D-Kyotorphin

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

MedKoo CAT#: 598076

CAS#: 70904-57-3

Description: D-Kyotorphin is a synthetic analogue of the neuropeptide kyotorphin and produces naloxone reversible analgesia.

Chemical Structure

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D-Kyotorphin
CAS# 70904-57-3
Instruction

Theoretical Analysis

MedKoo Cat#: 598076
Name: D-Kyotorphin
CAS#: 70904-57-3
Chemical Formula: C15H23N5O4
Exact Mass: 337.18
Molecular Weight: 337.380
Elemental Analysis: C, 53.40; H, 6.87; N, 20.76; O, 18.97

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: D-Kyotorphin; D Kyotorphin; H-L-Tyr-D-Arg-OH;

IUPAC/Chemical Name: L-tyrosyl-D-arginine

InChi Key: JXNRXNCCROJZFB-NWDGAFQWSA-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(N)NCCC[C@H](C(O)=O)NC([C@H](CC1=CC=C(O)C=C1)N)=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: >3 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Dzambazova EB, Landzhov BV, Bocheva AI, Bozhilova-Pastirova AA. Effects of D-kyotorphin on nociception and NADPH-d neurons in rat's periaqueductal gray after immobilization stress. Amino Acids. 2011 Oct;41(4):937-44. doi: 10.1007/s00726-010-0793-y. Epub 2010 Nov 3. PubMed PMID: 21046177.

2: Stone TW. A comparison of the effects of morphine, enkephalin, kyotorphin and D-phenylalanine on rat central neurones. Br J Pharmacol. 1983 May;79(1):305-12. PubMed PMID: 6871550; PubMed Central PMCID: PMC2044814.

3: Janicki PK, Lipkowski AW. Kyotorphin and D-kyotorphin stimulate Met-enkephalin release from rat striatum in vitro. Neurosci Lett. 1983 Dec 23;43(1):73-7. PubMed PMID: 6142436.

4: Satoh M, Wada T, Iwama T, Takagi H. Sites of analgesic actions of kyotorphin and D-kyotorphin in the central nervous system of rats. Neuropeptides. 1985 Feb;5(4-6):415-8. PubMed PMID: 4000414.

5: 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.

6: Bean AJ, Vaught JL. [D-Arg]Kyotorphin-induced ipsilateral rotation: evidence for in vivo effects independent of Met-enkephalin release. Brain Res. 1984 Nov 12;321(2):327-31. PubMed PMID: 6498522.

7: Arima T, Kitamura Y, Nishiya T, Takagi H, Nomura Y. Kyotorphin (L-tyrosyl-L-arginine) as a possible substrate for inducible nitric oxide synthase in rat glial cells. Neurosci Lett. 1996 Jul 5;212(1):1-4. PubMed PMID: 8823748.

8: Bean AJ, Vaught JL. Physical dependence produced by chronic intracerebroventricular infusion of [D-Arg]kyotorphin or thiorphan to rats. Eur J Pharmacol. 1984 Oct 15;105(3-4):333-7. PubMed PMID: 6096157.

9: 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.

10: Lopes SC, Fedorov A, Castanho MA. Chiral recognition of D-kyotorphin by lipidic membranes: relevance toward improved analgesic efficiency. ChemMedChem. 2006 Jul;1(7):723-8. PubMed PMID: 16902926.

11: Bocheva A. Effect of D-arginine on antinociception induced by kyotorphin, Tyr-cav, L-cav and Tyr(Cl2)-cav in rats. Methods Find Exp Clin Pharmacol. 2004 Jun;26(5):335-8. PubMed PMID: 15319811.

12: Jiang H, Hu Y, Keep RF, Smith DE. Enhanced antinociceptive response to intracerebroventricular kyotorphin in Pept2 null mice. J Neurochem. 2009 Jun;109(5):1536-43. doi: 10.1111/j.1471-4159.2009.06090.x. Epub 2009 Apr 4. PubMed PMID: 19383084; PubMed Central PMCID: PMC2898572.

13: 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.

14: Hirai K, Katayama Y. Effect of the endogenous analgesic dipeptide, kyotorphin, on transmitter release in sympathetic ganglia. Br J Pharmacol. 1985 Jul;85(3):629-34. PubMed PMID: 2862945; PubMed Central PMCID: PMC1916518.

15: Vaught JL, Chipkin RE. A characterization of kyotorphin (Tyr-Arg)-induced antinociception. Eur J Pharmacol. 1982 Apr 23;79(3-4):167-73. PubMed PMID: 7047176.

16: Sakurada T, Sakurada S, Watanabe S, Matsumura H, Kisara K, Akutsu Y, Sasaki Y, Suzuki K. Actions of intracerebroventricular administration of kyotorphin and an analog on thermoregulation in the mouse. Peptides. 1983 Nov-Dec;4(6):859-63. PubMed PMID: 6424102.

17: Godlevsky LS, Shandra AA, Mikhaleva II, Vastyanov RS, Mazarati AM. Seizure-protecting effects of kyotorphin and related peptides in an animal model of epilepsy. Brain Res Bull. 1995;37(3):223-6. PubMed PMID: 7627564.

18: Shiomi H, Kuraishi Y, Ueda H, Harada Y, Amano H, Takagi H. Mechanism of kyotorphin-induced release of Met-enkephalin from guinea pig striatum and spinal cord. Brain Res. 1981 Sep 21;221(1):161-9. PubMed PMID: 7272759.

19: Haseto S, Mizuma T, Ouchi H, Isoda T, Hayashi M, Awazu S. Preference of Peyer's patches to jejunal epithelium for intestinal absorption of oligopeptides, tyrosylglycylglycine and D-kyotorphin. Biol Pharm Bull. 1997 Sep;20(9):1024-5. PubMed PMID: 9331991.

20: 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.