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E6261

Sigma-Aldrich

β-Endorphin human

≥95% (HPLC)

Synonym(s):

β-Lipotropin 61-91, β-Lipotropin C-fragment, LPH (61-91)

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About This Item

Empirical Formula (Hill Notation):
C158H251N39O46S
CAS Number:
61214-51-5
Molecular Weight:
3464.98
MDL number:
MFCD00076383
UNSPSC Code:
12352202
PubChem Substance ID:
24894624
NACRES:
NA.32

Quality Level

200

assay

≥95% (HPLC)

UniProt accession no.

P01189

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc3ccccc3)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc4ccc(O)cc4)[C@@H](C)O)[C@@H](C)O)C(C)C)[C@@H](C)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc5ccc(O)cc5)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI

1S/C158H251N39O46S/c1-17-84(9)126(153(237)182-102(44-29-34-65-163)137(221)186-112(74-118(166)206)142(226)171-86(11)131(215)183-110(73-94-48-52-96(204)53-49-94)146(230)177-99(41-26-31-62-160)135(219)175-98(40-25-30-61-159)134(218)170-78-122(210)173-106(158(242)243)56-59-124(213)214)193-154(238)127(85(10)18-2)192-132(216)87(12)172-143(227)113(75-119(167)207)185-136(220)100(42-27-32-63-161)178-147(231)111(72-92-38-23-20-24-39-92)184-144(228)107(68-81(3)4)188-155(239)129(89(14)201)195-152(236)125(83(7)8)191-148(232)108(69-82(5)6)187-151(235)116-45-35-66-197(116)157(241)130(90(15)202)196-140(224)103(54-57-117(165)205)179-149(233)114(79-198)189-138(222)101(43-28-33-64-162)176-139(223)104(55-58-123(211)212)180-150(234)115(80-199)190-156(240)128(88(13)200)194-141(225)105(60-67-244-16)181-145(229)109(71-91-36-21-19-22-37-91)174-121(209)77-168-120(208)76-169-133(217)97(164)70-93-46-50-95(203)51-47-93/h19-24,36-39,46-53,81-90,97-116,125-130,198-204H,17-18,25-35,40-45,54-80,159-164H2,1-16H3,(H2,165,205)(H2,166,206)(H2,167,207)(H,168,208)(H,169,217)(H,170,218)(H,171,226)(H,172,227)(H,173,210)(H,174,209)(H,175,219)(H,176,223)(H,177,230)(H,178,231)(H,179,233)(H,180,234)(H,181,229)(H,182,237)(H,183,215)(H,184,228)(H,185,220)(H,186,221)(H,187,235)(H,188,239)(H,189,222)(H,190,240)(H,191,232)(H,192,216)(H,193,238)(H,194,225)(H,195,236)(H,196,224)(H,211,212)(H,213,214)(H,242,243)/t84-,85-,86-,87-,88+,89+,90+,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,125-,126-,127-,128-,129-,130-/m0/s1

InChI key

JMHFFDIMOUKDCZ-NTXHZHDSSA-N

Gene Information

human ... POMC(5443)

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Amino Acid Sequence

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-Ala-Tyr-Lys-Lys-Gly-Glu

General description

β-Endorphin is a potent endogenous opioid protein that is derived from propiomelanocortin, a protein found in the brain, anterior pituitary, skin, immune system, and other peripheral sites. β-endorphin, however, is localized to the brain and spinal cord. It is one of the major opioid peptides, and is the derivative of the C-terminal of β-lipotropin. It is made of 31 amino acids.

Application

Human β-Endorphin is suitable for-
  • radioimmunoassay to determine the portal blood β-endorphin levels in lactating ewes, and its relation to bouts of suckling
  • to assess the melanogenesis, proliferation and dendricity of melanocytes
  • to assess the expression of μ-opioid receptor, in human skin organ culture, on exposure to β-endorphin
  • to examine the effects on cardiovascular functions of β-endorphin injection nucleus in amygdaloideus centralis (AC), into either nucleus paraventricularis (NPV) or rostral ventrolateral medulla (RVL)

Biochem/physiol Actions

β-Endorphin acts as a ligand for both μ and δ opioid receptors in different parts of the brain. It is released in response to painful stimuli and has potent antinociceptive activity. When given supraspinally, this activity is mediated through its action on ε-opioid receptors in brain that results in the release of Met-enkephalin. This activity is also mediated by its interaction with δ2-opioid receptors in the spinal cord. When introduced intrathecally, this function is an outcome of its interaction with μ and κ-opioid receptors in the rat. In autoimmune disorders, the elevated production of cytokines results in the production of β-endorphin, in pituitary and lymphocytes. This acts as a negative regulator of antibody production, and is thus, implicated in autoimmune diseases.
Potent endogenous opioid protein that is derived from propiomelanocortin, a protein found in the brain, anterior pituitary, skin, immune system, and other peripheral sites. It is released in response to painful stimuli and has potent antinociceptive activity that is mediated through its action on μ receptors in brain and by μ and κ receptors in the spinal cord.

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Andrzej T Slominski
The Journal of investigative dermatology, 126(9), 1934-1936 (2006-08-17)
The proopiomelanocortin (POMC) system is the central coordinator of the systemic endocrine responses to sustained stress. It has been recently discovered that mast cells also display regulated production of POMC peptides. Since at the tissue level mast cells integrate stress
Y H Ku et al.
Peptides, 22(9), 1465-1470 (2001-08-22)
It has been proved that input of specific electroacupuncture (EA) can activate beta-endorphin(beta-EP)ergic and noradrenergic neurons projecting to the rostral ventrolateral medulla (RVL), the latter acting upon the RVL-GABAergic interneurons, thereby produce depressor effect. The present study further shows that:
L F Tseng et al.
Naunyn-Schmiedeberg's archives of pharmacology, 351(5), 464-468 (1995-05-01)
The antinociception induced by beta-endorphin given supraspinally has been previously demonstrated to be mediated by the stimulation of epsilon-, but not mu-, delta- or kappa-opioid receptors in rats and mice. The present study was designed to determine what types of
M Narita et al.
Japanese journal of pharmacology, 76(3), 233-253 (1998-05-21)
Recently, mu-, delta- and kappa-opioid receptors have been cloned and relatively well-characterized. In addition to three major opioid receptor types, more extensive studies have suggested the possible existence of other opioid receptor types that can be classified as non-mu, non-delta
M Bigliardi-Qi et al.
The Journal of investigative dermatology, 114(3), 527-532 (2000-02-26)
It has been reported that opioid peptides modulate the differentiation of normal human keratinocytes and that mu-opiate receptors are expressed in human epidermis. The regulation of keratinocyte differentiation is particularly important in psoriasis, and one of the markers for hyperproliferative
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