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74675

Sigma-Aldrich

Novobiocin Natriumsalz

≥93% (HPLC)

Synonym(e):

Albamycin, Cathomycin, Novobiocin, Novobiocin, Monosodium Salt

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About This Item

Empirische Formel (Hill-System):
C31H35N2NaO11
CAS-Nummer:
1476-53-5
Molekulargewicht:
634.61
Beilstein:
3892910
EG-Nummer:
216-023-6
UNSPSC-Code:
51286504
NACRES:
NA.85

Assay

≥93% (HPLC)

Form

powder

Optische Aktivität

[α]20/D −48±3°, c = 1% in ethanol

Farbe

white to faint beige

Löslichkeit

H2O: soluble

Wirkungsspektrum von Antibiotika

Gram-positive bacteria

Wirkungsweise

DNA synthesis | interferes
enzyme | inhibits

Lagertemp.

2-8°C

SMILES String

[Na+].CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](Oc2ccc3C([O-])=C(NC(=O)c4ccc(O)c(C\C=C(\C)C)c4)C(=O)Oc3c2C)OC1(C)C

InChI

1S/C31H35N2O11.Na/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29;/h7,9-13,23,25-26,29,34,36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q-1;+1

InChIKey

AXOUUAINTJNFRS-UHFFFAOYSA-N

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Allgemeine Beschreibung

Chemical structure: coumarin-glycoside

Anwendung

Novobiocin is used to study heat shock protein inhibition and to produce positively supercoiled plasmid DNA. It is an inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase. It also is an inhibitor of retrovirus RNA-dependent DNA-polymerase.
Für die Produktion von positiv superspiralisierter Plasmid-DNA. Inhibitor von bakterieller DNA-Gyrase und eukaryotischer DNA-Topoisomerase. Inhibitor von RNA-abhängiger DNA-Polymerase aus Retroviren.

Biochem./physiol. Wirkung

Novobiocin inhibits DNA synthesis by inhibiting bacterial DNA gyrase targeting the GyrB subunit of the enzyme involved in energy transduction. Novobiocin acts as a competitive inhibitors of the ATPase reaction catalysed by GyrB . It is also a Hsp90 inhibitor . Antimicrobial spectrum: Gram-positive bacterial.
Wirkungsweise: Hemmt die DNA-Synthese durch Hemmen des Enzyms Topoisomerase II.
Antimikrobielles Spektrum: Grampositiv, bakteriell.

Verpackung

1g, 5g

Sonstige Hinweise

Keep container tightly closed in a dry and well-ventilated place. Light sensitive. Store under inert gas. Keep in a dry place.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Y Sumiyoshi et al.
The Journal of general virology, 64 (Pt 10), 2329-2333 (1983-10-01)
Inhibitors of bacterial DNA gyrase and eukaryotic DNA topoisomerase (novobiocin and nalidixic acid) were investigated with respect to their effect on the activity of RNA-dependent DNA polymerases from murine and avian retroviruses. Purified RNA-dependent DNA polymerase from AKR virus was
N R Cozzarelli
Science (New York, N.Y.), 207(4434), 953-960 (1980-02-29)
Negative supercoiling of bacterial DNA by DNA gyrase influences all metabolic processes involving DNA and is essential for replication. Gyrase supercoils DNA by a mechanism called sign inversion, whereby a positive supercoil is directly inverted to a negative one by
Jeffery D Eskew et al.
BMC cancer, 11, 468-468 (2011-11-02)
The molecular chaperone, heat shock protein 90 (Hsp90) has been shown to be overexpressed in a number of cancers, including prostate cancer, making it an important target for drug discovery. Unfortunately, results with N-terminal inhibitors from initial clinical trials have
Rudi K Allan et al.
The Journal of biological chemistry, 281(11), 7161-7171 (2006-01-20)
The C-terminal domain of Hsp90 displays independent chaperone activity, mediates dimerization, and contains the MEEVD motif essential for interaction with tetratricopeptide repeat-containing immunophilin cochaperones assembled in mature steroid receptor complexes. An alpha-helical region, upstream of the MEEVD peptide, helps form
Huiping Zhao et al.
Bioorganic & medicinal chemistry letters, 23(2), 552-557 (2012-12-14)
Hsp90 is a promising therapeutic target for the treatment of cancer. Novobiocin is the first Hsp90 C-terminal inhibitor ever identified and recent structure-activity relationship studies on the noviose sugar identified several commercially available amines as suitable surrogates. In an effort
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