Psora-4
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MedKoo CAT#: 526438

CAS#: 724709-68-6

Description: Psora-4 is an inhibitor of voltage-gated potassium channels (Kv1.3). It is selective for Kv1.3 but does inhibit the Kv1.5 channel. Psora 4 selectively binds to the C-type inactivated state of the Kv1.3 channel and inhibits potassium current in a use-dependent manner. It has immunosuppressive activity, inhibiting proliferation of human and rat myelin-specific effector memory T cells in vitro.

Chemical Structure

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Psora-4
CAS# 724709-68-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526438
Name: Psora-4
CAS#: 724709-68-6
Chemical Formula: C21H18O4
Exact Mass: 334.12
Molecular Weight: 334.370
Elemental Analysis: C, 75.43; H, 5.43; O, 19.14

Price and Availability

Size Price Availability Quantity
1mg USD 205
5mg USD 405
10mg USD 640
25mg USD 1150
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Synonym: Psora-4

IUPAC/Chemical Name: 5-(4-Phenylbutoxy)psoralen

InChi Key: JJAWGNIQEOFURP-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C1OC2=CC3=C(C=CO3)C(OCCCCC4=CC=CC=C4)=C2C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Psora-4 is an inhibitor of Kv1.3 (EC50 = 3 nM). It is selective for Kv1.3 over Kv1.1, Kv1.2, Kv1.4, Kv1.7, and Kv3.1 channels (EC50s = 62, 49, 202, 100, and 1,500 nM, respectively).
In vitro activity: Psora-4 blocked Kv1.3 in a use-dependent manner, with a Hill coefficient of 2 and an EC50 value of 3 nM. Psora-4 exhibited 17- to 70-fold selectivity for Kv1.3 over Kv1.1, Kv1.2, Kv1.4, and Kv1.7 with the exception of Kv1.5 (EC50, 7.7 nM) and showed no effect on Kv3.1; IKCa1, SK1-SK3, and BKCa; or the neuronal NaV1.2 channel. Reference: Mol Pharmacol. 2004 Jun;65(6):1364-74. https://pubmed.ncbi.nlm.nih.gov/15155830/
In vivo activity: Psora-4 extends lifespan in C. elegans. This study reports that Psora-4 increases the production of free radicals and modulates genes related to stress response. Its effect intersects closely with the target set of caloric restriction genes, suggesting that Psora-4, in part, acts as caloric restriction mimetic. Reference: Geroscience. 2022 Apr;44(2):1029-1046. https://pubmed.ncbi.nlm.nih.gov/33988831/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 29.91

Preparing Stock Solutions

The following data is based on the product molecular weight 334.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Hamilton DL, Beall C, Jeromson S, Chevtzoff C, Cuthbertson DJ, Ashford ML. Kv1.3 inhibitors have differential effects on glucose uptake and AMPK activity in skeletal muscle cell lines and mouse ex vivo skeletal muscle. J Physiol Sci. 2014 Jan;64(1):13-20. doi: 10.1007/s12576-013-0285-4. Epub 2013 Sep 17. PMID: 24043354. 2. Vennekamp J, Wulff H, Beeton C, Calabresi PA, Grissmer S, Hänsel W, Chandy KG. Kv1.3-blocking 5-phenylalkoxypsoralens: a new class of immunomodulators. Mol Pharmacol. 2004 Jun;65(6):1364-74. doi: 10.1124/mol.65.6.1364. PMID: 15155830. 3. Labbaf A, Dellin M, Komadowski M, Chetkovich DM, Decher N, Pape HC, Seebohm G, Budde T, Zobeiri M. Characterization of Kv1.2-mediated outward current in TRIP8b-deficient mice. Biol Chem. 2023 Mar 1;404(4):291-302. doi: 10.1515/hsz-2023-0116. PMID: 36852869. 4. Admasu TD, Barardo D, Ng LF, Batchu KC, Cazenave-Gassiot A, Wenk MR, Gruber J. A small-molecule Psora-4 acts as a caloric restriction mimetic to promote longevity in C. elegans. Geroscience. 2022 Apr;44(2):1029-1046. doi: 10.1007/s11357-021-00374-6. Epub 2021 May 14. PMID: 33988831; PMCID: PMC9135947.
In vitro protocol: 1. Hamilton DL, Beall C, Jeromson S, Chevtzoff C, Cuthbertson DJ, Ashford ML. Kv1.3 inhibitors have differential effects on glucose uptake and AMPK activity in skeletal muscle cell lines and mouse ex vivo skeletal muscle. J Physiol Sci. 2014 Jan;64(1):13-20. doi: 10.1007/s12576-013-0285-4. Epub 2013 Sep 17. PMID: 24043354. 2. Vennekamp J, Wulff H, Beeton C, Calabresi PA, Grissmer S, Hänsel W, Chandy KG. Kv1.3-blocking 5-phenylalkoxypsoralens: a new class of immunomodulators. Mol Pharmacol. 2004 Jun;65(6):1364-74. doi: 10.1124/mol.65.6.1364. PMID: 15155830.
In vivo protocol: 1. Labbaf A, Dellin M, Komadowski M, Chetkovich DM, Decher N, Pape HC, Seebohm G, Budde T, Zobeiri M. Characterization of Kv1.2-mediated outward current in TRIP8b-deficient mice. Biol Chem. 2023 Mar 1;404(4):291-302. doi: 10.1515/hsz-2023-0116. PMID: 36852869. 2. Admasu TD, Barardo D, Ng LF, Batchu KC, Cazenave-Gassiot A, Wenk MR, Gruber J. A small-molecule Psora-4 acts as a caloric restriction mimetic to promote longevity in C. elegans. Geroscience. 2022 Apr;44(2):1029-1046. doi: 10.1007/s11357-021-00374-6. Epub 2021 May 14. PMID: 33988831; PMCID: PMC9135947.

