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ALX-380-042

Revised 05-May-08

Doxorubicin . hydrochloride
SYNONYMS	DXR . HCl 14-Hydroxydaunomycin . HCl Adriamycin . HCl
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-042-M005		5 mg	60.00 USD
ALX-380-042-M010		10 mg	110.00 USD
ALX-380-042-M025		25 mg	250.00 USD

Product Specification

FORMULA:	C₂₇H₂₉NO₁₁ . HCl
MW:	543.5 . 36.5
CAS NUMBER:	25316-40-9
MERCK INDEX:	14: 3439
RTECS:	QI9295900
SOURCE/HOST:	Isolated from Streptomyces peucetius var. caesius.
PURITY:	≥98%
APPEARANCE:	Red solid.
SOLUBILITY:	Soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HAZARD:	MAY BE CARCINOGENIC. MAY BE TERATOGENIC. TOXIC. MAY BE MUTAGENIC.

Product Description

Antitumor antibiotic. Induces DNA damage by intercalating into DNA and inhibiting topoisomerase II. Binds covalently to DNA. Inhbibits reverse transcriptase, RNA polymerase and the catalytic activity of Dnmt1. Immunosuppressive. Antineoplastic. Induces apoptosis.

Product Specific Literature References

Adriamycin and daunomycin induce programmed cell death (apoptosis) in tumour cells: A. Skladanowski & J. Konopa; Biochem. Pharmacol. 46, 375 (1993) Abstract
A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin: D.A. Gewirtz; Biochem. Pharmacol. 57, 727 (1999) Abstract
Doxorubicin treatment activates a Z-VAD-sensitive caspase, which causes deltapsim loss, caspase-9 activity, and apoptosis in Jurkat cells: S. Gamen, et al.; Exp. Cell Res. 258, 223 (2000) Abstract
Involvement of cyclin-dependent kinases in doxorubicin-induced apoptosis in human tumor cells: Y. Lu, et al.; Mol. Carcinog. 29, 1 (2000) Abstract
Characterization of Adriamycin-Induced G2 Arrest and Its Abrogation by Caffeine in FL-Amnion Cells with or without p53: Y. Minemoto, et al.; Exp. Cell Res. 262, 37 (2001) Abstract
Enhancement of Fas-mediated apoptosis in renal cell carcinoma cells by adriamycin: X.X. Wu, et al.; Cancer Res. 60, 2912 (2000) Abstract
Doxorubicin-induced apoptosis in endothelial cells and cardiomyocytes is ameliorated by nitrone spin traps and ebselen. Role of reactive oxygen and nitrogen species: S. Kotamraju, et al.; J. Biol. Chem. 275, 33585 (2000) Abstract; Full Text
The power and potential of doxorubicin-DNA adducts: S.M. Cutts, et al.; IUBMB Life 57, 73 (2005), Review Abstract
Adriamycin-induced interference with cardiac mitochondrial calcium homeostasis: K.B. Wallace; Cardiovasc. Toxicol. 7, 101 (2007), Review Abstract
Doxorubicin-induced cardiomyopathy from the cardiotoxic mechanisms to managemen: G. Takemura & H. Fujiwara; Prog. Cardiovasc. Dis. 49, 330 (2007), Review Abstract

Further Categories Containing This Product:

Other Toxins • Antitumor Agents (Apoptosis Inducers) • Antibiotics - Topoisomerase Inhibitors • Antibiotics - Immunomodulators • Antitumor Agents (Enzyme Inhibitors) • DNA Intercalators & Crosslinkers • Antibiotics - Apoptosis Inducers & Inhibitors • Antitumor Agents (DNA Interaction & Gene Regulation)

ALX-380-043

Revised 03-Apr-08

Daunorubicin . hydrochloride
SYNONYMS	Daunomycin . HCl
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-043-M010		10 mg	95.00 USD

Product Specification

FORMULA:	C₂₇H₂₉NO₁₀. HCl
MW:	527.5 . 36.5
CAS NUMBER:	23541-50-6
MERCK INDEX:	14: 2832
SOURCE/HOST:	Isolated from Streptomyces spec.
PURITY:	≥98% (HPLC)
APPEARANCE:	Orange to red solid.
SOLUBILITY:	Soluble in water or methanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	TOXIC.

Product Description

Anthracycline anticancer antibiotic. Induces DNA damage by intercalating into DNA and inhibiting topoisomerase I and II. Inhibits RNA and DNA synthesis. Induces DNA single strand breaks and apoptosis in tumor cells.

