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AmmTX3

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

AmmTX3 is a peptide that can be isolated from the venom of Androctonus mauretanicus and belongs scorpion toxin of the α-KTX15 subfamily. It is a specific potassium 4 (Kv4) channel blocker and could reduce the A-type potassium current in mouse cerebellar granule neurons through this channel. It has specific high-affinity blockade for Kv4.2 and Kv4.3 channels of mice because of expression of dipeptidyl peptidase-like proteins (DPP) DPP6 and DPP10. It also has a small blocking effect on hERG channels without alteration of the gating kinetics.

Category

Peptide Inhibitors

Catalog number

BAT-010307

Molecular Formula

C158H262N50O48S6

Molecular Weight

3822.47

Specification
Reference Reading

IUPAC Name

(2S)-1-[(2S)-2-[[(1R,4S,7R,12R,15S,18S,21S,24S,30S,33S,36S,42S,45R,50R,53S,62S,65R,72S,78S,81S,86S,89S,92S)-50-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-4-amino-2-[[(2S,3R)-2-[[(2S)-4-carboxy-2-[[(2S,3S)-3-methyl-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]butanoyl]amino]-3-hydroxybutanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]hexanoyl]amino]-18,42-bis(4-aminobutyl)-78-(2-amino-2-oxoethyl)-53-(3-amino-3-oxopropyl)-24,81-bis[(2S)-butan-2-yl]-15,72-bis(3-carbamimidamidopropyl)-62,89-bis(hydroxymethyl)-33,36,86-trimethyl-2,5,13,16,19,22,25,28,31,34,37,40,43,51,54,57,60,63,71,74,77,80,83,84,87,90,93-heptacosaoxo-4,21,30,92-tetra(propan-2-yl)-9,10,47,48,67,68-hexathia-3,6,14,17,20,23,26,29,32,35,38,41,44,52,55,58,61,64,70,73,76,79,82,85,88,91,94-heptacosazatricyclo[43.24.14.1112,65]tetranonacontane-7-carbonyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxylic acid

Purity

>98%

Sequence

XIETNKKC(1)QGGSC(2)ASVC(3)RKVIGVAAGKC(1)INGRC(2)VC(3)YP(Modifications: X = Glp)

Storage

Store at -20°C

InChI

InChI=1S/C158H262N50O48S6/c1-19-77(12)121-147(246)176-64-115(221)200-117(73(4)5)148(247)179-81(16)126(225)177-80(15)125(224)173-62-113(219)181-86(33-22-26-50-159)130(229)196-105-72-262-258-68-101(194-134(233)89(35-24-28-52-161)184-132(231)88(34-23-27-51-160)186-138(237)96(59-109(165)215)191-154(253)124(83(18)211)207-137(236)94(46-49-116(222)223)189-152(251)122(78(13)20-2)204-136(235)93-45-48-110(216)180-93)142(241)188-92(44-47-107(163)213)128(227)174-60-111(217)172-61-112(218)183-98(65-209)139(238)197-100-67-257-261-71-104(195-131(230)87(37-30-54-170-157(166)167)182-114(220)63-175-129(228)95(58-108(164)214)190-153(252)123(79(14)21-3)205-146(105)245)145(244)203-119(75(8)9)150(249)199-103(144(243)192-97(57-84-40-42-85(212)43-41-84)155(254)208-56-32-39-106(208)156(255)256)70-260-259-69-102(198-149(248)118(74(6)7)202-140(239)99(66-210)193-127(226)82(17)178-141(100)240)143(242)187-91(38-31-55-171-158(168)169)133(232)185-90(36-25-29-53-162)135(234)201-120(76(10)11)151(250)206-121/h40-43,73-83,86-106,117-124,209-212H,19-39,44-72,159-162H2,1-18H3,(H2,163,213)(H2,164,214)(H2,165,215)(H,172,217)(H,173,224)(H,174,227)(H,175,228)(H,176,246)(H,177,225)(H,178,240)(H,179,247)(H,180,216)(H,181,219)(H,182,220)(H,183,218)(H,184,231)(H,185,232)(H,186,237)(H,187,242)(H,188,241)(H,189,251)(H,190,252)(H,191,253)(H,192,243)(H,193,226)(H,194,233)(H,195,230)(H,196,229)(H,197,238)(H,198,248)(H,199,249)(H,200,221)(H,201,234)(H,202,239)(H,203,244)(H,204,235)(H,205,245)(H,206,250)(H,207,236)(H,222,223)(H,255,256)(H4,166,167,170)(H4,168,169,171)/t77-,78-,79-,80-,81-,82-,83+,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,117-,118-,119-,120-,121-,122-,123-,124-/m0/s1

InChI Key

SVJLXERVUUOWID-PKTDLBDVSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC2CSSCC3C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(NC(=O)C(NC2=O)C(C)C)C(=O)NC(CC4=CC=C(C=C4)O)C(=O)N5CCCC5C(=O)O)C(=O)NC(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)NC(CSSCC(C(=O)NC(C(=O)NCC(=O)NCC(=O)NC(C(=O)N3)CO)CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CC(=O)N)NC(=O)C(C(C)O)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)CC)NC(=O)C6CCC(=O)N6)C(=O)N1)CCCCN)C)C)C(C)C)C(C)CC)C(C)C)CCCCN)CCCNC(=N)N)C(C)C)CO)C)CCCNC(=N)N)CC(=O)N

1. Regulation of Rostral Nucleus of the Solitary Tract Responses to Afferent Input by A-type K+ Current

J B Travers, D H Terman, S P Travers, Z Chen Neuroscience . 2022 Jul 15;495:115-125. doi: 10.1016/j.neuroscience.2022.05.036.

