1742-95-6

Basic information

• Product Name: 4-AMINO-1,8-NAPHTHALIMIDE
• Synonyms: 6-amino-1h-benz(de)isoquinoline-3(2h)-dione;6-amino-1h-benz[de]isoquinoline-3(2h)-dione;dfp1;6-AMINO-BENZO[DE]ISOQUINOLINE-1,3-DIONE;4-ANI;4-AMINO-1,8-NAPHTHALIMIDE;4-aminonaphthalene-1,8-dicarboximide;4-AMINO-1,8-NAPHTHALIMIDE 98%
• CAS NO: 1742-95-6
• Molecular Formula: C₁₂H₈N₂O₂
• Molecular Weight: 212.2
• EINECS: 217-110-1
• Product Categories: 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
• Mol File: 1742-95-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 360 °C
• Boiling Point: 352.04°C (rough estimate)
• Flash Point: 282.8 °C
• Appearance: orange amorphous powder
• Density: 1.105 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.75E-12mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO
• PKA: 9.53±0.20(Predicted)
• Water Solubility: 354mg/L at 25℃
• CAS DataBase Reference: 4-AMINO-1,8-NAPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-1,8-NAPHTHALIMIDE(1742-95-6)
• EPA Substance Registry System: 4-AMINO-1,8-NAPHTHALIMIDE(1742-95-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: DE4081000
• TSCA: Yes
• Hazardous Substances Data: 1742-95-6(Hazardous Substances Data)

Usage

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.

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.

InChI:InChI=1/C12H8N2O2/c13-9-5-4-8-10-6(9)2-1-3-7(10)11(15)14-12(8)16/h1-5H,13H2,(H,14,15,16)

Upstream product

• 39061-35-3 4-nitro-1,8-naphthalic anhydride 
• 6492-86-0 4-amino-1,8-naphthalic anhydride 
• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 52559-36-1 4-bromonaphthalene-1,8-dicarboximide 
• 6642-29-1 4-nitronaphthalic-1,8-anhydride 
• 26848-63-5 4-sulfo-naphthalene-1,8-dicarboxylic acid 

Downstream Products

• 1103778-33-1 4-(2-bromobenzyl)amino-N-(4'-Boc-aminomethylbenzyl)-1,8-naphthalimide 
• 1103778-30-8 4-amino-N-(4'-Boc-aminomethylbenzyl)-1,8-naphthalimide 
• 943530-68-5 4-[(2-bromobenzyl)(methyl)amino]-N-benzyl-1,8-naphthalimide 
• 943530-67-4 4-[benzyl(2-bromobenzyl)amino]-N-benzyl-1,8-naphthalimide 
• 943530-66-3 4-[(2-bromobenzyl)amino]-N-benzyl-1,8-naphthalimide 
• 1026163-02-9 4-[(2-bromobenzyl)amino]-N-(methoxymethyl)-1,8-naphthalimide 
• 943530-71-0 C₃₂H₃₁BN₂O₄ 
• 943530-69-6 C₃₈H₃₅BN₂O₄ 
• 926649-39-0 C₄₇H₅₇BrN₂O₄ 
• 34418-97-8 6-amino-2-benzyl-1Hbenzo[de]isoquinoline-1,3(2H)-dione 
• 893421-20-0 1,4-dibromo-2-octyloxy-5-(2-(4-amino-1,8-naphthalimide-9-yl)ethyloxy)benzene 

Relevant articles and documents

15N-,13C- and 1H-NMR Spectroscopy characterization and growth inhibitory potency of a combi-molecule synthesized by acetylation of an unstable monoalkyltriazene

6-(3-Methyltriaz-1-en-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione referred to as EG22 (8a), is an open-chain 3-alkyl-1,2,3-triazene termed “combi-molecule” designed to inhibit poly(adenosine diphosphate ribose) polymerase (PARP) and damage DNA. To delay its hydrolysis, acetylation of N3 was required. Being a monoalkyl-1,2,3-triazene, EG22 could assume two tautomers in solution or lose nitrogen during the reaction, thereby leading to several acetylated compounds. Instead, one compound was observed and to unequivocally assign its structure, we introduced isotopically labeled reagents in its preparation, with the purpose of incorporating 15N at N2 and 13C in the 3-methyl group. The results showed that the 1,2,3-triazene moiety remained intact, as confirmed by 15N-NMR, coupling patterns between the 15N-labeled N2 and the 13C-labeled methyl group. Furthermore, we undertook heteronuclear single quantum coherence (HSQC) and heteronuclear multiple bond correlation (HMBC) experiments that permitted the detection and assignment of all four nitrogens in 6-(3-acetyl-3-methyltriaz-1-en-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione, referred to as ZSM02 (9a), whose structure was further confirmed by X-ray crystallography. The structure showed a remarkable coplanarity between the N-acetyltriazene and the naphtalimide moiety. Thus, we unequivocally assigned 9a as the product of the reaction and compared its growth inhibitory activity with that of its precursor, EG22. ZSM02 exhibited identical growth inhibitory profile as EG22, suggesting that it may be a prodrug of EG22.

Fluorescent compound used for APN inhibitor and application of fluorescent compound

The invention discloses a fluorescent compound used for an APN inhibitor and application of the fluorescent compound. The general molecular formula of the compound is (I) or (II). In the general molecular formula, R1is hydrogen, methyl, ethyl, propyl, butyl, amyl, hexyl, benzyl, 2-amino ethyl, 2, 2-N, N-dimethylethyl or hydroxyl; R2 is hydrogen, halogen or a hydrophilic carboxyl group; and R is methyl or ethyl. The inhibitor can be used as an aminopeptidase N inhibitor, and is used for detecting tissue distribution of aminopeptidase N and cancer cells and Doppler tissue imaging; and the inhibitor can be used as an anti-solid tumor medicine, and is used for detection of abnormal expression of aminopeptidase N and disease diagnosis.

NUCLEOPHILIC DISPLACEMENT OF THE NITRO GROUP IN 2- AND 4-NITRONAPHTHALIC-1,8-ANHYDRIDES AND THEIR DERIVATIVES

The nitro group in 2- and 4-nitronaphthalic-1,8-anhydrides can be substituted by amines in certain cases with retention of the anhydride grouping.