Product Specific Literature References

Ceramide synthase mediates daunorubicin-induced apoptosis: an alternative mechanism for generating death signals: R. Bose, et al.; Cell 82, 405 (1995) Abstract
Daunorubicin activates NFkappaB and induces kappaB-dependent gene expression in HL-60 promyelocytic and Jurkat T lymphoma cells: M.P. Boland, et al.; J. Biol. Chem. 272, 12952 (1997) Abstract; Full Text
Alteration of the daunorubicin-triggered sphingomyelin-ceramide pathway and apoptosis in MDR cells: influence of drug transport abnormalities: M.G. Come, et al.; Int. J. Cancer 81, 580 (1999) Abstract
A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin: D.A. Gewirtz; Biochem. Pharmacol. 57, 727 (1999) Abstract
Altered multidrug resistance phenotype caused by anthracycline analogues and cytosine arabinoside in myeloid leukemia: X.F. Hu, et al.; Blood 93, 4086 (1999) Abstract
Implication of radical oxygen species in ceramide generation, c-Jun N- terminal kinase activation and apoptosis induced by daunorubicin: V. Mansat-de Mas, et al.; Mol. Pharmacol. 56, 867 (1999) Abstract
The phosphoinositide 3-kinase/Akt pathway is activated by daunorubicin in human acute myeloid leukemia cell lines: I. Plo, et al.; FEBS Lett 452, 150 (1999) Abstract
Caspase-3-like activity is necessary but not sufficient for daunorubicin-induced apoptosis in Jurkat human lymphoblastic leukemia cells: K.J. Turnbull, et al.; Leukemia 13, 1056 (1999) Abstract
Regulation of phospholipase D activity and ceramide production in daunorubicin-induced apoptosis in A-431 cells: J. Chen, et al.; Biochim. Biophys. Acta. 1488, 219 (2000) Abstract
Signaling pathways activated by daunorubicin:: G. Laurent & J. P. Jaffrezou; Blood 98, 913 (2001), Review Abstract

Further Categories Containing This Product:

Antitumor Agents (Apoptosis Inducers) • Antibiotics - Topoisomerase Inhibitors • Antibiotics - Immunomodulators • Antitumor Agents (Enzyme Inhibitors) • DNA Intercalators & Crosslinkers • Antibiotics - Apoptosis Inducers & Inhibitors • Antitumor Agents (DNA Interaction & Gene Regulation)

ALX-380-065

Revised 24-Sep-08

Fostriecin
SYNONYMS	Phosphotrienin CI-920
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Topoisomerase Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-065-C010		10 µg	150.00 USD

Product Specification

FORMULA:	C₁₉H₂₆O₉PNa
MW:	452.4
CAS NUMBER:	87860-39-7
RTECS:	UQ0600000
SOURCE/HOST:	Isolated from Streptomyces pulveraceous subsp. fostreus.
PURITY:	≥98% (HPLC)
APPEARANCE:	Colorless solid.
SOLUBILITY:	Soluble in water (50mg/ml), methanol (10mg/ml) or 100% ethanol (10mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stable for at least 1 year when stored at -20°C. Use fresh solution.
HANDLING:	Protect from light. Packaged under inert gas. Hygroscopic.

Product Description

Antitumor antibiotic. Catalytic inhibitor of topoisomerase II. Strong protein phosphatase 2A (PP2A) inhibitor (IC₅₀=3.2nM). Weak inhibitor for PP1 (IC₅₀=131µM). No apparent effect on PP2B. The binding site for fostriecin on PP2A is different from that of okadaic acid (see Prod. No. ALX-350-003).