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1: Venturini E, Leanza L, Azzolini M, Kadow S, Mattarei A, Weller M, Tabatabai G, Edwards MJ, Zoratti M, Paradisi C, Szabò I, Gulbins E, Becker KA. Targeting the Potassium Channel Kv1.3 Kills Glioblastoma Cells. Neurosignals. 2017 Sep 1;25(1):26-38. doi: 10.1159/000480643. [Epub ahead of print] PubMed PMID: 28869943.

2: Kidd MW, Bulley S, Jaggar JH. Angiotensin II reduces the surface abundance of K(V) 1.5 channels in arterial myocytes to stimulate vasoconstriction. J Physiol. 2017 Mar 1;595(5):1607-1618. doi: 10.1113/JP272893. Epub 2017 Feb 5. PubMed PMID: 27958660; PubMed Central PMCID: PMC5330887.

3: Nishijima Y, Cao S, Chabowski DS, Korishettar A, Ge A, Zheng X, Sparapani R, Gutterman DD, Zhang DX. Contribution of K(V)1.5 Channel to Hydrogen Peroxide-Induced Human Arteriolar Dilation and Its Modulation by Coronary Artery Disease. Circ Res. 2017 Feb 17;120(4):658-669. doi: 10.1161/CIRCRESAHA.116.309491. Epub 2016 Nov 21. PubMed PMID: 27872049; PubMed Central PMCID: PMC5315616.

4: Zhou YY, Hou GQ, He SW, Xiao Z, Xu HJ, Qiu YT, Jiang S, Zheng H, Li ZY. Psora-4, a Kv1.3 Blocker, Enhances Differentiation and Maturation in Neural Progenitor Cells. CNS Neurosci Ther. 2015 Jul;21(7):558-67. doi: 10.1111/cns.12402. Epub 2015 May 15. PubMed PMID: 25976092.

5: Ueyama A, Imura K, Kasai-Yamamoto E, Tai N, Nagira M, Shichijo M, Yasui K. Kv1.3 blockers ameliorate allergic contact dermatitis by preferentially suppressing effector memory T cells in a rat model. Clin Exp Dermatol. 2013 Dec;38(8):897-903. doi: 10.1111/ced.12097. PubMed PMID: 24252082.

6: Hamilton DL, Beall C, Jeromson S, Chevtzoff C, Cuthbertson DJ, Ashford ML. Kv1.3 inhibitors have differential effects on glucose uptake and AMPK activity in skeletal muscle cell lines and mouse ex vivo skeletal muscle. J Physiol Sci. 2014 Jan;64(1):13-20. doi: 10.1007/s12576-013-0285-4. Epub 2013 Sep 17. PubMed PMID: 24043354.

7: Wulff H, Yarov-Yarovoy V. Channels: Sticking to nooks and crannies. Nat Chem Biol. 2013 Aug;9(8):473-4. doi: 10.1038/nchembio.1292. PubMed PMID: 23868316.

8: Marzian S, Stansfeld PJ, Rapedius M, Rinné S, Nematian-Ardestani E, Abbruzzese JL, Steinmeyer K, Sansom MS, Sanguinetti MC, Baukrowitz T, Decher N. Side pockets provide the basis for a new mechanism of Kv channel-specific inhibition. Nat Chem Biol. 2013 Aug;9(8):507-13. doi: 10.1038/nchembio.1271. Epub 2013 Jun 2. PubMed PMID: 23728494; PubMed Central PMCID: PMC4539245.

9: Leanza L, Trentin L, Becker KA, Frezzato F, Zoratti M, Semenzato G, Gulbins E, Szabo I. Clofazimine, Psora-4 and PAP-1, inhibitors of the potassium channel Kv1.3, as a new and selective therapeutic strategy in chronic lymphocytic leukemia. Leukemia. 2013 Aug;27(8):1782-5. doi: 10.1038/leu.2013.56. Epub 2013 Feb 21. PubMed PMID: 23426166.

