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Key Documents

C7802

Sigma-Aldrich

Charybdotoxin

≥90% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C176H277N57O55S7
CAS Number:
Molecular Weight:
4295.89
MDL number:
UNSPSC Code:
51111800
NACRES:
NA.32

Quality Level

Assay

≥90% (HPLC)

form

powder

storage temp.

−20°C

InChI

1S/C176H277N57O55S7/c1-81(2)58-106-149(263)213-110(62-91-67-191-80-197-91)152(266)215-112(64-127(183)246)156(270)231-135(85(8)240)170(284)219-114(69-234)157(271)200-95(36-25-54-192-174(185)186)138(252)196-68-130(249)199-96(32-17-21-50-177)139(253)222-120-75-291-295-79-124(226-159(273)116(71-236)218-167(281)132(82(3)4)228-155(269)113(65-128(184)247)216-169(283)134(84(7)239)230-154(268)108(59-88-28-13-12-14-29-88)210-145(259)102-44-47-129(248)198-102)166(280)232-137(87(10)242)172(286)233-136(86(9)241)171(285)220-115(70-235)158(272)204-98(34-19-23-52-179)141(255)206-104(45-48-131(250)251)147(261)225-122-77-292-290-74-119(223-143(257)99(35-20-24-53-180)201-140(254)97(33-18-22-51-178)203-153(267)111(63-126(182)245)214-148(262)105(49-57-289-11)208-162(120)276)161(275)205-101(38-27-56-194-176(189)190)144(258)224-121(164(278)211-107(60-89-39-41-92(243)42-40-89)150(264)221-118(73-238)173(287)288)76-293-294-78-123(163(277)207-103(43-46-125(181)244)146(260)202-100(142(256)209-106)37-26-55-193-175(187)188)227-168(282)133(83(5)6)229-160(274)117(72-237)217-151(265)109(212-165(122)279)61-90-66-195-94-31-16-15-30-93(90)94/h12-16,28-31,39-42,66-67,80-87,95-124,132-137,195,234-243H,17-27,32-38,43-65,68-79,177-180H2,1-11H3,(H2,181,244)(H2,182,245)(H2,183,246)(H2,184,247)(H,191,197)(H,196,252)(H,198,248)(H,199,249)(H,200,271)(H,201,254)(H,202,260)(H,203,267)(H,204,272)(H,205,275)(H,206,255)(H,207,277)(H,208,276)(H,209,256)(H,210,259)(H,211,278)(H,212,279)(H,213,263)(H,214,262)(H,215,266)(H,216,283)(H,217,265)(H,218,281)(H,219,284)(H,220,285)(H,221,264)(H,222,253)(H,223,257)(H,224,258)(H,225,261)(H,226,273)(H,227,282)(H,228,269)(H,229,274)(H,230,268)(H,231,270)(H,232,280)(H,233,286)(H,250,251)(H,287,288)(H4,185,186,192)(H4,187,188,193)(H4,189,190,194)/t84-,85-,86-,87-,95+,96+,97+,98+,99+,100+,101+,102+,103+,104+,105+,106+,107+,108+,109+,110+,111+,112+,113+,114+,115+,116+,117+,118+,119+,120+,121+,122+,123+,124+,132+,133+,134+,135+,136+,137+/m1/s1

InChI key

CNVQLPPZGABUCM-LIGYZCPXSA-N

Gene Information

human ... KCNA3(3738)
mouse ... KCNA3(16491)
rat ... KCNA3(29731)

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Amino Acid Sequence

Glp-Phe-Thr-Asn-Val-Ser-Cys-Thr-Thr-Ser-Lys-Glu-Cys-Trp-Ser-Val-Cys-Gln-Arg-Leu-His-Asn-Thr-Ser-Arg-Gly-Lys-Cys-Met-Asn-Lys-Lys-Cys-Arg-Cys-Tyr-Ser [Disulfide Bridges: 7-28, 13-33, 17-35]

Application

Charybdotoxin has been used:
  • in the inhibition of endothelium-derived hyperpolarizing factor responses
  • in electrophysiological studies, as calcium channel blockers
  • as a transport inhibitor

Biochem/physiol Actions

Charybdotoxin (ChTX) is a scorpion venom, which blocks a voltage-gated potassium channel, by binding to the extracellular loop of the potassium channel.
High (BK) or intermediate (IK1) conductance calcium-activated and voltage-gated (Kv1.3) channel blocker.
Potent and selective inhibitor of the Ca2+-activated K+ channel present in GH3 anterior pituitary cells and primary bovine aortic smooth muscle cells.

Other Notes

Peptide found in the venom of the scorpion Leiurus quinquestriatus.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J M Doughty et al.
The American journal of physiology, 276(3 Pt 2), H1107-H1112 (1999-03-10)
In rat mesenteric artery, endothelium-derived hyperpolarizing factor (EDHF) is blocked by a combination of apamin and charybdotoxin (ChTX). The site of action of these toxins has not been established. We compared the effects of ChTX and apamin applied selectively to
Solution structure of extracellular loop of human beta4 subunit of BK channel and its biological implication on ChTX sensitivity
Wang Y, et al.
Scientific Reports, 8(1), 4571-4571 (2018)
Transepithelial impedance analysis of chloride secretion.
Ashvani K Singh et al.
Methods in molecular medicine, 70, 129-142 (2002-03-29)
Cultured heart cells from oyster: an experimental approach for evaluation of the toxicity of the marine pollutant tributyltin
Droguet M, et al.
Aquatic Living Resources, 25(2), 185-194 (2012)
Dan Gordon et al.
The journal of physical chemistry. B, 116(6), 1933-1941 (2012-01-20)
Using a novel rigid body Brownian dynamics algorithm, we investigate how a spherically asymmetrical polyamine molecule, a branched analogue of spermine, interacts with the external vestibule of the voltage-gated potassium channel, Kv1.2. Simulations reveal that the blocker, with a charge

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