Product Specific Literature References

Novel antitumor agents CI-920, PD 113,270 and PD 113,271. II. Isolation and characterization: S.S. Stampwala, et al.; J. Antibiot. (Tokyo) 36, 1601 (1983) Abstract
Novel antitumor agents CI-920, PD 113,270 and PD 113,271. I. Taxonomy, fermentation and biological properties: J.B. Tunac, et al.; J. Antibiot. (Tokyo) 36, 1595 (1983) Abstract
Studies on the biochemical mechanism of the novel antitumor agent, CI- 920: D.W. Fry, et al.; Cancer Chemother. Pharmacol. 13, 171 (1984) Abstract
Anticancer activity of the structurally novel antibiotic Cl-920 and its analogues: W.R. Leopold, et al.; Cancer Res. 44, 1928 (1984) Abstract
Inhibition of type II topoisomerase by fostriecin: T.J. Boritzki, et al.; Biochem. Pharmacol. 37, 4063 (1988) Abstract
Comparison of effects of fostriecin, novobiocin, and camptothecin, inhibitors of DNA topoisomerases, on DNA replication and repair in human cells: C.M. Gedik & A.R. Collins; Nucl. Acids Res. 18, 1007 (1990) Abstract
The cell cycle related differences in susceptibility of HL-60 cells to apoptosis induced by various antitumor agents: W. Gorczyca, et al.; Cancer Res. 53, 3186 (1993) Abstract
Induction of DNA strand breaks associated with apoptosis during treatment of leukemias: W. Gorczyca, et al.; Leukemia 7, 659 (1993) Abstract
Antitumor drug fostriecin inhibits the mitotic entry checkpoint and protein phosphatases 1 and 2A: M. Roberge, et al.; Cancer Res. 54, 6115 (1994) Abstract
Fostriecin: a review of the preclinical data: R.S. de Jong, et al.; Anticancer Drugs 8, 413 (1997) Abstract
Fostriecin, an antitumor antibiotic with inhibitory activity against serine/threonine protein phosphatases types 1 (PP1) and 2A (PP2A), is highly selective for PP2A: A.H. Walsh, et al.; FEBS Lett. 416, 230 (1997) Abstract
Fostriecin, an inhibitor of protein phosphatase 2A, limits myocardial infarct size even when administered after onset of ischemia: C. Weinbrenner, et al.; Circulation 98, 899 (1998) Abstract
Phase I and pharmacokinetic study of the topoisomerase II catalytic inhibitor fostriecin: R.S. de Jong, et al.; Br. J. Cancer 79, 882 (1999) Abstract
Fostriecin: chemistry and biology: D.S. Lewy, et al.; Curr. Med. Chem. 9, 2005 (2002) Abstract

Further Categories Containing This Product:

Antibiotics - Other Signal Transduction Pathway Modulators • Antitumor Antibiotics • Antitumor Agents (Enzyme Inhibitors) • PP2A / Related Products

ALX-380-073

Revised 12-Oct-07

Chartreusin
SYNONYMS	Lambdamycin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-073-M005		5 mg	50.00 USD
ALX-380-073-M025		25 mg	200.00 USD

Product Specification

FORMULA:	C₃₂H₃₂O₁₄
MW:	640.6
CAS NUMBER:	6377-18-0
MERCK INDEX:	14: 2045
SOURCE/HOST:	Isolated from Streptomyces chartreusis.
PURITY:	≥98%
APPEARANCE:	Yellow solid.
SOLUBILITY:	Soluble in acetone; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HAZARD:	TOXIC.

Product Description

Antitumor antibiotic which inhibits topoisomerase II. Induces single-strand scission in DNA in the presence of reducing agents.

Product Specific Literature References

Chartreusin, a New Antibiotic Produced by Streptomyces chartreusis, a New Species: B. E. Leach, et al.; J. Am. Chem. Soc. 75, 4011 (1953)
Chartreusin, a glycosidic antitumour antibiotic from Streptomyces: J.A. Beisler; Prog. Med. Chem. 19, 247 (1982), (Review) Abstract
Biochemical characterisation of elsamicin and other coumarin-related antitumour agents as potent inhibitors of human topoisomerase II: A. Lorico & B.H. Long; Eur. J. Cancer 14, 1985 (1993) Abstract
Chartreusin, elsamicin A and related anti-cancer antibiotics: J. Portugal; Curr. Med. Chem. Anticancer Agents 3, 411 (2003), Review Abstract

Further Categories Containing This Product:

Antibiotics - Topoisomerase Inhibitors • Antitumor Agents (Enzyme Inhibitors) • Antitumor Agents (DNA Interaction & Gene Regulation)

ALX-380-079

Revised 08-Apr-08

Rebeccamycin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-079-C250		250 µg	120.00 USD
ALX-380-079-M001		1 mg	360.00 USD

Product Specification

FORMULA:	C₂₇H₂₁Cl₂N₃O₇
MW:	570.4
CAS NUMBER:	93908-02-2
SOURCE/HOST:	Isolated from Streptomyces sp.
PURITY:	≥98% (HPLC)
APPEARANCE:	Yellow solid.
SOLUBILITY:	Soluble in DMSO.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stock solutions are stable for at least 3 months when stored at -20°C.
HANDLING:	After reconstitution, prepare aliquots and store at -20°C. Protect from light.

