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2,4-(OH)₂-PhAcAsn533Arg

General Description

NameValue
LevelS-1 / C-2
Discovered1986 / A. lobata
SynonymAR 636 / Arg 636 / Argiopine / Argiotoxin 636 / ArgTX 636 / ATX / AVTX 636
Molecular formulaC₂₉H₅₂N₁₀O₆
CAS144576-90-9
SMILESO=C(NC(CC(N)=O)C(NCCCCCNCCCNCCCNC(C(N)CCCNC(N)=N)=O)=O)CC1=CC=C(O)C=C1O
InChIInChI=1S/C29H52N10O6/c30-22(7-4-15-38-29(32)33)27(44)36-16-6-13-35-12-5-11-34-10-2-1-3-14-37-28(45)23(19-25(31)42)39-26(43)17-20-8-9-21(40)18-24(20)41/h8-9,18,22-23,34-35,40-41H,1-7,10-17,19,30H2,(H2,31,42)(H,36,44)(H,37,45)(H,39,43)(H4,32,33,38)
Precursor 1 [M+H]⁺637.41441
Precursor 2 [M+2H]²⁺319.21084
Precursor 3
HDX15
Precursor HDX 1 [M(D₁₅)+D]⁺653.51483
Precursor HDX 2 [M(D₁₅)+2D]²⁺327.76419
Precursor HDX 3
Rt
Rt HDX

Calculated MS/MS fragments

#abctazytz
1265.08190247.07133248.05535282.10845214.16624197.13969231.19279
2350.17105332.16048333.14450367.19760271.22409254.19754288.25064
3407.22890389.21833390.20235424.25545356.31324339.28669373.33978
4464.28675446.27618447.26020637.41441470.35616453.32961487.38271

Additional MS/MS fragments

m/zAnnotation
123.04406a’

