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WS009 B

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Category Bioactive by-products
Catalog number BBF-01639
CAS
Molecular Weight 535.52
Molecular Formula C24H25NO11S

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

WS009 B is an endothelin receptor antagonists isolated from Streptomyces sp. no. 89009. II. The IC50 is 6.7 X 10(-7) mol/L.

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Synonyms WS-009B
IUPAC Name 3-[(4a,6,8,12a,12b-pentahydroxy-3-methyl-1,7,12-trioxo-5,6-dihydro-4H-benzo[a]anthracen-6a-yl)sulfanyl]-2-acetamidopropanoic acid
Canonical SMILES CC1=CC(=O)C2(C(C1)(CC(C3(C2(C(=O)C4=C(C3=O)C(=CC=C4)O)O)SCC(C(=O)O)NC(=O)C)O)O)O
InChI InChI=1S/C24H25NO11S/c1-10-6-15(28)23(35)21(34,7-10)8-16(29)22(37-9-13(20(32)33)25-11(2)26)19(31)17-12(4-3-5-14(17)27)18(30)24(22,23)36/h3-6,13,16,27,29,34-36H,7-9H2,1-2H3,(H,25,26)(H,32,33)
InChI Key JTSMUTXXQIUBJR-UHFFFAOYSA-N
Appearance White Powder
Melting Point 156-159°C
1. WS009 A and B, new endothelin receptor antagonists isolated from Streptomyces sp. no. 89009. II. Biological characterization and pharmacological characterization of WS009 A and B
S Miyata, M Hashimoto, K Fujie, M Shouho, K Sogabe, S Kiyoto, M Okuhara, M Kohsaka J Antibiot (Tokyo). 1992 Jul;45(7):1041-6. doi: 10.7164/antibiotics.45.1041.
WS009 A and B, produced by Streptomyces sp. No. 89009, were found to be competitive and specific antagonists against endothelin (ET)-1 receptors in in vitro studies and also active in in vivo studies. Furthermore, WS009 A and B were specific antagonists for vascular ET-1 receptors (ETA receptors) and significantly prevented the accumulation of intracellular inositol 1,4,5-triphosphate (IP3) in endothelin treated rat aorta tissues.
2. WS009 A and B, new endothelin receptor antagonists isolated from Streptomyces sp. no. 89009. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
S Miyata, N Ohhata, H Murai, Y Masui, M Ezaki, S Takase, M Nishikawa, S Kiyoto, M Okuhara, M Kohsaka J Antibiot (Tokyo). 1992 Jul;45(7):1029-40. doi: 10.7164/antibiotics.45.1029.
WS009 A and B novel endothelin receptor antagonists, have been isolated from the fermentation broth of Streptomyces sp. No. 89009. These antagonists were purified from the culture filtrate followed by Diaion SP-207, DEAE Toyopearl column chromatography and HPLC. WS009 A and B showed selective activity in an endothelin receptor binding assay with IC50 of 5.8 x 10(-6) M and 6.7 x 10(-7) M, respectively. On the basis of spectroscopic and chemical evidence, the structures of WS009 A and B have been established as 1 and 3, and are highly hydroxylated benz[a]anthraquinone chromophores.

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