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Huwentoxin XVI

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

Huwentoxin XVI is a potent and selective N-type Ca2+ channel blocker (IC50 ~ 60 nM) with no inhibitory effect on T-type Ca2+ channels, K+ channels or Na+ channels. Huwentoxin XVI exhibits analgesic effects in vivo.

Category

Peptide Inhibitors

Catalog number

BAT-010274

CAS number

1600543-88-1

Molecular Formula

C196H292N50O56S6

Molecular Weight

4437.13

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-2-[[(2S)-2-[[(1R,2aR,4S,7S,7aR,10aS,13S,16S,16aS,19S,19aS,22S,28S,31S,34S,37S,40S,43S,46S,49R,54R,57S,60S,66S,69S,72S,75S,78R,81S,87S,93S,99S)-2a-amino-7,37-bis(4-aminobutyl)-69-(2-amino-2-oxoethyl)-28,99-bis[(2S)-butan-2-yl]-57-(3-carbamimidamidopropyl)-72,93-bis(2-carboxyethyl)-66,75-bis(carboxymethyl)-16-[(1R)-1-hydroxyethyl]-10a,40-bis(hydroxymethyl)-34,43,46-tris[(4-hydroxyphenyl)methyl]-22-(1H-imidazol-4-ylmethyl)-31-(1H-indol-3-ylmethyl)-4,16a,19-tris(2-methylpropyl)-1a,2,5,8,8a,11a,14,14a,17,17a,20,20a,23,26,27a,29,32,35,38,41,44,47,56,59,65,68,71,74,77,80,86,89,92,95,98-pentatriacontaoxo-19a,87-di(propan-2-yl)-4a,5a,23a,24a,51,52-hexathia-a,3,6,9,9a,12a,15,15a,18,18a,21,21a,24,26a,27,30,33,36,39,42,45,48,55,58,64,67,70,73,76,79,85,88,91,94,97-pentatriacontazahexacyclo[76.43.4.254,107.09,13.060,64.081,85]heptacosahectane-49-carbonyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-aminohexanoyl]amino]-6-aminohexanoic acid

Appearance

White Lyophilized Solid

Purity

>98%

Sequence

C(1)IGEGVPC(2)DENDPRC(3)C(1)SGLVC(2)LKPTLHGIWYKSYYC(3)YKK

Storage

Store at -20°C

InChI

InChI=1S/C196H292N50O56S6/c1-16-102(13)158-188(294)211-85-148(255)213-121(58-60-152(259)260)162(268)208-86-150(257)239-157(101(11)12)194(300)246-69-31-40-145(246)186(292)237-142-94-307-308-95-143-182(288)221-126(71-98(5)6)169(275)219-123(36-22-26-64-199)192(298)244-67-30-41-146(244)187(293)243-160(104(15)249)191(297)229-127(72-99(7)8)170(276)226-133(78-110-83-205-96-212-110)163(269)209-87-151(258)240-159(103(14)17-2)190(296)230-132(77-109-82-207-117-33-19-18-32-115(109)117)175(281)223-128(73-105-42-50-111(250)51-43-105)171(277)216-119(35-21-25-63-198)166(272)233-138(89-248)179(285)224-130(75-107-46-54-113(252)55-47-107)173(279)222-131(76-108-48-56-114(253)57-49-108)174(280)235-139(180(286)225-129(74-106-44-52-112(251)53-45-106)172(278)215-118(34-20-24-62-197)165(271)220-124(195(301)302)37-23-27-65-200)92-305-306-93-141(184(290)236-140(91-304-303-90-116(201)161(267)242-158)183(289)232-137(88-247)164(270)210-84-149(256)214-125(70-97(3)4)178(284)241-156(100(9)10)189(295)238-143)234-167(273)120(38-28-66-206-196(203)204)218-185(291)144-39-29-68-245(144)193(299)136(81-155(265)266)231-176(282)134(79-147(202)254)227-168(274)122(59-61-153(261)262)217-177(283)135(80-154(263)264)228-181(142)287/h18-19,32-33,42-57,82-83,96-104,116,118-146,156-160,207,247-253H,16-17,20-31,34-41,58-81,84-95,197-201H2,1-15H3,(H2,202,254)(H,205,212)(H,208,268)(H,209,269)(H,210,270)(H,211,294)(H,213,255)(H,214,256)(H,215,278)(H,216,277)(H,217,283)(H,218,291)(H,219,275)(H,220,271)(H,221,288)(H,222,279)(H,223,281)(H,224,285)(H,225,286)(H,226,276)(H,227,274)(H,228,287)(H,229,297)(H,230,296)(H,231,282)(H,232,289)(H,233,272)(H,234,273)(H,235,280)(H,236,290)(H,237,292)(H,238,295)(H,239,257)(H,240,258)(H,241,284)(H,242,267)(H,243,293)(H,259,260)(H,261,262)(H,263,264)(H,265,266)(H,301,302)(H4,203,204,206)

