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Merck
CN

I2784

Sigma-Aldrich

INH2BP

≥98% (HPLC), solid

Synonym(s):

5-Iodo-6-amino-1,2-benzopyrone

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About This Item

Empirical Formula (Hill Notation):
C9H6INO2
CAS Number:
137881-27-7
Molecular Weight:
287.05
MDL number:
MFCD00912555
UNSPSC Code:
12352202
PubChem Substance ID:
24724511

Key Documents

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Assay

≥98% (HPLC)

form

solid

solubility

DMSO: soluble 31 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

Nc1ccc2OC(=O)C=Cc2c1I

InChI

1S/C9H6INO2/c10-9-5-1-4-8(12)13-7(5)3-2-6(9)11/h1-4H,11H2

InChI key

WWRAFPGUBABZSD-UHFFFAOYSA-N

Biochem/physiol Actions

Inhibitor of poly (ADP-ribose) polymerase-1 (PARP-1); anti-apoptotic.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
035K4713

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C Szabó et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(7), 3867-3872 (1998-05-09)
Peroxynitrite, a cytotoxic oxidant formed from nitric oxide (NO) and superoxide, induces DNA strand breakage, which activates the nuclear enzyme poly(ADP-ribose) synthase (PARS; EC 2.4.2.30). The cellular function of PARS was determined in fibroblast lines from PARS knockout animals (PARS-/-)
Raquel M Forsythe et al.
Shock (Augusta, Ga.), 17(3), 180-184 (2002-03-20)
Studies indicate that endotoxin (LPS) causes intestinal injury, increases inducible nitric oxide synthase (iNOS) activity, leads to increased NO production, and promotes bacterial translocation (BT). To investigate the mechanism by which LPS causes gut injury and to test the hypothesis
P I Bauer et al.
Biochimie, 77(5), 374-377 (1995-01-01)
A non-covalently binding inhibitory ligand of poly(ADP-ribose) polymerase, 5-iodo-6-amino-1,2-benzopyrone, when incubated at 5-600 microM external concentration with an E-ras-transformed tumorigenic cell line or with human prostatic carcinoma cells for 40 to 60 days converts both cancer cells to a non-tumorigenic
G S Scott et al.
Journal of neuroimmunology, 117(1-2), 78-86 (2001-06-30)
Peroxynitrite formation has been demonstrated during experimental allergic encephalomyelitis (EAE). Furthermore, peroxynitrite has been identified as an activator of poly(ADP-ribose) synthetase (PARS), an enzyme implicated in neurotoxicity. In the current study, we examined the role of PARS activation in the
Lina Du et al.
The Journal of biological chemistry, 278(20), 18426-18433 (2003-03-11)
Poly(ADP-ribosylation), primarily via poly(ADP-ribose) polymerase-1 (PARP-1), is a pluripotent cellular process important for maintenance of genomic integrity and RNA transcription in cells. However, during conditions of oxidative stress and energy depletion, poly(ADP-ribosylation) paradoxically contributes to mitochondrial failure and cell death.
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