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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:
1290541-46-6
Molecular Weight:
339.39
MDL number:
MFCD03294274
UNSPSC Code:
12352200
PubChem Substance ID:
329825366
NACRES:
NA.77

Quality Level

100

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Inhibition of DNA repair protein RAD51 affects porcine preimplantation embryo development
Jin ZL, et al.
Reproduction (Cambridge, England), 157(3) (2019)
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
Zhe-Long Jin et al.
Reproduction (Cambridge, England), 157(3), 223-234 (2019-03-01)
Homologous recombination (HR) plays a critical role in facilitating replication fork progression when the polymerase complex encounters a blocking DNA lesion, and it also serves as the primary mechanism for error-free DNA repair of double-stranded breaks. DNA repair protein RAD51
Arthur Aubry et al.
Oncogene, 39(31), 5338-5357 (2020-06-24)
Local intravitreal or intra-arterial chemotherapy has improved therapeutic success for the pediatric cancer retinoblastoma (RB), but toxicity remains a major caveat. RB initiates primarily with RB1 loss or, rarely, MYCN amplification, but the critical downstream networks are incompletely understood. We
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