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SML0364

Sigma-Aldrich

RAD51 Inhibitor B02

≥98% (HPLC)

Synonym(s):

3-(Phenylmethyl)-2-[(1E)-2-(3-pyridinyl)ethenyl]-4(3H)-quinazolinone

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About This Item

Empirical Formula (Hill Notation):
C22H17N3O
CAS Number:
Molecular Weight:
339.39
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to dark brown

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

O=C1N(CC2=CC=CC=C2)C(/C=C/C3=CN=CC=C3)=NC4=C1C=CC=C4

InChI

1S/C22H17N3O/c26-22-19-10-4-5-11-20(19)24-21(13-12-17-9-6-14-23-15-17)25(22)16-18-7-2-1-3-8-18/h1-15H,16H2/b13-12+

InChI key

GEKDQXSPTHHANP-OUKQBFOZSA-N

Application

RAD51 Inhibitor B02 has been used:
  • to test its effect on the polar body extrusion (PBE) rate in porcine oocytes
  • for RAD51 inhibition in porcine embryos
  • as RAD51 inhibitor and to test its effect on targeted nucleotide substitution (TNS) in induced pluripotent stem cells (iPSCs)

Biochem/physiol Actions

B02 (3-(Phenylmethyl)-2-[(1E)-2-(3-pyridinyl)ethenyl]-4(3H)-quinazolinone), a pyridinylvinyl-quinazolinone compound is cell-permeable. B02 inhibits human RAD51 recombinase and subsequent nucleofilaments formation. It halts homologous recombination (HR) repair events in cancer cells. B02 favors apoptosis in multiple myeloma and is crucial for sensitizing them to doxorubicin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Ivana Murfuni et al.
PLoS genetics, 9(10), e1003910-e1003910 (2013-11-10)
In checkpoint-deficient cells, DNA double-strand breaks (DSBs) are produced during replication by the structure-specific endonuclease MUS81. The mechanism underlying MUS81-dependent cleavage, and the effect on chromosome integrity and viability of checkpoint deficient cells is only partly understood, especially in human
A small-molecule inhibitor of RAD51 reduces homologous recombination and sensitizes multiple myeloma cells to doxorubicin
Alagpulinsa DA, et al.
Frontiers in Oncology, 4, 289-289 (2014)
RAD51 maintains chromosome integrity and mitochondrial distribution during porcine oocyte maturation in vitro
Jin ZL and Kim NH
Journal of Reproduction and Development (2017)
Inhibition of DNA repair protein RAD51 affects porcine preimplantation embryo development
Jin ZL, et al.
Reproduction (Cambridge, England), 157(3) (2019)
X Chen et al.
Oncogene, 35(1), 22-34 (2015-04-22)
Fanconi anemia (FA) is a genetic disease of bone marrow failure, cancer susceptibility, and sensitivity to DNA crosslinking agents. FANCD2, the central protein of the FA pathway, is monoubiquitinated upon DNA damage, such as crosslinkers and replication blockers such as

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