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PZ0188

Sigma-Aldrich

PF-3644022 hydrate

≥98% (HPLC)

Synonym(s):

(10R)-9,10,11,12-tetrahydro-10-methyl-3-(6-methyl-3-pyridinyl)-8H-[1,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one hydrate

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About This Item

Empirical Formula (Hill Notation):
C21H18N4OS · xH2O
Molecular Weight:
374.46 (anhydrous basis)
MDL number:
MFCD21363374
UNSPSC Code:
51111800
PubChem Substance ID:
329823762
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: ≥15 mg/mL

storage temp.

2-8°C

SMILES string

O.C[C@@H]1CNc2c(sc3ccc4nc(ccc4c23)-c5ccc(C)nc5)C(=O)N1

InChI

1S/C21H18N4OS.H2O/c1-11-3-4-13(10-22-11)15-6-5-14-16(25-15)7-8-17-18(14)19-20(27-17)21(26)24-12(2)9-23-19;/h3-8,10,12,23H,9H2,1-2H3,(H,24,26);1H2/t12-;/m1./s1

InChI key

WHVUIWUUCVXAGR-UTONKHPSSA-N

Application

PF-3644022 hydrate has been used for the inhibition of mitogen-activated protein kinase 2 (MK2) in human osteosarcoma cells (U2OS) and in colorectal carcinoma cells (CT26).

Biochem/physiol Actions

PF-3644022 is a potent inhibitor of mitogen-activated protein kinase-activated protein kinase 2 (MK2; Ki = 3 nM). PF-3644022 inhibits TNFa and IL-6 production in LPS-stimulated human whole blood (IC50 = 1.6 and 10.3 μM, respectively) and blocks TNFα production and paw swelling in a streptococcal cell wall-induced arthritis in rats.

Features and Benefits

This compound is featured on the MAPKAPs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

PF3644022 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the PF3644022 probe summary on the Chemical Probes Portal website.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

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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Induction of oxidative metabolism by the p38alpha/MK2 pathway.
Trempolec N, et al.
Scientific Reports, 7(1), 11367-11367 (2017)
Oncogenic RAS signaling promotes tumor immunoresistance by stabilizing PD-L1 mRNA.
Coelho MA, et al.
Immunity, 47(6), 1083-1099 (2017)
Natalia Ronkina et al.
Journal of immunology (Baltimore, Md. : 1950), 203(8), 2291-2300 (2019-09-19)
Tristetraprolin (TTP) is an RNA-binding protein and an essential factor of posttranscriptional repression of cytokine biosynthesis in macrophages. Its activity is temporally inhibited by LPS-induced p38MAPK/MAPKAPK2/3-mediated phosphorylation, leading to a rapid increase in cytokine expression. We compared TTP expression and
Nuria Gutierrez-Prat et al.
Proceedings of the National Academy of Sciences of the United States of America, 118(29) (2021-07-18)
Cell survival in response to stress is determined by the coordination of various signaling pathways. The kinase p38α is activated by many stresses, but the intensity and duration of the signal depends on the stimuli. How different p38α-activation dynamics may
I-Ting Chen et al.
EMBO reports, 22(12), e52254-e52254 (2021-10-12)
Promyelocytic leukemia protein (PML) is a tumor suppressor possessing multiple modes of action, including induction of apoptosis. We unexpectedly find that PML promotes necroptosis in addition to apoptosis, with Pml-/- macrophages being more resistant to TNF-mediated necroptosis than wild-type counterparts

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