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74675

Sigma-Aldrich

Novobiocin sodium salt

≥93% (HPLC)

Synonym(s):

Albamycin, Cathomycin, Novobiocin, Novobiocin, Monosodium Salt

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About This Item

Empirical Formula (Hill Notation):
C31H35N2NaO11
CAS Number:
1476-53-5
Molecular Weight:
634.61
Beilstein/REAXYS Number:
3892910
EC Number:
216-023-6
UNSPSC Code:
51286504
NACRES:
NA.85

assay

≥93% (HPLC)

form

powder

optical activity

[α]20/D −48±3°, c = 1% in ethanol

color

white to faint beige

solubility

H2O: soluble

antibiotic activity spectrum

Gram-positive bacteria

mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

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

InChI key

AXOUUAINTJNFRS-UHFFFAOYSA-N

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General description

Chemical structure: coumarin-glycoside

Application

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.
For the production of positively supercoiled plasmid DNA. Inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase. Inhibitor of retrovirus RNA-dependent DNA-polymerase.

Biochem/physiol Actions

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.
Mode of Action: Inhibits DNA synthesis by inhibiting the enzyme Topoisomerase II.
Antimicrobial spectrum: Gram-positive bacterial.

Packaging

1g, 5g

Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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