4-AMINO-1,8-NAPHTHALIMIDE

Names

[ Name ]:
4-AMINO-1,8-NAPHTHALIMIDE

[Synonym ]:
6-aminobenzo[de]isoquinoline-1,3-dione
EINECS 217-092-5
4-Amino-1,8-naphthalimide
6-Amino-1H-benzo[de]isoquinoline-1,3(2H)-dione
MFCD00001892

Biological Activity

[Description]:

4-Aminonaphthalimide is a potent PARP inhibitor and potentiates the cytotoxicity of γ-radiation in cancer cells[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Epigenetics >> PARP

Signaling Pathways >> Cell Cycle/DNA Damage >> PARP

[References]

[1]. Schlicker 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.

Chemical & Physical Properties

[ Density]:
1.105 g/mL at 25ºC(lit.)

[ Boiling Point ]:
544.1ºC at 760 mmHg

[ Melting Point ]:
360ºC

[ Molecular Formula ]:
C₁₂H₈N₂O₂

[ Molecular Weight ]:
212.20

[ Flash Point ]:
282.8ºC

[ Exact Mass ]:
212.05900

[ PSA ]:
75.95000

[ LogP ]:
1.64270

[ Vapour Pressure ]:
6.75E-12mmHg at 25°C

[ Index of Refraction ]:
1.764

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DE4081000

CHEMICAL NAME :: 1H-Benz(de)isoquinoline-1,3(2H)-dione, 6-amino-

CAS REGISTRY NUMBER :: 1742-95-6

BEILSTEIN REFERENCE NO. :: 0177185

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H8-N2-O2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GISAAA Gigiena i Sanitariya. For English translation, see HYSAAV. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1936- Volume(issue)/page/year: 42(1),111,1977

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DE4081000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

A new polymerizable fluorescent PET chemosensor of fluoride (F-) based on naphthalimide-thiourea dye.

Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 90 , 85-92, (2012)

A novel N-allyl-4-amino-substituted 1,8-naphthalimide dye, containing thiourea functional group with intense yellow-green fluorescence was successfully synthesized. Copolymerization was done with styr...

Preventing oxidation of cellular XRCC1 affects PARP-mediated DNA damage responses.

DNA Repair (Amst.) 12(9) , 774-85, (2013)

Poly(ADP-ribose) polymerase-1 (PARP-1) binds intermediates of base excision repair (BER) and becomes activated for poly(ADP-ribose) (PAR) synthesis. PAR mediates recruitment and functions of the key B...

[Effect of PARP-1 inhibitor 4-amino-1 ,8-naphthalimide on the on the sensitivity of adriamycin].

Wei Sheng Yan Jiu 41(2) , 173-9, (2012)

To explore the effect of inhibition of poly (ADP-ribose) polymerase-1 (PARP-1) on the sensitivity of cells to adriamycin (ADM).Mouse embryonic fibroblasts (MEFs) were divided into two groups according...