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S1014

Sigma-Aldrich

Streptonigrin

from Streptomyces flocculus, ≥98% (HPLC), powder, apoptosis inducer

Synonym(s):

Bruneomycin, Nigrin

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1 MG
$122.00
5 MG
$444.00

About This Item

Empirical Formula (Hill Notation):
C25H22N4O8
CAS Number:
Molecular Weight:
506.46
Beilstein/REAXYS Number:
599390
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

$122.00


Available to ship onApril 08, 2025Details


Request a Bulk Order

Product Name

Streptonigrin from Streptomyces flocculus, ≥98%

Quality Level

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

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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.

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Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 1 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Mi Huang et al.
Veterinary research, 52(1), 48-48 (2021-03-21)
Iron is essential for most bacteria to survive, but excessive iron leads to damage by the Fenton reaction. Therefore, the concentration of intracellular free iron must be strictly controlled in bacteria. Riemerella anatipestifer (R. anatipestifer), a Gram-negative bacterium, encodes the
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)
Nilanjana Chatterjee et al.
Journal of bacteriology, 202(14) (2020-05-13)
Group A streptococcus (GAS) produces millions of infections worldwide, including mild mucosal infections, postinfection sequelae, and life-threatening invasive diseases. During infection, GAS readily acquires nutritional iron from host heme and hemoproteins. Here, we identified a new heme importer, named SiaFGH
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.
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

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