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46531

Supelco

Novobiocin sodium salt

VETRANAL®, analytical standard

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About This Item

Empirical Formula (Hill Notation):
C31H35N2NaO11
CAS Number:
1476-53-5
Molecular Weight:
634.61
Beilstein:
3892910
EC Number:
216-023-6
UNSPSC Code:
41116107
PubChem Substance ID:
24870266
NACRES:
NA.24

grade

analytical standard

Quality Level

100

product line

VETRANAL®

Assay

97.9% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

antibiotic activity spectrum

Gram-positive bacteria

application(s)

clinical testing

format

neat

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

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
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

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

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317,H319

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK2243
BCCB6920
SZBF069XV
SZBE203XV
SZBE094XV

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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
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
Bhaskar Reddy Kusuma et al.
Bioorganic & medicinal chemistry letters, 21(23), 7170-7174 (2011-10-22)
Novobiocin analogs lacking labile glycosidic ether have been designed, synthesized and evaluated for Hsp90 inhibitory activity. Replacement of the synthetically complex noviose sugar with simple aromatic side chains produced analogs that maintain moderate cytotoxic activity against MCF7 and SkBR3 breast
Sidharth Chopra et al.
The Journal of antimicrobial chemotherapy, 67(2), 415-421 (2011-11-05)
New classes of drugs are needed to treat tuberculosis (TB) in order to combat the emergence of resistance to existing agents and shorten the duration of therapy. Targeting DNA gyrase is a clinically validated therapeutic approach using fluoroquinolone antibiotics to
Roman Pantůček et al.
Systematic and applied microbiology, 36(2), 90-95 (2013-01-16)
Thirteen coagulase-negative, oxidase-negative, and novobiocin-susceptible staphylococci were isolated from human clinical specimens. The isolates were differentiated from known staphylococcal species on the basis of 16S rRNA, hsp60, rpoB, dnaJ, tuf, and gap gene sequencing, automated ribotyping, (GTG)5-PCR fingerprinting, and MALDI-TOF
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