ChemicalBook CAS DataBase List 1276123-71-7

1276123-71-7

Name	L-Phenylalaninamide, L-tyrosyl-L-prolyl-L-tryptophyl-, acetate (1:1)
CAS	1276123-71-7
Molecular Formula	C36H42N6O7
Molecular Weight	670.77
MOL File	1276123-71-7.mol

Chemical Properties

form	Solid
color	White to off-white

Hazard Information

Uses

Endomorphin 1 acetate, a high affinity, highly selective agonist of the μ-opioid receptor (Ki: 1.11 nM), displays reasonable affinities for kappa3 binding sites, with Ki value between 20 and 30 nM. Endomorphin 1 acetate has antinociceptive properties[1][2][4].

in vivo

Endomorphin 1 (i.c.v.) acetate shows antinociceptive properties in mice, with an ED₅₀ value of 6.16 nM^[2].
Endomorphin 1 (50 μg/kg, i.v., rats) acetate alleviates myocardial ischemia/reperfusion injury (MIRI) by inhibiting the inflammatory response^[3].

Animal Model:	ICR mice^[2].
Dosage:	6.16 nM (ED₅₀)
Administration:	Intracerebroventricularly (i.c.v.) injection
Result:	Inhibited dose-dependently the tail-flick response.

Animal Model:	Rats^[3].
Dosage:	50 μg/kg
Administration:	Intravenously following LAD ligation for 25 min, subsequently the LAD was reperfused for 120 min.
Result:	Alleviated MIRI by reducing the production of free radicals. Dncreased LDH and CK-MB activities. Increased SOD activity and decreased MDA content. Decreased IL-6 and TNF-α plasma content.

IC 50

μ Opioid Receptor/MOR: 1.11 nM (Ki)

References

[1] Goldberg IE, et al. Pharmacological characterization of endomorphin-1 and endomorphin-2 in mouse brain. J Pharmacol Exp Ther. 1998 Aug;286(2):1007-13. PMID:9694962
[2] Tseng LF. The antinociceptive properties of endomorphin-1 and endomorphin-2 in the mouse. Jpn J Pharmacol. 2002 Jul;89(3):216-20. DOI:10.1254/jjp.89.216
[3] Zhang WP, et al. Effects of endomorphin-1 postconditioning on myocardial ischemia/reperfusion injury and myocardial cell apoptosis in a rat model. Mol Med Rep. 2016 Oct;14(4):3992-8. DOI:10.3892/mmr.2016.5695
[4] Koda Y, et al. Synthesis and in vitro evaluation of a library of modified endomorphin 1 peptides. Bioorg Med Chem. 2008 Jun 1;16(11):6286-96. DOI:10.1016/j.bmc.2008.04.020
[5] Harrison C, et al. The effects of endomorphin-1 and endomorphin-2 in CHO cells expressing recombinant mu-opioid receptors and SH-SY5Y cells. Br J Pharmacol. 1999 Sep;128(2):472-8. DOI:10.1038/sj.bjp.0702798
[6] Neudeck BL, et al. Endomorphin-1 alters interleukin-8 secretion in Caco-2 cells via a receptor mediated process. Immunol Lett. 2002 Dec 3;84(3):217-21. DOI:10.1016/s0165-2478(02)00198-0
[7] Fujita T, et al. Inhibition by endomorphin-1 and endomorphin-2 of excitatory transmission in adult rat substantia gelatinosa neurons. Neuroscience. 2006;139(3):1095-105. DOI:10.1016/j.neuroscience.2006.01.010

Supplier

Send Inquriy