Recorded MS/MS spectra

pdfPrecursorCo-elutingSpiderSourceAuthor

References

TitleReferenceSpiderNameContentLink
Structure-functional characterization of argiopin - An ion channel blocker from the venom of spider Argiope lobataE. V. Grishin, T. M. Volkova, A. S. Arseniev, V. V. Onoprienko, L. G. Magazanik, S. M. Antonov, I. M. Fedorova, Bioorg. Kim. 1986, 12, 1121A. lobataArg 636Link
Effects of the spider Argiope lobata crude venom and its low-molecular weight component, argiopin, on the postsynaptic membraneL. G. Magazanic, S. M. Antonov, I. M. Fedorova, T. M. Volkova, E. V. Grishin, Biol. Membr. 1986, 3, 1204-1219A. lobataLink
Structures and biological activities of three synaptic antagonists from orb weaver spider venomM. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, V. J Venema, Biochem. Biophys. Res. Com. 1987, 148, 678-683A. aurantiaAR 636Synthesis, NMR (ns), Amino acid analysis, Activity-studiesLink
Argiopin blocks the glutamate response and sensorimotor transmission in motoneurones of isolated frog spinal cordS. M. Antonov, E. V. Grishin, L. G. Magazanik, O. V. Shupliakov, N. P. Vesselkin, T. M. Volkova, Neurosci. Lett. 1987, 83, 179-184A. aurantiaArgiopinActivity-studiesLink
The total synthesis of argiopine (argiotoxin-636)T. L. Shih, J. Ruiz-Sanchez, H. Mrozik, Tetrahedron Letters 1987, 28, 6015-6018Argiopinine / Argiotoxin 636 (1)Synthesis, NMR (ns), IRLink
Isolation and characterisation of glutamate receptor antagonists from venoms of orb-web spidersT. Budd, P. Clinton, A. Dell, I. R. Duce, S. J. Johnson, D. L. J. Quicke, G. W. Taylor, P. N. R. Usherwood, G. Usoh, Brain Res. 1988, 448, 30-39A. florida & A. trifasciataArg 636NMR, Amino acid analysis, Activity-studiesLink
Single channel studies of non-competitive antagonism of a quiqualate-sensitive glutamate receptor by argiotoxin636 - a fraction isolated from orb-web spider venom.C. J. Kerry, R. L. Ramsey, M. S. P. Sansom, P. N. R. Usherwood, Brain Res. 1988, 459, 312-327A. gemma & Argiope sp.Argiotoxin 636Activity-studiesLink
The total synthesis of argiotoxins 636, 659 and 673V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, R. A. Volkmann, Tetrahedron Letters 1988, 29, 6223-6226Arg 636Synthesis, NMRLink
Synthesis of argiopineE. A. Elin, B. F. de Macedo, V. V. Onoprienko, N. E. Osokina, O. B. Tikhhomirova, Bioorganicheskaya Khimiya 1988, 14, 704-706ArgiopinineSynthesis
Glutamate receptor anatgonists from the spider Argiope lobata venomE. V. Grishin, T. M. Volkova, A. S. Arseniev, Biorg. Khim. 1988, 14, 883-892
Argiopine as an antagonist of glutamate effect on frog spinal motoneuronsS. M. Antonov, O. V. Shuplyakov, L. G. Magazanik, N. P. Veselkin, T. M. Volkova, E. V. Grishin, Doklady Akademii Nauk SSSR 1988, 298, 505-508Link
Isolation and structure analysis of components from venom of the spider Argiope lobataE. V. Grishin, T. M. Volkova, A. S. Arseniev, Toxicon 1989, 27, 541-549A. lobataArgiopinNMR (ns), Amino acid analysis, Activity-studiesLink
Argiopine blocks glutamate-activated single-channel currents on crayfish muscle by two mechanismS. M. Antonov, J. Dudel, C. Franke, H. Hatt, J. Physiol. 1989, 419, 569-587A. lobataArgiopineActivity-studiesLink
Argiotoxin-636 blocks excitatory synaptic transmission in rat hippocampal CA1 pyramidal neuronsJ. H. Ashe, C. L. Cox, M. E. Adams, Brain Res. 1989, 480, 234-241AR 636Activity-studiesLink
Antagonism of responses to excitatory amino acids on rat cortical neurones by the spider toxin, argiotoxin 636T. Pristley, G. N. Woodruff, J. A. Kemp, Br. J. Pharmacol. 1989, 97, 1315-1323Argiotoxin 636Activity-studiesLink
