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Application Area

Acetyl-β-Endorphin (human)

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

Category

Others

Catalog number

BAT-015147

CAS number

80102-04-1

Molecular Formula

C160H253N39O47S

Molecular Weight

3507.07

Specification
Reference Reading

IUPAC Name

(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]-6-aminohexanoyl]amino]-3-hydroxypropanoyl]amino]-5-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]-6-aminohexanoyl]amino]-4-amino-4-oxobutanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-6-aminohexanoyl]amino]-4-amino-4-oxobutanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-aminohexanoyl]amino]-6-aminohexanoyl]amino]acetyl]amino]pentanedioic acid

Synonyms

Ac-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-OH; N-acetyl-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-alanyl-L-tyrosyl-L-lysyl-L-lysyl-glycyl-L-glutamic acid

Appearance

White Powder

Purity

≥95%

Sequence

Ac-YGGFMTSEKSQTPLVTLFKNAIIKNAYKKGE

Storage

Store at -20°C

Solubility

Soluble in DMSO, Water

InChI

InChI=1S/C160H253N39O47S/c1-18-85(9)128(155(240)184-103(45-30-35-66-165)139(224)188-114(75-120(167)209)144(229)172-87(11)133(218)185-112(74-96-49-53-98(207)54-50-96)148(233)179-100(42-27-32-63-162)137(222)177-99(41-26-31-62-161)135(220)171-79-124(213)175-107(160(245)246)57-60-126(216)217)195-156(241)129(86(10)19-2)194-134(219)88(12)173-145(230)115(76-121(168)210)187-138(223)101(43-28-33-64-163)180-149(234)113(72-94-39-24-21-25-40-94)186-146(231)108(69-82(3)4)190-157(242)131(90(14)203)197-154(239)127(84(7)8)193-150(235)109(70-83(5)6)189-153(238)118-46-36-67-199(118)159(244)132(91(15)204)198-142(227)104(55-58-119(166)208)181-151(236)116(80-200)191-140(225)102(44-29-34-65-164)178-141(226)105(56-59-125(214)215)182-152(237)117(81-201)192-158(243)130(89(13)202)196-143(228)106(61-68-247-17)183-147(232)111(71-93-37-22-20-23-38-93)176-123(212)78-169-122(211)77-170-136(221)110(174-92(16)205)73-95-47-51-97(206)52-48-95/h20-25,37-40,47-54,82-91,99-118,127-132,200-204,206-207H,18-19,26-36,41-46,55-81,161-165H2,1-17H3,(H2,166,208)(H2,167,209)(H2,168,210)(H,169,211)(H,170,221)(H,171,220)(H,172,229)(H,173,230)(H,174,205)(H,175,213)(H,176,212)(H,177,222)(H,178,226)(H,179,233)(H,180,234)(H,181,236)(H,182,237)(H,183,232)(H,184,240)(H,185,218)(H,186,231)(H,187,223)(H,188,224)(H,189,238)(H,190,242)(H,191,225)(H,192,243)(H,193,235)(H,194,219)(H,195,241)(H,196,228)(H,197,239)(H,198,227)(H,214,215)(H,216,217)(H,245,246)/t85-,86-,87-,88-,89+,90+,91+,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,127-,128-,129-,130-,131-,132-/m0/s1

InChI Key

FOABCKXRBHNWGH-JONIBSFZSA-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(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CCC(=O)O)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)NC(=O)C

1. alpha N-acetyl human beta-endorphin-(1-31) alleviates the morphine withdrawal syndrome in rodents: a comparative study with clonidine

J Garzón, P Sánchez-Blázquez Life Sci. 1992;50(26):2099-109. doi: 10.1016/0024-3205(92)90576-b.

The potential effect of intracerebroventricular (icv) alpha N-acetyl human beta-endorphin-(1-31) on morphine dependence was examined in mice and rats. Animals were rendered tolerant-dependent by subcutaneous (sc) implantation of an oily suspension (10 ml/Kg mouse and 3 ml/Kg rat) containing 0.1 g/ml of morphine. After 72 h of chronic morphine, 1 mg/Kg sc naloxone precipitated in both species a withdrawal syndrome that was moderate in animals pretreated with the acetylated derivative of beta-endorphin. Doses of 28 fmols/rat or 80 fmols/mouse alpha N-acetyl human beta-endorphin-(1-31) reduced the number of animals presenting the jumping behaviour, as well as the number of jumps recorded. Moreover, less than half of the rats presented the other withdrawal signs evaluated: squeak on touch, diarrhoea, chattering, chewing, ptosis and body shakes. This activity could be observed when alpha N-acetyl human beta-endorphin was injected 1 h to 24 h before naloxone; longer intervals resulted in a significant loss of this activity. The alpha 2 agonist clonidine given icv at pmol-nmol doses decreased the incidence of morphine withdrawal syndrome. Combinations of these two substances generally did not produce any further enhancement of the effects of clonidine and alpha N-acetyl beta-endorphin when used alone. Icv injections of the antagonist of alpha 2-adrenoceptors yohimbine prevented both clonidine and alpha N-acetyl beta-endorphin-(1-31) from reducing the jumping behaviour displayed by morphine-abstinent mice. It is suggested that alpha N-acetyl beta-endorphin produces this alleviation of the morphine withdrawal syndrome by improving the efficiency of alpha 2-mediated agonist effects after acting on a neural substrate that is distinct from the mu opioid receptor binding site.

