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PZ0186

Sigma-Aldrich

PF-477736

≥98% (HPLC)

Synonym(s):

(2R)-2-Amino-2-cyclohexyl-N-[2-(1-methyl-1H-pyrazol-4-yl)-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl]-acetamide, PF-00477736

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About This Item

Empirical Formula (Hill Notation):
C22H25N7O2
CAS Number:
952021-60-2
Molecular Weight:
419.48
MDL number:
MFCD16038847
UNSPSC Code:
12352200
PubChem Substance ID:
329823760
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

yellow

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

Cn1cc(cn1)-c2[nH]c3cc(NC(=O)[C@H](N)C4CCCCC4)cc5C(=O)NN=Cc2c35

InChI

1S/C22H25N7O2/c1-29-11-13(9-25-29)20-16-10-24-28-21(30)15-7-14(8-17(27-20)18(15)16)26-22(31)19(23)12-5-3-2-4-6-12/h7-12,19,27H,2-6,23H2,1H3,(H,26,31)(H,28,30)/t19-/m1/s1

InChI key

NDEXUOWTGYUVGA-LJQANCHMSA-N

Application

PF-477736 has been used as a checkpoint protein 1 (CHK1) inhibitor to study the effect of CHK1 in cell cycle regulation in primary breast and lung primary epithelial cells.

Biochem/physiol Actions

PF-00477736 is a potent, selective ATP-competitive small-molecule inhibitor that inhibits Chk1 with a Ki of 0.49 nM. The compound abrogates cell cycle arrest induced by DNA damage and enhances cytotoxicity of clinically important chemotherapeutic agents, including gemcitabine and carboplatin.
PF-477736 may be effectively used to resensitize platinum resistant ovarian cancer cells. PF-477736 alone or in combination with other chemotherapeutic agents may be used to treat triple-negative breast cancer.

Other Notes

PF-477736 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the PF-477736 probe summary on the Chemical Probes Portal website.

Legal Information

Sold for research purposes under agreement from Pfizer Inc.

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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Abstract NTOC-095: THE SYNERGISTIC EFFECTS OF CARBOPLATIN AND PF--477736, A SMALL MOLECULE CHECKPOINT KINASE 1 INHIBITOR ON A PLATINUM RESISTANT OVARIAN CANCER CELL LINE
Lee J, et al.
Clinical Cancer Research, 9(3), 1-7 (2017)
Marijn T M van Jaarsveld et al.
Oncogenesis, 9(3), 35-35 (2020-03-15)
Cancer is a life-threatening disease that affects one in three people. Although most cases are sporadic, cancer risk can be increased by genetic factors. It remains unknown why certain genes predispose for specific forms of cancer only, such as checkpoint
Cell-type-specific role of CHK2 in mediating DNA damage-induced G2 cell cycle arrest
van Jaarsveld MTM, et al.
Oncogenesis, 9(3), 1-7 (2020)
Chk1 inhibition as a novel therapeutic strategy for treating triple-negative breast and ovarian cancers
Bryant C, et al.
BMC Cancer, 14(1), 570-570 (2014)
Stéphanie Arnould et al.
Oncotarget, 8(56), 95206-95222 (2017-12-10)
Reduction in nucleotide pools through the inhibition of mitochondrial enzyme dihydroorotate dehydrogenase (DHODH) has been demonstrated to effectively reduce cancer cell proliferation and tumour growth. The current study sought to investigate whether this antiproliferative effect could be enhanced by combining

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