Need Assistance?

US & Canada:
+
UK: +

Our Highlights

GMP Grade Efficient workshop for GMP production.
Optimal Prices Buying products on this site guarantees the best price!
Commercial Batches Independent GMP manufacturing suites that handle commercial batches
Prompt Delivery Warehouses in multiple cities to ensure timely delivery
Flexible Quantity Quantities available from milligrams to ton

Kaliotoxin

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Potent blocker of voltage-sensitive K+ channels (IC50 values are 0.1, 1.1 and 25 nM for KV1.3, KV1.1 and KV1.2 channels) respectively). Also inhibits Ca2+-activated K+ channels.

Category

Peptide Inhibitors

Catalog number

BAT-010733

CAS number

145199-73-1

Molecular Formula

C171H283N55O49S8

Molecular Weight

4149.94

Specification
Reference Reading

IUPAC Name

6-amino-2-[[1-[2-[[47-[[6-amino-2-[[2-[[4-amino-2-[[2-[[2-[[2-[(2-aminoacetyl)amino]-3-methylbutanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]-15,39,75,92-tetrakis(4-aminobutyl)-81-(2-amino-2-oxoethyl)-65-(3-amino-3-oxopropyl)-33-benzyl-30,78-bis(3-carbamimidamidopropyl)-18-(carboxymethyl)-50,56-bis(hydroxymethyl)-4-(1H-imidazol-4-ylmethyl)-21-methyl-89-(2-methylpropyl)-27,84-bis(2-methylsulfanylethyl)-2,5,13,16,19,22,25,28,31,34,37,40,48,51,54,57,63,66,74,77,80,83,86,87,90,93,99-heptacosaoxo-9,10,44,45,70,71-hexathia-a,3,6,14,17,20,23,26,29,32,35,38,41,49,52,55,58,64,67,73,76,79,82,85,88,91,94-heptacosazapentacyclo[40.30.14.1412,68.058,62.094,98]hectane-7-carbonyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]hexanoic acid

Appearance

White lyophilised powder

Purity

98 % (HPLC).

Sequence

GVEXNVKC(1)SGSPQC(2)LKPC(3)KDAGMRFGKC(1)MNRKC(2)HC(3)XPK

Storage

stable in freeze-dried state. In solution, keep at -20 °C.

Solubility

Well in water and saline

InChI

InChI=1S/C171H283N55O49S8/c1-13-89(8)134(222-148(253)101(48-50-130(237)238)204-163(268)132(87(4)5)220-126(233)72-178)165(270)212-110(70-125(181)232)153(258)221-133(88(6)7)164(269)203-97(39-20-26-56-175)144(249)216-117-82-281-278-79-114-154(259)201-103(52-65-277-12)147(252)210-109(69-124(180)231)152(257)199-98(42-29-59-187-170(182)183)140(245)197-96(38-19-25-55-174)143(248)215-116-81-280-279-80-115(217-145(250)100(47-49-123(179)230)202-160(265)120-44-32-62-225(120)167(272)113(78-228)196-129(236)76-191-138(243)112(77-227)213-158(117)263)156(261)207-106(66-86(2)3)150(255)205-104(40-21-27-57-176)166(271)224-61-31-45-121(224)162(267)219-118(83-282-283-84-119(218-151(256)108(209-157(116)262)68-93-73-186-85-192-93)159(264)223-135(91(10)229)168(273)226-63-33-46-122(226)161(266)206-105(169(274)275)41-22-28-58-177)155(260)200-95(37-18-24-54-173)141(246)211-111(71-131(239)240)149(254)193-90(9)136(241)189-74-127(234)195-102(51-64-276-11)146(251)198-99(43-30-60-188-171(184)185)142(247)208-107(67-92-34-15-14-16-35-92)137(242)190-75-128(235)194-94(139(244)214-114)36-17-23-53-172/h14-16,34-35,73,85-91,94-122,132-135,227-229H,13,17-33,36-72,74-84,172-178H2,1-12H3,(H2,179,230)(H2,180,231)(H2,181,232)(H,186,192)(H,189,241)(H,190,242)(H,191,243)(H,193,254)(H,194,235)(H,195,234)(H,196,236)(H,197,245)(H,198,251)(H,199,257)(H,200,260)(H,201,259)(H,202,265)(H,203,269)(H,204,268)(H,205,255)(H,206,266)(H,207,261)(H,208,247)(H,209,262)(H,210,252)(H,211,246)(H,212,270)(H,213,263)(H,214,244)(H,215,248)(H,216,249)(H,217,250)(H,218,256)(H,219,267)(H,220,233)(H,221,258)(H,222,253)(H,223,264)(H,237,238)(H,239,240)(H,274,275)(H4,182,183,187)(H4,184,185,188)

