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Technology Process of Streptonigrin

Streptonigrin

Base Information
  • Chemical Name:Streptonigrin
  • CAS No.:3930-19-6
  • Molecular Formula:C25H22 N4 O8
  • Molecular Weight:506.51
  • Hs Code.:
  • European Community (EC) Number:223-501-8
  • NSC Number:83950,56748,45383
  • UNII:261Q3JB310
  • DSSTox Substance ID:DTXSID00960034
  • Nikkaji Number:J2.203I,J2.999.943K,J2.999.944I
  • Wikipedia:Streptonigrin
  • Wikidata:Q15427845,Q104984816
  • NCI Thesaurus Code:C844
  • Pharos Ligand ID:CDXGPAMZ849V
  • Metabolomics Workbench ID:50024
  • ChEMBL ID:CHEMBL11417
  • Mol file:3930-19-6.mol
Streptonigrin

Synonyms:Brunemycin;Bruneomycin;Nigrin;NSC 45383;NSC-45383;NSC45383;Rufocromomycin;Streptonigrin

Suppliers and Price of Streptonigrin
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • Streptonigrin
  • 1mg
  • $ 490.00
  • TRC
  • Streptonigrin from Streptomyces flocculus
  • 2.5mg
  • $ 395.00
  • Sigma-Aldrich
  • Streptonigrin from Streptomyces flocculus ≥98%
  • 1mg
  • $ 100.00
  • Sigma-Aldrich
  • Streptonigrin from Streptomyces flocculus ≥98%
  • 5mg
  • $ 361.00
  • Cayman Chemical
  • Streptonigrin
  • 5mg
  • $ 315.00
  • Cayman Chemical
  • Streptonigrin
  • 1mg
  • $ 90.00
  • Biosynth Carbosynth
  • 5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid
  • 5 mg
  • $ 700.00
  • Biosynth Carbosynth
  • 5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid
  • 2 mg
  • $ 420.00
  • Biosynth Carbosynth
  • 5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid
  • 1 mg
  • $ 250.00
Total 34 raw suppliers
Chemical Property of Streptonigrin
Chemical Property:
  • Vapor Pressure:0mmHg at 25°C 
  • Melting Point:301-303℃ 
  • Refractive Index:1.6000 (estimate) 
  • Boiling Point:719°Cat760mmHg 
  • PKA:6.2-6.4 (1:1 aq dioxane) 
  • Flash Point:388.7°C 
  • PSA：197.18000 
  • Density:1.54g/cm3 
  • LogP:3.59940 
  • Storage Temp.:2-8°C 
  • XLogP3:1.8
  • Hydrogen Bond Donor Count:4
  • Hydrogen Bond Acceptor Count:12
  • Rotatable Bond Count:6
  • Exact Mass:506.14376367
  • Heavy Atom Count:37
  • Complexity:944
Purity/Quality:

97% *data from raw suppliers

Streptonigrin *data from reagent suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes:T+ 
  • Statements: 28 
  • Safety Statements: 53-28-36/37/39-45 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Canonical SMILES:CC1=C(C(=C(N=C1C(=O)O)C2=NC3=C(C=C2)C(=O)C(=C(C3=O)N)OC)N)C4=C(C(=C(C=C4)OC)OC)O
  • Description Streptonigrin is a phenylpyridylquinoline originally isolated from S. flocculus with diverse biological activities. Streptonigrin (2.5-12.5 μM) induces DNA cleavage by calf thymus topoisomerase II in a concentration-dependent manner. It induces phage production in S. typhimurium when used at concentrations ranging from 1 to 10 μg/ml. Streptonigrin (10 μg/ml) inhibits DNA synthesis in and reduces survival of S. typhimurium bacteria. Streptonigrin is bactericidal against E. coli in an iron-dependent manner, an effect that is blocked by the iron chelators deferoxamine and orthophenanthroline. Streptonigrin (40 nM) is cytotoxic to human HT-29 colon carcinoma cells but not to BE colon carcinoma cells in which NAD(P)H:quinone oxidoreductase is not expressed. Streptonigrin (0.001-0.1 μg/ml) inhibits mitosis and induces chromatin breaks in human leukocytes in a concentration-dependent manner. In vivo, streptonigrin (0.05 mg/kg, i.p.) increases the mean survival time in rats infected with Rauscher virus.
  • Uses Streptonigrin 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 Streptonigrin are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated. Streptonigrin from Streptomyces flocculus Streptonigrin is an unusual aminoquinone with broad biological activity against bacteria, fungi, nematodes, viruses and tumour cells. Streptonigrin acts as a bioreductive agent, highly dependent on interactions with metal ions, notably iron, and plays an important role in free radical production through redox cycling of NAD(P)H:quinone oxidoreductase (NQO1).
Refernces

Synthesis of a Helical Ferrocene

10.1021/ja00365a087

The research includes three distinct studies. The first study investigates the biosynthetic pathway of streptonigrin, utilizing [U - L3C6] glucose to elucidate the complex process, with erythrose-4-phosphate and 4-aminoanthranilic acid being key intermediates. The second study details the synthesis of a helical ferrocene. It involves creating a helical structure with cyclopentadienyl rings, using 2,7-dihydroxynaphthalene, vinyl ketone cyclization, and photocyclization. The final product is obtained by reacting the lithium salt of the helical structure with FeCl?. The third study examines the catalytic hydrolysis of esters of p-nitrophenol bound by amylose in a Me?SO-H?O mixed-solvent system, focusing on the conformational changes and rate accelerations in this unique environment.

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