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APETx2

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

APETx2, an ion channel 3 (ASIC3) channel blocker, has been found to exhibit analgesic properties against acid-induced and inflammatory pain.

Category

Peptide Inhibitors

Catalog number

BAT-010318

CAS number

713544-47-9

Molecular Formula

C196H280N54O61S6

Molecular Weight

4561.06

Specification
Reference Reading

IUPAC Name

2-[2-[[1-[2-[[52-[2-[[2-[(2-aminoacetyl)amino]-3-hydroxybutanoyl]amino]propanoylamino]-34-(4-aminobutyl)-40-(2-amino-2-oxoethyl)-19,69-dibenzyl-28-butan-2-yl-13,75,96-tris(3-carbamimidamidopropyl)-99-(carboxymethyl)-2a,60,87-tris(1-hydroxyethyl)-4,37,49,81-tetrakis(hydroxymethyl)-16,25,72,90-tetrakis[(4-hydroxyphenyl)methyl]-22-(1H-indol-3-ylmethyl)-66-(2-methylpropyl)-1a,3,4a,6,10a,12,15,17a,18,21,24,27,30,33,36,39,42,45,48,51,59,62,65,68,71,74,77,80,83,86,89,92,95,98-tetratriacontaoxo-12a,13a,19a,20a,54,55-hexathia-a,2,3a,5,9a,11,14,16a,17,20,23,26,29,32,35,38,41,44,47,50,58,61,64,67,70,73,76,79,82,85,88,91,94,97-tetratriacontazapentacyclo[55.53.7.446,78.07,11.0105,109]henicosahectane-15a-carbonyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]propanoylamino]butanedioic acid

Synonyms

APETx2; 713544-47-9; AKOS024458355; H-Gly-DL-xiThr-DL-Ala-DL-Cys(1)-DL-Ser-DL-Cys(2)-Gly-DL-Asn-DL-Ser-DL-Lys-Gly-DL-xiIle-DL-Tyr-DL-Trp-DL-Phe-DL-Tyr-DL-Arg-DL-Pro-DL-Ser-DL-Cys(3)-DL-Pro-DL-xiThr-DL-Asp-DL-Arg-Gly-DL-Tyr-DL-xiThr-Gly-DL-Ser-DL-Cys(2)-DL-Arg-DL-Tyr-DL-Phe-DL-Leu-Gly-DL-xiThr-DL-Cys(1)-DL-Cys(3)-DL-xiThr-DL-Pro-DL-Ala-DL-Asp-OH

Appearance

White Solid

Purity

>98%

Sequence

GTAC(1)SC(2)GNSKGIYWFYRPSC(3)PTDRGYTGSC(2)RYFLGTC(1)C(3)TPAD

Storage

Store at -20°C

InChI

InChI=1S/C196H280N54O61S6/c1-12-94(4)152-186(303)230-125(71-107-48-56-112(263)57-49-107)169(286)229-126(72-108-77-209-114-34-20-19-33-113(108)114)170(287)228-122(67-103-31-17-14-18-32-103)167(284)227-123(69-105-44-52-110(261)53-45-105)165(282)223-118(38-25-61-208-196(204)205)190(307)248-62-26-40-141(248)183(300)235-133(86-254)177(294)241-139-92-317-316-91-138(181(298)247-157(101(11)259)192(309)250-64-28-39-140(250)182(299)215-95(5)158(275)232-129(193(310)311)75-151(273)274)239-180(297)137-90-315-313-88-135(236-159(276)96(6)216-187(304)154(98(8)256)242-144(265)76-198)179(296)234-132(85-253)176(293)237-134(163(280)213-79-146(267)218-127(73-143(199)264)171(288)233-131(84-252)175(292)221-115(35-21-22-58-197)160(277)211-81-148(269)243-152)87-312-314-89-136(178(295)222-117(37-24-60-207-195(202)203)164(281)225-124(70-106-46-54-111(262)55-47-106)168(285)226-121(66-102-29-15-13-16-30-102)166(283)224-119(65-93(2)3)162(279)212-82-149(270)244-155(99(9)257)188(305)240-137)238-174(291)130(83-251)219-147(268)80-214-185(302)153(97(7)255)245-173(290)120(68-104-42-50-109(260)51-43-104)217-145(266)78-210-161(278)116(36-23-59-206-194(200)201)220-172(289)128(74-150(271)272)231-189(306)156(100(10)258)246-184(301)142-41-27-63-249(142)191(139)308/h13-20,29-34,42-57,77,93-101,115-142,152-157,209,251-263H,12,21-28,35-41,58-76,78-92,197-198H2,1-11H3,(H2,199,264)(H,210,278)(H,211,277)(H,212,279)(H,213,280)(H,214,302)(H,215,299)(H,216,304)(H,217,266)(H,218,267)(H,219,268)(H,220,289)(H,221,292)(H,222,295)(H,223,282)(H,224,283)(H,225,281)(H,226,285)(H,227,284)(H,228,287)(H,229,286)(H,230,303)(H,231,306)(H,232,275)(H,233,288)(H,234,296)(H,235,300)(H,236,276)(H,237,293)(H,238,291)(H,239,297)(H,240,305)(H,241,294)(H,242,265)(H,243,269)(H,244,270)(H,245,290)(H,246,301)(H,247,298)(H,271,272)(H,273,274)(H,310,311)(H4,200,201,206)(H4,202,203,207)(H4,204,205,208)