InChI Key

VRARWAGTAUYUOO-UHFFFAOYSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)NC(CCCCN)C(=O)NC1CSSCC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC3CSSCC(C(=O)NC(C(=O)NC(C(=O)N4CCCC4C(=O)NC(CSSCC(NC(=O)C(NC3=O)CC5=CNC=N5)C(=O)NC(C(C)O)C(=O)N6CCCC6C(=O)NC(CCCCN)C(=O)O)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N2)CCCCN)CC7=CC=CC=C7)CCCNC(=N)N)CCSC)C)CC(=O)O)CCCCN)CCCCN)CC(C)C)NC(=O)C(NC(=O)C8CCCN8C(=O)C(NC(=O)CNC(=O)C(NC1=O)CO)CO)CCC(=O)N)CCCCN)CCCNC(=N)N)CC(=O)N)CCSC)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)C)NC(=O)CN

1. Neuro-Modulation of Immuno-Endocrine Response Induced by Kaliotoxin of Androctonus Scorpion Venom

Marie-France Martin-Eauclaire, Amina Ladjel-Mendil, Fatima Laraba-Djebari J Biochem Mol Toxicol . 2016 Dec;30(12):580-587. doi: 10.1002/jbt.21824.

Kaliotoxin (KTX), a specific blocker of potassium channels, exerts various toxic effects due to its action on the central nervous system. Its use in experimental model could help the understanding of the cellular and molecular mechanisms involved in the neuropathological processes related to potassium channel dysfunctions. In this study, the ability of KTX to stimulate neuro-immuno-endocrine axis was investigated. As results, the intracerebroventricular injection of KTX leads to severe structural-functional alterations of both hypothalamus and thyroid. These alterations were characterized by a massive release of hormones' markers of thyroid function associated with damaged tissue which was infiltrated by inflammatory cell and an imbalanced redox status. Taken together, these data highlight that KTX is able to modulate the neuro-endocrine response after binding to its targets leading to the hypothalamus and the thyroid stimulation, probably by inflammatory response activation and the installation of oxidative stress in these organs.

2. Total chemical synthesis and X-ray structure of kaliotoxin by racemic protein crystallography

Michael R Sawaya, Brad L Pentelute, Zachary P Gates, Todd O Yeates, Kalyaneswar Mandal, Stephen B H Kent Chem Commun (Camb) . 2010 Nov 21;46(43):8174-6. doi: 10.1039/c0cc03148h.

Here we report the total synthesis of kaliotoxin by 'one pot' native chemical ligation of three synthetic peptides. A racemic mixture of D- and L-kaliotoxin synthetic protein molecules gave crystals in the centrosymmetric space group P1 that diffracted to atomic-resolution (0.95 Å), enabling the X-ray structure of kaliotoxin to be determined by direct methods.

3. Kaliotoxin, a Kv1.1 and Kv1.3 channel blocker, improves associative learning in rats

C Mourre, B Soumireu-Mourat, S Kourrich Behav Brain Res . 2001 Apr 8;120(1):35-46. doi: 10.1016/s0166-4328(00)00356-9.

Olfactory associative learning was used to investigate the involvement of Kv channels containing Kv1.1 and Kv1.3 alpha-subunits in learning and memory. Kaliotoxin (KTX), a specific inhibitor of these Kv channels, was injected intracerebroventricularly in the rat brain, at a dose of 10 ng that did not disturb the rats' locomotor activity or drinking behaviour. In the first paradigm (odour-reward training), KTX improved learning but not information consolidation. Moreover, KTX increased the long-term retrieval of an odour-reward association tested by a reversal test 1 month after the odour-reward training. The second paradigm (successive odour-pair training) tested reference memory. The first session was an acquisition session where the rats learned a new odour-discrimination problem with the same procedure. The second was a retention session held 24 h later to test retrieval of the learned information. KTX injected before the acquisition or retention session improved performance, but no effect was found when KTX was injected immediately after acquisition. We showed that these effects were not due to the action of KTX on attention processes. Thus, these results suggest that the blockage of Kv1.1 or Kv1.3 channels by KTX facilitates cognitive processes as learning, in particular in a reference representation.