Kyotorphin

  • CAT Number: I014425
  • CAS Number: 70904-56-2
  • Molecular Formula: C15H23N5O4
  • Molecular Weight: 337.38
  • Purity: ≥95%
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Kyotorphin (Cat.No:I014425) is a naturally occurring neuropeptide derived from the enzymatic breakdown of hemoglobin in the brain. It acts as an endogenous analgesic and has been shown to have potent pain-relieving effects in various animal models. Kyotorphin is of interest in pain research and may have potential therapeutic applications in pain management.

Catalog Number I014425
CAS Number 70904-56-2
Molecular Formula

C15H23N5O4

Purity 95%
Solubility Soluble in DMSO
InChI 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
InChIKey JXNRXNCCROJZFB-RYUDHWBXSA-N
SMILES N[C@@H](Cc1ccc(O)cc1)C(N[C@@H](CCCNC(N)=N)C(O)=O)=O
Reference

</br>1: Tsukahara T, Yamagishi S, Neyama H, Ueda H. Tyrosyl-tRNA synthetase: A potential kyotorphin synthetase in mammals. Peptides. 2018 Mar;101:60-68. doi: 10.1016/j.peptides.2017.12.026. Epub 2017 Dec 28. PubMed PMID: 29289698.</br>2: Bahamondes C, Wilson L, Guzmán F, Illanes A. Mathematical determination of kinetic parameters for assessing the effect of the organic solvent on the selectivity of peptide synthesis with immobilized α-chymotrypsin. J Biosci Bioeng. 2017 Dec;124(6):618-622. doi: 10.1016/j.jbiosc.2017.06.017. Epub 2017 Aug 25. PubMed PMID: 28847579.</br>3: Perazzo J, Lima C, Heras M, Bardají E, Lopes-Ferreira M, Castanho M. Neuropeptide Kyotorphin Impacts on Lipopolysaccharide-Induced Glucocorticoid-Mediated Inflammatory Response. A Molecular Link to Nociception, Neuroprotection, and Anti-Inflammatory Action. ACS Chem Neurosci. 2017 Aug 16;8(8):1663-1667. doi: 10.1021/acschemneuro.7b00007. Epub 2017 May 9. PubMed PMID: 28472878.</br>4: Figueira TN, Freire JM, Cunha-Santos C, Heras M, Gonçalves J, Moscona A, Porotto M, Salomé Veiga A, Castanho MA. Quantitative analysis of molecular partition towards lipid membranes using surface plasmon resonance. Sci Rep. 2017 Mar 30;7:45647. doi: 10.1038/srep45647. PubMed PMID: 28358389; PubMed Central PMCID: PMC5372468.</br>5: Perazzo J, Castanho MA, Sá Santos S. Pharmacological Potential of the Endogenous Dipeptide Kyotorphin and Selected Derivatives. Front Pharmacol. 2017 Jan 12;7:530. doi: 10.3389/fphar.2016.00530. eCollection 2016. Review. PubMed PMID: 28127286; PubMed Central PMCID: PMC5226936.</br>6: Perazzo J, Lopes-Ferreira M, Sá Santos S, Serrano I, Pinto A, Lima C, Bardaji E, Tavares I, Heras M, Conceição K, Castanho MA. Endothelium-Mediated Action of Analogues of the Endogenous Neuropeptide Kyotorphin (Tyrosil-Arginine): Mechanistic Insights from Permeation and Effects on Microcirculation. ACS Chem Neurosci. 2016 Aug 17;7(8):1130-40. doi: 10.1021/acschemneuro.6b00099. Epub 2016 Jun 15. PubMed PMID: 27244291.</br>7: Bi W, Bi Y, Gao X, Yan X, Zhang Y, Xue P, Bammert CE, Legalley TD, Michael Gibson K, Bi L, Wang JX. Anti-inflammatory, analgesic and antioxidant activities of novel kyotorphin-nitroxide hybrid molecules. Bioorg Med Chem Lett. 2016 Apr 15;26(8):2005-13. doi: 10.1016/j.bmcl.2016.02.086. Epub 2016 Mar 3. PubMed PMID: 26961795.</br>8: Sá Santos S, Santos SM, Pinto AR, Ramu VG, Heras M, Bardaji E, Tavares I, Castanho MA. Amidated and Ibuprofen-Conjugated Kyotorphins Promote Neuronal Rescue and Memory Recovery in Cerebral Hypoperfusion Dementia Model. Front Aging Neurosci. 2016 Jan 26;8:1. doi: 10.3389/fnagi.2016.00001. eCollection 2016. PubMed PMID: 26858637; PubMed Central PMCID: PMC4726799.