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Merck
CN

N8010

4-Nitrophenyl 4-guanidinobenzoate hydrochloride

protease substrate, ≥95.0% (TLC), powder

Synonym(s):

4-Guanidinobenzoic acid 4-nitrophenylester hydrochloride, NPGB, pNPGB

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About This Item

Empirical Formula (Hill Notation):
C14H12N4O4 · HCl
CAS Number:
Molecular Weight:
336.73
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352204
EC Number:
242-831-3
MDL number:
Beilstein/REAXYS Number:
8024554
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Product Name

4-Nitrophenyl 4-guanidinobenzoate hydrochloride, protease inhibitor and substrate

InChI key

PKSBDZOBYIKNGY-UHFFFAOYSA-N

InChI

1S/C14H12N4O4.ClH/c15-14(16)17-10-3-1-9(2-4-10)13(19)22-12-7-5-11(6-8-12)18(20)21;/h1-8H,(H4,15,16,17);1H

SMILES string

Cl[H].NC(=N)Nc1ccc(cc1)C(=O)Oc2ccc(cc2)[N+]([O-])=O

assay

≥95.0% (TLC)

form

powder

solubility

formic acid: soluble 49.00-51.00 mg/mL

storage temp.

−20°C

Quality Level

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Application

4-Nitrophenyl 4-guanidinobenzoate hydrochloride has been used:
  • as a substrate for trypsin for active site titration experiments
  • for pre-treating of mosquito eggs in the interplasmid transposition assay
  • as a component of isotonic buffer to moisten filter paper for mosquito embryo collection

Biochem/physiol Actions

4-Nitrophenyl 4-guanidinobenzoate hydrochloride (pNPGB) inhibits phenoloxidase enzyme and delays embryo chorionic membrane hardening.

General description

4-Nitrophenyl 4-guanidinobenzoate hydrochloride (pNPGB) is a trypsin substrate. It is more water-soluble than 4-methylumbelliferyl 4-guanidinobenzoate and is preferred in spectrophotometric assay.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Studies on the Molecular Mechanism of Mersalyl and 4-Aminophenylmercuric Acetate Re-activation of Trypsin-Thiol Complexes
STEVEN FS and GRIFFIN MM
European Journal of Biochemistry, 109(2), 567-573 (1980)
J E Dravland et al.
The Journal of experimental zoology, 232(1), 117-128 (1984-10-01)
Previous studies from this laboratory have suggested a role for sperm trypsinlike activity in the membrane events of the hamster sperm acrosome reaction, but these conclusions have been disputed by studies done with guinea pig, mouse, and ram sperm. This
Mekdes Debela et al.
Scientific reports, 8(1), 10705-10705 (2018-07-18)
Human KLK8/neuropsin, a kallikrein-related serine peptidase, is mostly expressed in skin and the hippocampus regions of the brain, where it regulates memory formation by synaptic remodeling. Substrate profiles of recombinant KLK8 were analyzed with positional scanning using fluorogenic tetrapeptides and
D Collen et al.
The Journal of biological chemistry, 268(11), 8284-8289 (1993-04-15)
The mechanism of activation of human plasminogen by recombinant staphylokinase (STAR) was studied using the active site titrant p-nitrophenyl-p'-guanidinobenzoate (NPGB). NPGB prevented active site exposure in equimolar mixtures of plasminogen and STAR but reacted stoichiometrically with mixtures preincubated in the
S P Leytus et al.
Biochimica et biophysica acta, 788(1), 74-86 (1984-07-17)
A theory and experimental method are presented to characterize the kinetics of fast-acting, irreversible proteinase inhibitors. The theory is based upon formal analysis of the case of an irreversible inhibitor competing with a substrate for the active-site of a proteinase.

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