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  • 85885 - Streptonigrin from Streptomyces flocculus

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85885 Fluka

Streptonigrin from Streptomyces flocculus

≥98.0% (TLC)

Synonym: Bruneomycin, Nigrin

  • CAS Number 3930-19-6

  • Empirical Formula (Hill Notation) C25H22N4O8

  • Molecular Weight 506.46

  •  Beilstein Registry Number 599390

  •  EC Number 223-501-8

  •  MDL number MFCD00063401

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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

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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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)

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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)

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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)

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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)

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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)

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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)

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[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)

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[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)

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[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)

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

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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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)

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Merck 14,8827

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