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From Wikipedia, the free encyclopedia

TGOT
Clinical data
Other namesTG-OT; TgOT; [Thr4,Gly7]-oxytocin; [Thr4,Gly7]-OT
Drug classOxytocin receptor agonist
ATC code
  • None
Identifiers
  • (2S)-N-[(2R)-1-[[2-[[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-3-sulfanylpropan-2-yl]-2-[[(2S,3R)-2-[[(2S,3S)-2-[[(2S)-2-[[(2R)-2-amino-3-sulfanylidenepropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]butanediamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
Chemical and physical data
FormulaC39H61N11O12S2
Molar mass940.10 g·mol−1
3D model (JSmol)
  • CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CS)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)NC(=O)[C@H](CC1=CC=C(C=C1)O)NC(=O)[C@H](C=S)N
  • InChI=1S/C39H61N11O12S2/c1-6-19(4)31(49-37(60)25(46-33(56)23(40)16-63)12-21-7-9-22(52)10-8-21)38(61)50-32(20(5)51)39(62)47-26(13-28(41)53)36(59)48-27(17-64)35(58)44-15-30(55)45-24(11-18(2)3)34(57)43-14-29(42)54/h7-10,16,18-20,23-27,31-32,51-52,64H,6,11-15,17,40H2,1-5H3,(H2,41,53)(H2,42,54)(H,43,57)(H,44,58)(H,45,55)(H,46,56)(H,47,62)(H,48,59)(H,49,60)(H,50,61)/t19-,20+,23-,24-,25-,26-,27-,31-,32-/m0/s1
  • Key:SJRRTEZQOSELMP-IKNHWLCZSA-N

TGOT, also known as [Thr4,Gly7]-oxytocin, is a synthetic peptide oxytocin receptor agonist which is widely used in scientific research.[1][2] It is a potent and selective agonist of the oxytocin receptor.[1][2] The drug has very high affinity and selectivity for the oxytocin receptor in rodents but the same is not true in humans, and hence it shows no advantage over oxytocin in humans.[1][3][4]

TGOT has been found to partially reverse the adverse behavioral changes caused by social isolation in rodents, for instance social avoidance and aggression.[5][6] It shows partially dissociable effects from those of oxytocin in rodents, which may be related to comparative selectivity against vasopressin receptors.[7]

TGOT was first described in the scientific literature by 1977.[8] TGOT, or [Thr4,Gly7]-oxytocin, should not be confused with triglycyl-oxytocin, which is also known by the acronym TGOT but is a different peptide oxytocin analogue that is far less-known in comparison.[9][10]

See also

[edit]

References

[edit]
  1. 1 2 3 Jurek B, Neumann ID (July 2018). "The Oxytocin Receptor: From Intracellular Signaling to Behavior". Physiological Reviews. 98 (3): 1805–1908. doi:10.1152/physrev.00031.2017. PMID 29897293.
  2. 1 2 Manning M, Misicka A, Olma A, Bankowski K, Stoev S, Chini B, et al. (April 2012). "Oxytocin and vasopressin agonists and antagonists as research tools and potential therapeutics". Journal of Neuroendocrinology. 24 (4): 609–628. doi:10.1111/j.1365-2826.2012.02303.x. PMC 3490377. PMID 22375852.
  3. ↑ Busnelli M, Chini B (2018). "Molecular Basis of Oxytocin Receptor Signalling in the Brain: What We Know and What We Need to Know". Current Topics in Behavioral Neurosciences. 35: 3–29. doi:10.1007/7854_2017_6. ISBN 978-3-319-63738-9. PMID 28812263.
  4. ↑ Busnelli M, Bulgheroni E, Manning M, Kleinau G, Chini B (August 2013). "Selective and potent agonists and antagonists for investigating the role of mouse oxytocin receptors". The Journal of Pharmacology and Experimental Therapeutics. 346 (2): 318–327. doi:10.1124/jpet.113.202994. PMC 3716315. PMID 23723434.
  5. ↑ Krimberg JS, Lumertz FS, Orso R, Viola TW, de Almeida RM (March 2022). "Impact of social isolation on the oxytocinergic system: A systematic review and meta-analysis of rodent data". Neuroscience and Biobehavioral Reviews. 134 104549. doi:10.1016/j.neubiorev.2022.104549. hdl:10923/25707. PMID 35074312.
  6. ↑ Tan O, Musullulu H, Raymond JS, Wilson B, Langguth M, Bowen MT (September 2019). "Oxytocin and vasopressin inhibit hyper-aggressive behaviour in socially isolated mice". Neuropharmacology. 156 107573. doi:10.1016/j.neuropharm.2019.03.016. PMID 30885607.
  7. ↑ Suraev AS, Bowen MT, Ali SO, Hicks C, Ramos L, McGregor IS (May 2014). "Adolescent exposure to oxytocin, but not the selective oxytocin receptor agonist TGOT, increases social behavior and plasma oxytocin in adulthood". Hormones and Behavior. 65 (5): 488–496. doi:10.1016/j.yhbeh.2014.03.002. PMID 24631584.
  8. ↑ Lowbridge J, Manning M, Haldar J, Sawyer WH (January 1977). "Synthesis and some pharmacological properties of [4-threonine, 7-glycine]oxytocin, [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine, 7-glycine]oxytocin (hydroxy[Thr4, Gly7]oxytocin), and [7-Glycine]oxytocin, peptides with high oxytocic-antidiuretic selectivity". Journal of Medicinal Chemistry. 20 (1): 120–123. doi:10.1021/jm00211a025. PMID 833810.
  9. ↑ Stevenson RW, Robinson IC, Parsons JA (February 1982). "Activation and clearance of a hormonogen, triglycyl-oxytocin, in the conscious dog". Acta Endocrinologica. 99 (2). Copenh: 211–217. doi:10.1530/acta.0.0990211. PMID 7058681.
  10. ↑ PubChem. "oxytocin, tri-Gly-". PubChem. Retrieved 19 July 2026.
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