₅₀	0.61 μg/mL Compound: 1a	Cytotoxicity against mouse lymphoblastic leukemia cell culture (L-1210) Cytotoxicity against mouse lymphoblastic leukemia cell culture (L-1210)	[PMID: 3656364]
MDA-MB-231	IC₅₀	30.5 μM Compound: 8	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay	[PMID: 38870832]
P388	IC₅₀	0.045 μg/mL Compound: 1a	Cytotoxicity against P388 mouse leukemia cell culture (9PS(P388)) Cytotoxicity against P388 mouse leukemia cell culture (9PS(P388))	[PMID: 3656364]
SH-SY5Y	IC₅₀	0.05 μM Compound: 1	Cytotoxicity against human wild type SH-SY5Y cells Cytotoxicity against human wild type SH-SY5Y cells	[PMID: 12027749]
SH-SY5Y	IC₅₀	4.6 μM Compound: 1	Cytotoxicity against human SH-SY5Y cells overexpressing dominant negative mutant of p53 Cytotoxicity against human SH-SY5Y cells overexpressing dominant negative mutant of p53	[PMID: 12027749]
SK-MEL-2	IC₅₀	0.02 μg/mL Compound: Streptonigrin	In vitro cytotoxic activity against SK-MEL-2 (melanoma) using SRB (sulforhodamine B) assay In vitro cytotoxic activity against SK-MEL-2 (melanoma) using SRB (sulforhodamine B) assay	[PMID: 10328288]
SK-MEL-2	IC₅₀	0.02 μg/mL Compound: 1	Cytotoxicity against Homo sapiens (human) SK-MEL-2 cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) SK-MEL-2 cells after 72 hr by MTT assay	10.1007/s00044-004-0032-8
SK-OV-3	IC₅₀	0.28 μg/mL Compound: Streptonigrin	In vitro cytotoxic activity against SK-OV-3 (ovarian) using SRB (sulforhodamine B) assay In vitro cytotoxic activity against SK-OV-3 (ovarian) using SRB (sulforhodamine B) assay	[PMID: 10328288]
SK-OV-3	IC₅₀	0.28 μg/mL Compound: 1	Cytotoxicity against Homo sapiens (human) SKOV3 cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) SKOV3 cells after 72 hr by MTT assay	10.1007/s00044-004-0032-8
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL10-induced Stat3 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL10-induced Stat3 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL10-induced Stat3 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL10-induced Stat3 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL15-induced Stat5 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL15-induced Stat5 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL15-induced Stat5 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL15-induced Stat5 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL4-induced Stat5 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL4-induced Stat5 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL4-induced Stat5 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL4-induced Stat5 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL4-induced Stat6 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL4-induced Stat6 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL4-induced Stat6 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL4-induced Stat6 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL6-induced Stat1 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL6-induced Stat1 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL6-induced Stat1 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL6-induced Stat1 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL6-induced Stat3 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL6-induced Stat3 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL6-induced Stat3 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL6-induced Stat3 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL7-induced Stat5 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL7-induced Stat5 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated IL7-induced Stat5 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated IL7-induced Stat5 phosphorylation in BALB/c mouse CD8+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
T-cell	IC₅₀	<20 μM Compound: 1, NSC-45383	Inhibition of JAK-mediated interferon-gamma-induced Stat1 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry Inhibition of JAK-mediated interferon-gamma-induced Stat1 phosphorylation in BALB/c mouse CD4+ T cells by Phospho-Flow cytometry	[PMID: 18157122]
XF498	IC₅₀	0.31 μg/mL Compound: Streptonigrin	In vitro cytotoxic activity against XF 498 (CNS) using SRB (sulforhodamine B) assay In vitro cytotoxic activity against XF 498 (CNS) using SRB (sulforhodamine B) assay	[PMID: 10328288]
XF498	IC₅₀	0.31 μg/mL Compound: 1	Cytotoxicity against Homo sapiens (human) XF498 cells after 72 hr by MTT assay Cytotoxicity against Homo sapiens (human) XF498 cells after 72 hr by MTT assay	10.1007/s00044-004-0032-8

In Vitro

Streptonigrin (10 μM) shows cytotoxicity towards both cancerous U2OS and normal NIH 3T3 cell lines^[1].
Streptonigrin (0-5 μM; 24 h) inhibits the proliferation of SW480 cells, AGS cells and HEK293 cells transfected with β-catenin in a dose-dependent manner^[2].
Streptonigrin (0.1-5 μM) does not influence the basal activity of soluble guanylate cyclase but causes concentration-dependent inhibition of enzyme activation by SNP (IC₅₀ of 4.16 μM) and also by spermineNONO^[3].
Streptonigrin (0-1 μM; 10 min) inhibits SENP1 activity with an IC₅₀ of 0.518 μM when SUMO1 is used as a substrate^[4].
Streptonigrin (2 μM; 16 h) reduces HIF1α protein level in HCT116 cells transfected with HIF1α expression plasmid^[4].
Streptonigrin (1 nM-10 μM; 4 h) shows a concentration-dependent effect on nuclear morphology in NIH 3T3 cells, promoting heterochromatin formation^[5].
Streptonigrin (2.5-500 μM; 60 min) inhibits the catalytic activity of purified calf thymus DNA topoisomerase II by relaxation of pBR322 DNA^[6].
Streptonigrin (72 h) selectively suppresses B-cell proliferation induced by LPS, with an IC₅₀ value of 0.29 ng/mL^[8].
Streptonigrin (10-100 nM) increases p53 and Apoptosis in ACHN and CAKI-1 cells^[9].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[8]

