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alpha-Dendrotoxin

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

alpha-Dendrotoxin is from the venom of the Eastern green mamba, Dendroaspis angusticeps. It selectively blocks voltage-gated activation of the K+ channels in the synaptosomes.

Category

Peptide Inhibitors

Catalog number

BAT-015148

CAS number

74504-53-3

Molecular Formula

C305H472N98O84S6

Molecular Weight

7048.11

Specification
Reference Reading

IUPAC Name

(4S)-4-amino-5-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2R)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[(2S)-2-[[2-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S,3S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-5-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-5-amino-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2R)-1-[[2-[[2-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S,3R)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-5-carbamimidamido-1-[[(2S)-5-carbamimidamido-1-[[(2S,3R)-1-[[(2R)-1-[[(2S,3S)-1-(carboxymethylamino)-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-1,4-dioxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-oxopentanoic acid

Synonyms

α-Dendrotoxin (reduced); α-DTX; Pyr-Pro-Arg-Arg-Lys-Leu-Cys-Ile-Leu-His-Arg-Asn-Pro-Gly-Arg-Cys-Tyr-Asp-Lys-Ile-Pro-Ala-Phe-Tyr-Tyr-Asn-Gln-Lys-Lys-Lys-Gln-Cys-Glu-Arg-Phe-Asp-Trp-Ser-Gly-Cys-Gly-Gly-Asn-Ser-Asn-Arg-Phe-Lys-Thr-Ile-Glu-Glu-Cys-Arg-Arg-Thr-Cys-Ile-Gly-OH (Disulfide bridge: Cys7-Cys57, Cys16-Cys40, Cys32-Cys53); Toxin C13S2C3 (Dendroaspis angusticeps reduced)

Appearance

White Lyophilized Powder

Purity

≥98% by HPLC

Sequence

pEPRRKLCILHRNPGRCYDKIPAFYYNQKKKQCERFDWSGCGGNSNRFKTIEECRRTCIG (Disulfide bridge: Cys7-Cys57, Cys16-Cys40, Cys32-Cys53)