Argiopine differentiates between vertebrate and invertebrate glutamine binding sitesJ. M. Schaeffer, J. Ruiz-Sanchez, T. L. Shih, H. Mrozik, Pesticide Biochemistry and Physiology 1989, 35, 26-32ArgiopineActivity-studiesLink
Argiopine, argiopinines, and pseudoargiopinines as glutamate receptor blockers in hippocampal neuronsN. I. Kiskin, O. A. Kryshtal, A. Y. Tsyndrenko, T. M. Volkova, E. V. Grishin, Neurophysiology 1990, 21, 525-532A. lobataArgiopineActivity-studiesLink
Argiotoxin-636 blocks effects of N-methyl-D-aspartate on lateral line of Xenopus laevis at concentrations which do not alter spontaneous or evoked neural activityS. L. Guth, D. A. Scapini, M. J. Drescher, D. G. Drescher, Life Sciences 1990, 47, 1437-1445ATXActivity-studiesLink
Argiotoxin 636 inhibits NMDA-activated ion channels expressed in xenopus oocytesA. Draguhn, W. Jahn, V. Witzemann, Neurosci Lett. 1991, 132, 187-190Argiotoxin 636 / ATXActivity-studiesLink
Arylamine spider toxins antagonize NMDA receptor-mediated synaptic transmission in rat hippocampal slicesA. L. Mueller, B. C. Albensi, A. H. Ganong, L. S. Reynolds, H. Jackson, Synapse 1991, 9, 244-250Argiotoxin 636Activity-studiesLink
Comparison of some arthropod toxins and toxin fragments as antagonists of excitatory amino acid-induced excitation of rat spinal neuronsM. G. Jones, D. Lodge, European Journal of Pharmacology 1991, 204, 203-209Argiotoxin / ATXActivity-studiesLink
The spider toxin, argiotoxin636, binds to Mg2+ site on the N-methyl-D-aspartate receptor complexI. J. Reynolds, Br. J. Pharmacol. 1991, 103, 1373-1376Argiotoxin 636Activity-studiesLink
Anesthesia and muscle relaxation with intrathecal injection of AR636 and AG489, two acylpolyamine spider toxins, in ratE. E. Herold, T. L. Yaksh, Anesthesiology 1992, 77, 507-512A. aurantiaAR 636Activity-studiesLink
Polyamine spider toxins are potent un-competitive antagonists of rat cortex excitatory amino acid receptorsM. S. Davies, M. P. Baganoff, E. V. Grishin, T. H. Lanthorn, T. M. Volkova, G. B. Watson, R. C. Wiegand, Eur J Pharmacol. 1992, 227, 51-56A. lobataArgiopinActivity-studiesLink
Synthesis of argiopine (Argiotoxin 636)E. A. Elin, B. Flores de Macedo, V. V. Onoprienko, N. E. Osokina, O. B. Tikhomirova, Boletin de la Sociedad Quimica del Peru 1992, 58, 96-99Argiopine / Argiotoxin 636Synthesis
Antropod toxins as leads for novel insecticides: An assessment of polyamine amides as glutamate antagonistsI. S. Blagbrough, P. T. H. Brackley, M. Bruce, B. W. Bycroft, A. J. Mather, S. Millington, H. L. Sudan, P. N. R. Usherwood, Toxicon 1992, 30, 303-322ArgTX 636ReviewLink
Effects of Agelenopsis aperta toxins on the N-methyl-D-aspartate receptor: Polyamine-like and high-affinity antagonist actionsK. Williams, J. Pharmacol. Exp. Ther. 1993, 266, 231-236Argiotoxin 6363Activity-studiesLink
Selective anatgonism of native and cloned kainate and NMDA receptors by polyamine-containing toxinsP. T. Brackley, D. R. Bell, S. K. Choi, K. Nakanishi, P. N. Usherwood, J. Pharmacol. Exp. Ther. 1993, 266, 1573-1580Argiotoxin 636 / Arg 636Activity-studiesLink
Interaction of bovine brain glycoprotein with glutamate and argiopininsT. M. Volkova, N. A. Avetisyan, T. G. Galkina, A. B. Kudelin, E. V. Grishin, Chemistry of Peptides and Proteins 1993, 5⁄6, 741-749Activity-studies
Synthesis and assay of hybrid analogs of argiotoxin-636 and philanthotoxin-433: Glutamate receptor antagonistsS.-K. Choi, K. Nakanishi, P. N. R. Usherwood, Tetrahedron 1993, 49, 5777-5790Argiotoxin 636 (2)Synthesis, NMRLink
