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Agelenin

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Agelenin
Names
Other names U1-agatoxin-Aop1a, U1-AGTX-Aop1a
Identifiers
3D model (JSmol)
ChemSpider
  • none
KEGG
InChI
  • InChI=1S/C160H259N51O46S6/c1-14-82(12)126(155(254)197-99(55-85-61-176-88-32-19-18-31-87(85)88)141(240)195-103(59-125(224)225)144(243)202-108(68-214)145(244)186-92(36-25-45-174-159(168)169)133(232)205-113(73-261)150(249)199-105(157(256)257)53-81(10)11)209-146(245)109(69-215)203-139(238)97(51-79(6)7)191-135(234)94(40-41-124(222)223)188-130(229)89(33-20-22-42-161)187-148(247)111(71-259)204-132(231)90(34-21-23-43-162)184-137(236)95(49-77(2)3)182-122(220)64-178-128(227)106(66-212)201-151(250)114(74-262)208-152(251)115(75-263)206-134(233)93(37-26-46-175-160(170)171)189-153(252)116-38-27-47-210(116)123(221)65-179-129(228)107(67-213)200-138(237)96(50-78(4)5)190-127(226)83(13)181-136(235)101(57-118(164)216)194-149(248)112(72-260)207-140(239)98(54-84-29-16-15-17-30-84)192-131(230)91(35-24-44-173-158(166)167)185-143(242)102(58-119(165)217)193-142(241)100(56-86-62-172-76-180-86)196-154(253)117-39-28-48-211(117)156(255)104(52-80(8)9)198-147(246)110(70-258)183-121(219)63-177-120(218)60-163/h15-19,29-32,61-62,76-83,89-117,126,176,212-215,258-263H,14,20-28,33-60,63-75,161-163H2,1-13H3,(H2,164,216)(H2,165,217)(H,172,180)(H,177,218)(H,178,227)(H,179,228)(H,181,235)(H,182,220)(H,183,219)(H,184,236)(H,185,242)(H,186,244)(H,187,247)(H,188,229)(H,189,252)(H,190,226)(H,191,234)(H,192,230)(H,193,241)(H,194,248)(H,195,240)(H,196,253)(H,197,254)(H,198,246)(H,199,249)(H,200,237)(H,201,250)(H,202,243)(H,203,238)(H,204,231)(H,205,232)(H,206,233)(H,207,239)(H,208,251)(H,209,245)(H,222,223)(H,224,225)(H,256,257)(H4,166,167,173)(H4,168,169,174)(H4,170,171,175)/t82-,83-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,126-/m0/s1Key: ZUAKRHLBADVPFO-XJXDTQAOSA-N
SMILES
  • NCC(=O)NCC(=O)N()(CS)C(=O)N()(CC(C)C)C(=O)N1()(CCC1)C(=O)N()(CC1=CN=C-N1)C(=O)N()(CC(=O)N)C(=O)N()(CCCNC(=N)N)C(=O)N()(Cc1ccccc1)C(=O)N()(CS)C(=O)N()(CC(=O)N)C(=O)N()(C)C(=O)N()(CC(C)C)C(=O)N()(CO)C(=O)NCC(=O)N1()(CCC1)C(=O)N()(CCCNC(=N)N)C(=O)N()(CS)C(=O)N()(CS)C(=O)N()(CO)C(=O)NCC(=O)N()(CC(C)C)C(=O)N()(CCCCN)C(=O)N()(CS)C(=O)N()(CCCCN)C(=O)N()(CCC(=O)O)C(=O)N()(CC(C)C)C(=O)N()(CO)C(=O)N()(()(CC)C)C(=O)N()(CC(=CN2)C1=C2C=CC=C1)C(=O)N()(CC(=O)O)C(=O)N()(CO)C(=O)N()(CCCNC(=N)N)C(=O)N()(CS)C(=O)N()(CC(C)C)C(=O)O
Properties
Molar mass 3500 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Agelenin (toxicologically named as U1-agatoxin-Aop1a and abbreviated as U1-AGTX-Aop1a) is a neurotoxic peptide isolated from the venom of the spider Allagelena opulenta which consists of 35 amino acids. It is an antagonist of the presynaptic P-type calcium channel in insects.

Sources

Agelenin is an insecticidal toxin of the venom of the species Allagelena opulenta. It was first discovered in 1990.

Chemistry

Agelenin consists of a polypeptide chain of 35 amino acid residues. It has a short anti-parallel β-sheet connected by three disulfide bonds and four β-turns that form the compact core structure. The three amino acid residues that are thought to be essential for the inhibiting activity of agelenin are Phe9, Ser28 and Arg33.

The structure of agelenin is similar to the structure of ICK toxins like ω-Aga-IVA and ω-ACTXHv1a in that they all consist of three disulfide bonds with the same bonding pattern. An important difference between agelenin and ω-Aga-IVA and ω-ACTXHv1a is that ω-Aga-IVA and ω-ACTXHv1a have functional C-terminal tails.

Agelenin belongs to toxin group of agatoxins. The amino acid structure of agelenin is Gly-Gly-Cys-Leu-Pro-His-Asn-Arg-Phe-Cys-Asn-Ala-Leu-Ser-Gly-Pro-Arg-Cys-Cys-Ser-Gly-Leu-Lys-Cys-Lys-Glu-Leu-Ser-Ile-Trp-Asp-Ser-Arg-Cys-Leu (GGCLPHNRFCNALSGPRCCSGLKCKELSIWDSRCL).

Target

Agelenin is directed against P-subtype calcium channels in insects.

Toxicity

Agelenin is not toxic in mammals, but has a PD50 of 291 pmol/g in crickets where it causes rapid, reversible paralysis. In preparations of neuromuscular junctions of lobsters agelenin causes a non-reversible paralysis due to the suppression of excitatory postsynaptic potentials, presumably by inhibition of the presynaptic calcium influx.

References

  1. ^ Institute for Molecular Bioscience. (2010) “U2-agatoxin-Aop1a”, Arachnoserver. Accessed on: 11 October 2015.
  2. ^ Hagiwara, K., Sakai, T., Miwa, A., Kawai, N. and Nakajima, T. (1990). "Complete amino acid sequence of a new type of neurotoxin from the venom of the spider, Agelena opulenta". BioMed Research International. 11: 181–186. doi:10.2220/biomedres.11.181.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Yamaji, N., Sugase, K., Nakajima, T., Miki, T., Wakamori, M., More, Y. and Iwashita, T. (2007). "Solution structure of agelenin, an intisecticidal peptide isolated from the spider Agelena opulenta, and its structural similarities to insect-specific calcium channel inhibitors". FEBS Letters. 581 (20): 3789–3794. Bibcode:2007FEBSL.581.3789Y. doi:10.1016/j.febslet.2007.06.077. PMID 17644092.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Rash, L.D. and Hodgson, W.C. (2002). "Pharmacology and biochemistry of spider venoms". Toxicon. 40 (3): 225–254. Bibcode:2002Txcn...40..225R. doi:10.1016/S0041-0101(01)00199-4. PMID 11711120.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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