Cell Line:

A20.2J, M12.4.5, YAC-I, P815, FDC.P2
Concentration:
Incubation Time:

48 h
Result:

Showed relatively low inhibitory effect on the proliferation of A20.2J cells, with an IC₅₀ value of 10.9 ng/mL.
Showed relatively low inhibitory effect on the proliferation of M12.4.5 cells, with an IC₅₀ value of 28.8 ng/mL.
Showed inhibitory effect on the proliferation of YAC-I cells, with an IC₅₀ value of 0.3 ng/mL.
Showed a certain inhibitory effect on the proliferation of P815 cells, with an IC₅₀value of 0.78 ng/mL.
Had a good inhibitory effect on the proliferation of FDC.P2 cells, with an IC₅₀value of 0.07 ng/mL.

In Vivo

Streptonigrin (0.2 mg/kg; i.p or 0.5 mg/kg; p.o.) shows antiviral activity in mice infected with the Rauscher murine leukemia virus, reducing the spleen weight^[7].
Streptonigrin (0.1-0.2 mg/kg; i.p.; on day 0, 2, 4, and 6; until day 7) significantly suppresses the proliferative response of T-cells rather than that of B-cells in C57BL/6 mice^[8].
Streptonigrin (0.1 mg/kg; p.o.; once a day; 5 days a week) increases the expression of p53 in tumors, and decreases the expression of Ki67 in the xenograft model of human renal cell carcinoma in BALB/c nude mice^[9].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Female BALB/c mice (5-week-old) infected with Rauscher murine leukemia virus^[7]
Dosage:

0.05 mg/kg, 0.2 mg/kg, 0.5 mg/kg
Administration:

i.p. or p.o.
Result:

Significantly reduced splenomegaly, with the maximum effect at 0.2 mg/kg i.p. or 0.5 mg/kg p.o..
Prolonged the survival time of infected mice.

Chemical Information

No. CAS 3930-19-6
Appearance Solid
Peso molecular 506.46
Fòrmula C₂₅H₂₂N₄O₈
Color Light brown to brown
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
Synonyms

Bruneomycin
Structure Classification
- Alkaloids
- Pyridine Alkaloids
- Quinones
- Benzene Quinones
- Phenols
- Monophenols
Initial Source
- Microorganisms
Streptomyces flocculus
Envío

Room temperature in continental US; may vary elsewhere.

Almacenamiento

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Publications (1)

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Sci Signal

SUMOylated IL-33 in the nucleus stabilizes the transcription factor IRF1 in hepatocellular carcinoma cells to promote immune escape. [Abstract]

2023 Mar 14;16(776):eabq3362. PMID: 36917642

Streptonigrin purchased from MedChemExpress. Usage Cited in: Sci Signal. 2023 Mar 14;16(776):eabq3362. [Abstract]

Streptonigrin (SUMOylation agonist; 2, 4, 8 μM; 48 h) markedly increases the amount of IL-33 protein SUMOylation in Huh7 cells transfected with wild-type IL-33.

Pureza y Documentación

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Pureza: 99.98%

Assay: 99.98%

ee.: 99.98%

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COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Instrucciones de manejo (2659 KB)

Referencias

[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. [Content Brief]

[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. [Content Brief]

[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. [Content Brief]

[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. [Content Brief]

[5]. Loyola AC, et al. Streptonigrin at low concentration promotes heterochromatin formation. Sci Rep. 2020 Feb 26;10(1):3478. [Content Brief]

[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. [Content Brief]

[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. [Content Brief]

[8]. Suzuki H, et al. Immunosuppressive activity of streptonigrin in vitro and in vivo. Biosci Biotechnol Biochem. 1996 May;60(5):789-93. [Content Brief]

[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. [Content Brief]

[10]. Long GV, et al. Interaction of the antitumour antibiotic streptonigrin with DNA and oligonucleotides. Anticancer Drug Des. 1997 Sep;12(6):453-72. [Content Brief]

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Streptonigrin

1 Cited Publications

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Streptonigrin

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Publications Citing Use of MedChemExpress (MCE) Streptonigrin

Ver todos los productos específicos de isoformas Antibiotic

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Streptonigrin

Natural Product Library Plus

Publications Citing Use of MedChemExpress (MCE) Streptonigrin

Ver todos los productos específicos de isoformas Antibiotic

Ver todos los productos específicos de isoformas HIF/HIF Prolyl-Hydroxylase

Actividad biológica

Chemical Information

Publications (1)

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Help & FAQs

Streptonigrin Related Classifications

HY-124586 Related Classifications