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β-Endorphin (rat)

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

β-Endorphin is an endogenous 31-amino acid neuropeptide that binds to μ-, δ-, and κ-opioid receptors (Kis = 3.73, 5.02, and 32.7 nM, respectively, in COS-1 cells expressing rat receptors).

Category

Peptide Inhibitors

Catalog number

BAT-015150

CAS number

309246-19-3

Molecular Formula

C157H254N42O44S

Molecular Weight

3466.02

Specification
Reference Reading

IUPAC Name

(2S)-5-amino-2-[[2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoyl]amino]hexanoyl]amino]acetyl]amino]-5-oxopentanoic acid

Synonyms

H-Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Val-His-Lys-Lys-Gly-Gln-OH; L-tyrosyl-glycyl-glycyl-L-phenylalanyl-L-methionyl-L-threonyl-L-seryl-L-alpha-glutamyl-L-lysyl-L-seryl-L-glutaminyl-L-threonyl-L-prolyl-L-leucyl-L-valyl-L-threonyl-L-leucyl-L-phenylalanyl-L-lysyl-L-asparagyl-L-alanyl-L-isoleucyl-L-isoleucyl-L-lysyl-L-asparagyl-L-valyl-L-histidyl-L-lysyl-L-lysyl-glycyl-L-glutamine

Appearance

Lyophilized Powder

Purity

≥95%

Density

1.3±0.1 g/cm3

Boiling Point

2966.7±65.0°C at 760 mmHg

Sequence

YGGFMTSEKSQTPLVTLFKNAIIKNVHKKGQ

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C157H254N42O44S/c1-18-84(11)125(152(237)183-100(45-30-35-62-162)135(220)186-111(72-118(167)209)146(231)192-123(82(7)8)150(235)189-109(70-93-73-168-79-172-93)144(229)179-97(42-27-32-59-159)133(218)176-96(41-26-31-58-158)132(217)171-76-121(212)174-104(157(242)243)52-55-116(165)207)195-153(238)126(85(12)19-2)194-130(215)86(13)173-140(225)110(71-117(166)208)185-134(219)98(43-28-33-60-160)178-143(228)108(69-91-39-24-21-25-40-91)184-141(226)105(65-80(3)4)188-154(239)128(88(15)203)197-151(236)124(83(9)10)193-145(230)106(66-81(5)6)187-149(234)114-46-36-63-199(114)156(241)129(89(16)204)198-138(223)101(51-54-115(164)206)180-147(232)112(77-200)190-136(221)99(44-29-34-61-161)177-137(222)102(53-56-122(213)214)181-148(233)113(78-201)191-155(240)127(87(14)202)196-139(224)103(57-64-244-17)182-142(227)107(68-90-37-22-20-23-38-90)175-120(211)75-169-119(210)74-170-131(216)95(163)67-92-47-49-94(205)50-48-92/h20-25,37-40,47-50,73,79-89,95-114,123-129,200-205H,18-19,26-36,41-46,51-72,74-78,158-163H2,1-17H3,(H2,164,206)(H2,165,207)(H2,166,208)(H2,167,209)(H,168,172)(H,169,210)(H,170,216)(H,171,217)(H,173,225)(H,174,212)(H,175,211)(H,176,218)(H,177,222)(H,178,228)(H,179,229)(H,180,232)(H,181,233)(H,182,227)(H,183,237)(H,184,226)(H,185,219)(H,186,220)(H,187,234)(H,188,239)(H,189,235)(H,190,221)(H,191,240)(H,192,231)(H,193,230)(H,194,215)(H,195,238)(H,196,224)(H,197,236)(H,198,223)(H,213,214)(H,242,243)/t84-,85-,86-,87+,88+,89+,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,123-,124-,125-,126-,127-,128-,129-/m0/s1

InChI Key

KSZMZNRVPCEDEO-KFHPFRHLSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)NC(CC1=CN=CN1)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CCC(=O)N)C(=O)O)NC(=O)C(C)NC(=O)C(CC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC(C)C)NC(=O)C(C(C)O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C3CCCN3C(=O)C(C(C)O)NC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CCSC)NC(=O)C(CC4=CC=CC=C4)NC(=O)CNC(=O)CNC(=O)C(CC5=CC=C(C=C5)O)N

1. [INFLUENCE OF Р-ENDORPHIN ON FUNCTIONAL ACTIVITY OF ISOLATED RAT HEART]

V R Rembovskiy, A S Radilov, S G Petunov, D V Bobkov, D S Laptev Ross Fiziol Zh Im I M Sechenova . 2016 Nov;102(11):1343-51.

