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Merck

P4157

Sigma-Aldrich

Phe-Arg β-naphthylamide dihydrochloride

cathepsin substrate, fluorogenic, ≥98% (TLC), powder

Sinónimos:

PAβN

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About This Item

Fórmula empírica (notación de Hill):
C25H30N6O2 · 2HCl
Número de CAS:
Peso molecular:
519.47
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

product name

Phe-Arg β-naphthylamide dihydrochloride, cathepsin substrate

Quality Level

assay

≥98% (TLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

Cl.NC(Cc1ccccc1)C(=O)NC(CCCNC(N)=N)C(=O)Nc2ccc3ccccc3c2

InChI

1S/C25H30N6O2.ClH/c26-21(15-17-7-2-1-3-8-17)23(32)31-22(11-6-14-29-25(27)28)24(33)30-20-13-12-18-9-4-5-10-19(18)16-20;/h1-5,7-10,12-13,16,21-22H,6,11,14-15,26H2,(H,30,33)(H,31,32)(H4,27,28,29);1H

InChI key

ZMTAZQYLEGNUTJ-UHFFFAOYSA-N

General description

Phe-Arg β-naphthylamide, a peptidomimetic compound, is an efflux pump inhibitor (EPI). It acts on the major multidrug resistance efflux transporters of Gram-negative bacteria. Phe-Arg -naphthylamide lowers fluoroquinolone resistance in Pseudomonas aeruginosa.

Application

Phe-Arg -naphthylamide dihydrochloride has been used to evaluate the contribution of efflux pumps to antimicrobial resistance. It has also been used for minimal inhibitory concentration testing in the presence of an efflux pump inhibitor.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Substrates

Substrate for dipeptidyl aminopeptidase I (cathepsin C).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

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Commonality among fluoroquinolone-resistant sequence type ST131 extraintestinal Escherichia coli isolates from humans and companion animals in Australia
Platell JL, et al.
Antimicrobial Agents and Chemotherapy, 55(8), 3782-3787 (2011)
Proof of an Outer Membrane Target of the Efflux Inhibitor Phe-Arg-beta-Naphthylamide from Random Mutagenesis
Schuster S, et al.
Molecules (Basel), 24(3), 470-470 (2019)
Fluoroquinolone resistance mechanisms in multidrug-resistant Escherichia coli isolated from extraintestinal infections in dogs
Gibson JS, et al.
Veterinary Microbiology, 146(1-2), 161-166 (2010)
Nagakumar Bharatham et al.
Nature communications, 12(1), 5400-5400 (2021-09-15)
OqxB is an RND (Resistance-Nodulation-Division) efflux pump that has emerged as a factor contributing to the antibiotic resistance in Klebsiella pneumoniae. OqxB underwent horizontal gene transfer and is now seen in other Gram-negative bacterial pathogens including Escherichia coli, Enterobacter cloacae
Christopher Concha et al.
Microorganisms, 7(12) (2019-12-19)
Despite their great importance for human therapy, quinolones are still used in Chilean salmon farming, with flumequine and oxolinic acid currently approved for use in this industry. The aim of this study was to improve our knowledge of the mechanisms

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