Storage

Store at -20°C

Solubility

Soluble in Acetic Acid, Water

InChI

InChI=1S/C305H480N98O85S6/c1-16-154(9)238(290(481)349-142-237(433)434)395-286(477)217(150-494)394-293(484)242(159(14)406)399-265(456)188(75-50-116-343-305(333)334)361-252(443)183(70-45-111-338-300(323)324)366-282(473)213(146-490)392-262(453)192(95-101-233(425)426)368-260(451)193(96-102-234(427)428)372-291(482)240(156(11)18-3)397-294(485)243(160(15)407)400-264(455)181(67-36-42-108-311)362-268(459)197(123-162-56-25-21-26-57-162)375-256(447)185(72-47-113-340-302(327)328)365-277(468)206(132-225(317)415)383-281(472)211(144-405)389-276(467)204(130-223(315)413)353-228(418)139-345-227(417)138-346-246(437)212(145-489)354-230(420)140-347-245(436)210(143-404)388-274(465)202(128-167-136-344-174-61-30-29-60-172(167)174)380-280(471)208(135-236(431)432)385-272(463)198(124-163-58-27-22-28-59-163)376-255(446)184(71-46-112-339-301(325)326)360-259(450)191(94-100-232(423)424)370-283(474)214(147-491)391-261(452)190(93-98-222(314)412)367-250(441)178(64-33-39-105-308)356-248(439)176(62-31-37-103-306)355-249(440)177(63-32-38-104-307)358-258(449)189(92-97-221(313)411)369-278(469)205(131-224(316)414)382-271(462)200(126-165-81-87-170(409)88-82-165)378-270(461)199(125-164-79-85-169(408)86-80-164)377-269(460)196(122-161-54-23-20-24-55-161)373-244(435)158(13)351-288(479)219-77-53-119-403(219)297(488)241(157(12)19-4)398-263(454)180(66-35-41-107-310)363-279(470)207(134-235(429)430)384-273(464)201(127-166-83-89-171(410)90-84-166)379-284(475)215(148-492)390-247(438)175(68-43-109-336-298(319)320)352-229(419)141-348-287(478)218-76-51-118-402(218)296(487)209(133-226(318)416)387-257(448)186(73-48-114-341-303(329)330)364-275(466)203(129-168-137-335-151-350-168)381-266(457)195(121-153(7)8)386-292(483)239(155(10)17-2)396-285(476)216(149-493)393-267(458)194(120-152(5)6)374-254(445)179(65-34-40-106-309)357-251(442)182(69-44-110-337-299(321)322)359-253(444)187(74-49-115-342-304(331)332)371-289(480)220-78-52-117-401(220)295(486)173(312)91-99-231(421)422/h20-30,54-61,79-90,136-137,151-160,173,175-220,238-243,344,404-410,489-494H,16-19,31-53,62-78,91-135,138-150,306-312H2,1-15H3,(H2,313,411)(H2,314,412)(H2,315,413)(H2,316,414)(H2,317,415)(H2,318,416)(H,335,350)(H,345,417)(H,346,437)(H,347,436)(H,348,478)(H,349,481)(H,351,479)(H,352,419)(H,353,418)(H,354,420)(H,355,440)(H,356,439)(H,357,442)(H,358,449)(H,359,444)(H,360,450)(H,361,443)(H,362,459)(H,363,470)(H,364,466)(H,365,468)(H,366,473)(H,367,441)(H,368,451)(H,369,469)(H,370,474)(H,371,480)(H,372,482)(H,373,435)(H,374,445)(H,375,447)(H,376,446)(H,377,460)(H,378,461)(H,379,475)(H,380,471)(H,381,457)(H,382,462)(H,383,472)(H,384,464)(H,385,463)(H,386,483)(H,387,448)(H,388,465)(H,389,467)(H,390,438)(H,391,452)(H,392,453)(H,393,458)(H,394,484)(H,395,477)(H,396,476)(H,397,485)(H,398,454)(H,399,456)(H,400,455)(H,421,422)(H,423,424)(H,425,426)(H,427,428)(H,429,430)(H,431,432)(H,433,434)(H4,319,320,336)(H4,321,322,337)(H4,323,324,338)(H4,325,326,339)(H4,327,328,340)(H4,329,330,341)(H4,331,332,342)(H4,333,334,343)/t154-,155-,156-,157-,158-,159+,160+,173-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,185-,186-,187-,188-,189-,190-,191-,192-,193-,194-,195-,196-,197-,198-,199-,200-,201-,202-,203-,204-,205-,206-,207-,208-,209-,210-,211-,212-,213-,214-,215-,216-,217-,218-,219-,220-,238-,239-,240-,241-,242-,243-/m0/s1

InChI Key

VTZVGBZAMQCGPU-IXCSVPCASA-N

Canonical SMILES

CCC(C)C(C(=O)NCC(=O)O)NC(=O)C(CS)NC(=O)C(C(C)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CS)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)CC)NC(=O)C(C(C)O)NC(=O)C(CCCCN)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(=O)N)NC(=O)C(CO)NC(=O)C(CC(=O)N)NC(=O)CNC(=O)CNC(=O)C(CS)NC(=O)CNC(=O)C(CO)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CC(=O)O)NC(=O)C(CC4=CC=CC=C4)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)O)NC(=O)C(CS)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CC5=CC=C(C=C5)O)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CC7=CC=CC=C7)NC(=O)C(C)NC(=O)C8CCCN8C(=O)C(C(C)CC)NC(=O)C(CCCCN)NC(=O)C(CC(=O)O)NC(=O)C(CC9=CC=C(C=C9)O)NC(=O)C(CS)NC(=O)C(CCCNC(=N)N)NC(=O)CNC(=O)C1CCCN1C(=O)C(CC(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC1=CN=CN1)NC(=O)C(CC(C)C)NC(=O)C(C(C)CC)NC(=O)C(CS)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C1CCCN1C(=O)C(CCC(=O)O)N

1. [VGKC-complex antibodies]

Osamu Watanabe Brain Nerve . 2013 Apr;65(4):401-11.