10: Leanza L, Henry B, Sassi N, Zoratti M, Chandy KG, Gulbins E, Szabò I. Inhibitors of mitochondrial Kv1.3 channels induce Bax/Bak-independent death of cancer cells. EMBO Mol Med. 2012 Jul;4(7):577-93. doi: 10.1002/emmm.201200235. Epub 2012 Apr 11. PubMed PMID: 22496117; PubMed Central PMCID: PMC3407946.

11: Xu R, Cao M, Wu X, Wang X, Ruan L, Quan X, Lü C, He W, Zhang C. Kv1.3 channels as a potential target for immunomodulation of CD4+ CD28null T cells in patients with acute coronary syndrome. Clin Immunol. 2012 Feb;142(2):209-17. doi: 10.1016/j.clim.2011.10.009. Epub 2011 Nov 9. PubMed PMID: 22169811.

12: Straub SV, Perez SM, Tan B, Coughlan KA, Trebino CE, Cosgrove P, Buxton JM, Kreeger JM, Jackson VM. Pharmacological inhibition of Kv1.3 fails to modulate insulin sensitivity in diabetic mice or human insulin-sensitive tissues. Am J Physiol Endocrinol Metab. 2011 Aug;301(2):E380-90. doi: 10.1152/ajpendo.00076.2011. Epub 2011 May 17. PubMed PMID: 21586699.

13: Hao B, Chen ZW, Zhou XJ, Zimin PI, Miljanich GP, Wulff H, Wang YX. Identification of phase-I metabolites and chronic toxicity study of the Kv1.3 blocker PAP-1 (5-(4-phenoxybutoxy)psoralen) in the rat. Xenobiotica. 2011 Mar;41(3):198-211. doi: 10.3109/00498254.2010.532886. Epub 2010 Nov 11. PubMed PMID: 21070145; PubMed Central PMCID: PMC3644211.

14: Cheong A, Li J, Sukumar P, Kumar B, Zeng F, Riches K, Munsch C, Wood IC, Porter KE, Beech DJ. Potent suppression of vascular smooth muscle cell migration and human neointimal hyperplasia by KV1.3 channel blockers. Cardiovasc Res. 2011 Feb 1;89(2):282-9. doi: 10.1093/cvr/cvq305. Epub 2010 Sep 29. PubMed PMID: 20884640; PubMed Central PMCID: PMC3020133.

15: Hyodo T, Oda T, Kikuchi Y, Higashi K, Kushiyama T, Yamamoto K, Yamada M, Suzuki S, Hokari R, Kinoshita M, Seki S, Fujinaka H, Yamamoto T, Miura S, Kumagai H. Voltage-gated potassium channel Kv1.3 blocker as a potential treatment for rat anti-glomerular basement membrane glomerulonephritis. Am J Physiol Renal Physiol. 2010 Dec;299(6):F1258-69. doi: 10.1152/ajprenal.00374.2010. Epub 2010 Sep 1. PubMed PMID: 20810612; PubMed Central PMCID: PMC3006300.

16: Tobin AA, Joseph BK, Al-Kindi HN, Albarwani S, Madden JA, Nemetz LT, Rusch NJ, Rhee SW. Loss of cerebrovascular Shaker-type K(+) channels: a shared vasodilator defect of genetic and renal hypertensive rats. Am J Physiol Heart Circ Physiol. 2009 Jul;297(1):H293-303. doi: 10.1152/ajpheart.00991.2008. Epub 2009 May 1. PubMed PMID: 19411284; PubMed Central PMCID: PMC2711739.

17: Stokely ME, Garg P, Bhat MA, Koulen P. Transient 5-(4-phenylbutoxy)psoralen (PAP-1) treatment dissociates developing pathologies in autoimmune optic neuritis into two distinct pathology profiles. J Neurosci Res. 2008 Jul;86(9):2111-24. doi: 10.1002/jnr.21645. PubMed PMID: 18335521.

18: Pereira LE, Villinger F, Wulff H, Sankaranarayanan A, Raman G, Ansari AA. Pharmacokinetics, toxicity, and functional studies of the selective Kv1.3 channel blocker 5-(4-phenoxybutoxy)psoralen in rhesus macaques. Exp Biol Med (Maywood). 2007 Nov;232(10):1338-54. PubMed PMID: 17959847; PubMed Central PMCID: PMC2390884.

19: Liebau S, Pröpper C, Böckers T, Lehmann-Horn F, Storch A, Grissmer S, Wittekindt OH. Selective blockage of Kv1.3 and Kv3.1 channels increases neural progenitor cell proliferation. J Neurochem. 2006 Oct;99(2):426-37. PubMed PMID: 17029597.

20: Li Y, Wang P, Xu J, Desir GV. Voltage-gated potassium channel Kv1.3 regulates GLUT4 trafficking to the plasma membrane via a Ca2+-dependent mechanism. Am J Physiol Cell Physiol. 2006 Feb;290(2):C345-51. PubMed PMID: 16403947.