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Mambalgin 1

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

Mambalgin 1, a toxin isolated from black mamba venom, is a disulfide-rich polypeptide consisting of 57 amino acids and belongs to the family of three-finger toxins. Mambalgin 1 is a selective ASIC1a inhibitor (IC50= 192 and 72 nM for human ASIC1a and ASIC1a/1b dimer, respectively), and binds to closed/inactive channel.

Category

Peptide Inhibitors

Catalog number

BAT-010241

CAS number

1609937-15-6

Molecular Formula

C272H429N85O84S10

Molecular Weight

6554.51

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-2-[[(4R,7S,10S,13S,16S,19R)-19-[[(4R,7S,10S,13S,16S,19S,22S,25S,28R)-28-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(1R,2aS,4S,5aS,7S,8aS,10S,11aS,13S,19S,25S,28S,31S,34S,37S,40S,43S,46S,49S,52S,58R,63R,66S,69S,72S,75S,81S,84S,87S,90R,96S,99S)-90-[[(2S)-6-amino-2-[[(2S)-2-amino-4-methylpentanoyl]amino]hexanoyl]amino]-40,75,99-tris(4-aminobutyl)-10,34-bis(2-amino-2-oxoethyl)-52,84-bis(3-amino-3-oxopropyl)-28,96-dibenzyl-46-[(2S)-butan-2-yl]-8a,31-bis(3-carbamimidamidopropyl)-5a-(carboxymethyl)-13,66-bis[(1R)-1-hydroxyethyl]-4,87-bis[(4-hydroxyphenyl)methyl]-7,11a,81-tris(1H-imidazol-4-ylmethyl)-37,43,49-tris(2-methylpropyl)-2a,19-bis(2-methylsulfanylethyl)-1a,2,4a,5,7a,8,10a,11,13a,14,17,20,26,29,32,35,38,41,44,47,50,53,56,65,68,71,74,77,80,83,86,89,95,98-tetratriacontaoxo-69,72-di(propan-2-yl)-60,61,92-trithia-a,3,3a,6,6a,9,9a,12,12a,15,18,21,27,30,33,36,39,42,45,48,51,54,57,64,67,70,73,76,79,82,85,88,94,97-tetratriacontazatricyclo[61.30.20.021,25]tridecahectane-58-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-7-(4-aminobutyl)-10,13-bis(2-amino-2-oxoethyl)-16,22-bis(2-carboxyethyl)-19-[(1R)-1-hydroxyethyl]-25-(hydroxymethyl)-6,9,12,15,18,21,24,27-octaoxo-1,2-dithia-5,8,11,14,17,20,23,26-octazacyclononacosane-4-carbonyl]amino]-7-(3-carbamimidamidopropyl)-10-(carboxymethyl)-13-[(1R)-1-hydroxyethyl]-16-(hydroxymethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]amino]-4-amino-4-oxobutanoyl]amino]-6-aminohexanoic acid

Synonyms

LKCYQHGKVVTCHRDMKFCYHNTGMPFRNLKLILQGCSSSCSETENNKCCSTDRCNK

Appearance

Lyophilized Powder

Purity

>98%

Sequence

LKC(1)YQHGKVVTC(2)HRDMKFC(1)YHNTGMPFRNLKLILQGC(2)SSSC(3)SETENNKC(3)C(4)STDRC(4)NK(Modifications: Disulfide bridge: 3-19, 12-37, 41-49, 50-55)

Storage

Store at -20°C

InChI

InChI=1S/C272H429N85O84S9/c1-21-134(14)211-264(435)336-165(90-130(6)7)232(403)315-157(66-70-195(280)369)217(388)299-110-204(378)307-188(254(425)340-183(114-360)249(420)338-182(113-359)248(419)339-184(115-361)250(421)347-190-121-447-449-123-192(346-224(395)153(52-32-38-80-277)311-239(410)174(99-197(282)371)331-242(413)177(102-200(285)374)330-227(398)159(68-72-205(379)380)319-265(436)213(136(16)364)354-230(401)160(69-73-206(381)382)317-247(418)181(112-358)341-257(190)428)259(430)348-191-122-448-446-120-189(255(426)333-175(100-198(283)372)240(411)320-163(269(440)441)53-33-39-81-278)345-225(396)156(56-42-84-298-272(291)292)314-244(415)180(105-208(385)386)337-266(437)214(137(17)365)355-251(422)185(116-362)342-258(191)429)119-445-450-124-193-256(427)328-172(97-144-107-294-126-303-144)237(408)313-155(55-41-83-297-271(289)290)222(393)334-179(104-207(383)384)243(414)318-161(74-86-442-19)228(399)309-151(50-30-36-78-275)220(391)323-167(92-139-44-24-22-25-45-139)236(407)344-187(118-444-117-186(343-223(394)150(49-29-35-77-274)308-216(387)148(279)88-128(2)3)252(423)324-168(94-141-58-62-146(367)63-59-141)233(404)316-158(67-71-196(281)370)226(397)326-171(96-143-106-293-125-302-143)218(389)300-109-202(376)305-149(48-28-34-76-273)229(400)350-209(132(10)11)262(433)351-210(133(12)13)263(434)356-215(138(18)366)267(438)349-193)253(424)325-169(95-142-60-64-147(368)65-61-142)235(406)327-173(98-145-108-295-127-304-145)238(409)332-178(103-201(286)375)246(417)353-212(135(15)363)261(432)301-111-203(377)306-162(75-87-443-20)268(439)357-85-43-57-194(357)260(431)335-170(93-140-46-26-23-27-47-140)234(405)312-154(54-40-82-296-270(287)288)221(392)329-176(101-199(284)373)241(412)322-164(89-129(4)5)231(402)310-152(51-31-37-79-276)219(390)321-166(91-131(8)9)245(416)352-211/h22-27,44-47,58-65,106-108,125-138,148-194,209-215,358-368H,21,28-43,48-57,66-105,109-124,273-279H2,1-20H3,(H2,280,369)(H2,281,370)(H2,282,371)(H2,283,372)(H2,284,373)(H2,285,374)(H2,286,375)(H,293,302)(H,294,303)(H,295,304)(H,299,388)(H,300,389)(H,301,432)(H,305,376)(H,306,377)(H,307,378)(H,308,387)(H,309,399)(H,310,402)(H,311,410)(H,312,405)(H,313,408)(H,314,415)(H,315,403)(H,316,404)(H,317,418)(H,318,414)(H,319,436)(H,320,411)(H,321,390)(H,322,412)(H,323,391)(H,324,423)(H,325,424)(H,326,397)(H,327,406)(H,328,427)(H,329,392)(H,330,398)(H,331,413)(H,332,409)(H,333,426)(H,334,393)(H,335,431)(H,336,435)(H,337,437)(H,338,420)(H,339,419)(H,340,425)(H,341,428)(H,342,429)(H,343,394)(H,344,407)(H,345,396)(H,346,395)(H,347,421)(H,348,430)(H,349,438)(H,350,400)(H,351,433)(H,352,416)(H,353,417)(H,354,401)(H,355,422)(H,356,434)(H,379,380)(H,381,382)(H,383,384)(H,385,386)(H,440,441)(H4,287,288,296)(H4,289,290,297)(H4,291,292,298)

InChI Key

JRVGGBDTNREHFW-UHFFFAOYSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(CSSCC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)C(C)O)C(C)C)C(C)C)CCCCN)CC3=CNC=N3)CCC(=O)N)CC4=CC=C(C=C4)O)NC(=O)C(CCCCN)NC(=O)C(CC(C)C)N)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N5CCCC5C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CC(C)C)CCCCN)CC(C)C)CC(=O)N)CCCNC(=N)N)CC6=CC=CC=C6)CCSC)C(C)O)CC(=O)N)CC7=CNC=N7)CC8=CC=C(C=C8)O)CC9=CC=CC=C9)CCCCN)CCSC)CC(=O)O)CCCNC(=N)N)CC1=CNC=N1)C(=O)NC(CO)C(=O)NC(CO)C(=O)NC(CO)C(=O)NC1CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CO)CCC(=O)O)C(C)O)CCC(=O)O)CC(=O)N)CC(=O)N)CCCCN)C(=O)NC1CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CO)C(C)O)CC(=O)O)CCCNC(=N)N)C(=O)NC(CC(=O)N)C(=O)NC(CCCCN)C(=O)O)CCC(=O)N)CC(C)C