Product Description

Antibiotic. Weak topoisomerase I inhibitor structurally similar to staurosporine (Prod. No. ALX-380-014). Does not show any inhibitory activity against protein kinases. Shows significant antitumor properties in vitro (IC₅₀=480nM against mouse B16 melanoma cells and IC₅₀=500nM against P388 leukemia cells).

Product Specific Literature References

Production and biological activity of rebeccamycin, a novel antitumor agent: J.A. Bush, et al.; J. Antibiot. (Tokyo) 40, 668 (1987) Abstract
Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group: F. Anizon, et al.; J. Med. Chem. 40, 3456 (1997) Abstract
DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin: C. Bailly, et al.; Biochemistry 36, 3917 (1997) Abstract
Calories from carbohydrates: energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition: C. Bailly, et al.; Chem. Biol. 6, 277 (1999) Abstract

Further Categories Containing This Product:

Antibiotics - Topoisomerase Inhibitors • Antitumor Agents (Enzyme Inhibitors)

ALX-380-092

Revised 03-Jul-08

Radicicol
SYNONYMS	Monorden 1aS-(1aR,2Z,4E,14,15aR*)]-8-Chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-6H-oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Antifungal

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-092-M001		1 mg	75.00 USD
ALX-380-092-M005		5 mg	295.00 USD

Product Specification

FORMULA:	C₁₈H₁₇ClO₆
MW:	364.8
CAS NUMBER:	12772-57-5
MERCK INDEX:	14: 6253
RTECS:	RR1105000
SOURCE/HOST:	Isolated from Humicola fuscoatra.
PURITY:	≥98% (HPLC)
APPEARANCE:	White to light yellow powder.
SOLUBILITY:	Soluble in DMSO, methanol or acetone.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
HAZARD:	MAY BE CARCINOGENIC. HARMFUL.

Product Description

Antifungal macrocyclic lactone antibiotic with antimalarial activity. Potent inhibitor of HSP90. Binds more strongly to HSP90 (nanomolar affinity) than to Grp94. Also binds to yeast HSP90, E. coli HtpG and TRAP-1. Non-competitive inhibitor of ATP citrate lyase. Anti-angiogenic. Specifically inhibits the interaction between HIF-1α/Arnt heterodimer and the hypoxia-responsive element (HRE), reducing VEGF expression. Protein tyrosine kinase inhibitor, e.g. p60^v-src(IC₅₀=0.27nM). Inhibitor of cyclooxygenase-2 (COX-2) expression (IC₅₀=27nM) without affecting COX-1 expression in LPS-stimulated macrophages. Induces the differentiation of HL-60 cells into macrophages, blocking cell cycle at G1 and G2. Suppressor of NIH 3T3 cell transformation by diverse oncogenes such as mos, ras and src in part by blocking the key signal transduction intermediates such as MAP kinase and GAP-associated p62. Inhibitor of AP-1-, NF-κB- and serum response factor (SRF)-mediated transcription (e.g. expression of iNOS). Represses the transcriptional function of the estrogen receptor. Inhibits archeal growth and DNA topoisomerase VI (a Topo IIB family topoisomerase). Blocks replication of negative-strand RNA viruses.