We have studied the effect of Р-endorphin (an endogenous opioid peptide) on the functional characteristics of isolated rat heart. In physiological concentrations (6.3 X 10-10 M) Р-endorphin induces a negative inotropic effect, accompanied by a slight decrease in the heart rate, and has no effect on the perfusion pressure of the coronary vessels. It is shown that the effect of Р-endorphin is mediated by 5-opioid receptors. ATP-dependent K+-channels contribute the greatest contribution to the implementation of the effect of Р-endorphin on the isolated heart of a rat. The role of voltage-dependent K+-channels and NO-mediated mechanisms in the implementation of the effects of Р-endorphin is minor.

2. Extracellular biotransformation of beta-endorphin in rat striatum and cerebrospinal fluid

B Reed, J M Bidlack, B T Chait, M J Kreek J Neuroendocrinol . 2008 May;20(5):606-16. doi: 10.1111/j.1365-2826.2008.01705.x.

Numerous studies have investigated the behavioural effects of beta-endorphin, both endogenous and exogenously applied. However, the potential for biotransformation of beta-endorphin in the extracellular space of the brain has not been previously directly addressed in vivo. Utilising microinfusion/microdialysis and matrix-assisted laser desorption/ionisation mass spectrometry, we investigated beta-endorphin biotransformation in the striatum of rats. We infused 1.0 nmol beta-endorphin into the striatum of adult male Fischer rats and observed rapid cleavage resulting in beta-endorphin 1-18, as well as several fragments resulting from further N-terminal degradation. In vitro studies with incubation of full-length beta-endorphin, with and without protease inhibitors, in the incubation fluid of isolated striatal slices indicate that beta-endorphin is initially cleaved predominantly at the Phe(18)-Lys(19), position, as well as at the Leu(17)-Phe(18) position. Investigations of cerebrospinal fluid revealed similar enzymatic cleavage of beta-endorphin. The observed pattern of cleavage sites (Phe(18)-Lys(19) and Leu(17)-Phe(18)) is consistent with published in vitro studies of purified insulin-degrading enzyme cleavage of beta-endorphin. The binding affinities of full-length beta-endorphin, as well as previously identified beta-endorphin fragments alpha-endorphin (beta-endorphin 1-16) and gamma-endorphin (beta-endorphin 1-17), and the fragment identified in the present study, beta-endorphin 1-18, at heterologously expressed mu, delta and kappa-opioid receptors, respectively, were determined; the affinity of the truncation fragments is reduced at each of the receptors compared to the affinity of full length beta-endorphin.

3. Characterization of the effects of acute ethanol administration on the release of beta-endorphin peptides by the rat hypothalamus

C Gianoulakis Eur J Pharmacol . 1990 May 3;180(1):21-9. doi: 10.1016/0014-2999(90)90588-w.

In the present studies the direct effect of ethanol on the release of beta-endorphin by the rat hypothalamus was investigated. When various concentrations of ethanol (10-120 mM) were added into the incubation medium, it was noticed that though low concentrations of ethanol (10, 20 and 30 mM) induced a pronounced increase in the release of beta-endorphin-like peptides from the hypothalamus, high concentrations of ethanol (40, 60 and 120 mM) induced a less pronounced increase. Exposure of hypothalamus to depolarizing concentrations of potassium chloride (following washing of the ethanol), provoked a significant release of beta-endorphin-like peptides, regardless of the ethanol concentration the tissues were exposed prior to the stimulation with the potassium chloride. Chromatographic analysis of the incubation media with Sephadex-G-75 revealed that the hypothalamus released mainly beta-endorphin-sized peptides. Analysis of the beta-endorphin-sized peptides with reverse-phase high performance liquid chromatography indicated the presence of beta-endorphin-(1-31) as well as non-acetyl and acetyl beta-endorphin-(1-27). Thus ethanol exerts a biphasic effect on the release of beta-endorphin-like peptides by the rat hypothalamus, with low concentrations inducing a dose-dependent increase, reaching maximum at 20 mM ethanol, and with higher concentrations of ethanol inducing a less pronounced increase in the release of beta-endorphin-like peptides, leading to an inverted U-shaped dose response relationship of ethanol and release of beta-endorphin-like peptides from the rat hypothalamus.