ChemicalBook--->CAS DataBase List--->1742-95-6

1742-95-6

1742-95-6 Structure

1742-95-6 Structure
IdentificationBack Directory
[Name]

4-AMINO-1,8-NAPHTHALIMIDE
[CAS]

1742-95-6
[Synonyms]

dfp1
4-ANI
TIMTEC-BB SBB003425
4-amino-naphthalimid
4-aminonaphthalimide
4-AMINO-1,8-NAPHTHALIMIDE
4-AMINO-1,8-NAPHTHALIMIDE 98%
4-Amino-1,8-naphthalimide,98%
4-Amino-1,8-naphthalenedicarbimide
4-Aminonaphthalene-1,8-dicarbimide
4-Amino-1,8-naphthalenedicarboximide
4-aminonaphthalene-1,8-dicarboximide
6-AMINO-BENZO[DE]ISOQUINOLINE-1,3-DIONE
6-Amino-2H-benzo[de]isoquinoline-1,3-dione
6-amino-1h-benz(de)isoquinoline-3(2h)-dione
6-amino-1h-benz[de]isoquinoline-3(2h)-dione
6-amino-1h-benz(de)isoquinoline-1,3(2h)-dione
3(2H)-dione,6-amino-1H-Benz[de]isoquinoline-1
1H-Benzdeisoquinoline-1,3(2H)-dione, 6-amino-
6-AMino-1H-benzo[de]isoquinoline-1,3(2H)-dione
6-Amino-2,3-dihydro-1H-benzo[de]isoquinoline-1,3-dione
[EINECS(EC#)]

217-110-1
[Molecular Formula]

C12H8N2O2
[MDL Number]

MFCD00006921
[MOL File]

1742-95-6.mol
[Molecular Weight]

212.2
Chemical PropertiesBack Directory
[Appearance]

orange amorphous powder
[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)
Hazard InformationBack Directory
[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.
[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.
[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.
[storage]

Store at -20°C
[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.
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-37/39
[WGK Germany ]

3
[RTECS ]

DE4081000
[TSCA ]

Yes
[HS Code ]

29251995
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Acetic acid-->Nitric acid-->Ammonia-->Sodium dichromate dihydrate-->ACENAPHTHYLENE
Spectrum DetailBack Directory
[Spectrum Detail]

4-AMINO-1,8-NAPHTHALIMIDE(1742-95-6)MS
4-AMINO-1,8-NAPHTHALIMIDE(1742-95-6)1HNMR
4-AMINO-1,8-NAPHTHALIMIDE(1742-95-6)IR1
4-AMINO-1,8-NAPHTHALIMIDE(1742-95-6)Raman
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