Product Specific Literature References

Potent and specific inhibition of p60v-src protein kinase both in vivo and in vitro by radicicol: H.J. Kwon, et al.; Cancer Res. 52, 6926 (1992) Abstract
Radicicol, a microbial cell differentiation modulator, inhibits in vivo angiogenesis: T. Oikawa, et al.; Eur. J. Pharmacol. 241, 221 (1993) Abstract
Radicicol, a protein tyrosine kinase inhibitor, suppresses the expression of mitogen-inducible cyclooxygenase in macrophages stimulated with lipopolysaccharide and in experimental glomerulonephritis: P. Chanmugam, et al.; J. Biol. Chem. 270, 5418 (1995) Abstract; Full Text
Suppression of RAS and MOS transformation by radicicol: J.F. Zhao, et al.; Oncogene 11, 161 (1995) Abstract
Induction of differentiation of HL-60 cells by the anti-fungal antibiotic, radicicol: Y. Shimada, et al.; J. Antibiot. 48, 824 (1995) Abstract
Radicicol inhibits tyrosine phosphorylation of the mitotic Src substrate Sam68 and retards subsequent exit from mitosis of Src-transformed cells: I. Pillay, et al.; Cell Growth Differ. 7, 1487 (1996) Abstract
Radicicol leads to selective depletion of Raf kinase and disrupts K-Ras-activated aberrant signaling pathway: S. Soga, et al.; J. Biol. Chem. 273, 822 (1998) Abstract; Full Text
Antimalarial activity of radicicol, heptelidic acid and other fungal metabolites: Y. Tanaka, et al.; J. Antibiot. 51, 153 (1998) Abstract
Targeting of the protein chaperone, HSP90, by the transformation suppressing agent, radicicol: S.V. Sharma, et al.; Oncogene 16, 2369 (1998) Abstract
Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin: S.M. Roe, et al.; J. Med. Chem. 42, 260 (1999) Abstract
T.W. Schulte, et al.; Mol. Endocrinol. 13, 1435 (1999) Abstract; Full Text
Radicicol suppresses expression of inducible nitric-oxide synthase by blocking p38 kinase and nuclear factor-kappaB/Rel in lipopolysaccharide-stimulated macrophages: Y.J. Jeon, et al.; J. Pharmacol. Exp. Ther. 294, 548 (2000) Abstract; Full Text
Radicicol binds and inhibits mammalian ATP citrate lyase: S.W. Ki, et al.; J. Biol. Chem. 275, 39231 (2000) Abstract; Full Text
Radicicol suppresses transformation and restores tropomyosin-2 expression in both ras- and MEK-transformed cells without inhibiting the Raf/MEK/ERK signaling cascade: P.N. Kim, et al.; Cell Growth Differ. 12, 543 (2001) Abstract; Full Text
Radicicol-sensitive peptide binding to the N-terminal portion of GRP94: S. Vogen, et al.; J. Biol. Chem. 277, 40742 (2002) Abstract; Full Text
Reduction of hypoxia-induced transcription through the repression of hypoxia-inducible factor-1alpha/aryl hydrocarbon receptor nuclear translocator DNA binding by the 90-kDa heat-shock protein inhibitor radicicol: E. Hur, et al.; Mol. Pharmacol. 62, 975 (2002) Abstract; Full Text
Radicicol represses the transcriptional function of the estrogen receptor by suppressing the stabilization of the receptor by heat shock protein 90: M.O. Lee, et al.; Mol. Cell Endocrinol. 188, 47 (2002) Abstract
Development of radicicol analogues: S. Soga, et al.; Curr. Cancer Drug Targets 3, 359 (2003) Abstract
Heat shock protein 90 (Hsp90) chaperone complex inhibitor, radicicol, potentiated radiation-induced cell killing in a hormone-sensitive prostate cancer cell line through degradation of the androgen receptor: K. Harashima, et al.; Int. J. Radiat. Biol. 81, 63 (2005) Abstract
Inhibition of archaeal growth and DNA topoisomerase VI activities by the Hsp90 inhibitor radicicol: D. Gadelle, et al.; Nucleic Acid Res. 33, 2310 (2005) Abstract
Geldanamycin, radicicol, and chimeric inhibitors of the Hsp90 N-terminal ATP binding site: M.K. Hadden, et al.; Curr. Top. Med. Chem. 6, 1173 (2006), Review Abstract
The topoisomerase II-Hsp90 complex: a new chemotherapeutic target?: C.R. Barker, et al.; Int. J. Cancer 118, 2685 (2006) Abstract
Structural basis for topoisomerase VI inhibition by the anti-Hsp90 drug radicicol: K.D. Corbett & J.M. Berger; Nucleic Acids Res. 34, 4269 (2006) Abstract
Chemistry and biology of resorcylic acid lactones: N. Winssinger & S. Barluenga; Chem. Commun. (Camb.) 22 (2007) Abstract
Antiviral activity and RNA polymerase degradation following Hsp90 inhibition in a range of negative strand viruses: J.H. Connor, et al.; Virology 362, 109 (2007) Abstract

Further Categories Containing This Product:

HSP90 / HtpG / Related Products • Tyrosine Kinase Inhibitors • Antibiotics - Topoisomerase Inhibitors • Antitumor Agents (Hormone-related) • Estrogen & Estrogen Receptors / Related Products • Malaria / Related Products • Antibiotics - Antimalarial • Antibiotics for Cell Cycle Research • Antibiotics - NF-kB Inhibitors • Antibiotics - Nitric Oxide Pathway Modulators • Antibiotics for Angiogenesis Research • Antibiotics - Protein Kinase Inhibitors • RNA Polymerases / Related Products • Cell Cycle Blockers & Inhibitors / Related Products • NF-kB Pathway Inhibitors

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)