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P6124

Sigma-Aldrich

5-(4-Phenoxybutoxy)psoralen

≥98% (HPLC), solid

Synonym(s):

PAP-1

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About This Item

Empirical Formula (Hill Notation):
C21H18O5
CAS Number:
870653-45-5
Molecular Weight:
350.36
MDL number:
MFCD11114059
UNSPSC Code:
12352200
PubChem Substance ID:
24724583
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

storage condition

protect from light

color

white

solubility

DMSO: 9 mg/mL

storage temp.

2-8°C

SMILES string

O=C1Oc2cc3occc3c(OCCCCOc4ccccc4)c2C=C1

InChI

1S/C21H18O5/c22-20-9-8-16-19(26-20)14-18-17(10-13-24-18)21(16)25-12-5-4-11-23-15-6-2-1-3-7-15/h1-3,6-10,13-14H,4-5,11-12H2

InChI key

KINMYBBFQRSVLL-UHFFFAOYSA-N

Biochem/physiol Actions

5-(4-Phenoxybutoxy)psoralen (PAP-1) is derived from 5-methoxypsoralen, a natural compound. PAP-1 show higher selectivity for Kv1.3 (voltage-gated potassium channels) than other Kv1 family members. Kv1.3 is predominant on cell membranes of activated effector memory T-cells. Inhibition of Kv1.3 results in membrane depolarization. In rat models, PAP-1 is known to delay the onset of diabetes. It might be used in the treatment of psoriasis and effector memory T cells mediated autoimmune diseases. Oral, intraperitoneal and topical administration of PAP-1 prevents allergic contact dermatitis induced by oxazolone.
Selective inhibitor of Kv1.3, voltage-gated K+ channel. PAP-1 (EC50=2 nM) potently inhibits human T effector memory cell proliferation and delayed hypersensitivity. Effective orally or intraperitoneally. 5-(4-Phenoxybutoxy)psoralen has 23-fold selectivity for Kv1.3 over Kv1.5, and 33-125-fold selectivity over other Kv1 family channels.

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

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H334

Precautionary Statements

P261 - P284 - P501

Hazard Classifications

Resp. Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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4-Phenoxybutoxy-substituted heterocycles-A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1. 3
Bodendiek SB, et al.
European Journal of Medicinal Chemistry, 44(5), 1838-1852 (2009)
Pharmacokinetics, toxicity, and functional studies of the selective Kv1. 3 channel blocker 5-(4-phenoxybutoxy) psoralen in rhesus macaques
Pereira LE, et al.
Exp. Biol. Med, 232(10), 1338-1354 (2007)
Dai-Chao Ma et al.
Experimental neurology, 332, 113399-113399 (2020-07-12)
After cerebral ischemia/reperfusion injury, pro-inflammatory M1-like and anti-inflammatory M2-like phenotypes of microglia are involved in neuroinflammation, in which NLRP3 inflammasome plays an essential role. Kv1.3 channel has been recognized as neuro-immunomodulatory target, but it is not clear as to its
Identification of phase-I metabolites and chronic toxicity study of the Kv1. 3 blocker PAP-1 (5-(4-phenoxybutoxy) psoralen) in the rat
Hao B, et al.
Xenobiotica, 41(3), 198-211 (2011)
Joaquim Bobi et al.
Translational research : the journal of laboratory and clinical medicine, 224, 40-54 (2020-06-12)
The modulation of voltage-gated K+ (Kv) channels, involved in cell proliferation, arises as a potential therapeutic approach for the prevention of intimal hyperplasia present in in-stent restenosis (ISR) and allograft vasculopathy (AV). We studied the effect of PAP-1, a selective
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