484400

Nitrocefin

≥95% (UV), solid, β-lactamase substrate, Calbiochem^®

• Synonym(s): Nitrocefin, 3-(2,4-Dinitrostyryl)-(6R, 7R)-7-(2-thienylacetamido)-ceph-3-em-4-carboxylic Acid, E-isomer
• Empirical Formula (Hill Notation): C₂₁H₁₆N₄O₈S₂
• CAS Number: 41906-86-9
• Molecular Weight: 516.50
• MDL number: MFCD12165893
• UNSPSC Code: 12352200
• NACRES: NA.21

Properties

• Product Name: Nitrocefin, A chromogenic β-lactamase substrate that undergoes distinctive color change from yellow as the amide bond in the β-lactam ring is hydrolyzed by β-lactamase.
• Quality Level: 200
• assay: ≥95% (UV)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: orange-yellow
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: [s]1c(ccc1)CC(=O)N[C@H]2[C@H]3SCC(=C(N3C2=O)C(=O)O)\C=C\c4c(cc(cc4)[N+](=O)[O-])[N+](=O)[O-]
• 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

Description

General description

A chromogenic β-lactamase substrate that undergoes distinctive color change from yellow (λ_max = 390 nm at pH 7.0) to red (λ_max = 486 nm at pH 7.0) as the amide bond in the β-lactam ring is hydrolyzed by β-lactamase. Nitrocefin is sensitive to hydrolysis by all known lactamases produced by Gram-positive and Gram-negative bacteria. Also useful for the detection of β-lactamase patterns from bacterial cell extracts by isoelectric focusing. Has been used in competitive inhibition studies in developmental work on β-lactamase-resistant antibiotics.

Packaging

Packaged under inert gas

Warning

Toxicity: Flammable (J)

Preparation Note

Preparing a Nitrocefin (500 µg/ml) Solution

• Dissolve 1 mg Nitrocefin in 100 µl dimethylsulfoxide (DMSO) and vortex.

• Add 1.9 ml phosphate buffer (100 mM, pH 7) to produce 2 ml total volume.

• This yields a working Nitrocefin solution of 500 µg/ml (~1 mM), which is suitable for most applications.

• Nitrocefin, particularly in solution, is very sensitive to light.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solution may be stored at -20°C for up to 2 weeks.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Guay, R., et al. 1980. IRCS Med. Science 8, 209.
King, A., et al. 1980. Antimicrob. Agents Chemother. 17, 165.
Matthew, M., et al. 1975. J. Gen. Microbiol. 88, 169.
O’Callaghan, C.H., et al. 1972. Antimicrob. Agents Chemother. 1, 283.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H315,H317,H318
• pcodes: P261 - P264 - P272 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3