Iberiotoxin

Iberiotoxin is a toxin isolated from Buthus tamulus scorpion venom. Iberiotoxin is a selective high conductance high conductance Ca2+-activated K+ channel inhibitor with a Kd of ~1 nM. Iberiotoxin does not block other types of voltage-dependent ion channels.

Product information

CAS Number: 129203-60-7

Molecular Weight: 4230.85

Formula: C179H274N50O55S7

Chemical Name: 5-amino-2-[[2-[[10-[[6-amino-2-[[6-amino-2-[[2-[[2-[[7, 34-bis(4-aminobutyl)-37-[[2-[[2-[[2-[[10-(4-aminobutyl)-22-[[3-carboxy-2-[[2-[[3-carboxy-2-[[3-hydroxy-2-[[2-[(5-oxopyrrolidine-2-carbonyl)amino]-3-phenylpropanoyl]amino]butanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-7-(2-carboxyethyl)-13, 19-bis(hydroxymethyl)-6, 9, 12, 15, 18, 21-hexaoxo-16-propan-2-yl-1, 2-dithia-5, 8, 11, 14, 17, 20-hexazacyclotricosane-4-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylbutanoyl]amino]-25-benzyl-13-(3-carbamimidamidopropyl)-16, 31-bis(carboxymethyl)-28-(2-methylpropyl)-6, 9, 12, 15, 18, 21, 24, 27, 30, 33, 36-undecaoxo-19-propan-2-yl-1, 2-dithia-5, 8, 11, 14, 17, 20, 23, 26, 29, 32, 35-undecazacyclooctatriacontane-4-carbonyl]amino]-4-methylsulfanylbutanoyl]amino]acetyl]amino]hexanoyl]amino]hexanoyl]amino]-7-(3-carbamimidamidopropyl)-6, 9-dioxo-1, 2-dithia-5, 8-diazacycloundecane-4-carbonyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoic acid

Smiles: CC(O)C(NC(=O)C(CC1C=CC=CC=1)NC(=O)C1CCC(=O)N1)C(=O)NC(CC(O)=O)C(=O)NC(C(C)C)C(=O)NC(CC(O)=O)C(=O)NC1CSSCC(NC(=O)C(CCC(O)=O)NC(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C(NC(=O)C(CO)NC1=O)C(C)C)C(=O)NC(CC1=CNC2=CC=CC=C12)C(=O)NC(CO)C(=O)NC(C(C)C)C(=O)NC1CSSCC(NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CCCNC(N)=N)NC(=O)C(CC(O)=O)NC(=O)C(NC(=O)CNC(=O)C(CC2C=CC=CC=2)NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)NC(=O)C(CCCCN)NC1=O)C(C)C)C(=O)NC(CCSC)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC1CSSCC(NC(=O)C(CCCNC(N)=N)NC1=O)C(=O)NC(CC1C=CC(O)=CC=1)C(=O)NC(CCC(N)=O)C(O)=O

InChiKey: VDNVVLOBNHIMQA-UHFFFAOYSA-N

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)

Technical Data

Appearance: Solid Power

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Iberiotoxin reversibly blocks Ca2+-activated K+ channel in excised membrane patches from bovine aortic smooth muscle. Iberiotoxin acts exclusively at the outer face of the channel and functions with IC50 values of about 250 pM. Iberiotoxin is a partial inhibitor of 125I-charybdotoxin binding in bovine aortic sarcolemmal membrane vesicles (Ki of 250 pM). Iberiotoxin functions as a noncompetitive inhibitor of charybdotoxin binding. Iberiotoxin treatment affects rat mesenchymal stem cells (rMSCs) migration in the absence of platelet lysate (PL) by inducing a decrease in cell migration suggesting that BK channels regulate rMSCs migration in basal conditions. 10 nM of Iberiotoxin abolishes the PL-induced migration effect on MSCs.

In Vivo:

Male Wistar rats (6-7 weeks old) with chronic heart failure (CHF), Iberiotoxin (0.125 nmol/nl, 1.25 nmol/nl and 12.5 nmol/nl) is infused into paraventricular hypothalamic nucleus (PVN) by osmotic minipumps. After perfusion of Iberiotoxin by microinjection of rAAV2-KCNMB4 shRNA virus, right ventricular weight/body weight and lung weight/body weight ratio as well as left ventricular end-diastolic diameter are increased and left ventricular ejection fraction is decreased.

References:

1. A 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. J Biol Chem. 1990 Jul 5;265(19):11083-90.
2. Santiago Echeverry, et al. Activation of BK Channel Contributes to PL-Induced Mesenchymal Stem Cell Migration. Front Physiol. 2020 Mar 24;11:210.
3. S Candia, et al. Mode of Action of Iberiotoxin, a Potent Blocker of the Large Conductance Ca(2+)-activated K+ Channel. Biophys J. 1992 Aug;63(2):583-90.

Products are for research use only. Not for human use.