WB-3559A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01617 |
| CAS | 96053-97-3 |
| Molecular Weight | 638.9 |
| Molecular Formula | C36H66N2O7 |
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Description
WB-3559A is a fibrinolytic metabolite produced by Flavobacterium sp.
Specification
| Synonyms | WB-3559 A; WB 3559 A |
| IUPAC Name | (2S)-3-hydroxy-2-[[2-[[(3R)-14-methyl-3-[(E)-13-methyltetradec-4-enoyl]oxypentadecanoyl]amino]acetyl]amino]propanoic acid |
| Canonical SMILES | CC(C)CCCCCCCCCCC(CC(=O)NCC(=O)NC(CO)C(=O)O)OC(=O)CCC=CCCCCCCCC(C)C |
| InChI | InChI=1S/C36H66N2O7/c1-29(2)22-18-14-10-6-5-7-13-17-21-25-35(42)45-31(24-20-16-12-9-8-11-15-19-23-30(3)4)26-33(40)37-27-34(41)38-32(28-39)36(43)44/h13,17,29-32,39H,5-12,14-16,18-28H2,1-4H3,(H,37,40)(H,38,41)(H,43,44)/b17-13+/t31-,32+/m1/s1 |
| InChI Key | LVBXUDKEAOBSPR-DYITVEONSA-N |
Properties
| Melting Point | 144-145°C |
Reference Reading
1. Studies on WB-3559 A, B, C and D, new potent fibrinolytic agents. II. Structure elucidation and synthesis
I Uchida, K Yoshida, Y Kawai, S Takase, Y Itoh, H Tanaka, M Kohsaka, H Imanaka J Antibiot (Tokyo). 1985 Nov;38(11):1476-86. doi: 10.7164/antibiotics.38.1476.
The structures of WB-3559 A, B, C and D, new fibrinolytic agents isolated from Flavobacterium sp. No. 3559, have been elucidated to be as shown in 1, 2, 3 and 4, respectively, on the basis of chemical and spectroscopic evidence. Total synthesis of WB-3559 D (4) was achieved starting from the optically active aldehyde 14.
2. Studies on WB-3559 A, B, C and D, new potent fibrinolytic agents. I. Discovery, identification, isolation and characterization
K Yoshida, M Iwami, Y Umehara, M Nishikawa, I Uchida, M Kohsaka, H Aoki, H Imanaka J Antibiot (Tokyo). 1985 Nov;38(11):1469-75. doi: 10.7164/antibiotics.38.1469.
WB-3559 A, B, C and D were produced by a bacterium which was classified as a member of the genus Flavobacterium. These compounds were purified by solvent extraction followed by chromatography on silica gel and then isolated by HPLC. The chemical structures were determined on the basis of chemical and spectroscopic evidence as in the succeeding papers. WB-3559 A, B, C and D stimulated rabbit plasma euglobulin clot lysis time. A chemically synthesized compound (WB-3559 D-syn) stimulated mouse plasma euglobulin clot lysis time when injected intravenously.
3. Genomic study and lipidomic bioassay of Leeuwenhoekiella parthenopeia: A novel rare biosphere marine bacterium that inhibits tumor cell viability
Giuliano Gattoni, Rafael R de la Haba, Jesús Martín, Fernando Reyes, Cristina Sánchez-Porro, Antonia Feola, Candida Zuchegna, Shaday Guerrero-Flores, Mario Varcamonti, Ezio Ricca, Nelly Selem-Mojica, Antonio Ventosa, Paulina Corral Front Microbiol. 2023 Jan 6;13:1090197. doi: 10.3389/fmicb.2022.1090197. eCollection 2022.
The fraction of low-abundance microbiota in the marine environment is a promising target for discovering new bioactive molecules with pharmaceutical applications. Phenomena in the ocean such as diel vertical migration (DVM) and seasonal dynamic events influence the pattern of diversity of marine bacteria, conditioning the probability of isolation of uncultured bacteria. In this study, we report a new marine bacterium belonging to the rare biosphere, Leeuwenhoekiella parthenopeia sp. nov. Mr9T, which was isolated employing seasonal and diel sampling approaches. Its complete characterization, ecology, biosynthetic gene profiling of the whole genus Leeuwenhoekiella, and bioactivity of its extract on human cells are reported. The phylogenomic and microbial diversity studies demonstrated that this bacterium is a new and rare species, barely representing 0.0029% of the bacterial community in Mediterranean Sea metagenomes. The biosynthetic profiling of species of the genus Leeuwenhoekiella showed nine functionally related gene cluster families (GCF), none were associated with pathways responsible to produce known compounds or registered patents, therefore revealing its potential to synthesize novel bioactive compounds. In vitro screenings of L. parthenopeia Mr9T showed that the total lipid content (lipidome) of the cell membrane reduces the prostatic and brain tumor cell viability with a lower effect on normal cells. The lipidome consisted of sulfobacin A, WB 3559A, WB 3559B, docosenamide, topostin B-567, and unknown compounds. Therefore, the bioactivity could be attributed to any of these individual compounds or due to their synergistic effect. Beyond the rarity and biosynthetic potential of this bacterium, the importance and novelty of this study is the employment of sampling strategies based on ecological factors to reach the hidden microbiota, as well as the use of bacterial membrane constituents as potential novel therapeutics. Our findings open new perspectives on cultivation and the relationship between bacterial biological membrane components and their bioactivity in eukaryotic cells, encouraging similar studies in other members of the rare biosphere.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
