4-AMINO-1,8-NAPHTHALIMIDE

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

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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)

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Safety

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

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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.

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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

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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

ACENAPHTHYLENE Sodium dichromate dihydrate Nitric acid Acetic acid Ammonia

Preparation Products

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4-AMINO-1,8-NAPHTHALIMIDE Suppliers

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

4-Amino-N-2,4-xylyl-1,8-naphthalimide 4-AMINO-1,8-NAPHTHALIMIDE LUCIFER YELLOW CH DILITHIUM SALT ACID YELLOW 7 1,8-Naphthalimide LUCIFER YELLOW ETHYLENEDIAMINE 6-(4-ACETAMIDO-1 8-NAPHTHALAMIDO) HEXANO LUCIFER YELLOW CADAVERINE H-LYS(DABSYL)-SER-GLU-VAL-ASN-LEU-ASP-ALA-GLU-PHE-ARG-GLN-LUCIFER YELLOW LUCIFER YELLOW CH DIPOTASSIUM SALT LUCIFER YELLOW VS DILITHIUM SALT 4-AMINO-1,8-NAPHTHALIMIDE 4-N,N-BIS-(2-PYRIDYL) AMINO-1,8,NAPHTHALIMIDE 4-(DI-TERT-BUTOXYCARBONYL)AMINO-1,8 –NAPHTHALIMIDE 6-AMINO-2-(3-HYDROXY-PHENYL)-BENZO[DE]ISOQUINOLINE-1,3-DIONE 4-(6-NITRO-1,3-DIOXO-1H,3H-BENZO[DE]ISOQUINOLIN-2-YL)-BENZOIC ACID 6-AMINO-2-(2-HYDROXY-ETHYL)-1,3-DIOXO-2,3-DIHYDRO-1H-BENZO[DE]ISOQUINOLINE-5-SULFONIC ACID 2-(4-AMINOPHENYL)-6-NITRO-1H-BENZO[DE]ISOQUINOLINE-1,3(2H)-DIONE

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