Nitrocefin
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| Category | Others |
| Catalog number | BBF-03759 |
| CAS | 41906-86-9 |
| Molecular Weight | 516.50 |
| Molecular Formula | C21H16N4O8S2 |
| Purity | 90% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-03759 | 100 mg | $1100 | In stock | |
| BBF-03759 | 1 g | $5500 | In stock |
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Add to cartDescription
Nitrocefin is a chromogenic cephalosporin substrate routinely used to detect the presence of beta-lactamase enzymes produced by various microbes.
Specification
| Synonyms | 3-(2,4-Dinitrostyryl)-(6R,7R)-7-(2-thienylacetamido)-ceph-3-em-4-carboxylic acid; UNII-EWP54G0J8F; EWP54G0J8F |
| Storage | Store at -20°C, Under Inert Atmosphere |
| IUPAC Name | (6R,7R)-3-[(E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CS3)C(=O)O)C=CC4=C(C=C(C=C4)[N+](=O)[O-])[N+](=O)[O-] |
| InChI | InChI=1S/C21H16N4O8S2/c26-16(9-14-2-1-7-34-14)22-17-19(27)23-18(21(28)29)12(10-35-20(17)23)4-3-11-5-6-13(24(30)31)8-15(11)25(32)33/h1-8,17,20H,9-10H2,(H,22,26)(H,28,29)/b4-3+/t17-,20-/m1/s1 |
| InChI Key | LHNIIDJCEODSHA-OQRUQETBSA-N |
| Source | Synthetic |
Properties
| Appearance | Orange to Yellow Powder |
| Boiling Point | 872°C at 760 mmHg |
| Density | 1.67 g/cm3 |
| Solubility | Soluble in DMSO (1.0 mg/ml) |
Reference Reading
1.Refined models of New Delhi metallo-beta-lactamase-1 with inhibitors: an QM/MM modeling study.
Wang YT1,2, Cheng TL2. J Biomol Struct Dyn. 2016 Jan 6:1-10. [Epub ahead of print]
New Delhi metallo-beta-lactamase 1 (NDM-1) has been identified as a potential target for the treatment of multi-drug resistance bacterial infections. We used molecular docking, normal MD, SIE, QM/MM MD simulations, QM/MM GBSA binding free energy, and QM/MM GBSA alanine-scanning mutagenesis techniques to investigate interactions of the NDM-1 with 11 inhibitors (Tigecycline, BAL30072, D-captopril, Penicillin G, Ampicillin, Carbenicillin, Cephalexin, Cefaclor, Nitrocefin, Meropenem, and Imipenem). From our normal MD and QM/MM simulations, the correlation coefficients between the predicted binding free energies and experimental values are .88 and .93, respectively. Then simulations, which combined QM/MM/GBSA and alanine-scanning mutagenesis techniques, were performed and our results show that two residues (Lys211 and His250) have the strongest impact on the binding affinities of the 11 NDM-1/inhibitors. Therefore, our approach theoretically suggests that the two residues (Lys211 and His250) are responsible for the selectivity of NDM-1 associated inhibitors.
2.Novel Piperazine Arylideneimidazolones Inhibit the AcrAB-TolC Pump in Escherichia coli and Simultaneously Act as Fluorescent Membrane Probes in a Combined Real-Time Influx and Efflux Assay.
Bohnert JA1, Schuster S2, Kern WV2, Karcz T3, Olejarz A3, Kaczor A3, Handzlik J3, Kieć-Kononowicz K3. Antimicrob Agents Chemother. 2016 Mar 25;60(4):1974-83. doi: 10.1128/AAC.01995-15. Print 2016 Apr.
In this study, we tested five compounds belonging to a novel series of piperazine arylideneimidazolones for the ability to inhibit the AcrAB-TolC efflux pump. The biphenylmethylene derivative (BM-19) and the fluorenylmethylene derivative (BM-38) were found to possess the strongest efflux pump inhibitor (EPI) activities in the AcrAB-TolC-overproducingEscherichia colistrain 3-AG100, whereas BM-9, BM-27, and BM-36 had no activity at concentrations of up to 50 μM in a Nile red efflux assay. MIC microdilution assays demonstrated that BM-19 at 1/4 MIC (intrinsic MIC, 200 μM) was able to reduce the MICs of levofloxacin, oxacillin, linezolid, and clarithromycin 8-fold. BM-38 at 1/4 MIC (intrinsic MIC, 100 μM) was able to reduce only the MICs of oxacillin and linezolid (2-fold). Both compounds markedly reduced the MIC of rifampin (BM-19, 32-fold; and BM-38, 4-fold), which is suggestive of permeabilization of the outer membrane as an additional mechanism of action.
3.Involvement of a Novel Class C Beta-Lactamase in the Transglutaminase Mediated Cross-Linking Cascade of Streptomyces mobaraensis DSM 40847.
Zindel S1, Ehret V1, Ehret M1, Hentschel M1, Witt S1, Krämer A1, Fiebig D1, Jüttner N1, Fröls S2, Pfeifer F2, Fuchsbauer HL1. PLoS One. 2016 Feb 17;11(2):e0149145. doi: 10.1371/journal.pone.0149145. eCollection 2016.
Streptomyces mobaraensis DSM 40847 secretes transglutaminase that cross-links proteins via γ-glutamyl-ε-lysine isopeptide bonds. Characterized substrates are inhibitory proteins acting against various serine, cysteine and metalloproteases. In the present study, the bacterial secretome was examined to uncover additional transglutaminase substrates. Fractional ethanol precipitation of the exported proteins at various times of culture growth, electrophoresis of the precipitated proteins, and sequencing of a 39 kDa protein by mass spectrometry revealed the novel beta-lactamase Sml-1. As indicated by biotinylated probes, Sml-1, produced in E. coli, exhibits glutamine and lysine residues accessible for transglutaminase. The chromogenic cephalosporin analogue, nitrocefin, was hydrolyzed by Sml-1 with low velocity. The obtained Km and kcat values of the recombinant enzyme were 94.3±1.8 μM and 0.39±0.03 s-1, respectively. Penicillin G and ampicillin proved to be weak inhibitors of nitrocefin hydrolysis (Ki of 0.
4.Contribution of PBP3 Substitutions and TEM-1, TEM-15, and ROB-1 Beta-Lactamases to Cefotaxime Resistance in Haemophilus influenzae and Haemophilus parainfluenzae.
Søndergaard A1, Nørskov-Lauritsen N1. Microb Drug Resist. 2015 Dec 18. [Epub ahead of print]
AIMS: To investigate the relative contributions of naturally occurring penicillin-binding protein 3 (PBP3) substitutions, and TEM-1, TEM-15, and ROB-1 beta-lactamases on resistance to a third-generation cephalosporin in Haemophilus influenzae and Haemophilus parainfluenzae.
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
