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C0496

Sigma-Aldrich

CRT0044876

≥98% (HPLC)

Synonym(s):

7-Nitro-1H-indole-2-carboxylic acid, 7-Nitroindole-2carboxylic acid, NSC 69877

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About This Item

Empirical Formula (Hill Notation):
C9H6N2O4
CAS Number:
6960-45-8
Molecular Weight:
206.15
EC Number:
230-154-6
MDL number:
MFCD00044720
UNSPSC Code:
12352200
PubChem Substance ID:
329774800
NACRES:
NA.25

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: >20 mg/mL

storage temp.

room temp

SMILES string

OC(=O)c1cc2cccc([N+]([O-])=O)c2[nH]1

InChI

1S/C9H6N2O4/c12-9(13)6-4-5-2-1-3-7(11(14)15)8(5)10-6/h1-4,10H,(H,12,13)

InChI key

BIUCOFQROHIAEO-UHFFFAOYSA-N

Biochem/physiol Actions

CRT0044876 targets the apurinic endonuclease (APE1) active site and inhibits its 3′-phosphodiesterase and 3′-phosphatase activities—essential steps in excision repair—with minimal effects on endonuclease IV, BamH1 restriction endonuclease, or topoisomerase I even at concentrations as high as 100 μM. At non-cytotoxic concentrations, CRT0044876 potentiates the cytotoxicity of several DNA base-targeting compounds, with accumulation of apurinic sites.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H319,H334

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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De-Sheng Pei et al.
Nucleic acids research, 39(8), 3156-3165 (2010-12-22)
DNA repair is required to maintain genome stability in stem cells and early embryos. At critical junctures, oxidative damage to DNA requires the base excision repair (BER) pathway. Since early zebrafish embryos lack the major polymerase in BER, DNA polymerase
Junqiu Zhai et al.
Nucleic acids research, 45(6), e45-e45 (2016-12-08)
Human apurinic/apyrimidinic endonuclease/redox effector factor 1 (APE1) is an essential DNA repair protein. Herein, we demonstrate that avidin-oriented abasic site-containing DNA strands (AP-DNA) on the surface of silica coated magnetic nanoparticles (SiMNP) can selectively respond to APE1 while resist the
Jeroen E J Guikema et al.
The Journal of experimental medicine, 204(12), 3017-3026 (2007-11-21)
Antibody class switch recombination (CSR) occurs by an intrachromosomal deletion requiring generation of double-stranded breaks (DSBs) in switch-region DNA. The initial steps in DSB formation have been elucidated, involving cytosine deamination by activation-induced cytidine deaminase and generation of abasic sites
Prachi Verma et al.
Biochimie, 144, 122-133 (2017-11-04)
Dihydroxy-1-selenolane (DHS) previously reported to exhibit radioprotective activity was investigated to understand its mechanism of action in CHO cells of epithelial origin. DHS pre-treatment at 25 μM for 16 h significantly protected CHO cells from radiation (4-11 Gy)-induced delayed mitotic cell death. Further
Leonardo Pereira Franchi et al.
Journal of photochemistry and photobiology. B, Biology, 211, 111992-111992 (2020-08-18)
Photodynamic therapy (PDT) is an anticancer modality depicting an induced oxidative stress as the mechanism of action that ultimately culminates in cell death. The apurinic/apyrimidinic endonuclease 1/redox factor-1 (APE1/Ref-1) is a key protein promoting bad prognostic in several cancer types.
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