4-AMINO-1,8-NAPHTHALIMIDE Struktur

4-Aminonaphthalin-1,8-dicarboximid

Bezeichnung:4-Aminonaphthalin-1,8-dicarboximid

CAS-Nr1742-95-6

Englisch Name:4-AMINO-1,8-NAPHTHALIMIDE

CBNumberCB0774002

SummenformelC12H8N2O2

Molgewicht212.2

MOL-Datei1742-95-6.mol

Synonyma

4-Aminonaphthalin-1,8-dicarboximid

4-Aminonaphthalin-1,8-dicarboximid physikalisch-chemischer Eigenschaften

Schmelzpunkt	360 °C
Siedepunkt	352.04°C (rough estimate)
Dichte	1.105 g/mL at 25 °C(lit.)
Dampfdruck	0Pa at 25℃
Brechungsindex	1.6000 (estimate)
storage temp.	-20°C
Löslichkeit	Soluble in DMSO
Aggregatzustand	Orange solid.
pka	9.53±0.20(Predicted)
Farbe	Yellow to brown
Wasserlöslichkeit	354mg/L at 25℃
LogP	1.08
CAS Datenbank	1742-95-6
EPA chemische Informationen	1H-Benz[de]isoquinoline-1,3(2H)-dione, 6-amino- (1742-95-6)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39
WGK Germany	3
RTECS-Nr.	DE4081000
TSCA	Yes
HS Code	29251995

Gefahreninformationscode (GHS)

4-AMINO-1,8-NAPHTHALIMIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
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.
Chemische Eigenschaften
orange amorphous powder
Verwenden
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.
Enzyminhibitor
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.
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

4-Aminonaphthalin-1,8-dicarboximid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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