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