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P4157

Phe-Arg β-naphthylamide dihydrochloride

Name: Phe-Arg &#946;-naphthylamide dihydrochloride
Brand: SIGMA

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

Synonym(s):

PAβN

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About This Item

Empirical Formula (Hill Notation):

C₂₅H₃₀N₆O₂ · 2HCl

CAS Number:

100929-99-5

Molecular Weight:

519.47

UNSPSC Code:

12352204

PubChem Substance ID:

24898508

NACRES:

NA.32

MDL number:

MFCD00058046

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Product Name

Phe-Arg β-naphthylamide dihydrochloride, cathepsin substrate

Quality Level

200

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.

Substrate for dipeptidyl aminopeptidase I (cathepsin C).

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

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)

Structure and function relationship of OqxB efflux pump from Klebsiella pneumoniae.

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

Characterization of Mechanisms Lowering Susceptibility to Flumequine among Bacteria Isolated from Chilean Salmonid Farms.

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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Global Trade Item Number

SKU	GTIN
P4157-25MG	04061834373643
P4157-250MG	04061834373636

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