Kv1.3-blocking 5-phenylalkoxypsoralens: A new class of immunomodulators

Molecular Pharmacology

Volumn 65, Issue 6, 2004, Pages 1364-1374

  Vennekamp, Julia ^a   Wulff, Heike ^b   Beeton, Christine ^c   Calabresi, Peter A ^d   Grissmer, Stephan ^e   Hänsel, Wolfram ^a   Chandy, K George ^c,f  

^a UNIVERSITY OF KIEL   (Germany)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d JOHNS HOPKINS HOSPITAL   (United States)

^e UNIVERSITY OF ULM   (Germany)

^f UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (4 PHENYLBUTOXY)PSORALEN; 5 PHENYLPSORALEN DERIVATIVE; AUTOANTIGEN; IMMUNOMODULATING AGENT; POTASSIUM CHANNEL; POTASSIUM CHANNEL BLOCKING AGENT; PSORALEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AUTOIMMUNE DISEASE; BODY WEIGHT; CELL PROLIFERATION; CELLULAR IMMUNITY; CONTROLLED STUDY; DRUG POTENCY; HUMAN; HUMAN CELL; IMMUNOMODULATION; IMMUNOSUPPRESSIVE TREATMENT; IN VIVO STUDY; MEMORY CELL; MULTIPLE SCLEROSIS; PATCH CLAMP; PATHOGENESIS; PRIORITY JOURNAL;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; CELL DIVISION; CELL LINE; CELLS, CULTURED; HUMANS; KV1.3 POTASSIUM CHANNEL; POTASSIUM CHANNEL BLOCKERS; POTASSIUM CHANNELS; POTASSIUM CHANNELS, VOLTAGE-GATED; PSORALENS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2442660257     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.65.6.1364     Document Type: Article

References (47)

