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Merck

C7802

Sigma-Aldrich

Charybdotoxin

≥90% (HPLC)

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About This Item

Empirische Formel (Hill-System):
C176H277N57O55S7
CAS-Nummer:
Molekulargewicht:
4295.89
MDL-Nummer:
UNSPSC-Code:
51111800
NACRES:
NA.32

Qualitätsniveau

Assay

≥90% (HPLC)

Form

powder

Lagertemp.

−20°C

SMILES String

S1SC[C@@H]2NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CSSC[C@@H]5NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)

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

InChIKey

CNVQLPPZGABUCM-LIGYZCPXSA-N

Angaben zum Gen

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]

Anwendung

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. Wirkung

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.
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.

Sonstige Hinweise

Peptide found in the venom of the scorpion Leiurus quinquestriatus.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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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)
M Hanner et al.
The Journal of biological chemistry, 273(26), 16289-16296 (1998-06-20)
Coexpression of alpha and beta subunits of the high conductance Ca2+-activated K+ (maxi-K) channel leads to a 50-fold increase in the affinity for 125I-charybdotoxin (125I-ChTX) as compared with when the alpha subunit is expressed alone (Hanner, M., Schmalhofer, W. A.
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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