ALEXIS Biochemicals: Novobiocin . sodium salt

ALX-380-093

Revised 16-Jun-08

Novobiocin . sodium salt
SYNONYMS	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
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Other Signal Transduction Pathway Modulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-093-G001		1 g	30.00 USD

Product Specification

FORMULA:	C₃₁H₃₅N₂O₁₁ . Na
MW:	611.6 . 23.0
CAS NUMBER:	1476-53-5
MERCK INDEX:	14: 6722
RTECS:	RD5425000
PURITY:	≥95%
APPEARANCE:	White to pale yellow solid.
SOLUBILITY:	Soluble in water (100mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HANDLING:	Protect from light.
HAZARD:	HARMFUL. IRRITANT.

Product Description

Antibiotic. Inhibitor of HSP90. Interacts with the C-terminal ATP-binding domain of HSP90 in contrast to the benzoquinone ansamycins 17-AAG (Prod. No. ALX-380-091), geldanamycin (Prod. No. ALX-380-054), herbimycin A (Prod. No. ALX-350-029), and the chemically unrelated radicicol (Prod. No. ALX-380-092), 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.

Product Specific Literature References

Novobiocin-a specific inhibitor of semiconservative DNA replication in permeabilized Escherichia coli cells: W.L. Staudenbauer; J. Mol. Biol. 96, 201 (1975) Abstract
Novobiocin and coumermycin inhibit DNA supercoiling catalyzed by DNA gyrase: M. Gellert, et al.; PNAS 73, 4474 (1976) 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
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
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 and D.R. Morris; Nucleic Acids Res. 11, 2999 (1983) Abstract
Structure-activity relationships in DNA gyrase inhibitors: S. Radl; Pharmacol. Ther. 48, 1 (1990), (Review) 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
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
Mechanism of inhibition of vaccinia DNA topoisomerase by novobiocin and coumermycin: J. Sekiguchi, et al.; J. Biol. Chem. 271, 2313 (1996) 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
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
Novobiocin is a novel inducer of CD38 on cells of the myelomonocytic lineage: A. Thiele, et al.; Biochim. Biophys. Acta 1542, 32 (2002) Abstract
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
Alteration of Escherichia coli topoisomerase IV to novobiocin resistance: C.D. Hardy and N.R. Cozzarelli; Antimicrob. Agents Chemother. 47, 941 (2003) Abstract; Full Text
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
A coumermycin/novobiocin-regulated gene expression system: H.F. Zhao, et al.; Hum. Gene Ther. 14, 1619 (2003) Abstract
Destabilization of the non-pathogenic, cellular prion-protein by a small molecular drug: H.J. Ochel and 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
Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90: J.A. Burlison, et al.; JACS 128, 15529 (2006) Abstract

Further Categories Containing This Product:

Protein Synthesis Other Products • HSP90/HtpG/Related Products • Antibiotics - Topoisomerase Inhibitors • Anti-inflammatory Agents Other Products

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