Chemistry:Joro toxin

Joro toxin

Names
Preferred 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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:245409 N
ChEMBL	ChEMBL119582 Y
ChemSpider	106778 Y
IUPHAR/BPS	4229
KEGG	C13931 Y
PubChem CID	119582
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 Y Key: SJLRBGDPTALRDM-QFIPXVFZSA-N Y
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

Tracking categories (test):

• SizeSet

Joro spider toxin (joro toxin, JSTX) - a toxin which was originally extracted from the spider Nephila clavata venom. The compound has demonstrated the ability to selectively block postsynaptic glutamate potentials, AMPA glutamate receptors, and to antagonise the effect of NMDA receptors in the CNS of vertebrates. However, it does not affect aspartate-induced neural depolarization, resting membrane potential, nerve terminal spontaneous signalling, or inhibitory postsynaptic potentials.

Literature

• Kawai, Nobufumi; Niwa, Akiko; Abe, Takashi (1982). "Spider venom contains specific receptor blocker of glutaminergic synapses". Brain Research 247 (1): 169–71. doi:10.1016/0006-8993(82)91044-7. PMID 6127145. 
• 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): 82–5. doi:10.1016/0168-0102(87)90026-5. PMID 2829068. 
• Jackson, Jaewan; Lee, P.N.R. (1988). "Spider toxins as tools for dissecting elements of excitatory amino acid transmission". Trends in Neurosciences 11 (6): 278–83. doi:10.1016/0166-2236(88)90112-9. PMID 2465627. 
• 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. 
• 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): 200–10. doi:10.1016/0168-0102(91)90057-6. PMID 1677747. 
• 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. 
• 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): 244–50. doi:10.1002/syn.890090403. PMID 1662833.