Glidobactin C
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| Category | Antibiotics |
| Catalog number | BBF-01249 |
| CAS | 108351-52-6 |
| Molecular Weight | 548.72 |
| Molecular Formula | C29H48N4O6 |
| Purity | ≥95% |
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Description
It is produced by the strain of Polyangium brachysporum sp. No. K481-B-101. It is an anti-tumor antibiotic. It has the activity against pathogenic fungi and yeast, the activity of Glidobactin C is the strongest. Glidobactin C has anti-candida albicans and aspergillus fumigatus activity with MIC of 0.8 μg/mL. It also extends the survival of mice inoculated with leukemia P388 cells.
Specification
| Synonyms | Antibiotic BU-2867TC; BU-2867TC; 2,4-Tetradecadienamide, N-(2-hydroxy-1-(((10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)amino)carbonyl)propyl)-, (5S-(3E,5R*,8R*(1R*(2E,4E),2S*),10R*))- |
| IUPAC Name | (2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]tetradeca-2,4-dienamide |
| Canonical SMILES | CCCCCCCCCC=CC=CC(=O)NC(C(C)O)C(=O)NC1CC(CCNC(=O)C=CC(NC1=O)C)O |
| InChI | InChI=1S/C29H48N4O6/c1-4-5-6-7-8-9-10-11-12-13-14-15-26(37)33-27(22(3)34)29(39)32-24-20-23(35)18-19-30-25(36)17-16-21(2)31-28(24)38/h12-17,21-24,27,34-35H,4-11,18-20H2,1-3H3,(H,30,36)(H,31,38)(H,32,39)(H,33,37)/b13-12+,15-14+,17-16-/t21-,22+,23-,24-,27-/m0/s1 |
| InChI Key | UHXDSKADPILIPT-OHIHYABUSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi; Yeast |
| Boiling Point | 898.2 °C at 760 mmHg |
| Melting Point | 273-275 °C |
| Density | 1.14 g/cm3 |
| Solubility | Soluble in Methanol, DMSO, Ethanol; Fairly soluble in Ethyl Acetate, Acetonitrile, Chloroform; Insoluble in Water |
Reference Reading
1. A proteasome inhibitor produced by Burkholderia pseudomallei modulates intracellular growth
Sariqa Wagley, Muthita Vanaporn, Darawan Rinchai, Laura Conejero, Ganjana Lertmemongkolchai, Gregory J Bancroft, Richard W Titball Microb Pathog. 2017 Jun;107:175-180. doi: 10.1016/j.micpath.2017.03.015. Epub 2017 Mar 18.
The NRPS/PKS cluster encodes the enzymes necessary for glidobactin synthesis it is partially conserved in various members of the Burkholderia genus including B. pseudomallei. In this study we have shown that the insertional inactivation or deletion of glbC in this cluster in B. pseudomallei could reduce the ability of the bacterium to survive or grow in murine macrophages or in human neutrophils. Exogenously added proteasome inhibitors were able to chemically complement the mutation. The insertional inactivation or deletion of glbC increased virulence in an acute model of infection in Balb/c or C57BL/6 mice but virulence in a chronic model of infection was similar to that of the wild type. Our findings contrast with the previous finding that inactivation of the glb gene cluster in B. pseudomallei strain 1026b resulted in marked attenuation, and provides evidence of differential roles for some genes in virulence of different strains of B. pseudomallei.
2. Competitive Metabolite Profiling of Natural Products Reveals Subunit Specific Inhibitors of the 20S Proteasome
Atul Pawar, Michael Basler, Heike Goebel, Gerardo Omar Alvarez Salinas, Marcus Groettrup, Thomas Böttcher ACS Cent Sci. 2020 Feb 26;6(2):241-246. doi: 10.1021/acscentsci.9b01170. Epub 2020 Jan 21.
We have developed a syringolin-based chemical probe and explored its utility for the profiling of metabolite extracts as potent inhibitors of the 20S proteasome. Activity-guided fractionation by competitive labeling allowed us to isolate and identify glidobactin A and C as well as luminmycin A from a Burkholderiales strain. The natural products exhibited unique subunit specificities for the proteolytic subunits of human and mouse constitutive and immunoproteasome in the lower nanomolar range. In particular, glidobactin C displayed an unprecedented β2/β5 coinhibition profile with single-digit nanomolar potency in combination with sufficiently high cell permeability. These properties render glidobactin C a promising live cell proteasome inhibitor with potent activity against human breast cancer cell lines and comparably low immunotoxicity.
3. The chemical arsenal of Burkholderia pseudomallei is essential for pathogenicity
John B Biggins, Hahk-Soo Kang, Melinda A Ternei, David DeShazer, Sean F Brady J Am Chem Soc. 2014 Jul 2;136(26):9484-90. doi: 10.1021/ja504617n. Epub 2014 Jun 24.
Increasing evidence has shown that small-molecule chemistry in microbes (i.e., secondary metabolism) can modulate the microbe-host response in infection and pathogenicity. The bacterial disease melioidosis is conferred by the highly virulent, antibiotic-resistant pathogen Burkholderia pseudomallei (BP). Whereas some macromolecular structures have been shown to influence BP virulence (e.g., secretion systems, cellular capsule, pili), the role of the large cryptic secondary metabolome encoded within its genome has been largely unexplored for its importance to virulence. Herein we demonstrate that BP-encoded small-molecule biosynthesis is indispensible for in vivo BP pathogenicity. Promoter exchange experiments were used to induce high-level molecule production from two gene clusters (MPN and SYR) found to be essential for in vivo virulence. NMR structural characterization of these metabolites identified a new class of lipopeptide biosurfactants/biofilm modulators (the malleipeptins) and syrbactin-type proteasome inhibitors, both of which represent overlooked small-molecule virulence factors for BP. Disruption of Burkholderia virulence by inhibiting the biosynthesis of these small-molecule biosynthetic pathways may prove to be an effective strategy for developing novel melioidosis-specific therapeutics.
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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 ╳
