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Merck

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:
Molekulargewicht:
634.61
Beilstein:
3892910
EG-Nummer:
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

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.
Novobiocin is used to study heat shock protein inhibition [1] and to produce positively supercoiled plasmid DNA.[2] It is an inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase.[3] It also is an inhibitor of retrovirus RNA-dependent DNA-polymerase.[4]

Biochem./physiol. Wirkung

Wirkungsweise: Hemmt die DNA-Synthese durch Hemmen des Enzyms Topoisomerase II.
Antimikrobielles Spektrum: Grampositiv, bakteriell.
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 [5]. It is also a Hsp90 inhibitor [1]. Antimicrobial spectrum: Gram-positive bacterial.

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

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


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Die Dokumentenbibliothek aufrufen

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
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
D Lockshon et al.
Nucleic acids research, 11(10), 2999-3017 (1983-05-25)
A procedure has been developed whereby the relative amounts of the topoisomers of E. coli plasmid can be determined for cells grown under a variety of conditions. Several applications of the procedure are presented. Addition of either novobiocin or oxolinic
A Maxwell
Molecular microbiology, 9(4), 681-686 (1993-08-01)
The coumarin group of antibiotics have as their target the bacterial enzyme DNA gyrase. The drugs bind to the B subunit of gyrase and inhibit DNA supercoiling by blocking the ATPase activity. Recent data show that the binding site for
Patricia L Taylor et al.
ACS chemical biology, 7(9), 1547-1555 (2012-06-16)
Multi-drug-resistant infections caused by Gram-negative pathogens are rapidly increasing, highlighting the need for new chemotherapies. Unlike Gram-positive bacteria, where many different chemical classes of antibiotics show efficacy, Gram-negatives are intrinsically insensitive to many antimicrobials including the macrolides, rifamycins, and aminocoumarins

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