ChemicalBook > CAS DataBase List > 4-AMINO-1,8-NAPHTHALIMIDE

4-AMINO-1,8-NAPHTHALIMIDE

Product Name
4-AMINO-1,8-NAPHTHALIMIDE
CAS No.
1742-95-6
Chemical Name
4-AMINO-1,8-NAPHTHALIMIDE
Synonyms
dfp1;4-ANI;TIMTEC-BB SBB003425;4-aminonaphthalimide;4-amino-naphthalimid;4-AMINO-1,8-NAPHTHALIMIDE;4-Amino-1,8-naphthalimide,98%;4-AMINO-1,8-NAPHTHALIMIDE 98%;4-amino-1-hydroxy-7H-purin-6-ol;4-Amino-1,8-naphthalenedicarbimide
CBNumber
CB0774002
Molecular Formula
C12H8N2O2
Formula Weight
212.2
MOL File
1742-95-6.mol
More
Less

4-AMINO-1,8-NAPHTHALIMIDE Property

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℃
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)
More
Less

Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39
WGK Germany 
3
RTECS 
DE4081000
TSCA 
Yes
HS Code 
29251995
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A0966
Product name
4-Amino-1,8-naphthalimide
Packaging
20mg
Price
$169
Updated
2024/03/01
Alfa Aesar
Product number
J64358
Product name
4-Amino-1,8-naphthalimide, 95%
Packaging
100mg
Price
$48.65
Updated
2024/03/01
Alfa Aesar
Product number
J64358
Product name
4-Amino-1,8-naphthalimide, 95%
Packaging
1g
Price
$201.65
Updated
2024/03/01
Cayman Chemical
Product number
18509
Product name
4-amino-1,8-Naphthalimide
Purity
≥95%
Packaging
10mg
Price
$44
Updated
2024/03/01
Cayman Chemical
Product number
18509
Product name
4-amino-1,8-Naphthalimide
Purity
≥95%
Packaging
50mg
Price
$193
Updated
2024/03/01
More
Less

4-AMINO-1,8-NAPHTHALIMIDE Chemical Properties,Usage,Production

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

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.

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.

4-AMINO-1,8-NAPHTHALIMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

4-AMINO-1,8-NAPHTHALIMIDE Suppliers

Carbosynth
Tel
--
Fax
--
Email
sales@carbosynth.com
Country
United Kingdom
ProdList
6005
Advantage
58
Apin Chemicals Limited (UK)
Tel
--
Fax
--
Email
info@apinchemicals.com
Country
United Kingdom
ProdList
6184
Advantage
60
CARBONE SCIENTIFIC CO.,LTD
Tel
--
Fax
--
Email
sales@carbonesci.com
Country
United Kingdom
ProdList
6666
Advantage
30

1742-95-6, 4-AMINO-1,8-NAPHTHALIMIDERelated Search:


  • 4-Amino-1,8-naphthalenedicarbimide
  • 4-Amino-1,8-naphthalenedicarboximide
  • 4-Aminonaphthalene-1,8-dicarbimide
  • 6-Amino-2,3-dihydro-1H-benzo[de]isoquinoline-1,3-dione
  • 6-Amino-2H-benzo[de]isoquinoline-1,3-dione
  • 4-Amino-1,8-naphthalimide,98%
  • 6-amino-1h-benz(de)isoquinoline-3(2h)-dione
  • 6-amino-1h-benz[de]isoquinoline-3(2h)-dione
  • 4-aminonaphthalimide
  • 6-amino-1h-benz(de)isoquinoline-1,3(2h)-dione
  • 6-AMino-1H-benzo[de]isoquinoline-1,3(2H)-dione
  • 4-amino-1-hydroxy-7H-purin-6-ol
  • 4-aminonaphthalene-1,8-dicarboximide
  • dfp1
  • 6-AMINO-BENZO[DE]ISOQUINOLINE-1,3-DIONE
  • 4-ANI
  • 4-AMINO-1,8-NAPHTHALIMIDE
  • 1H-Benzdeisoquinoline-1,3(2H)-dione, 6-amino-
  • 4-AMINO-1,8-NAPHTHALIMIDE 98%
  • TIMTEC-BB SBB003425
  • 3(2H)-dione,6-amino-1H-Benz[de]isoquinoline-1
  • 4-amino-naphthalimid
  • 10-amino-3-azatricyclo[7.3.1.0,13]trideca-1(13),5,7,9,11-pentaene-2,4-dione
  • 4-Aminonaphthalin-1,8-dicarboximid
  • Inhibitor,4amino1,8Naphthalimide,4-Aminonaphthalimide,PARP,inhibit,poly ADP ribose polymerase,4 amino 1,8 Naphthalimide
  • 4-Aminonaphthalimide, PARP-1 inhibitor
  • 1742-95-6
  • PARP Regulators
  • PARP
  • Cell Signaling and Neuroscience
  • Cell Biology
  • BioChemical
  • Apoptosis and Cell Cycle
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • PARP (Poly(ADP-Ribose) polymerase)
  • PARP InhibitorsEnzyme Inhibitors by Enzyme
  • PARP Poly(ADP-ribose) PolymeraseCancer Research
  • Antitumor Agents
  • Apoptosis and Cell Cycle
  • P to
  • Therapy Adjuncts