Argiotoxin detects molecular differences in AMPA receptor channelsS. Herlitz, M. Raditsch, J. P. Ruppersberg, W. Jahn, H. Monyer, R. Schoepfer, V. Witzmann, Neuron 1993, 10, 1131-1140ATXActivity-studiesLink
Inhibition of voltage-activated calcium currents from cultured sensory neurons by spermine, argiotoxin-636 and a synthetic arginine polyamineK. G. Sutton, A. C. Dolphin, R. H. Scott, Molecular Neuropharmacology 1993, 3, 37-43Argiotoxin 636
Subunit-specific block of cloned NMDA receptors by argiotoxin636M. Raditsch, J. P. Ruppersberg, T. Kuner, W. Günther, R. Schoepfer, P. H. Seeburg, W. Jahn, V. Witzemann, FEBS 1993, 324, 63-66Argiotoxin 636Activity-studiesLink
Polyamine toxins from spiders and waspsA. Schäfer, H. Benz, W. Fiedler, A. Guggisberg, S. Bienz, M. Hesse, The Alkaloids 1994, 45, 1-125div.AR 636 / Arg 636 / Argiopine / Argiotoxin / Argiotoxin 636 / ArgTX 636ReviewLink
Pharmacology of polyamine toxins from spider and waspsA. L. Mueller, R. Roeloffs, H. Jackson, The Alkaloids, Chapter 2 1995, 46, 63-94A. lobataArg 636ReviewLink
Total synthesis of polyamine amide spider toxin argiotoxin-636 by a practical reductive alkylation strategyI. S. Blagbrough, E. Moya, Tetrahedron Letters 1995, 36, 9393-9396ArgTX 636SynthesisLink
Action of argiotoxin636 on N-methyl-D-aspartate channels in cerebellar cellsL. Fagni, J. Bockaert, NeuroReport 1995, 6, 1037-1040Argiotoxin 636Activity-studies
Conformational analysis of argiopine molecule obtained from Argiope lobata spider venomN. M. Godjayev, I. N. Aliyeva, S. Akyüz, C. I. Aliyev, Journal of Molecular Structure 1995, 350, 173-183ArgiopineActivity-studiesLink
Conformational analysis of argiopine molecule obtained from Argiope lobata spider venomN. M. Godjayev, I. N. Aliyeva, S. Akyüz, C. I. Aliyev, Journal of Molecular Structure 1995, 350, 173-183Argiotoxin 636Activity-studiesLink
Polyamine spider toxins and mammalian N-methyl-D-aspartate receptors - Structural basis for channel blocking and binding of argiotoxin636M. Raditsch, M. Geyer, H. R. Kalbitzer, W. Jahn, J. P. Ruppersberg, V. Witzemann, Eur. J. Biochem. 1996, 240, 416-426Argiotoxin 636Synthesis, NMR, Activity-studiesLink
Polyamine amides are neuroprotective in cerebellar granule cell cultures challenged with excitatory amino acidsA. C. Green, K. Nakanishi, P. N. R. Usherwood, Brain Research 1996, 717, 135-146ArgTX 636Activity-studiesLink
Multiple actions of arylalkylamine arthropod toxins on the N-methyl-D-aspartate receptorS. D. Donevan, M. A. Rogawski, Neuroscience 1996, 70, 361-375Arg 636Activity-studiesLink
Diversity of Joro spider toxinsM. Yoshioka, 1997, 117, 700-714A. lobataargiopineReviewLink
Potent and voltage-dependent block by philanthotoxin-343 of neuronal nicotinic receptor/channels in PC12 cellsM. Liu, K. Nakazawa , K. Inoue, Y. Ohno, British Journal of Pharmacology 1997, 122, 379-385Argiotoxin 636Activity-studiesLink
Inhibition of voltage-activated K+ currents in cultured sensory neurons by the polyamine spider toxin argiotoxin-636 may involve a polyamine transporter and an intracellular site of actionR. H. Scott, M. T. Gibson, Biochemical Society Transaction 1998, 26, 614-620Argiotoxin 636Link
Extracellular or intracellular application of argiotoxin-636 has inhibitory actions on membrane excitability and voltage-activated currents in cultured rat sensory neuronesR. H. Scott, N. M. Thatcher, A. Ayar, S. J. Mitchell, J. Pollock, M. T. Gibson, I. R. Duce, E. Moya, I. S. Blagbrough, Neuropharmacology 1998, 37, 1563-1578Argiotoxin 636Activity-studiesLink