1. One-pot hydrazide-based native chemical ligation for efficient chemical synthesis and structure determination of toxin Mambalgin-1

Yiming Li, Changlin Tian, Yao He, Fangming Wu, Sijian Li, Ming Wen, Longhua Zhang, Demeng Sun, Man Pan Chem Commun (Camb) . 2014 Jun 4;50(44):5837-9. doi: 10.1039/c4cc00779d.

An efficient one-pot chemical synthesis of snake venom toxin Mambalgin-1 was achieved using an azide-switch strategy combined with hydrazide-based native chemical ligation. Synthetic Mambalgin-1 exhibited a well-defined structure after sequential folding in vitro. NMR spectroscopy revealed a three-finger toxin family structure, and the synthetic toxin inhibited human acid-sensing ion channel 1a.

2. Effects of systemic inhibitors of acid-sensing ion channels 1 (ASIC1) against acute and chronic mechanical allodynia in a rodent model of migraine

Eric Lingueglia, Sylvie Diochot, Anne Baron, Michel Lanteri-Minet, Emilie Piquet, Clément Verkest, Mélodie Dauvois Br J Pharmacol . 2018 Nov;175(21):4154-4166. doi: 10.1111/bph.14462.

Background and purpose:Acid-sensing ion channels (ASICs) are neuronal proton sensors emerging as potential therapeutic targets in pain of the orofacial region. Amiloride, a non-specific ASIC blocker, has been shown to exert beneficial effects in animal models of migraine and in patients. We explored the involvement of the ASIC1-subtype in cutaneous allodynia, a hallmark of migraine affecting cephalic and extra-cephalic regions in about 70% of migrainers.Experimental approach:We investigated the effects of systemic injections of amiloride and mambalgin-1, a specific inhibitor of ASIC1a- and ASIC1b-containing channels, on cephalic and extra-cephalic mechanical sensitivity in a rodent model of acute and chronic migraine induced by i.p. injections of isosorbide dinitrate.Key results:I.v. injections of these inhibitors reversed cephalic and extra-cephalic acute cutaneous mechanical allodynia in rats, a single injection inducing a delay in the subsequent establishment of chronic allodynia. Both mambalgin-1 and amiloride also reversed established chronic allodynia. The anti-allodynic effects of mambalgin-1 were not altered in ASIC1a-knockout mice, showing the ASIC1a subtype is not involved in these effects which were comparable to those of the anti-migraine drug sumatriptan and of the preventive drug topiramate on acute and chronic allodynia respectively. A single daily injection of mambalgin-1 also had a significant preventive effect on allodynia chronification.Conclusions and implications:These pharmacological data support the involvement of peripheral ASIC1-containing channels in migraine cutaneous allodynia as well as in its chronification. They highlight the therapeutic potential of ASIC1 inhibitors as both an acute and prophylactic treatment for migraine.

3. Site-specific fluorescence spectrum detection and characterization of hASIC1a channels upon toxin mambalgin-1 binding in live mammalian cells

Ying Xiong, Liang Xiao, Changlin Tian, Ming Wen, Jin Bao, Tian Xue, Longhua Zhang, Xiaoqi Guo, Juan Li, Peibei Sun Chem Commun (Camb) . 2015 May 11;51(38):8153-6. doi: 10.1039/c5cc01418b.

The synthesis of fluorescent unnatural amino-acid Anap was optimized and the Anap was incorporated into four sites in an acid-pocket or a transmembrane region of human acid-sensing ion channel-1a (hASIC1a). Combinational Anap fluorescence spectra and patch-clamp electrophysiology data illustrated site-specific conformational responses upon toxin mambalgin-1 binding. This combinational approach can be used to analyse conformational properties of many different eukaryotic proteins in their functional states, in a site-specific manner in live mammalian cells.