Replaces Prod. #: ALX-380-093
Antibiotic. Inhibitor of HSP90. Interacts with the C-terminal ATP-binding domain of HSP90 in contrast to the benzoquinone ansamycins 17-AAG (Prod. No. BML-EI308), geldanamycin (Prod. No. BML-EI280), herbimycin A (Prod. No. BML-EI227) and the chemically unrelated radicicol (Prod. No. BML-EI285), which bind to the N-terminal ATP-binding site of HSP90. Inhibitor of DNA gyrase. Useful for the production of positively supercoiled plasma DNA, targeting the nucleotide-binding site of gyrase B. Inhibits retrovirus RNA-dependent DNA polymerase. Potent inhibitor of ADP ribosylation. Inhibits LPS-induced production of pro-inflammatory cytokines, such as TNF-α, IL-1, IL-6 and IL-10. Inhibits protein synthesis and alters the phosphorylation state of several cytosolic proteins. Reverses etoposide resistance in non-P-glycoprotein expressing multidrug resistant (MDR) tumor cell lines. Inducer of CD38 on cells of the myelomonocytic lineage. Forms ion channels in lipid bilayers. Inhibitor of breast cancer resistance protein (BCRP)
Product Details
| Alternative Name: | Albamycin, Streptonivicin, N-[7-[[3-O-Aminocarbonyl-6-deoxy-5-C-methyl-4-O-β-L-lyxo-hexapyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-4-hydroxy-3-(3-methyl-2-butenyl)benzamide |
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| Formula: | C31H35N2O11 . Na |
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| MW: | 634.6 |
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| CAS: | 1476-53-5 |
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| MI: | 14: 6722 |
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| RTECS: | RD5425000 |
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| Excitation maximum: | 307nm |
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| Appearance: | White to off-white powder. |
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| Activity: | ~900 µg/mg |
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| Solubility: | Soluble in water (100mg/ml), ethanol or DMSO. |
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| Shipping: | Ambient Temperature |
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| Long Term Storage: | +4°C |
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| Handling: | Protect from light. |
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| Regulatory Status: | RUO - Research Use Only |
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Product Literature References
Specific inhibitors of the breast cancer resistance protein (BCRP): A. Pick, et al.; Chem. Med. Chem.
5, 1498 (2010),
Abstract;
Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90: J.A. Burlison, et al.; JACS
128, 15529 (2006),
Abstract;
Destabilization of the non-pathogenic, cellular prion-protein by a small molecular drug: H.J. Ochel & G. Gademann; Antivir. Ther.
9, 441 (2004),
Abstract;
Novobiocin induces a distinct conformation of Hsp90 and alters Hsp90-cochaperone-client interactions: B.G. Yun, et al.; Biochemistry
43, 8217 (2004),
Abstract;
Reversal of breast cancer resistance protein (BCRP/ABCG2)-mediated drug resistance by novobiocin, a coumermycin antibiotic: K. Shiozawa,et al.; Int. J. Cancer
108, 146 (2004),
Abstract;
A coumermycin/novobiocin-regulated gene expression system: H.F. Zhao, et al.; Hum. Gene Ther.
14, 1619 (2003),
Abstract;
Active-site residues of Escherichia coli DNA gyrase required in coupling ATP hydrolysis to DNA supercoiling and amino acid substitutions leading to novobiocin resistance: C.H. Gross, et al.; Antimicrob. Agents Chemother.
47, 1037 (2003),
Abstract;
Full Text
Alteration of Escherichia coli topoisomerase IV to novobiocin resistance: C.D. Hardy & N.R. Cozzarelli; Antimicrob. Agents Chemother.
47, 941 (2003),
Abstract;
Full Text
Evidence that the novobiocin-sensitive ATP-binding site of the heat shock protein 90 (hsp90) is necessary for its autophosphorylation: T. Langer, et al.; Cell Biol. Int.
