Cepabactin

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Cepabactin
Category Antibiotics
Catalog number BBF-03257
CAS 72731-33-0
Molecular Weight 155.15
Molecular Formula C7H9NO3

Online Inquiry

Description

Cepabactin is an antibiotic produced by Pseudomonas sp. BN-227. It has anti-gram-positive and negative bacteria activity.

Specification

Synonyms Antibiotic BN 227; BN 227; Antibiotic G 1549; 1-Hydroxy-5-methoxy-6-methyl-2(1H)-pyridinone
IUPAC Name 1-hydroxy-5-methoxy-6-methylpyridin-2-one
Canonical SMILES CC1=C(C=CC(=O)N1O)OC
InChI InChI=1S/C7H9NO3/c1-5-6(11-2)3-4-7(9)8(5)10/h3-4,10H,1-2H3
InChI Key SVCUBTJFRYLVSI-UHFFFAOYSA-N

Properties

Appearance Colorless Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 298.5±50.0°C at 760 mmHg
Melting Point 115°C
Density 1.3±0.1 g/cm3
Solubility Soluble in Methanol, ethanol, chloroform, acetone, ethyl acetate

Reference Reading

1. Burkholderia pseudomallei known siderophores and hemin uptake are dispensable for lethal murine melioidosis
Brian H Kvitko, Andrew Goodyear, Katie L Propst, Steven W Dow, Herbert P Schweizer PLoS Negl Trop Dis. 2012;6(6):e1715. doi: 10.1371/journal.pntd.0001715. Epub 2012 Jun 26.
Burkholderia pseudomallei is a mostly saprophytic bacterium, but can infect humans where it causes the difficult-to-manage disease melioidosis. Even with proper diagnosis and prompt therapeutic interventions mortality rates still range from >20% in Northern Australia to over 40% in Thailand. Surprisingly little is yet known about how B. pseudomallei infects, invades and survives within its hosts, and virtually nothing is known about the contribution of critical nutrients such as iron to the bacterium's pathogenesis. It was previously assumed that B. pseudomallei used iron-acquisition systems commonly found in other bacteria, for example siderophores. However, our previous discovery of a clinical isolate carrying a large chromosomal deletion missing the entire malleobactin gene cluster encoding the bacterium's major high-affinity siderophore while still being fully virulent in a murine melioidosis model suggested that other iron-acquisition systems might make contributions to virulence. Here, we deleted the major siderophore malleobactin (mba) and pyochelin (pch) gene clusters in strain 1710b and revealed a residual siderophore activity which was unrelated to other known Burkholderia siderophores such as cepabactin and cepaciachelin, and not due to increased secretion of chelators such as citrate. Deletion of the two hemin uptake loci, hmu and hem, showed that Hmu is required for utilization of hemin and hemoglobin and that Hem cannot complement a Hmu deficiency. Prolonged incubation of a hmu hem mutant in hemoglobin-containing minimal medium yielded variants able to utilize hemoglobin and hemin suggesting alternate pathways for utilization of these two host iron sources. Lactoferrin utilization was dependent on malleobactin, but not pyochelin synthesis and/or uptake. A mba pch hmu hem quadruple mutant could use ferritin as an iron source and upon intranasal infection was lethal in an acute murine melioidosis model. These data suggest that B. pseudomallei may employ a novel ferritin-iron acquisition pathway as a means to sustain in vivo growth.
2. Burkholderia Bacteria Produce Multiple Potentially Novel Molecules that Inhibit Carbapenem-Resistant Gram-Negative Bacterial Pathogens
Eliza Depoorter, Evelien De Canck, Tom Coenye, Peter Vandamme Antibiotics (Basel). 2021 Feb 2;10(2):147. doi: 10.3390/antibiotics10020147.
Antimicrobial resistance in Gram-negative pathogens represents a global threat to human health. This study determines the antimicrobial potential of a taxonomically and geographically diverse collection of 263 Burkholderia (sensu lato) isolates and applies natural product dereplication strategies to identify potentially novel molecules. Antimicrobial activity is almost exclusively present in Burkholderia sensu stricto bacteria and rarely observed in the novel genera Paraburkholderia, Caballeronia, Robbsia, Trinickia, and Mycetohabitans. Fourteen isolates show a unique spectrum of antimicrobial activity and inhibited carbapenem-resistant Gram-negative bacterial pathogens. Dereplication of the molecules present in crude spent agar extracts identifies 42 specialized metabolites, 19 of which represented potentially novel molecules. The known identified Burkholderia metabolites include toxoflavin, reumycin, pyrrolnitrin, enacyloxin, bactobolin, cepacidin, ditropolonyl sulfide, and antibiotics BN-227-F and SF 2420B, as well as the siderophores ornibactin, pyochelin, and cepabactin. Following semipreparative fractionation and activity testing, a total of five potentially novel molecules are detected in active fractions. Given the molecular formula and UV spectrum, two of those putative novel molecules are likely related to bactobolins, and another is likely related to enacyloxins. The results from this study confirm and extend the observation that Burkholderia bacteria present exciting opportunities for the discovery of potentially novel bioactive molecules.
3. Protocol for efficient solid-phase synthesis of peptides containing 1-hydroxypyridine-2-one (1,2-HOPO)
Danah Al Shaer, Beatriz G de la Torre, Fernando Albericio MethodsX. 2020 Sep 28;7:101082. doi: 10.1016/j.mex.2020.101082. eCollection 2020.
·Metal chelation has found many applications that directly affect human's life.·Natural siderophores are one of the most potent chelators for Fe (III)·1-Hydroxypyridine-2-one (1,2-HOPO) (Fig. 1a), which is shown in 4-carboxy-1-hydroxypyridin-2-one (1,2-HOPO-4-COOH) (Fig. 1b), is a moiety that electronically resembles the hydroxamate group found in natural siderophores (Fig. 1c). Of note, 1,2-HOPO moiety is present in the natural siderophore cepabactin [1]·Synthesis of 1,2-HOPO containing chelators has been carried in solid phase using carboxylic acid derivatives of 1,2-HOPO and required the protection of the reactive hydroxyl group usually with benzyl group (Bzl). After the peptide elongation, the Bzl group has been removed on the same solid phase using a bit harsh conditions: 0.1 M BBr3 in DCM for 60 min [2], 10% HBr in AcOH for 14 h [3]; in solution: 1 M BCl3 in DCM for 2 d [4], 50% HCl in AcOH for 4 d [5], H2-Pd/C, AcOH-MeOH [6].·First of all, a method for the incorporation of the 1,2-HOPO-4-COOH through its carboxyl group into the peptide backbone without protecting the N-OH is proposed (the presence of the carboxyl group facilitates the attachment).·Furthermore, in the cases that Bzl protection is required for the N-OH, a friendlier method for removing the Bzl is described. The removal of the Bzl is done concomitantly to the global deprotection and cleavage of the peptide from the resin using TFA- TFMSA-H2O (8:3:1).

Recommended Products

BBF-00664 Alternariol Inquiry
BBF-03756 Amygdalin Inquiry
BBF-01737 Cordycepin Inquiry
BBF-00586 Brefeldin A Inquiry
BBF-05781 Emodepside Inquiry
BBF-03908 Miltefosine Inquiry

Bio Calculators

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* 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
g/mol
g

Recently viewed products

Online Inquiry

Verification code

Copyright © 2024 BOC Sciences. All rights reserved.

cartIcon
Inquiry Basket