Various antibodies are associated with voltage-gated potassium channels (VGKCs). Representative antibodies to VGKCs were first identified by radioimmunoassays using radioisotope-labeled alpha-dendrotoxin-VGKCs solubilized from rabbit brain. These antibodies were detected only in a proportion of patients with acquired neuromyotonia (Isaacs' syndrome). VGKC antibodies were also detected in patients with Morvan's syndrome and in those with a form of autoimmune limbic encephalitis. Recent studies indicated that the "VGKC" antibodies are mainly directed toward associated proteins (for example LGI-1 and CASPR-2) that complex with the VGKCs themselves. The "VGKC" antibodies are now commonly known as VGKC-complex antibodies. In general, LGI-1 antibodies are most commonly detected in patients with limbic encephalitis with syndrome of inappropriate secretion of antidiuretic hormone. CASPR-2 antibodies are present in the majority of patients with Morvan's syndrome. These patients develop combinations of CNS symptoms, autonomic dysfunction, and peripheral nerve hyperexcitability. Furthermore, VGKC-complex antibodies are tightly associated with chronic idiopathic pain. Hyperexcitability of nociceptive pathways has also been implicated. These antibodies may be detected in sera of some patients with neurodegenerative diseases (for example, amyotrophic lateral sclerosis and Creutzfeldt-Jakob disease).

2. The alpha-dendrotoxin footprint on a mammalian potassium channel

E Carmeliet, T Debont, P Daenens, J Tytgat J Biol Chem . 1995 Oct 20;270(42):24776-81. doi: 10.1074/jbc.270.42.24776.

alpha-Dendrotoxin, a 59-amino acid basic peptide from the venom of Dendroaspis angusticeps (green mamba snake), potently blocks some but not all voltage-dependent potassium channels. Here we have investigated the relative contribution of the individual alpha-subunits constituting functional Kv1.1 potassium channels to alpha-dentroxin binding. Three residues critical for alpha-dentrotoxin binding and located in the loop between domains S5 and S6 were mutated (A352P, E353S, and Y379H), and multimeric cDNAs were constructed encoding homo- and heterotetrameric channels composed of all possible ratios of wild-type and mutant alpha-subunits. Complete mutant channels were about 200-fold less sensitive for the alpha-dendrotoxin block than complete wild-type channels, which is attributable to a smaller association rate. Analysis of the bimolecular reaction between alpha-dendrotoxin and the different homo- and heteromeric channel constructs revealed that the association rate depends on the number of wild-type alpha-subunits in the functional channel. Furthermore, we observed a linear relationship between the number of wild-type alpha-subunits in functional channels and the free energy for alpha-dendrotoxin binding, providing evidence that all four alpha-subunits must interact with alpha-dendrotoxin to produce a high affinity binding site.

3. Effects of alpha-dendrotoxin and dendrotoxin K on extracellular excitatory amino acids and on electroencephalograph spectral power in the hippocampus of anaesthetised rats

G Bagetta, L A Morrone, N G Bowery, D A Richards Neurosci Lett . 2000 Nov 3;293(3):183-6. doi: 10.1016/s0304-3940(00)01530-5.

Dendrotoxins, important pharmacological tools for studying K(+) channels, are potently convulsant in the central nervous system and evidence suggests that different members of the dendrotoxin family may act at pre- or post-synaptic sites. Using a combination of intrahippocampal infusion, microdialysis and electroencephalograph (EEG) recording, we have compared the effects of alpha-dendrotoxin and dendrotoxin K on extracellular levels of excitatory amino acids in anaesthetised rats. Our findings show that although infusion of 35 pmol of both peptides was associated with elevated extracellular aspartate and glutamate, these increased levels were more sustained with dendrotoxin K. Furthermore, there was EEG evidence of an associated transient functional change consistent with an action on pre-synaptic K(+) channels. In contrast, infusion of alpha-dendrotoxin produced only a brief effect on amino acid levels and no evidence of a functional consequence.