InChI Key

JEUFUDFTZMBKGH-UHFFFAOYSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC2C(=O)NC3CSSCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)N4CCCC4C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)N5CCCC5C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)N1)CC6=CNC=N6)CC(C)C)C(C)O)CCCCN)CC(C)C)NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC3=O)CO)CC(C)C)C(C)C)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N7CCCC7C(=O)NC(C(=O)N2)CCCNC(=N)N)CC(=O)O)CC(=O)N)CCC(=O)O)CC(=O)O)C(C)C)CCC(=O)O)C(C)CC)N)C(=O)NC(CC8=CC=C(C=C8)O)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)O)CC9=CC=C(C=C9)O)CC1=CC=C(C=C1)O)CO)CCCCN)CC1=CC=C(C=C1)O)CC1=CNC2=CC=CC=C21

1. Huwentoxin-XVI, an analgesic, highly reversible mammalian N-type calcium channel antagonist from Chinese tarantula Ornithoctonus huwena

Jianhua Tang, Zhenghua Sun, Zhonghua Liu, Weimin Zeng, Hanchun Chen, Xiongzhi Zeng, Songping Liang, Yucheng Xiao, Meichun Deng, Xuan Luo, Liping Jiang Neuropharmacology . 2014 Apr;79:657-67. doi: 10.1016/j.neuropharm.2014.01.017.

N-type calcium channels play important roles in the control of neurotransmission release and transmission of pain signals to the central nervous system. Their selective inhibitors are believed to be potential drugs for treating chronic pain. In this study, a novel neurotoxin named Huwentoxin-XVI (HWTX-XVI) specific for N-type calcium channels was purified and characterized from the venom of Chinese tarantula Ornithoctonus huwena. HWTX-XVI is composed of 39 amino acid residues including six cysteines that constitute three disulfide bridges. HWTX-XVI could almost completely block the twitch response of rat vas deferens to low-frequency electrical stimulation. Electrophysiological assay indicated that HWTX-XVI specifically inhibited N-type calcium channels in rat dorsal root ganglion cells (IC50 ~60 nM). The inhibitory effect of HWTX-XVI on N-type calcium channel currents was dose-dependent and similar to that of CTx-GVIA and CTx-MVIIA. However, the three peptides exhibited markedly different degrees of reversibility after block. The toxin had no effect on voltage-gated T-type calcium channels, potassium channels or sodium channels. Intraperitoneal injection of the toxin HWTX-XVI to rats elicited significant analgesic responses to formalin-induced inflammation pain. Toxin treatment also changed withdrawal latency in hot plate tests. Intriguingly, we found that intramuscular injection of the toxin reduced mechanical allodynia induced by incisional injury in Von Frey test. Thus, our findings suggest that the analgesic potency of HWTX-XVI and its greater reversibility could contribute to the design of a novel potential analgesic agent with high potency and low side effects.

2. Animal Venom Peptides Cause Antinociceptive Effects by Voltage-gated Calcium Channels Activity Blockage

Gabriela Trevisan, Sara Marchesan Oliveira Curr Neuropharmacol . 2022;20(8):1579-1599. doi: 10.2174/1570159X19666210713121217.

Pain is a complex phenomenon that is usually unpleasant and aversive. It can range widely in intensity, quality, and duration and has diverse pathophysiologic mechanisms and meanings. Voltage-gated sodium and calcium channels are essential to transmitting painful stimuli from the periphery until the dorsal horn of the spinal cord. Thus, blocking voltage-gated calcium channels (VGCCs) can effectively control pain refractory to treatments currently used in the clinic, such as cancer and neuropathic pain. VGCCs blockers isolated of cobra Naja naja kaouthia (α-cobratoxin), spider Agelenopsis aperta (ω-Agatoxin IVA), spider Phoneutria nigriventer (PhTx3.3, PhTx3.4, PhTx3.5, PhTx3.6), spider Hysterocrates gigas (SNX-482), cone snails Conus geographus (GVIA), Conus magus (MVIIA or ziconotide), Conus catus (CVID, CVIE and CVIF), Conus striatus (SO- 3), Conus fulmen (FVIA), Conus moncuri (MoVIA and MoVIB), Conus regularis (RsXXIVA), Conus eburneus (Eu1.6), Conus victoriae (Vc1.1.), Conus regius (RgIA), and spider Ornithoctonus huwena (huwentoxin-I and huwentoxin-XVI) venoms caused antinociceptive effects in different acute and chronic pain models. Currently, ziconotide is the only clinical used N-type VGCCs blocker peptide for chronic intractable pain. However, ziconotide causes different adverse effects, and the intrathecal route of administration also impairs its use in a more significant number of patients. In this sense, peptides isolated from animal venoms or their synthetic forms that act by modulating or blocking VGCCs channels seem to be a relevant prototype for developing new analgesics efficacious and well tolerated by patients.