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Merck
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Principaux documents

SML2706

Sigma-Aldrich

Jadomycin B

≥98% (HPLC)

Synonyme(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

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About This Item

Formule empirique (notation de Hill):
C30H31NO9
Numéro CAS:
149633-99-8
Poids moléculaire :
549.57
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Source biologique

Streptomyces venezuelae

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Solubilité

DMSO: 1 mg/mL

Température de stockage

−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

Clé InChI

BSBSCJRAEMDCHC-UHFFFAOYSA-N

Description générale

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

Actions biochimiques/physiologiques

Anti cancer, anti microbial

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

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)
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
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
Steven R Hall et al.
The Journal of pharmacology and experimental therapeutics, 363(2), 196-210 (2017-09-15)
Jadomycins are natural products that kill drug-sensitive and multidrug-resistant (MDR) breast cancer cells. To date, the cytotoxic activity of jadomycins has never been tested in MDR breast cancer cells that are also triple negative. Additionally, there is only a rudimentary
Liru Wang et al.
Microbiology (Reading, England), 148(Pt 4), 1091-1103 (2002-04-05)
Eight additional genes, jadX, O, P, Q, S, T, U and V, in the jad cluster of Streptomyces venezuelae ISP5230, were located immediately downstream of jadN by chromosome walking. Sequence analyses and comparisons implicated them in biosynthesis of the 2,6-dideoxysugar
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