SB-253514
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03402 |
| CAS | |
| Molecular Weight | 554.7 |
| Molecular Formula | C28H46N2O9 |
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Description
SB-253514 is an inhibitor of lipoprotein associated phospholipase A2 produced by Pseudomonas fluorescens DSM 11579.
Specification
| Synonyms | SB 253514; SB253514 |
| IUPAC Name | (3R)-N-[(2E)-2-[(7aS)-3-oxo-5,6,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl]-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxytetradecanamide |
| Canonical SMILES | CCCCCCCCCCCC(CC(=O)NC(=O)C=C1C2CCCN2C(=O)O1)OC3C(C(C(C(O3)C)O)O)O |
| InChI | InChI=1S/C28H46N2O9/c1-3-4-5-6-7-8-9-10-11-13-19(38-27-26(35)25(34)24(33)18(2)37-27)16-22(31)29-23(32)17-21-20-14-12-15-30(20)28(36)39-21/h17-20,24-27,33-35H,3-16H2,1-2H3,(H,29,31,32)/b21-17+/t18-,19+,20-,24-,25+,26+,27-/m0/s1 |
| InChI Key | CTDVHCGPSKGLNP-RQWRZHBRSA-N |
Properties
| Appearance | White Powder |
Reference Reading
1. Model membrane studies for characterization of different antibiotic activities of lipopeptides from Pseudomonas
Katrin Reder-Christ, Yvonne Schmidt, Marius Dörr, Hans-Georg Sahl, Michaele Josten, Jos M Raaijmakers, Harald Gross, Gerd Bendas Biochim Biophys Acta. 2012 Mar;1818(3):566-73. doi: 10.1016/j.bbamem.2011.08.007. Epub 2011 Aug 9.
Lipopeptides (LPs) are a structurally diverse class of amphipathic natural products that were in the past mainly known for their surfactant properties. However, the recent discovery of their antimicrobial and cytotoxic bioactivities have fueled and renewed the interest in this compound class. Propelled by the antimicrobial potential of this compound class, in this study a range of six underinvestigated LPs from Pseudomonads were examined with respect to their antibiotic activities towards bacteria. The assays revealed that only the glycosylated lipodipeptide SB-253514, produced by Pseudomonas strain SH-C52, showed significant antibacterial activity. Since the bioactivity of LPs is commonly attributed to membrane interactions, we analyzed the molecular interactions between the LPs and bacteria-like lipid model membranes in more detail via complementary biophysical approaches. Application of the quartz crystal microbalance (QCM) showed that all LPs possess a high binding affinity towards the model membranes. Despite their similar membrane affinity, monolayer studies displayed different tendencies of LPs to incorporate into the membrane. The degree of membrane incorporation could be correlated with specific structural features of the investigated LPs, such as distance between the peptidic macrocycle and the fatty acid, but did not fully reflect their respective antibacterial activity. Cyclic voltammetry (CV) experiments further demonstrated that SB-253514 showed no membrane permeabilization effects at inhibitory concentrations. Collectively, these results suggests that the antibacterial activity of SB-253514 cannot be explained by an unspecific detergent-like mechanism generally proposed for amphiphilic molecules but instead appears to occur via a defined structural target.
2. Biosynthetic origin of the antibiotic cyclocarbamate brabantamide A (SB-253514) in plant-associated Pseudomonas
Yvonne Schmidt, Menno van der Voort, Max Crüsemann, Jörn Piel, Michaele Josten, Hans-Georg Sahl, Henrike Miess, Jos M Raaijmakers, Harald Gross Chembiochem. 2014 Jan 24;15(2):259-66. doi: 10.1002/cbic.201300527.
Within the framework of our genome-based program to discover new antibiotic lipopeptides from Pseudomonads, brabantamides A-C were isolated from plant-associated Pseudomonas sp. SH-C52. Brabantamides A-C displayed moderate to high in vitro activities against Gram-positive bacterial pathogens. Their shared structure is unique in that they contain a 5,5-bicyclic carbamate scaffold. Here, the biosynthesis of brabantamide A (SB-253514) was studied by a combination of bioinformatics, feeding experiments with isotopically labelled precursors and in vivo and in vitro functional analysis of enzymes encoded in the biosynthetic pathway. The studies resulted in the deduction of all biosynthetic building blocks of brabantamide A and revealed an unusual feature of this metabolite: its biosynthesis occurs via an initially formed linear di-lipopeptide that is subsequently rearranged by a novel FAD-dependent Baeyer-Villiger monooxygenase.
3. Lp-PLA2 inhibitors (GlaxoSmithKline)
M L Booker IDrugs. 2001 Oct;4(10):1173-7.
GlaxoSmithKline is investigating a series of substituted pyrimidin-4-ones, including SB-435495, as reversible inhibitors of lipoprotein-associated phospholipase A(2) (Lp-PLA(2)) for the potential treatment of atherosclerosis [339220], [422380]. This series is being developed alongside a series of irreversible inhibitors such as SB-222657 and derivatives of SB-253514 [339220], [401355]. SB-435495 was discovered through the use of gene technology provided by Human Genome Sciences (HGS) [400047]. By October 2001, phase II trials of SB-435495 had been initiated [424613].
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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 ╳