26, 653 (2002),
Abstract;
Novobiocin is a novel inducer of CD38 on cells of the myelomonocytic lineage: A. Thiele, et al.; Biochim. Biophys. Acta
1542, 32 (2002),
Abstract;
Novobiocin and related coumarins and depletion of heat shock protein 90-dependent signaling proteins: M.G. Marcu, et al.; J. Natl. Cancer Inst.
92, 242 (2000),
Abstract;
The heat shock protein 90 antagonist novobiocin interacts with a previously unrecognized ATP-binding domain in the carboxyl terminus of the chaperone: M.G. Marcu, et al.; J. Biol. Chem.
275, 37181 (2000),
Abstract;
Full Text
Immunomodulating properties of the antibiotic novobiocin in human monocytes: A. Luhrmann, et al.; Antimicrob. Agents Chemother.
42, 1911 (1998),
Abstract;
Full Text
Mechanism of inhibition of vaccinia DNA topoisomerase by novobiocin and coumermycin: J. Sekiguchi, et al.; J. Biol. Chem.
271, 2313 (1996),
Abstract;
Full Text
The properties of ion channels formed by the coumarin antibiotic, novobiocin, in lipid bilayers: A.M. Feigin, et al.; Biochim. Biophys. Acta
1234, 43 (1995),
Abstract;
Nitric oxide activation of poly(ADP-ribose) synthetase in neurotoxicity: J. Zhang et al.; Science
263, 687 (1994),
Abstract;
Reversal of etoposide resistance in non-P-glycoprotein expressing multidrug resistant tumor cell lines by novobiocin: G. Rappa, et al.; Cancer Res.
53, 58487 (1993),
Abstract;
Cisplatin and novobiocin in the treatment of non-small cell lung cancer. A Southwest Oncology Group study.: G.K. Ellis et al.; Cancer
67, 2969 (1991),
Abstract;
Novobiocin treatment reverses radiation-induced alterations in higher-order DNA structure in L5178Y nucleoids.: M. Kapiszewska & M. Lange; Radation Res. 127, 285 (1991),
Structure-activity relationships in DNA gyrase inhibitors: S. Radl; Pharmacol. Ther.
48, 1 (1990), (Review),
Abstract;
The expression of the DNA ligase gene of Escherichia coli is stimulated by relaxation of chromosomal supercoiling.: J.C. Liebart et al.; Mol. Microbiol.
3, 269 (1989),
Abstract;
Inhibition of retrovirus RNA-dependent DNA polymerase by novobiocin and nalidixic acid: Y. Sumiyoshi, et al.; J. Gen. Virol.
64, 2329 (1983),
Abstract;
Positively supercoiled plasmid DNA is produced by treatment of Escherichia coli with DNA gyrase inhibitors: D. Lockshon & D.R. Morris; Nucleic Acids Res.
11, 2999 (1983),
Abstract;
Eukaryotic DNA repair is blocked at different steps by inhibitors of DNA topoisomerases and of DNA polymerases alpha and beta.: M.R. Mattern et al.; Biochim. Biophys. Acta
697, 6 (1982),
Abstract;
Effect of novobiocin and other DNA gyrase inhibitors on virus replication and DNA synthesis in herpes simplex virus type 1-infected BHK cells: B. Francke and J. Margolin; J. Gen. Virol.
52, 401 (1981),
Abstract;
Full Text
Energy coupling in DNA gyrase and the mechanism of action of novobiocin: A. Sugino, et al.; PNAS
75, 4838 (1978),
Abstract;
Full Text
Novobiocin and coumermycin inhibit DNA supercoiling catalyzed by DNA gyrase: M. Gellert, et al.; PNAS
73, 4474 (1976),
Abstract;
Full Text
Novobiocin-a specific inhibitor of semiconservative DNA replication in permeabilized Escherichia coli cells: W.L. Staudenbauer; J. Mol. Biol.
96, 201 (1975),
Abstract;
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