1,5-IsoquinolinediolAn inhibitor of PARP, NOS-2, and PARS

1,5-Isoquinolinediol (CAS 5154-02-9)

1,5-Isoquinolinediol | CAS 5154-02-9 is rated 5.0 out of 5 by 1.
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Synonym: 1,5-Dihydroxyisoquinoline; 5-Hydroxy-1(2H)-isoquinolinone; DiQ
Application: An inhibitor of PARP, NOS-2, and PARS
CAS Number: 5154-02-9
Purity: ≥97%
Molecular Weight: 161.2
Molecular Formula: C9H7NO2
* Refer to Certificate of Analysis for lot specific data (including water content).
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1,5-Isoquinolinediol is a small molecule with cell protective and neuroprotective properties. 1,5-isopuinolinediol is an inhibitor of both PARP-1 (poly (ADP-ribose) polymerase-1) and NOS2 (inducible nitric oxide synthase). PARP and NOS2 activations are implicated in deleterious inflammatory responses and suppression of their activity by 1,5 isoquinolinediol has been correlated to cellular protection and survival. The DNA excision-repair enzyme PARP (poly (ADP-ribose) synthetase, PARS) is activated by free radical oxidative cleavage of the DNA backbone, and excessive PARS activation leads to deplation of cellular NAD and ATP, progressing to cell death. A study demonstrates taht 1,5-isoquinolinediol protects against the neurotoxicity generated by NO-induced PARS activation and by NMDA in rat brain neurons. The Inhibition of PARP by 1,5-isoquinolinediol has also been correlated to a decrease in illegitimate recombination in gene targeting techniques, increasing the efficiency of specific alterations to chromosomal DNA.


References

1. Banasik, M., et al. 1992. J. Biol. Chem. 267: 1569-1575. PMID: 1530940
2. Zhang, J., et al. 1994. Science. 263: 687-689. PMID: 8080500
3. Dalmau, M., et al. 1996. Exp. Cell Res. 228: 14-18. PMID: 8892965
4. Semionov, A., et al. 2003. Biochem. Cell Biol. 81: 17-24. PMID: 12683632
5. Olszanecki, R., et al. 2006. J. Physiol. Pharmacol. 57: 109-117. PMID: 16601319

Physical State :
Solid
Solubility :
Soluble in DMSO (25 mg/ml), dimethyl formamide (25 mg/ml), warm ethanol (25 mg/ml), 0.1N NaOH (5.3 mg/ml), methanol (8 mg/ml), and water (partly miscible). Insoluble in 0.1N HCl.
Storage :
Store at room temperature
Melting Point :
279-281° C
Boiling Point :
~501.1° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.74
IC50 :
Poly [ADP-ribose] polymerase-1: IC50 = 390 nM (human); H9c2 (Cardiomyoblast cells): IC50 = 31267 nM (rat)
pK Values :
pKa: 8.38, pKb: 10.81
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
1340
MDL Number :
MFCD00006900
SMILES :
C1=CC2=C(C=CNC2=O)C(=C1)O

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Certificate of Analysis

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1,5-Isoquinolinediol  Product Citations

See how others have used 1,5-Isoquinolinediol. Click on the entry to view the PubMed entry .

Citations 1 to 4 of 4 total

PMID: # 28576564  Pant, R. et al. 2017. Neurosci. Lett. 653: 208-214.

PMID: # 24347828  Mohammad, G. et al. 2013. Mediators of inflammation. 2013: 510451.

PMID: # 18082271  Kujundzić, RN. et al. 2008. Immunol. Lett. 115: 153-159.

PMID: # 12897160  Leppard, JB. et al. 2003. Mol. Cell. Biol. 23: 5919-5927.

Citations 1 to 4 of 4 total
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Rated 5 out of 5 by from Leppard et al Leppard et al. (PubMed ID 12897160) used 1, 5-isoquinolinediol, a PARP-1 inhibitor, to prevent DNA damage-dependent association between DNA ligase III -XRCC1 complex and PARP-1. -SCBT Publication Review
Date published: 2015-05-31
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