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HomeProduct name list4-AMINO-1,8-NAPHTHALIMIDE

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: 2024-11-06 15:28:16
4-AMINO-1,8-NAPHTHALIMIDE Structural

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)
ghs
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.

Computed Descriptors for 4-AMINO-1,8-NAPHTHALIMIDE

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