Kyotorphin | CAS#70904-56-2 | Morphine-like dipeptide

MedKoo Cat#: 596864 | Name: Kyotorphin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Kyotorphin is a Morphine-like dipeptide from bovine brain.

Chemical Structure

Kyotorphin

CAS#70904-56-2

Theoretical Analysis

MedKoo Cat#: 596864

Name: Kyotorphin

CAS#: 70904-56-2

Chemical Formula: C15H23N5O4

Exact Mass: 337.1750

Molecular Weight: 337.38

Elemental Analysis: C, 53.40; H, 6.87; N, 20.76; O, 18.97

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
25mg	USD 750.00	2 Weeks

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Synonym

Kyotorphin; L-Tyrosyl-L-arginine; Tyr-arg; Kiotorphin;

IUPAC/Chemical Name

L-tyrosyl-L-arginine

InChi Key

JXNRXNCCROJZFB-RYUDHWBXSA-N

InChi Code

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

SMILES Code

N[C@@H](Cc1ccc(O)cc1)C(N[C@@H](CCCNC(N)=N)C(O)=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Kyotorphin is an endogenous neuroactive dipeptide with analgesic properties.

In vitro activity:

Kyotorphin abolished the stimulatory effect of norepinephrine on proliferation of cultured cells in vitro. Reference: Bull Exp Biol Med. 2006 Feb;141(2):223-5. https://pubmed.ncbi.nlm.nih.gov/16984102/

In vivo activity:

This study aimed to study the effects of the intracerebroventricular injection of effective antinociceptive doses of KTP (kyotorphin) on the motivational behavior, memory, and blood and hippocampal levels of the carbonylated proteins in healthy male adult Wistar rats. The present data showed that all single doses of KTP exerted an antinociceptive effect, but this effect was not observed after chronic administration. Reference: Folia Med (Plovdiv). 2021 Apr 30;63(2):189-196. https://pubmed.ncbi.nlm.nih.gov/33932008/

	Solvent	mg/mL	mM
Solubility
	DMSO	125.0	370.50
	Water	100.0	296.40

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 337.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Bronnikov GE, Kolaeva SG, Dolgacheva LP, Kramarova LI. Kyotorphin suppresses proliferation and Ca2+ signaling in brown preadipocytes. Bull Exp Biol Med. 2006 Feb;141(2):223-5. doi: 10.1007/s10517-006-0133-0. PMID: 16984102. 2. Angelova H, Krumova E, Dzhambazova E, Pechlivanova D. Effects of the antinociceptive dipeptide L-tyrosine-L-arginine (kyotorphin) on the motivation, anxiety, and memory in rats. Folia Med (Plovdiv). 2021 Apr 30;63(2):189-196. doi: 10.3897/folmed.63.e53912. PMID: 33932008. 3. Angelova H, Pechlivanova D, Krumova E, Miteva-Staleva J, Kostadinova N, Dzhambazova E, Landzhov B. Moderate protective effect of Kyotorphin against the late consequences of intracerebroventricular streptozotocin model of Alzheimer's disease. Amino Acids. 2019 Nov;51(10-12):1501-1513. doi: 10.1007/s00726-019-02784-5. Epub 2019 Sep 13. PMID: 31520285.

In vitro protocol:

In vivo protocol:

1. Angelova H, Krumova E, Dzhambazova E, Pechlivanova D. Effects of the antinociceptive dipeptide L-tyrosine-L-arginine (kyotorphin) on the motivation, anxiety, and memory in rats. Folia Med (Plovdiv). 2021 Apr 30;63(2):189-196. doi: 10.3897/folmed.63.e53912. PMID: 33932008. 2. Angelova H, Pechlivanova D, Krumova E, Miteva-Staleva J, Kostadinova N, Dzhambazova E, Landzhov B. Moderate protective effect of Kyotorphin against the late consequences of intracerebroventricular streptozotocin model of Alzheimer's disease. Amino Acids. 2019 Nov;51(10-12):1501-1513. doi: 10.1007/s00726-019-02784-5. Epub 2019 Sep 13. PMID: 31520285.

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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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.