4-AMINO-1,8-NAPHTHALIMIDE

CAS NO.：1742-95-6
Empirical Formula: C12H8N2O2
Molecular Weight: 212.2
MDL number: MFCD00006921
EINECS: 217-110-1
SAFETY DATA SHEET (SDS)
Update Date: 2026-03-13 23:13:44

What is 4-AMINO-1,8-NAPHTHALIMIDE?

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

The Uses of 4-AMINO-1,8-NAPHTHALIMIDE

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.

What are the applications of Application

4-Amino-1,8-naphthalimide is a PARP-1 inhibitor

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.

Properties of 4-AMINO-1,8-NAPHTHALIMIDE

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)
color	Yellow to brown
Water Solubility	354mg/L at 25℃
CAS DataBase Reference	1742-95-6
EPA Substance Registry System	1H-Benz[de]isoquinoline-1,3(2H)-dione, 6-amino- (1742-95-6)

Safety information for 4-AMINO-1,8-NAPHTHALIMIDE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.