SML2706
Jadomycin B
≥98% (HPLC)
别名:
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
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关于此项目
biological source
Streptomyces venezuelae
Quality Level
assay
≥98% (HPLC)
form
powder
storage condition
protect from light
solubility
DMSO: 1 mg/mL
storage temp.
−20°C
SMILES string
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
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
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
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
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
法规信息
涉药品监管产品
此项目有
Da-Hua Fu et al.
Molecular cancer therapeutics, 7(8), 2386-2393 (2008-08-30)
Aurora kinases have emerged as promising targets for cancer therapy because of their critical role in mitosis. These kinases are well-conserved in all eukaryotes, and IPL1 gene encodes the single Aurora kinase in budding yeast. In a virtual screening attempt
Susan M A Monro et al.
Bioorganic & medicinal chemistry, 19(11), 3357-3360 (2011-05-14)
The natural product jadomycin B, isolated from Streptomyces venezeulae ISP5230, has been found to cleave DNA in the presence of Cu(II) ions without the requirement for an external reducing agent. The efficiency of DNA cleavage was probed using supercoiled plasmid
Jadomycin, a novel 8H-benz[b]oxazolo[3,2-f]-phenanthridine antibiotic from streptomyces venezuelae ISP5230
Ayer S. W. et al
Tetrahedron Letters, 6301-6304 (1991)