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PZ0234

Sigma-Aldrich

PF-543 hydrochloride

≥98% (HPLC)

Synonym(s):

(2R)-1-[[4-[[3-Methyl-5-[(phenylsulfonyl)methyl]phenoxy]methyl]phenyl]methyl]-2-pyrrolidinemethanol hydrochloride, (R)-(1-(4-((3-Methyl-5-(phenylsulfonylmethyl)phenoxy)methyl)benzyl)pyrrolidin-2-yl)methanol hydrochloride, PF-05144543 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C27H31NO4S · HCl
CAS Number:
1415562-82-1
Molecular Weight:
502.07
MDL number:
MFCD28411614
UNSPSC Code:
12352200
PubChem Substance ID:
329823785
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to light brown

solubility

H2O: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

[H]Cl.CC1=CC(OCC2=CC=C(CN3[C@@H](CO)CCC3)C=C2)=CC(CS(C4=CC=CC=C4)(=O)=O)=C1

InChI

1S/C27H31NO4S.ClH/c1-21-14-24(20-33(30,31)27-7-3-2-4-8-27)16-26(15-21)32-19-23-11-9-22(10-12-23)17-28-13-5-6-25(28)18-29;/h2-4,7-12,14-16,25,29H,5-6,13,17-20H2,1H3;1H/t25-;/m1./s1

InChI key

WNKWAZFYPZMDGJ-VQIWEWKSSA-N

Biochem/physiol Actions

PF-543 hydrochloride is a novel, cell-permeable, potent and selective inhibitor of sphingosine kinase-1 (SphK1). PF-543 inhibits SphK1 with a Ki of 3.6 nM, is sphingosine competitive and is more than 100-fold selective for SphK1 over the SphK2 isoform. PF-543 decreased the level of endogenous S1P by 10-fold with proportional increase of the level of sphingosine.
PF-543 stimulates granular accumulation of microtubule-associated protein light chain 3 (LC3). It also induces LC3-I to LC3-II conversion, inhibited by autophagy inhibitors, wortmannin, 3-methyladenine (3-MA) and bafilomycin A1. In human head and neck squamous cell carcinoma (SCC) cells, PF-543 hydrochloride promotes necrosis,apoptosis and autophagy.

Storage Class Code

11 - Combustible Solids

WGK

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 autophagy by sphingosine kinase 1 inhibitor PF-543 in head and neck squamous cell carcinoma cells.
Hamada M. et al,
Cell death discovery, 3, 17047-17047 (2017)
Yuliya Fakhr et al.
International journal of molecular sciences, 23(7) (2022-04-13)
Preeclampsia (PE) involves inadequate placental function. This can occur due to elevated pro-inflammatory tumor necrosis factor-α (TNF-α). In other tissues, TNF-α signals via sphingosine kinase 1 (SphK1). SphK1 hinders syncytial formation. Whether this occurs downstream of TNF-α signaling is unclear.
Stephen J Blake et al.
Cell reports. Medicine, 2(12), 100464-100464 (2022-01-15)
Immune agonist antibodies (IAAs) are promising immunotherapies that target co-stimulatory receptors to induce potent anti-tumor immune responses, particularly when combined with checkpoint inhibitors. Unfortunately, their clinical translation is hampered by serious dose-limiting, immune-mediated toxicities, including high-grade and sometimes fatal liver
Gang Pei et al.
The EMBO journal, 40(13), e106272-e106272 (2021-05-05)
Cellular stress has been associated with inflammation, yet precise underlying mechanisms remain elusive. In this study, various unrelated stress inducers were employed to screen for sensors linking altered cellular homeostasis and inflammation. We identified the intracellular pattern recognition receptors NOD1/2

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