1. Bachmann A, Gutcher I, Kopp K, Brendel J, Bosch RF, Busch AE, and Gogelein H (2001) Characterization of a novel Kv1.5 channel blocker in Xenopus oocytes, CHO cells, human and rat cardiomyocytes. Naunyn-Schmiedeberg's Arch Pharmacol 364:472-478.
2. Bardien-Kruger S, Wulff H, Arieff Z, Brink P, Chandy KG, and Corfield V (2002) Characterization of the human voltage-gated potassium channel gene, KCNA7, a candidate gene for inherited cardiac disorders and its exclusion as a cause of progressive familial heart block I (PFHBI). Eur J Human Gen 10:36-43.
3. + channels improves experimental autoimmune encephalomyelitis and inhibits T cell activation. J Immunol 166:936-944.
4. + channels ameliorates experimental autoimmune encephalomyelitis, a model for multiple sclerosis. Proc Natl Acad Sci USA 98:13942-13947.
5. Beeton C, Wulff H, Singh S, Bosko S, Crossley G, Gutman GA, Cahalan MD, Pennington M, and Chandy KG (2003) A novel fluorescent toxin to detect and investigate Kv1.3-channel up-regulation in chronically activated T lymphocytes. J Biol Chem 278:9928-9937.
6. Bohuslavizki KH, Hansel W, Kneip A, Koppenhofer E, Niemoller E, and Sanmann K (1994) Mode of action of psoralens, benzofurans, acridones and coumarins on the ionic currents in intact myelinated nerve fibres and its significance in demyelinating diseases. Gen Physiol Biophys 13:309-328.
7. Bohuslavizki KH, Hinck-Kneip C, Kneip A, Koppenhöfer E, and Reimers A (1993) Reduction of MS-related scotoma by a new class of potassium channel blockers from Ruta graveolens. Neuroopthalmology 13:191-198.
8. Boiko T, Rasband MN, Levinson SR, Caldwell JH, Mandel G, Trimmer JS, and Matthews G (2001) Compact myelin dictates the differential targeting of two sodium channel isoforms in the same axon. Neuron 30:91-104.
9. Cahalan MD, Chandy KG, DeCoursey TE, and Gupta S (1985) A voltage-gated potassium channel in human T lymphocytes. J Physiol (Lond) 358:197-237.
10. Cahalan MD, Wulff H, and Chandy KG (2001) Molecular properties and physiological roles of ion channels in the immune system. J Clin Immunol 21:235-252.
11. Caporale G and Antonello C (1958) Sintesi di alcuni derivati furocumarinici. Il Farmaco Ed Sci 13:363-367.
12. Chandy KG, Cahalan MD, Pennington M, Norton RS, Wulff H, and Gutman GA (2001) Potassium channels in T lymphocytes: toxins to therapeutic immunosuppressants. Toxicon 39:1269-1276.
13. Coghlan MJ, Carrol WA, and Gopalakrishnan M (2001) Recent developments in the biology and medicinal chemistry of potassium channel modulators: update from a decade of progress. J Med Chem 44:1-27.
14. + channels in human T lymphocytes: a role in mitogenesis? Nature (Lond) 307:465-468.
15. During T, Gerst F, Hänsel W, Wulff H, and Koppenhöfer E (2000) Effects of three alkoxypsoralens on voltage gated ion channels in Ranvier nodes. Gen Physiol Biophys 19:345-364.
16. Fanger CM, Rauer H, Neben AL, Miller MJ, Rauer H, Wulff H, Rosa JC, Ganellin CR, Chandy KG, and Cahalan MD (2001) Calcium-activated potassium channels sustain calcium signaling in T lymphocytes. J Biol Chem 276:12249-12256.
17. + channel current. Circ Res 73:210-216.
18. + current in cultured adult human atrial myocytes. Circ Res 80:572-579.
19. Ghanshani S, Wulff H, Miller MJ, Rohm H, Neben A, Gutman GA, Cahalan MD, and Chandy KG (2000) Up-regulation of the IKCa1 potassium channel during T-cell activation: molecular mechanism and functional consequences. J Biol Chem 275:37137-37149.
20. + channels, types Kv1.1, 1.2, 1.3, 1.5, and 3.1, stably expressed in mammalian cell lines. Mol Pharmacol 45:1227-1234.
21. Hanner M, Schmalhofer WA, Green B, Bordallo C, Liu J, Slaughter RS, Kaczorowski GJ, and Garcia ML (1999) Binding of correolide to Kv1 family potassium channels. J Biol Chem 274:25237-25244.
22. Hansch C and Anderson SM (1967) The effect of intramolecular hydrophobic bonding on partition coefficients. J Org Chem 32:2583-2586.
23. Hanson DC, Nguyen A, Mather RJ, Rauer H, Koch K, Burgess LE, Rizzi JP, Donovan CB, Bruns MJ, Canniff PC, et al. (1999) UK-78,282, a novel piperidine compound that potently blocks the Kv1.3 voltage-gated potassium channel and inhibits human T cell activation. Br J Pharmacol 126:1707-1716.