Inhibitory actions of synthesised polyamine spider toxins and their analogues on Ca2+-activated Cl- currents recorded from cultured DRG neurones from neonatal ratsK. G. Sutton, S. R. Stapleton, R. H. Scott, Neuroscience Letters 1998, 251, 117-120Argiotoxin 636Activity-studiesLink
Design, synthesis and biological evaluation of spider toxin (argiotoxin-636) analogs as NMDA receptor antagonistsS. T. Moe, D. L. Smith, Y. Chien, J. L. Raszkiewicz, L. D. Artman, A. L. Mueller, Pharmaceutical Research 1998, 15, 31-38ARG 636 (1)Synthesis of analogues, Activity-studiesLink
Novel gating mechanism of polyamine block in the strong inward rectifier K channel Kir2.1J.-K. Lee, S. A. John, J. N. Weiss, J. Gen. Physiol. 1999, 113, 555-563ArgiotoxinActivity-studiesLink
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyaminesY. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52A. lobataArg 636ReviewLink
Long-term potentiation in the presence of NMDA receptor antagonist arylalkylamine spider toxinB. C. Albensi, N. Alasti, A. L. Mueller, Journal of Neuroscience Research 2000, 62, 177-185Arg 636Activity-studiesLink
An efficient and versatile synthesis of all structural types of acylpolyamine spider toxinsK. Nihei, M. J. Kato, T. Yamane, K. Konno, Tetrahedron 2006, 62, 8335-8350Arg 636 (8)Synthesis, NMR, ESI-MS/MSLink
Use of [3H]fluorowillardiine to study properties of AMPA receptor allosteric modulatorsM. Kessler, A. C. Arai, Brain Research 2006, 1076, 25-41Argiotoxin 636Activity studiesLink
Synthesis and biological activity of argiotoxin 636 and analogues: Selective antagonists for ionotropic glutamate receptorsJ. K. Nelson, S. U. Frolund, D. B. Tikhonov, A. S. Kristensen, K. Strømgaard, Angew. Chem. Int. Ed. 2009, 48, 3087-3091ArgTX 636 (1)Synthesis, Synthesis of analouges, Activity-studiesLink
The total large-scale synthesis of argiopineA. A. Formanovsky, I. S. Popova, I. V. Mikhura, Russian Journal of Bioorganic Chemistry 2009, 35, 752-758Argiopine (1)Synthesis, NMRLink
Argiotoxin in the closed AMPA receptor channel: Experimental and modeling studyO. I. Barygin, E. V. Grishin, D. B. Tikhonov, Biochemistry 2011, 50, 8213-8220ArgiotoxinActivity-studiesLink
Structure-activity relationship studies of argiotoxins: Selective and potent inhibitors of ionotropic glutamate receptorsM. H. Poulsen, S. Lucas, T. B. Bach, A. F. Barslund, C. Wenzler, C. B. Jensen, A. S. Kristensen, K. Strømgaard, J. Med. Chem. 2013, 56, 1171-1181ArgTX 636Synthesis of analogues, Activity-studiesLink
Binding ArgTX-636 in the NMDA receptor ion channelM. H. Poulsen, J. Anderson, R. Christensen, K. B. Hansen, S. F. Traynelis, K. Strømgaard, A. S. Kristensen, Journal of Molecular Biology 2015, 427, 176-189ArgTX 636Activity-studiesLink
ArgTX-636, a polyamine isolated from spider venom: A novel class of melanogenesis inhibitorsM. Verdoni, H. Roudaut, H. de Pomyers, D. Gigmes, D. Bertin, J. Luis, A. H. Bengeloune, K. Mabrouk, Bioorganic & Medicinal Chemistry 2016, 24, 5685-5692A. lobataArg 636Activity-studiesLink
Structural foundation for insect-selective activity of acylpolyamine toxins from spider Araneus ventricosusK. Lui, M. Wang, L. Jiang, X. Tang, Z. Liu, Z. Zhou, W. Hu, Z. Duan, S. Liang, Chemical Research in Toxicology 2019A. ventricosusAVTX 636NMRLink

Spider species

Spider speciesFamilyDiscovered
Araneus gemmaAraneidae1988 / C. J. Kerry
Araneus ventricosusAraneidae2019 / K. Lui
Argiope aurantiaAraneidae1987 / M. E. Adams
Argiope floridaAraneidae1988 / T. Budd
Argiope lobataAraneidae1986 / E. V. Grishin
Argiope sp.Araneidae1988 / C. J. Kerry
Argiope trifasciataAraneidae1988 / T. Budd

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