Responses in the rostral (gustatory) nucleus of the solitary tract (rNST) are modified by synaptic interactions within the nucleus and the constitutive membrane properties of the neurons themselves. The potassium current IAis one potential source of modulation. In the caudal NST, projection neurons with IAshow lower fidelity to afferent stimulation compared to cells without. We explored the role of an A-type K+ current (IA) in modulating the response to afferent stimulation and GABA-mediated inhibition in the rNST using whole cell patch clamp recording in transgenic mice that expressed channelrhodopsin (ChR2 H134R) in GABAergic neurons. The presence of IAwas determined in current clamp and the response to electrical stimulation of afferent fibers in the solitary tract was assessed before and after treatment with the specific Kv4 channel blocker AmmTX3. Blocking IAsignificantly increased the response to afferent stimulation by 53%. Using dynamic clamp to create a synthetic IAconductance, we demonstrated a significant 14% decrease in responsiveness to afferent stimulation in cells lacking IA. Because IAreduced excitability and is hyperpolarization-sensitive, we examined whether IAcontributed to the inhibition resulting from optogenetic release of GABA. Although blocking IAdecreased the percent suppression induced by GABA, this effect was attributable to the increased responsiveness resulting from AmmTX3, not to a change in the absolute magnitude of suppression. We conclude that rNST responses to afferent input are regulated independently by IAand GABA.

2. Kv4 potassium channels modulate hippocampal EPSP-spike potentiation and spatial memory in rats

Franck A Chaillan, François S Roman, Christine Manrique, Christiane Mourre, Bruno Truchet, Leam Sreng Learn Mem . 2012 Jun 14;19(7):282-93. doi: 10.1101/lm.025411.111.

Kv4 channels regulate the backpropagation of action potentials (b-AP) and have been implicated in the modulation of long-term potentiation (LTP). Here we showed that blockade of Kv4 channels by the scorpion toxin AmmTX3 impaired reference memory in a radial maze task. In vivo, AmmTX3 intracerebroventricular (i.c.v.) infusion increased and stabilized the EPSP-spike (E-S) component of LTP in the dentate gyrus (DG), with no effect on basal transmission or short-term plasticity. This increase in E-S potentiation duration could result from the combination of an increase in excitability of DG granular cells with a reduction of GABAergic inhibition, leading to a strong reduction of input specificity. Radioactive in situ hybridization (ISH) was used to evaluate the amounts of Kv4.2 and Kv4.3 mRNA in brain structures at different stages of a spatial learning task in naive, pseudoconditioned, and conditioned rats. Significant differences in Kv4.2 and Kv4.3 mRNA levels were observed between conditioned and pseudoconditioned rats. Kv4.2 and Kv4.3 mRNA levels were transiently up-regulated in the striatum, nucleus accumbens, retrosplenial, and cingulate cortices during early stages of learning, suggesting an involvement in the switch from egocentric to allocentric strategies. Spatial learning performance was positively correlated with the levels of Kv4.2 and Kv4.3 mRNAs in several of these brain structures. Altogether our findings suggest that Kv4 channels could increase the signal-to-noise ratio during information acquisition, thereby allowing a better encoding of the memory trace.

3. Expanding the scorpion toxin alpha-KTX 15 family with AmmTX3 from Androctonus mauretanicus

Marie-France Martin-Eauclaire, Meriem Alami, Lourival D Possani, Hélène Vacher, Marcel Crest, Pierre E Bougis Eur J Biochem . 2002 Dec;269(24):6037-41. doi: 10.1046/j.1432-1033.2002.03294.x.

A novel toxin, AmmTX3 (3823.5 Da), was isolated from the venom of the scorpion Androctonus mauretanicus. It showed 94% sequence homology with Aa1 from Androctonus australis and 91% with BmTX3 from Buthus martensi which, respectively, block A-type K+ current in cerebellum granular cells and striatum cultured neurons. Binding and displacement experiments using rat brain synaptosomes showed that AmmTX3 and Aa1 competed effectively with 125I-labelled sBmTX3 binding. They fully inhibited the 125I-labelled sBmTX3 binding (Ki values of 19.5 pm and 44.2 pm, respectively), demonstrating unambiguously that the three molecules shared the same target in rat brain. The specific binding parameters of 125I-labelled AmmTX3 for its site were determined at equilibrium (Kd = 66 pm, Bmax = 22 fmol per mg of protein). Finally, patch-clamp experiments on striatal neurons in culture demonstrated that AmmTX3 was able to inhibit the A-type K+ current (Ki = 131 nm).