• USA Home
  • S1014 - Streptonigrin from Streptomyces flocculus

EMAIL THIS PAGE TO A FRIEND

S1014 Sigma

Streptonigrin from Streptomyces flocculus

≥98%

Synonym: Bruneomycin, Nigrin

Purchase

Description

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.

Price and Availability


DISCOVER Bioactive Small Molecules

Duolink Webinar

Customers Also Viewed

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T+
Risk Statements (Europe) 
28
Safety Statements (Europe) 
53-28-36/37/39-45
RIDADR 
UN 3462 6.1 / PGI
WGK Germany 
3
RTECS 
TJ7350000

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Expression of a dominant negative I kappa B-alpha modulates hypersensitivity of ataxia telangiectasia fibroblasts to streptonigrin-induced apoptosis. Jung, M., et al. Radiat. Oncol. Investig. 5, 265-268, (1997)

Loading...


Chromosomal response of insect and mammalian cells to streptonigrin: a comparative study. Bolzan, A.D., et al. Environ. Mol. Mutagen. 32, 331-335, (1998)

Loading...


Antibiotic stress induces a large amount of outer membrane protein in Pseudomonas aeruginosa. Nakajima, A., et al. FEMS Microbiol. Lett. 165, 261-265, (1998)

Loading...


Vitamin D, race, and cardiovascular mortality: findings from a national US sample. Fiscella K and Franks P Ann. Fam. Med. 8(1), 11-8, (2010)

Loading...


Iron and citrate export by a major facilitator superfamily pump regulates metabolism and stress resistance in Salmonella Typhimurium. Frawley ER, Crouch ML, Bingham-Ramos LK, et al. Proc. Natl. Acad. Sci. U. S. A. 110(29), 12054-9, (2013)

Loading...


Scleromyxedema: a multicenter study of characteristics, comorbidities, course, and therapy in 30 patients. Rongioletti F, Merlo G, Cinotti E, et al. J. Am. Acad. Dermatol. 69(1), 66-72, (2013)

Loading...


Heteroaryl cross-coupling as an entry toward the synthesis of lavendamycin analogues: a model study. Verniest G, Wang X, De Kimpe N, et al. J. Org. Chem. 75(2), 424-33, (2010)

Loading...


[Evaluation of perioperative management of seven patients with pulmonary artery sling in recent seven years]. Sakaguchi R, Takayama W, Yoshikawa H, et al. Masui. 59(12), 1479-82, (2010)

Loading...


[Effects of statin use on intracranial hemorrhage and clinical outcome after intravenous rt-PA for acute ischemic stroke: SAMURAI rt-PA registry]. Makihara N, Okada Y, Koga M, et al. Rinsho. Shinkeigaku 50(4), 225-31, (2010)

Loading...


Current perspectives of fertility and pregnancy in thalassemia. Bajoria R and Chatterjee R Hemoglobin 33 Suppl 1, S131-5, (2009)

Loading...


Operative blood loss, blood transfusion, and 30-day mortality in older patients after major noncardiac surgery. Wu WC, Smith TS, Henderson WG, et al. Ann. Surg. 252(1), 11-7, (2010)

Loading...


Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

Loading...


High-content single-cell drug screening with phosphospecific flow cytometry. Peter O Krutzik et al Nat. Chem. Biol. 4, 132-42, (2008)

Loading...


Gold-catalyzed cycloisomerization of N-Propargylindole-2-carboxamides: application toward the synthesis of lavendamycin analogues. England DB and Padwa A Org. Lett. 10(16), 3631-4, (2008)

Loading...


A fluopol-ABPP HTS assay to identify PAD inhibitors. Knuckley B, Jones JE, Bachovchin DA, et al. Chem. Commun. (Camb.) 46(38), 7175-7, (2010)

Loading...


A novel streptococcal integrative conjugative element involved in iron acquisition. Heather Z, Holden MT, Steward KF, et al. Mol. Microbiol. 70(5), 1274-92, (2008)

Loading...


Gap junctional communication promotes apoptosis in a connexin-type-dependent manner. Kameritsch P, Khandoga N, Pohl U, et al. Cell Death Dis. 4, e584, (2013)

Loading...


Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis. Donohoe TJ, Jones CR, and Barbosa LC J. Am. Chem. Soc. 133(41), 16418-21, (2011)

Loading...


Lavendamycin antitumor agents: structure-based design, synthesis, and NAD(P)H:quinone oxidoreductase 1 (NQO1) model validation with molecular docking and biological studies. Hassani M, Cai W, Koelsch KH, et al. J. Med. Chem. 51(11), 3104-15, (2008)

Loading...


Borrelia burgdorferi, a pathogen that lacks iron, encodes manganese-dependent superoxide dismutase essential for resistance to streptonigrin. Troxell B, Xu H, and Yang XF J. Biol. Chem. 287(23), 19284-93, (2012)

Loading...


Characterization of streptonigrin biosynthesis reveals a cryptic carboxyl methylation and an unusual oxidative cleavage of a N-C bond. Xu F, Kong D, He X, et al. J. Am. Chem. Soc. 135(5), 1739-48, (2013)

Loading...


Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents. Cai W, Hassani M, Karki R, et al. Bioorg. Med. Chem. 18(5), 1899-909, (2010)

Loading...


Analysis of the activities of RAD54, a SWI2/SNF2 protein, using a specific small-molecule inhibitor. Deakyne JS, Huang F, Negri J, et al. J. Biol. Chem. 288(44), 31567-80, (2013)

Loading...


Relationship between heterochromatic interstitial telomeric sequences and chromosome damage induced by the radiomimetic compound streptonigrin in Chinese hamster ovary cells. Sánchez J, Bianchi MS, and Bolzán AD Mutat. Res. 684(1-2), 90-7, (2010)

Loading...


Streptonigrin inhibits β-Catenin/Tcf signaling and shows cytotoxicity in β-catenin-activated cells. Park S and Chun S Biochim. Biophys. Acta 1810(12), 1340-5, (2011)

Loading...


Specific IKKbeta inhibitor IV blocks Streptonigrin-induced NF-kappaB activity and potentiates its cytotoxic effect on cancer cells. Gavriil M, Tsao CC, Mandiyan S, et al. Mol. Carcinog. 48(8), 678-84, (2009)

Loading...


Streptonigrin induces delayed chromosomal instability involving interstitial telomeric sequences in Chinese hamster ovary cells. Mencucci MV, Bravo MV, Bianchi MS, et al. Mutat. Res. 747(1), 46-52, (2012)

Loading...


Novel non-active site inhibitor of Cryptosporidium hominis TS-DHFR identified by a virtual screen. W Edward Martucci et al Bioorg. Med. Chem. Lett. 19, 418-23, (2009)

Loading...


Novel immunoconjugates comprised of streptonigrin and 17-amino-geldanamycin attached via a dipeptide-p-aminobenzyl-amine linker system. Patrick J Burke et al Bioorg. Med. Chem. Lett. 19, 2650-3, (2009)

Loading...


Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors. Fabien Vincent et al Bioorg. Med. Chem. Lett. 19, 6793-6, (2009)

Loading...


Erwinia chrysanthemi iron metabolism: the unexpected implication of the inner membrane platform within the type II secretion system. Douet V, Expert D, Barras F, et al. J. Bacteriol. 191(3), 795-804, (2009)

Loading...


Iron transport in Francisella in the absence of a recognizable TonB protein still requires energy generated by the proton motive force. Crosa LM, Crosa JH, and Heffron F Biometals 22(2), 337-44, (2009)

Loading...


Analysis of spontaneous and streptonigrin-induced sister chromatid exchanges in peripheral lymphocytes of aircrew members of international flights. Sánchez J, Bianchi MS, Ciancio VR, et al. J. Environ. Pathol. Toxicol. Oncol. 27(4), 277-85, (2008)

Loading...


[Effects of endovascular therapy for renal artery stenosis on blood pressure and renal function: retrospective analysis of an unselected patient collective from 1994 to 2007]. Krug KB, Rehder O, Bovenschulte H, et al. Urologe. A 51(11), 1562-71, (2012)

Loading...


Merck 14,8827

Related Products

Technical Service:

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

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?