Streptonigrin (Bruneomycin, Nigrin, Rufocromomycin, Valacidin, Antibiotic RP 5278)

Streptonigrin is an unusual aminoquinone with broad biological activity against bacteria, fungi, nematodes, viruses and tumor 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). Streptonigrin from Streptomyces flocculus is an aminoquinone antitumor antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-kappaB. 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. Synonyms: 5278RP, AO 50165L302, Abbott Crystalline antibiotic, Bruneomycin, NSC 45383, NSC 56748, NSC 83950, Nigrin, Rufocromomycin, SN, STP, Streptonigran, Streptonigrin, 5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic Acid, (4R)-5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-2-pyridinecarboxylic Acid, (R)-Streptonigrin, CAS No: 3930-19-6, Molecular Formula: C??H??N?O?, Molecular Weight: 506.46, Source: Streptomyces sp. MST-AS5763, Apperance: Brown black solid, Purity: >98%, Solubility: Soluble in DMSO. Storage and Stability: May be stored at 4°C for short-term only. For long-term storage store at -20°C. Aliquots are stable for at least 12 months at -20°C. For maximum recovery of product, centrifuge the original vial after thawing and prior to removing the cap. Further dilutions can be made in assay buffer.