Kyotorphin

Kyotorphin
Chemical structure of kyotorphin
Chemical structure of kyotorphin
Names
IUPAC name
(2S)-2-[[(2S)-2-Amino-3-(4-hydroxyphenyl)propanoyl]amino]-5- (diaminomethylideneamino)pentanoic acid
Other names
Kiotorphin
L-Tyrosyl-L-arginine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C15H23N5O4/c16-11(8-9-3-5-10(21)6-4-9)13(22)20-12(14(23)24)2-1-7-19-15(17)18/h3-6,11-12,21H,1-2,7-8,16H2,(H,20,22)(H,23,24)(H4,17,18,19)/t11-,12-/m0/s1 checkY
    Key: JXNRXNCCROJZFB-RYUDHWBXSA-N checkY
  • InChI=1/C15H23N5O4/c16-11(8-9-3-5-10(21)6-4-9)13(22)20-12(14(23)24)2-1-7-19-15(17)18/h3-6,11-12,21H,1-2,7-8,16H2,(H,20,22)(H,23,24)(H4,17,18,19)/t11-,12-/m0/s1
    Key: JXNRXNCCROJZFB-RYUDHWBXBC
  • O=C(O)[C@@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)CCC/N=C(\N)N
Properties
C15H23N5O4
Molar mass 337.380 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Kyotorphin (L-tyrosyl-L-arginine) is a neuroactive dipeptide which plays a role in pain regulation in the brain. It was first isolated from bovine brain, by Japanese scientists in 1979. Kyotorphin was named for the site of its discovery, Kyoto, Japan and because of its morphine- (or endorphin-) like analgesic activity. Kyotorphin has an analgesic effect, but it does not interact with the opioid receptors. Instead, it acts by releasing met-enkephalin and stabilizing it from degradation. It may also possess properties of neuromediator/neuromodulator. It has been shown that kyotorphin is present in the human cerebrospinal fluid and that its concentration is lower in patients with persistent pain.

References

  1. ↑ Takagi H, Shiomi H, Ueda H, Amano H (November 1979). "A novel analgesic dipeptide from bovine brain is a possible Met-enkephalin releaser". Nature. 282 (5737): 410–2. Bibcode:1979Natur.282..410T. doi:10.1038/282410a0. PMID 228202.
  2. ↑ Perazzo, Juliana; Castanho, Miguel A. R. B.; Sá Santos, Sónia (2017). "Pharmacological Potential of the Endogenous Dipeptide Kyotorphin and Selected Derivatives". Frontiers in Pharmacology. 7: 530. doi:10.3389/fphar.2016.00530. PMC 5226936. PMID 28127286.
  3. ↑ Ueda, Hiroshi (2021). "Review of Kyotorphin Research: A Mysterious Opioid Analgesic Dipeptide and Its Molecular, Physiological, and Pharmacological Characteristics". Frontiers in Medical Technology. 3 662697. doi:10.3389/fmedt.2021.662697. PMC 8757751. PMID 35047919.
  4. ↑ Nishimura K, Kaya K, Hazato T, Ueda H, Satoh M, Takagi H (November 1991). "[Kyotorphin like substance in human cerebrospinal fluid of patients with persistent pain]". Masui (in Japanese). 40 (11): 1686–90. PMID 1766121.