InChI Key

HEHYILNFEUDIQC-UHFFFAOYSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC3CSSCC(NC(=O)C4CSSCC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N4)C(C)O)CC(C)C)CC5=CC=CC=C5)CC6=CC=C(C=C6)O)CCCNC(=N)N)NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C7CCCN7C3=O)C(C)O)CC(=O)O)CCCNC(=N)N)CC8=CC=C(C=C8)O)C(C)O)CO)C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)N1)CCCCN)CO)CC(=O)N)CO)NC(=O)C(C)NC(=O)C(C(C)O)NC(=O)CN)C(=O)NC(C(C)O)C(=O)N9CCCC9C(=O)NC(C)C(=O)NC(CC(=O)O)C(=O)O)CO)CCCNC(=N)N)CC1=CC=C(C=C1)O)CC1=CC=CC=C1)CC1=CNC2=CC=CC=C21)CC1=CC=C(C=C1)O

1. Modulation of Local Overactive Inflammation via Injectable Hydrogel Microspheres

Feng Cai, Jincheng Tang, Kun Xi, Yong Gu, Yichang Xu, Jiang Bian, Lianfu Deng, Liang Chen, Zhenzhou Tang, Wenguo Cui, Liang Wu, Hao Chen Nano Lett . 2021 Mar 24;21(6):2690-2698. doi: 10.1021/acs.nanolett.0c04713.

Although injectable hydrogel microsphere has demonstrated tremendous promise in clinical applications, local overactive inflammation in degenerative diseases could jeopardize biomaterial implantation's therapeutic efficacy. Herein, an injectable "peptide-cell-hydrogel" microsphere was constructed by covalently coupling of APETx2 and further loading of nucleus pulposus cells, which could inhibit local inflammatory cytokine storms to regulate the metabolic balance of ECMin vitro. The covalent coupling of APETx2 preserved the biocompatibility of the microspheres and achieved a controlled release of APETx2 for more than 28 days in an acidic environment. By delivering "peptide-cell-hydrogel" microspheres to a rat degenerative intervertebral disc at 4 weeks, the expression of ASIC-3 and IL-1β was significantly decreased for 3.53-fold and 7.29-fold, respectively. Also, the content of ECM was significantly recovered at 8 weeks. In summary, the proposed strategy provides an effective approach for tissue regeneration under overactive inflammatory responses.

2. The selective ASIC3 inhibitor APETx2 alleviates gastric mucosal lesion in the rat

Qun Jiang, Xi Chen, Weifeng Tu, Junlin Wen, Shaoqun Xu, Hongyan Zhou, Gaofeng Zhao Pharmazie . 2014 Jul;69(7):542-6.

This study aimed to assess the in vivo efficacy of acid sensing ion channel 3 (ASIC3) inhibitor APETx2 to alleviate acute gastric mucosal lesion (AGML) in a rat model. Thirty-six male Wistar rats were divided randomly into three groups: control group, water immersion restraint stress (WIRS) group, and APETx2 treatment group (n = 12). AGML was induced by WIRS for 6 h, and 25 microg/kg APETx2 was injected intraperitoneally before the onset of stress. Intragastric pH, ulcer index (UI) and gastric histopathological changes were measured, ASIC3 expression in thoracic dorsal root ganglia (DRG) neurons was examined by immunohistochemistry, PCR and Western blot analysis. Compared with control group, WIRS group showed obvious gastric injury with increased UI score, decreased intragastric pH and increased ASIC3 expression in DRG neurons (p < 0.05). APETx2 treatment before WIRS significantly alleviated gastric mucosal injury, decreased UI score, decreased gastric acidity and reduced ASIC3 expression in thoracic DRG neurons (p < 0.05). In conclusion, ASIC3 expression in DRG neurons projecting to the stomach is positively correlated with gastric mucosal lesion and acidosis in WIRS model. ASIC3 inhibitor APETx2 could improve gastric acidosis and alleviate AGML.

3. Functional expression in Escherichia coli of the disulfide-rich sea anemone peptide APETx2, a potent blocker of acid-sensing ion channel 3

Glenn F King, Mehdi Mobli, Lachlan D Rash, Raveendra Anangi Mar Drugs . 2012 Jul;10(7):1605-1618. doi: 10.3390/md10071605.

Acid-sensing ion channels (ASICs) are proton-gated sodium channels present in the central and peripheral nervous system of chordates. ASIC3 is highly expressed in sensory neurons and plays an important role in inflammatory and ischemic pain. Thus, specific inhibitors of ASIC3 have the potential to be developed as novel analgesics. APETx2, isolated from the sea anemone Anthopleura elegantissima, is the most potent and selective inhibitor of ASIC3-containing channels. However, the mechanism of action of APETx2 and the molecular basis for its interaction with ASIC3 is not known. In order to assist in characterizing the ASIC3-APETx2 interaction, we developed an efficient and cost-effective Escherichia coli periplasmic expression system for the production of APETx2. NMR studies on uniformly (13)C/(15)N-labelled APETx2 produced in E. coli showed that the recombinant peptide adopts the native conformation. Recombinant APETx2 is equipotent with synthetic APETx2 at inhibiting ASIC3 channels expressed in Xenopus oocytes. Using this system we mutated Phe15 to Ala, which caused a profound loss of APETx2's activity on ASIC3. These findings suggest that this expression system can be used to produce mutant versions of APETx2 in order to facilitate structure-activity relationship studies.