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S1014

Sigma-Aldrich

Streptonigrin

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

Synonyme(s) :

Bruneomycin, Nigrin

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About This Item

Formule empirique (notation de Hill):
C25H22N4O8
Numéro CAS:
3930-19-6
Poids moléculaire :
506.46
Numéro Beilstein :
599390
Numéro CE :
223-501-8
Numéro MDL:
MFCD00063401
Code UNSPSC :
12352200
ID de substance PubChem :
24899458
Nomenclature NACRES :
NA.77

product name

Streptonigrin from Streptomyces flocculus, ≥98%

Niveau de qualité

200

Pureté

≥98%

Spectre d'activité de l'antibiotique

viruses

Mode d’action

DNA synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

PVYJZLYGTZKPJE-UHFFFAOYSA-N

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Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300

Classification des risques

Acute Tox. 1 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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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
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)
Mary Hassani et al.
Journal of medicinal chemistry, 51(11), 3104-3115 (2008-05-07)
A 1H69 crystal structure-based in silico model of the NAD(P)H:quinone oxidoreductase 1 (NQO1) active site has been developed to facilitate NQO1-directed lavendamycin antitumor agent development. Lavendamycin analogues were designed as NQO1 substrates utilizing structure-based design criteria. Computational docking studies were
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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