Iberiotoxin

• CAT Number: R014712
• CAS Number: 129203-60-7
• Molecular Formula: C179H274N50O55S7
• Molecular Weight: 4230.876
• Purity: ≥95%
• Synonyms: 5-​Oxo-​L-​prolyl-​L-​phenylalanyl-​L-​threonyl-​L-​α-​aspartyl-​L-​valyl-​L-​α-​aspartyl-​L-​cysteinyl-​L-​seryl-​L-​valyl-​L-​seryl-​L-​lysyl-​L-​α-​glutamyl-​L-​cysteinyl-​L-​tryptophyl-​L-​seryl-​L-​valyl-​L-​cysteinyl-​L-​lysyl-​L-​α-​aspartyl-​
• Target: Potassium Channel
• Solubility: Soluble to 0.70 mg/ml in sterile water
• Storage: Desiccate at -20C
• InChI: InChI=1S/C179H274N50O55S7/c1-87(2)65-111-155(261)208-112(66-93-33-15-13-16-34-93)146(252)195-77-133(239)225-139(88(3)4)172(278)213-117(71-136(244)245)158(264)199-100(44-31-62-190-178(186)187)144(250)193-75-131(237)198-102(40-22-27-58-181)148(254)219-124(167(273)205-109(56-64-285-12)145(251)194-76-132(238)197-101(39-21-26-57-180)147(253)200-105(43-25-30-61-184)151(257)220-123-81-286-288-83-125(221-152(258)106(203-166(123)272)45-32-63-191-179(188)189)169(275)210-113(68-95-46-48-97(234)49-47-95)156(262)206-110(177(283)284)50-53-129(185)235)82-287-291-86-128(168(274)202-104(42-24-29-60-183)150(256)212-116(70-135(242)243)159(265)207-111)224-175(281)142(91(9)10)228-164(270)121(79-231)216-157(263)115(69-96-74-192-99-38-20-19-37-98(96)99)211-170(276)126-84-289-290-85-127(171(277)217-122(80-232)165(271)227-141(90(7)8)174(280)218-120(78-230)163(269)201-103(41-23-28-59-182)149(255)204-108(154(260)222-126)52-55-134(240)241)223-160(266)118(72-137(246)247)214-173(279)140(89(5)6)226-162(268)119(73-138(248)249)215-176(282)143(92(11)233)229-161(267)114(67-94-35-17-14-18-36-94)209-153(259)107-51-54-130(236)196-107/h13-20,33-38,46-49,74,87-92,100-128,139-143,192,230-234H,21-32,39-45,50-73,75-86,180-184H2,1-12H3,(H2,185,235)(H,193,250)(H,194,251)(H,195,252)(H,196,236)(H,197,238)(H,198,237)(H,199,264)(H,200,253)(H,201,269)(H,202,274)(H,203,272)(H,204,255)(H,205,273)(H,206,262)(H,207,265)(H,208,261)(H,209,259)(H,210,275)(H,211,276)(H,212,256)(H,213,278)(H,214,279)(H,215,282)(H,216,263)(H,217,277)(H,218,280)(H,219,254)(H,220,257)(H,221,258)(H,222,260)(H,223,266)(H,224,281)(H,225,239)(H,226,268)(H,227,271)(H,228,270)(H,229,267)(H,240,241)(H,242,243)(H,244,245)(H,246,247)(H,248,249)(H,283,284)(H4,186,187,190)(H4,188,189,191)
• InChIKey: VDNVVLOBNHIMQA-UHFFFAOYSA-N
• SMILES: CC(C)CC1C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)N1)CC(=O)O)CCCCN)NC(=O)C(C(C)C)NC(=O)C(CO)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C4CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N4)CCC(=O)O)CCCCN)CO)C(C)C)CO)NC(=O)C(CC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CC(=O)O)NC(=O)C(C(C)O)NC(=O)C(CC5=CC=CC=C5)NC(=O)C6CCC(=O)N6)C(=O)NC(CCSC)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC7CSSCC(NC(=O)C(NC7=O)CCCNC(=N)N)C(=O)NC(CC8=CC=C(C=C8)O)C(=O)NC(CCC(=O)N)C(=O)O)CCCCN)CCCNC(=N)N)CC(=O)O)C(C)C)CC9=CC=CC=C9

It is a highly selective blocker of the high conductance Ca2+-activated K+ channel. Iberiotoxin appears to modulate ChTX binding by an allosteric mechanism.37-amino acid peptide with 3 disulfide bridges.<!–C<SUB>179</SUB>H<SUB>274</SUB>N<SUB>50</SUB>O<SUB>55</SUB>S<SUB>7</SUB>–>Synthetic, originally from <I>Buthus tamulus</I> scorpion venom.As a specific blocker of Ca2+-activated K+ channels, Iberiotoxin does not affect other types of voltage-dependent K+ channels which are sensitive to inhibition by Charybdotoxin. Iberiotoxin blocks Ca2+-activated K+ channels by binding to their external mouth, and this binding is tighter and with an equilibrium dissociation constant 10-fold lower than that of Charybdotoxin.

Reference

– Galvez et al., /Purification and characterization of a unique, potent, peptidyl probe for the high conductance calcium-activated potassium channel from venom of the scorpion Buthus tamulus./<I> J. Biol. Chem. </I> (1990) 265(19):11083-11090- Candia et al., /Mode of action of Iberiotoxin, a potent blocker of the large conductance Ca2+-activated K+ channel./ Biophys. J. (1992). 63:583-590