jadomycin B Chemical Properties

Boiling point:

842.0±65.0 °C(Predicted)

Density 

1.48±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: 1mg/mL

pka

7.83±0.40(Predicted)

form 

powder

biological source

Streptomyces venezuelae

InChIKey

BSBSCJRAEMDCHC-UHFFFAOYSA-N

SMILES

N21C(OC(=O)C2C(CC)C)c3c(c(cc(c3)C)O)C4=C1C(=O)c5c(cccc5OC6OC(C(C(C6)O)O)C)C4=O

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

jadomycin B Usage And Synthesis

Uses

Jadomycin B, is produced by Streptomyces venezuelae fermentation. It is an angucycline antibiotic containing an unusual 8H-benz[b]oxazolo[3,2-f]-phenanthridine ring system and a rare carbohydrate, digitoxose.^1,2
Jadomycin B displays antimicrobial, anti-tumor, aurora-B kinase inhibition, DNA cleaving and more activities.^3,4,5,6
Jadomycin B was found to be active against a variety of staphylococci, including methicillin-resistant Staphylococcus aureus in a MIC of 1μg/ml.³ In addition, its anti-tumor activity was demonstrated as it kills drug-sensitive and multidrug-resistant breast cancer cell, through inhibition of type II topoisomerases and the induction of DNA damage and apoptosis. Jadomycin B (15 mM), 24-hour treatment significantly lowered the levels of topoisomerase IIa protein versus the vehicle control.⁴
It was also shown that Jadomycin B inhibits Aurora-B kinase activity by phosphorylation of histone H3 on Ser10 in a dose-dependent manner (10μg /mL Jadomycin B reduced H3 phosphorylation by 70%).⁵
Jadomycin B was also found to cleave DNA in the presence of Cu (II) by reducing it to Cu(I) which can further react with H₂O₂ to form hydroxyl radicals that causes DNA strand scission without the requirement of any external reducing agent. The EC50 value of Jadomycin B for single-strand scission was approximately 1.7μM.⁶

Biological Activity

Anti cancer, anti microbial

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