SML2706

Jadomycin B

≥98% (HPLC)

• Synonym(s): 1-(sec-butyl)-12-((4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-7-hydroxy-5-methyl-8H-benzo[b]oxazolo[3,2-f]phenanthridine-2,8,13(1H,3aH)-trione
• Empirical Formula (Hill Notation): C₃₀H₃₁NO₉
• CAS Number: 149633-99-8
• Molecular Weight: 549.57
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• biological source: Streptomyces venezuelae
• Quality Level: 100
• assay: ≥98% (HPLC)
• form: powder
• storage condition: protect from light
• solubility: DMSO: 1 mg/mL
• storage temp.: −20°C
• InChI: 1S/C30H31NO9/c1-5-13(3)24-30(37)40-29-16-9-12(2)10-17(32)21(16)23-25(31(24)29)28(36)22-15(27(23)35)7-6-8-19(22)39-20-11-18(33)26(34)14(4)38-20/h6-10,13-14,18,20,24,26,29,32-34H,5,11H2,1-4H3
• InChI key: BSBSCJRAEMDCHC-UHFFFAOYSA-N

Description

General description

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

Biochem/physiol Actions

Anti cancer, anti microbial

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable