Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

S1014

Sigma-Aldrich

Streptonigrin

from Streptomyces flocculus, ≥98% (HPLC), powder, antitumor antibiotic

Synonym(s):

Bruneomycin, Nigrin

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C25H22N4O8
CAS Number:
3930-19-6
Molecular Weight:
506.46
Beilstein:
599390
EC Number:
223-501-8
MDL number:
MFCD00063401
UNSPSC Code:
12352200
PubChem Substance ID:
24899458
NACRES:
NA.77

product name

Streptonigrin from Streptomyces flocculus, ≥98%

Quality Level

200

Assay

≥98%

antibiotic activity spectrum

viruses

Mode of action

DNA synthesis | interferes

storage temp.

2-8°C

SMILES string

COc1ccc(c(O)c1OC)-c2c(C)c(nc(c2N)-c3ccc4C(=O)C(OC)=C(N)C(=O)c4n3)C(O)=O

InChI

1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)

InChI key

PVYJZLYGTZKPJE-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Biochem/physiol Actions

Streptonigrin (SN) is an aminoquinone antitumour antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-κB. DNA cleavage reaction and chromosome damage by SN are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 1 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Wen-Chih Wu et al.
Annals of surgery, 252(1), 11-17 (2010-05-28)
Anemia and operative blood loss are common in the elderly, but evidence is lacking on whether intraoperative blood transfusions can reduce the risk of postoperative death. We analyzed retrospective data from 239,286 patients 65 years of older who underwent major
Kevin Fiscella et al.
Annals of family medicine, 8(1), 11-18 (2010-01-13)
Findings are conflicting about the relationship between vitamin D levels and cardiovascular mortality. We wanted to determine the contribution of vitamin D levels to black-white disparities in cardiovascular mortality. We examined the association of serum 25(OH)D levels with cardiovascular mortality
Ameen A Salahudeen et al.
Nature, 588(7839), 670-675 (2020-11-26)
The distal lung contains terminal bronchioles and alveoli that facilitate gas exchange. Three-dimensional in vitro human distal lung culture systems would strongly facilitate the investigation of pathologies such as interstitial lung disease, cancer and coronavirus disease 2019 (COVID-19) pneumonia caused
Zoe Heather et al.
Molecular microbiology, 70(5), 1274-1292 (2008-11-08)
In this study, we determined the function of a novel non-ribosomal peptide synthetase (NRPS) system carried by a streptococcal integrative conjugative element (ICE), ICESe2. The NRPS shares similarity with the yersiniabactin system found in the high-pathogenicity island of Yersinia sp.
Laura C C Cook et al.
mBio, 10(3) (2019-06-27)
Streptococcus pyogenes (group A streptococcus [GAS]) is a serious human pathogen with the ability to colonize mucosal surfaces such as the nasopharynx and vaginal tract, often leading to infections such as pharyngitis and vulvovaginitis. We present genome-wide transcriptome sequencing (RNASeq)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service