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S1014

Sigma-Aldrich

Streptonigrin

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

Synonym(s):

Bruneomycin, Nigrin

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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

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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.

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’.

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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
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
Timothy J Donohoe et al.
Journal of the American Chemical Society, 133(41), 16418-16421 (2011-09-29)
The synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted
Dylan B England et al.
Organic letters, 10(16), 3631-3634 (2008-07-17)
A series of N-propargylindole-2-carboxamides were found to undergo a AuCl 3-catalyzed cycloisomerization to give beta-carbolinones in high yield. The corresponding beta-chlorocarboline derivative was prepared and used for Pd(0)-catalyzed cross-coupling chemistry directed toward the synthesis of lavendamycin analogues.
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