Basic information Safety Supplier Related

4-AMINO-1,8-NAPHTHALIMIDE

Basic information Safety Supplier Related

4-AMINO-1,8-NAPHTHALIMIDE Basic information

Product Name:
4-AMINO-1,8-NAPHTHALIMIDE
Synonyms:
  • 4-Amino-1,8-naphthalenedicarbimide
  • 4-Amino-1,8-naphthalenedicarboximide
  • 4-Aminonaphthalene-1,8-dicarbimide
  • 6-Amino-2,3-dihydro-1H-benzo[de]isoquinoline-1,3-dione
  • 6-Amino-2H-benzo[de]isoquinoline-1,3-dione
  • 4-Amino-1,8-naphthalimide,98%
  • 6-amino-1h-benz(de)isoquinoline-3(2h)-dione
  • 6-amino-1h-benz[de]isoquinoline-3(2h)-dione
CAS:
1742-95-6
MF:
C12H8N2O2
MW:
212.2
EINECS:
217-110-1
Product Categories:
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • PARP (Poly(ADP-Ribose) polymerase)
  • PARP InhibitorsEnzyme Inhibitors by Enzyme
  • PARP Poly(ADP-ribose) PolymeraseCancer Research
  • Antitumor Agents
  • Apoptosis and Cell Cycle
  • P to
  • Therapy Adjuncts
Mol File:
1742-95-6.mol
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4-AMINO-1,8-NAPHTHALIMIDE Chemical Properties

Melting point:
360 °C
Boiling point:
352.04°C (rough estimate)
Density 
1.105 g/mL at 25 °C(lit.)
vapor pressure 
0Pa at 25℃
refractive index 
1.6000 (estimate)
storage temp. 
-20°C
solubility 
Soluble in DMSO
form 
Orange solid.
pka
9.53±0.20(Predicted)
Water Solubility 
354mg/L at 25℃
LogP
1.08
CAS DataBase Reference
1742-95-6
EPA Substance Registry System
1H-Benz[de]isoquinoline-1,3(2H)-dione, 6-amino- (1742-95-6)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39
WGK Germany 
3
RTECS 
DE4081000
TSCA 
Yes
HS Code 
29251995

MSDS

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4-AMINO-1,8-NAPHTHALIMIDE Usage And Synthesis

Description

The poly(ADP-ribose) polymerases (PARPs) form a family of enzymes with roles in DNA repair and apoptosis, particularly in response to reactive oxygen and nitrogen species. 4-amino-1,8-Naphthalimide (4-ANI) is an inhibitor of PARP (IC50 = 180 nM). It blocks radiation-induced PARP in cancer cells, potentiating the cytotoxicity of γ-radiation, although it is not cytotoxic in the absence of radiation. 4-ANI is used to study the role of PARP activity in various cell systems.

Chemical Properties

orange amorphous powder

Uses

The poly(ADP-ribose) polymerases (PARPs) form a family of enzymes with roles in DNA repair and apoptosis, particularly in response to reactive oxygen and nitrogen species. 4-amino-1,8-Naphthalimide (4-ANI) is an inhibitor of PARP (IC50 = 180 nM). It blocks radiation-induced PARP in cancer cells, potentiating the cytotoxicity of γ-radiation, although it is not cytotoxic in the absence of radiation. 4-ANI is used to study the role of PARP activity in various cell systems.

Definition

ChEBI: 4-amino-1,8-naphthalimide is a benzoisoquinoline and a dicarboximide.

Biochem/physiol Actions

4-Amino-1,8-naphthalimide sensitizes cells to radiation-induced cell damage and enhances the cytotoxicity of 1-methyl-3-nitro-1-nitrosoguanidine.

Enzyme inhibitor

This PARP inhibitor (FW = 212.21 g/mol) is a strong inhibitor of NAD:ADP-ribosyltransferase or poly(ADP-ribose) polymerase (IC50 = 0.18 μM). In addition, 4-Amino-1,8-naphthalimide is a radiation sensitizer at non-toxic and low concentrations.

References

[1]. schlicker a, peschke p, bürkle a, et al. 4-amino-1,8-naphthalimide: a novel inhibitor of poly(adp-ribose) polymerase and radiation sensitizer. int j radiat biol. 1999 jan;75(1):91-100.
[2]. davar d1, beumer jh, hamieh l, et al. role of parp inhibitors in cancer biology and therapy. curr med chem. 2012;19(23):3907-21.
[3]. banasik m, komura h, shimoyama m,et al. specific inhibitors of poly(adp-ribose) synthetase and mono(adp-ribosyl)transferase. j biol chem. 1992 jan 25;267(3):1569-75.
[4]. issaeva n, thomas hd, djureinovic t, et al. 6-thioguanine selectively kills brca2-defective tumors and overcomes parp inhibitor resistance. cancer res. 2010 aug 1;70(15):6268-76.

4-AMINO-1,8-NAPHTHALIMIDE Preparation Products And Raw materials

Raw materials

4-AMINO-1,8-NAPHTHALIMIDESupplier

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