24. Hirsh JK and Quandt FN (1996) Down-regulation of Na channel expression by A23187 in N1E-115 neuroblastoma cells. Brain Res 706:343-346.
25. + conductance is a post-activational event in rat T lymphocytes responsible for the adoptive transfer of experimental allergic encephalomyelitis. J Biomed Sci 4:98-110.
26. Judge SIV, Yeh ZJ, Mannie MD, Seifert LP, and Paterson PY (1997b) Potassium channel blockers inhibit adoptive transfer of experimental allergic encephalomyelitis by myelin-basic protein stimulated rat T lymphocytes. J Biomed Sci 4:169-178.
27. Leo A (2000) Octanol/water partition coefficients, in Handbook of Property Estimation Methods for Chemicals (Boethling RS and Mackay D eds) pp 89-114, Lewis Publishers, Boca Raton, FL.
28. Levy DI and Deutsch C (1996) Recovery from C-type inactivation is modulated by extracellular potassium. Biophys J 70:798-805.
29. Lewis RS and Cahalan MD (1995) Potassium and calcium channels in lymphocytes. Annu Rev Immunol 13:623-653.
30. Lin CS, Boltz RC, Blake JT, Nguyen M, Talento A, Fischer PA, Springer MS, Sigal NH, Slaughter RS, Garcia ML, et al. (1993) Voltage-gated potassium channels regulate calcium-dependent pathways involved in human T lymphocyte activation. J Exp Med 177:637-645.
31. Lipinski CA, Lombardo F, Dominy BW, and Feeney PJ (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev 23:3-25.
32. Lovett-Racke AE, Trotter JL, Lauber J, Perrin PJ, June CH, and Racke MK (1998) Decreased dependence of myelin basic protein-reactive T cells on CD28-mediated costimulation in multiple sclerosis patients: a marker of activated/memory T cells. J Clin Investig 101:725-730.
33. - costimulation-independent T cells in multiple sclerosis. J Clin Investig 108:1185-1194.
34. Nguyen A, Kath JC, Hanson DC, Biggers MS, Canniff PC, Donovan CB, Mather RJ, Bruns MJ, Rauer H, Aiyar J, et al. (1996) Novel nonpeptide agents potently block the C-type inactivated conformation of Kv1.3 and suppress T cell activation. Mol Pharmacol 50:1672-1679.
35. Sallusto F, Lenig D, Forster R, Lipp M, and Lanzavecchia A (1999) Two subsets of memory T lymphocytes with distinct homing potentials and effector functions. Nature (Lond) 401:708-712.
36. Schmalhofer WA, Bao J, McManus OB, Green B, Matyskiela M, Wunderler D, Bugianesi RM, Felix JP, Hanner M, Linde-Arias A-R, et al. (2002) Identification of a new class of inhibitors of the voltage-gated potassium channel, Kv1.3, with immunosuppressant properties. Biochemistry 18:7781-7794.
37. Schmalhofer WA, Slaughter RS, Matyskiela M, Felix JP, Tang YS, Rupprecht K, Kaczorowski GJ, and Garcia ML (2003) Di-substituted cyclohexyl derivatives bind to two identical sites with positive cooperativity on the voltage-gated potassium channel Kv1.3. Biochemistry 42:4733-4743.
38. Schoenberg A and Aziz G (1953) Furochromones and coumarins. VI. Demethylation of xantotoxin, khellin and khellol with aniline hydrochloride and magnesium iodide. J Am Chem Soc 75:3265-3266.
39. Scholz C, Anderson DE, Freeman GJ, and Hafler DA (1998) Expansion of autoreactive T cells in multiple sclerosis is independent of exogenous B7 costimulation. J Immunol 160:1532-1538.
40. + channel blocking alkoxypsoralens inhibit the immune response of encephalitogenic T line cells and lymphocytes from Lewis rats challenged for experimental autoimmune encephalomyelitis. Immunopharmacology 48:51-63.
41. Viglietta V, Kent SC, Orban T, and Hafler DA (2002) GAD65-reactive T cells are activated in patients with autoimmune type la diabetes. J Clin Investig 109:895-903.
42. + current similar to Kv1.5 cloned channel currents. Circ Res 73:1061-1076.
43. Wulff H, Beeton C, and Chandy KG (2003a) Potassium channels as therapeutic targets for autoimmune disorders. Curr Opin Drug Discov Dev 6:640-647.
44. + channel in effector memory T cells as new target for MS. J Clin Investig 111:1703-1713.
45. + channel, IKCa1: a potential immunosuppressant. Proc Natl Acad Sci USA 97:8151-8156.
46. + channels: synthesis and photoreactivity. J Med Chem 41:4542-4549.
47. Zhou Z, Gong Q, Ye B, Fan Z, Makielski JC, Robertson GA, and January CT (1998) Properties of HERG channels stably expressed in HEK 293 cells studied at physiological temperatures. Biophys J 74:230-241.