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P9872

Sigma-Aldrich

Psora-4

≥98% (HPLC)

Synonym(s):

5-(4-Phenylbutoxy)psoralen

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About This Item

Empirical Formula (Hill Notation):
C21H18O4
CAS Number:
724709-68-6
Molecular Weight:
334.37
UNSPSC Code:
12352200
PubChem Substance ID:
24278012
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

protect from light
under inert gas

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C1Oc2cc3occc3cc2C(OCCCCc4ccccc4)=C1

InChI

1S/C21H18O4/c22-20-10-9-16-19(25-20)14-18-17(11-13-23-18)21(16)24-12-5-4-8-15-6-2-1-3-7-15/h1-3,6-7,9-11,13-14H,4-5,8,12H2

InChI key

JJAWGNIQEOFURP-UHFFFAOYSA-N

Biochem/physiol Actions

The lymphocyte potassium channel Kv1.3 is regarded as a new target for immunosuppression. Psora-4 is the most potent small-molecule Kv1.3 blocker known. It blocked Kv1.3 in a use-dependent manner, with a Hill coefficient of 2 and an EC50 value of 3 nM, by preferentially binding to the C-type inactivated state of the channel. It exhibited 17- to 70-fold selectivity for Kv1.3 over closely related Kv1-family channels (Kv1.1, Kv1.2, Kv1.4, and Kv1.7) with the exception of Kv1.5 (EC50, 7.7 nM) and showed no effect on human ether-a-go-go-related channel, Kv3.1, the calcium-activated K+ channels (IKCa1, SK1-SK3, and BKCa), or the neuronal NaV1.2 channel. In a test of in vivo toxicity in rats, Psora-4 did not display any signs of acute toxicity after five daily subcutaneous injections at 33 mg/kg body weight. Psora-4 selectively suppressed the proliferation of human and rat myelin-specific effector memory T cells with EC50 values of 25 and 60 nM, respectively, without persistently suppressing peripheral blood naive and central memory T cells. Because autoantigen-specific effector memory T cells contribute to the pathogenesis of T cell-mediated autoimmune diseases such as multiple sclerosis, Psora-4 and other Kv1.3 blockers may be useful as immunomodulators for the therapy of autoimmune disord.

Features and Benefits

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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Julia Vennekamp et al.
Molecular pharmacology, 65(6), 1364-1374 (2004-05-25)
The lymphocyte potassium channel Kv1.3 is widely regarded as a promising new target for immunosuppression. To identify a potent small-molecule Kv1.3 blocker, we synthesized a series of 5-phenylalkoxypsoralens and tested them by whole-cell patch clamp. The most potent compound of
K George Chandy et al.
Trends in pharmacological sciences, 25(5), 280-289 (2004-05-04)
The voltage-gated Kv1.3 channel and the Ca(2+)-activated IKCa1 K(+) channel are expressed in T cells in a distinct pattern that depends on the state of lymphocyte activation and differentiation. The channel phenotype changes during the progression from the resting to
Janna Bednenko et al.
mAbs, 10(4), 636-650 (2018-03-02)
Identifying monoclonal antibodies that block human voltage-gated ion channels (VGICs) is a challenging endeavor exacerbated by difficulties in producing recombinant ion channel proteins in amounts that support drug discovery programs. We have developed a general strategy to address this challenge
Yu-Ye Zhou et al.
CNS neuroscience & therapeutics, 21(7), 558-567 (2015-05-16)
The self-repair ability of neural progenitor cells (NPCs) has been found to be activated and protected in several therapies helpful in multiple sclerosis (MS), an inflammatory demyelinating disease of the CNS. As a potential therapeutic target in MS, the role

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