Joro toxin

Joro toxin
Names
	IUPAC name (2S)-N1-{5-[3-({4-[(3-Aminopropyl)amino]butyl}amino)propanamido]pentyl}-N2-[(2,4-dihydroxyphenyl)acetyl]-L-glutaminamide
	Systematic IUPAC name (2S)-N1-{5-[3-({4-[(3-Aminopropyl)amino]butyl}amino)propanamido]pentyl}-2-[2-(2,4-dihydroxyphenyl)acetamido]butanediamide
	Other names Joro Spider toxin
Identifiers
CAS Number	112163-33-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34802 ;
ChEMBL	ChEMBL119582 ;
ChemSpider	106778 ;
ECHA InfoCard	100.217.900
IUPHAR/BPS	4229;
KEGG	C13931 ;
PubChem CID	119582;
CompTox Dashboard (EPA)	DTXSID50149933 ;
	InChI InChI=1S/C27H47N7O6/c28-10-6-13-30-11-4-5-12-31-16-9-25(38)32-14-2-1-3-15-33-27(40)22(19-24(29)37)34-26(39)17-20-7-8-21(35)18-23(20)36/h7-8,18,22,30-31,35-36H,1-6,9-17,19,28H2,(H2,29,37)(H,32,38)(H,33,40)(H,34,39)/t22-/m0/s1 Key: SJLRBGDPTALRDM-QFIPXVFZSA-N ;
	SMILES O=C(NCCCCCNC(=O)[C@@H](NC(=O)Cc1ccc(O)cc1O)CC(=O)N)CCNCCCCNCCCN;
Properties
Chemical formula	C27H47N7O6
Molar mass	565.716 g·mol−1
Appearance	White-grey powder
Density	1.196 g/cm3
Boiling point	979.883 °C (1,795.789 °F; 1,253.033 K)
Acidity (pKa)	9.53
Basicity (pKb)	10.573
Hazards
Flash point	546.414 °C (1,015.545 °F; 819.564 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Joro spider toxin (joro toxin, JSTX) – a toxin which was originally extracted from the venom of the joro spider (Trichonephila clavata), originally native to Japan.

Biochemical analysis

Joro toxin has demonstrated the ability to selectively block

postsynaptic glutamate potentials^[1] and
AMPA glutamate receptors.^[2]^[3]

It inhibits

NMDA receptors in the CNS of vertebrates.^[4]

Joro toxin does not affect

aspartate-induced neural depolarization,
resting membrane potential,
nerve terminal spontaneous signalling, or
inhibitory postsynaptic potentials.

Sources

Jackson, Jaewan; Lee, P.N.R. (1988). "Spider toxins as tools for dissecting elements of excitatory amino acid transmission". Trends in Neurosciences. 11 (6): 278–283. doi:10.1016/0166-2236(88)90112-9. PMID 2465627. S2CID 42853484.

Saito, Mitsuyoshi; Sahara, Yoshinori; Miwa, Akiko; Shimazaki, Kuniko; Nakajima, Terumi; Kawai, Nobufumi (1989). "Effects of a spider toxin (JSTX) on hippocampal CA1 neurons in vitro". Brain Research. 481 (1): 16–24. doi:10.1016/0006-8993(89)90480-0. PMID 2565131. S2CID 24856322.

Sahara, Yoshinori; Robinson, Hugh P.C.; Miwa, Akiko; Kawai, Nobufumi (1991). "A voltage-clamp study of the effects of Joro spider toxin and zinc on excitatory synaptic transmission in CA1 pyramidal cells of the guinea pig hippocampal slice". Neuroscience Research. 10 (3): 200–210. doi:10.1016/0168-0102(91)90057-6. PMID 1677747. S2CID 38895357.

References

^ Kawai, Nobufumi (1991). "Spider toxin and pertussis toxin differentiate post- and presynaptic glutamate receptors". Neuroscience Research. 12 (1): 3–12. doi:10.1016/0168-0102(91)90095-G. PMID 1660989. S2CID 23524210.
^ Shudo, Koichi; Endo, Yasuyuki; Hashimoto, Yuichi; Aramaki, Yoshio; Nakajima, Terumi; Kawai, Nobufumi (1987). "Newly synthesized analogues of the spider toxin block the crustacean glutamate receptor". Neuroscience Research. 5 (1): 82–85. doi:10.1016/0168-0102(87)90026-5. PMID 2829068. S2CID 41151994.
^ Kawai, Nobufumi; Niwa, Akiko; Abe, Takashi (1982). "Spider venom contains specific receptor blocker of glutaminergic synapses". Brain Research. 247 (1): 169–171. doi:10.1016/0006-8993(82)91044-7. PMID 6127145. S2CID 38772662.
^ Mueller, Alan L.; Albensi, Benedict C.; Ganong, Alan H.; Reynolds, Linda S.; Jackson, Hunter (1991). "Arylamine spider toxins antagonize NMDA receptor-mediated synaptic transmission in rat hippocampal slices". Synapse. 9 (4): 244–250. doi:10.1002/syn.890090403. PMID 1662833. S2CID 2546161.

[Kawai-1991-1] Kawai, Nobufumi (1991). "Spider toxin and pertussis toxin differentiate post- and presynaptic glutamate receptors". Neuroscience Research. 12 (1): 3–12. doi:10.1016/0168-0102(91)90095-G. PMID 1660989. S2CID 23524210.

[Shudo-Endo-etal-1987-2] Shudo, Koichi; Endo, Yasuyuki; Hashimoto, Yuichi; Aramaki, Yoshio; Nakajima, Terumi; Kawai, Nobufumi (1987). "Newly synthesized analogues of the spider toxin block the crustacean glutamate receptor". Neuroscience Research. 5 (1): 82–85. doi:10.1016/0168-0102(87)90026-5. PMID 2829068. S2CID 41151994.

[Kawai-Niwa-Abe-1982-3] Kawai, Nobufumi; Niwa, Akiko; Abe, Takashi (1982). "Spider venom contains specific receptor blocker of glutaminergic synapses". Brain Research. 247 (1): 169–171. doi:10.1016/0006-8993(82)91044-7. PMID 6127145. S2CID 38772662.

[Mueller-Albensi-etal-1991-4] Mueller, Alan L.; Albensi, Benedict C.; Ganong, Alan H.; Reynolds, Linda S.; Jackson, Hunter (1991). "Arylamine spider toxins antagonize NMDA receptor-mediated synaptic transmission in rat hippocampal slices". Synapse. 9 (4): 244–250. doi:10.1002/syn.890090403. PMID 1662833. S2CID 2546161.

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