2. Evidence of alpha-N-acetyl beta-endorphin in human cerebrospinal fluid

F Facchinetti, G Sances, E Martignoni, I Pagani, G Nappi, A R Genazzani Brain Res. 1992 Jul 17;586(1):1-5. doi: 10.1016/0006-8993(92)91363-j.

Alpha-N-acetyl-beta-endorphin (Ac-beta-EP) is a post-translational product of beta-endorphin (beta-EP) with no analgesic properties. Ac beta-EP is present in human fetal and adult pituitary gland and cross-reacts in all available beta-EP assays. This study evaluates levels of Ac-beta-EP in the cerebrospinal fluid (CSF) of 22 normal subjects and 15 chronic headache sufferers. Since dopamine may play a role in the acetylation process, homovanillic acid levels were also determined. After extraction and high performance liquid chromatographic (HPLC) fractionation of CSF, an immunoreactive Ac-beta-EP peak was detected coeluting with reference peptide. Ac-beta-EP was detectable in all but 5 normal subjects. In headache sufferers, Ac-beta-EP levels were always detectable and their mean value was significantly higher than that of healthy subjects (11.6 +/- 11.8 vs 3.9 +/- 3.6 fmol/ml; P less than 0.01). Conversely, CSF beta-endorphin (beta-EP) concentrations were decreased in headache patients (9.8 +/- 9.4 vs 15.7 +/- 9.7 fmol/ml; P less than 0.05), and as a consequence the beta-EP/Ac-beta-EP ratio was also markedly reduced (P less than 0.005). No difference was observed for CSF homovanillic acid concentrations. These data demonstrate that HPLC coupled to radioimmunoassay allows the identification of low but significant amounts of Ac beta-EP in human CSF. This compound represents a confounding factor when beta-EP immunoreactivity is assessed by conventional methods. In headache sufferers, Ac-beta-EP levels were higher than normal, whereas beta-EP concentrations were lower.(ABSTRACT TRUNCATED AT 250 WORDS)

3. Alpha-melanocyte-stimulating hormone and N-acetyl-beta-endorphin immunoreactivities are localized in the human pituitary but are not restricted to the zona intermedia

V R Evans, A B Manning, L H Bernard, B M Chronwall, W R Millington Endocrinology. 1994 Jan;134(1):97-106. doi: 10.1210/endo.134.1.8275975.

The adult human pituitary lacks a well defined intermediate lobe, and it is uncertain whether the POMC cells that remain in the zona intermedia represent melanotropes or corticotropes. In the present study, we investigated whether the N-acetylated beta-endorphin- and alpha-MSH-related peptides that are characteristically produced by melanotropes in the rat and other species are localized in the human pituitary. Sequential gel filtration and ion exchange HPLC analysis revealed that small amounts of alpha-N-acetyl-beta-endorphin-(1-31), as well as beta-endorphin-(1-27) and beta-endorphin-(1-26), were detectable in human pituitary extracts, although beta-endorphin-(1-31) was clearly the major form. Consistent with this analysis, low levels of alpha-MSH, but not N,O-diacetyl-alpha-MSH, were identified by reverse-phase HPLC, although again, the desacetyl form of alpha-MSH predominated. Immunohistochemistry revealed that N-acetyl-beta-endorphin immunoreactivity was colocalized with ACTH and beta-endorphin in a subpopulation of zona intermedia cells. Unexpectedly, immunoreactive N-acetyl-beta-endorphin was also observed in a comparable proportion of corticotropes dispersed throughout the anterior lobe. alpha-MSH immunoreactivity was similarly distributed. These results indicate that N-acetylation is not restricted to the zona intermedia, suggesting that the strict dichotomy between corticotrope and melanotrope POMC processing observed in the rat and other species does not extend to the human pituitary.