1,5-ISOQUINOLINEDIOL

Product Name1,5-ISOQUINOLINEDIOL
CAS5154-02-9
MFC9H7NO2
MW161.16
EINECS637-104-6
MOL File5154-02-9.mol

Chemical Properties

Melting point	270-275 °C
Boiling point	287.44°C (rough estimate)
Density	1.2480 (rough estimate)
refractive index	1.5050 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	DMSO: >36 mg/mL
form	solid
pka	8.52±0.20(Predicted)
color	off-white
InChI	InChI=1S/C9H7NO2/c11-8-3-1-2-7-6(8)4-5-10-9(7)12/h1-5,11H,(H,10,12)
InChIKey	LFUJIPVWTMGYDG-UHFFFAOYSA-N
SMILES	C1(=O)C2=C(C(O)=CC=C2)C=CN1
CAS DataBase Reference	5154-02-9(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	3
HS Code	29337900
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English

Usage And Synthesis

Description

The poly(ADP-ribose) polymerases (PARPs) form a family of enzymes with roles in DNA repair and apoptosis. 1,5-Isoquinolinediol is an inhibitor of poly(ADP-ribose) synthetase (PARP1; IC₅₀ = 0.39 μM). It has been used to study the role of PARP1 in both DNA repair and oxidant stress-induced cell death. This compound can be used with cells in culture and in animals.

Chemical Properties

white to off-white solid

Uses

Reagent used in the preparation of PARP inhibitor.

Uses

1,5-Isoquinolinediol can be used as a reagent in the preparation of PARP inhibitor.

Definition

ChEBI: An isoquinolinol that is isoquinoline in which the hydrogens at positions 1 and 5 are replaced by hydroxy groups.

General Description

A potent inhibitor of poly(ADP-ribose) polymerase (PARP; IC₅₀ = 390 nM). Reported to partially block SNAP (CN 487910)- induced cell death in SH-SYSY human neuroblastoma cells.

Biochem/physiol Actions

Cell permeable: yes

storage

+4°C

References

[1] M BANASIK. Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase.[J]. The Journal of Biological Chemistry, 1992, 267 3: 1569-1575.
[2] T RUSCETTI. Stimulation of the DNA-dependent protein kinase by poly(ADP-ribose) polymerase.[J]. The Journal of Biological Chemistry, 1998, 273 23: 14461-14467. DOI: 10.1074/jbc.273.23.14461
[3] PRABAL K. CHATTERJEE. Inhibitors of poly (ADP-ribose) synthetase reduce renal ischemia-reperfusion injury in the anesthetized rat in vivo[J]. FASEB Journal, 2000, 14 5: 641-651. DOI: 10.1096/fasebj.14.5.641
[4] J BOWES. Inhibitors of poly (ADP-ribose) synthetase protect rat cardiomyocytes against oxidant stress.[J]. Cardiovascular Research, 1999, 41 1: 126-134. DOI: 10.1016/s0008-6363(98)00221-1
[5] JOO-YUN BYUN. Reactive oxygen species-dependent activation of Bax and poly(ADP-ribose) polymerase-1 is required for mitochondrial cell death induced by triterpenoid pristimerin in human cervical cancer cells.[J]. Molecular Pharmacology, 2009, 76 4: 734-744. DOI: 10.1124/mol.109.056259
[6] YOUNG-HEE KANG. Caspase-independent cell death by arsenic trioxide in human cervical cancer cells: reactive oxygen species-mediated poly(ADP-ribose) polymerase-1 activation signals apoptosis-inducing factor release from mitochondria.[J]. Cancer research, 2004, 64 24: 8960-8967. DOI: 10.1158/0008-5472.can-04-1830

1,5-ISOQUINOLINEDIOL

Chemical Properties

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Usage And Synthesis

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