</br>9: Bahamondes C, Wilson L, Bernal C, Illanes A, Álvaro G, Guzmán F. Synthesis of the kyotorphin precursor benzoyl-L-tyrosine-L-argininamide with immobilized α-chymotrypsin in sequential batch with enzyme reactivation. Biotechnol Prog. 2016 Jan-Feb;32(1):54-9. doi: 10.1002/btpr.2187. Epub 2015 Nov 6. PubMed PMID: 26488135.</br>10: Conceição K, Magalhães PR, Campos SR, Domingues MM, Ramu VG, Michalek M, Bertani P, Baptista AM, Heras M, Bardaji ER, Bechinger B, Ferreira ML, Castanho MA. The anti-inflammatory action of the analgesic kyotorphin neuropeptide derivatives: insights of a lipid-mediated mechanism. Amino Acids. 2016 Jan;48(1):307-18. doi: 10.1007/s00726-015-2088-9. Epub 2015 Sep 7. PubMed PMID: 26347373.</br>11: Magalhães PR, Machuqueiro M, Baptista AM. Constant-pH Molecular Dynamics Study of Kyotorphin in an Explicit Bilayer. Biophys J. 2015 May 5;108(9):2282-90. doi: 10.1016/j.bpj.2015.03.052. PubMed PMID: 25954885; PubMed Central PMCID: PMC4423061.</br>12: Serrano ID, Ramu VG, Pinto AR, Freire JM, Tavares I, Heras M, Bardaji ER, Castanho MA. Correlation between membrane translocation and analgesic efficacy in kyotorphin derivatives. Biopolymers. 2015 Jan;104(1):1-10. doi: 10.1002/bip.22580. PubMed PMID: 25363470.</br>13: Voigt N, Henrich-Noack P, Kockentiedt S, Hintz W, Tomas J, Sabel BA. Toxicity of polymeric nanoparticles in vivo and in vitro. J Nanopart Res. 2014 Jun 1;16(6). pii: 2379. Epub 2014 May 6. PubMed PMID: 26420981; PubMed Central PMCID: PMC4584143.</br>14: Serrano ID, Freire JM, Carvalho MV, Neves M, Melo MN, Castanho MA. The mechanisms and quantification of the selective permeability in transport across biological barriers: the example of kyotorphin. Mini Rev Med Chem. 2014 Feb;14(2):99-110. Review. PubMed PMID: 24456269.</br>15: Santos SM, Garcia-Nimo L, Sá Santos S, Tavares I, Cocho JA, Castanho MA. Neuropeptide Kyotorphin (Tyrosyl-Arginine) has Decreased Levels in the Cerebro-Spinal Fluid of Alzheimer’s Disease Patients: Potential Diagnostic and Pharmacological Implications. Front Aging Neurosci. 2013 Oct 30;5:68. doi: 10.3389/fnagi.2013.00068. eCollection 2013. PubMed PMID: 24198785; PubMed Central PMCID: PMC3812564.</br>16: Popov M, Abu Hammad I, Bachar T, Grinberg S, Linder C, Stepensky D, Heldman E. Delivery of analgesic peptides to the brain by nano-sized bolaamphiphilic vesicles made of monolayer membranes. Eur J Pharm Biopharm. 2013 Nov;85(3 Pt A):381-9. doi: 10.1016/j.ejpb.2013.06.005. Epub 2013 Jun 18. PubMed PMID: 23791683.</br>17: Ribeiro MM, Santos SS, Sousa DSC, Oliveira M, Santos SM, Heras M, Bardaji E, Tavares I, Castanho MA. Side-effects of analgesic kyotorphin derivatives: advantages over clinical opioid drugs. Amino Acids. 2013 Jul;45(1):171-8. doi: 10.1007/s00726-013-1484-2. Epub 2013 Mar 8. PubMed PMID: 23471674.</br>18: Webster RI, Newmyer BA, Furuse M, Gilbert ER, Cline MA. The orexigenic effect of kyotorphin in chicks involves hypothalamus and brainstem activity and opioid receptors. Neuropeptides. 2013 Jun;47(3):193-8. doi: 10.1016/j.npep.2012.10.007. Epub 2012 Dec 20. PubMed PMID: 23261360.</br>19: Ribeiro MM, Franquelim HG, Torcato IM, Ramu VG, Heras M, Bardaji ER, Castanho MA. Antimicrobial properties of analgesic kyotorphin peptides unraveled through atomic force microscopy. Biochem Biophys Res Commun. 2012 Apr 13;420(3):676-9. doi: 10.1016/j.bbrc.2012.03.065. Epub 2012 Mar 17. PubMed PMID: 22450328.</br>20: Ribeiro MM, Pinto AR, Domingues MM, Serrano I, Heras M, Bardaji ER, Tavares I, Castanho MA. Chemical conjugation of the neuropeptide kyotorphin and ibuprofen enhances brain targeting and analgesia. Mol Pharm. 2011 Oct 3;8(5):1929-40. doi: 10.1021/mp2003016. Epub 2011 Aug 24. PubMed PMID: 21830793. </br> </br>

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