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Key Documents

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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
Pricing and availability is not currently available.

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

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Show Differences

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192420192400154903
甲醇 JIS special grade, ≥99.8%

192410

甲醇

甲醇 SAJ first grade, ≥99.5%

192420

甲醇

甲醇 SAJ special grade

192400

甲醇

甲醇 ACS spectrophotometric grade, ≥99.9%

154903

甲醇

assay

≥99.8%

assay

≥99.5%

assay

≥99.96% (GC)

assay

≥99.9%

form

liquid

form

liquid

form

liquid

form

liquid

bp

64.7 °C (lit.)

bp

64.7 °C (lit.)

bp

64.7 °C (lit.)

bp

64.7 °C (lit.)

expl. lim.

36 %

expl. lim.

36 %

expl. lim.

36 %

expl. lim.

36 %

mp

−98 °C (lit.)

mp

−98 °C (lit.)

mp

−98 °C (lit.)

mp

−98 °C (lit.)

Application

RAD51 Inhibitor B02 has been used:
  • to test its effect on the polar body extrusion (PBE) rate in porcine oocytes [1]
  • for RAD51 inhibition in porcine embryos[2]
  • as RAD51 inhibitor and to test its effect on targeted nucleotide substitution (TNS) in induced pluripotent stem cells (iPSCs)[3]

Biochem/physiol Actions

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000405550
    0000405553
    0000405553
    0000405550
    0000356262

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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)
    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
    Inhibition of DNA repair protein RAD51 affects porcine preimplantation embryo development
    Jin ZL, et al.
    Reproduction (Cambridge, England), 157(3) (2019)
    RAD51 maintains chromosome integrity and mitochondrial distribution during porcine oocyte maturation in vitro
    Jin ZL and Kim NH
    Journal of Reproduction and Development (2017)
    View All Related Papers

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