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'''Endomorphin-1''' ('''EM-1''') ([[amino acid sequence]] Tyr-Pro-Trp-Phe-NH<sub>2</sub>) is an [[endogenous]] [[opioid peptide]] and one of the two [[endomorphin]]s.<ref name="BodnarCommons2002">{{cite book| vauthors = Bodnar RJ, Commons KG, Pfaff DW |title=Central Neural States Relating Sex and Pain|url=https://books.google.com/books?id=4KeQEC4nHSkC&pg=PA67|date=3 April 2002|publisher=JHU Press|isbn=978-0-8018-6827-6|pages=67–}}</ref> It is a high [[affinity (pharmacology)|affinity]], highly selective [[agonist]] of the [[μ-opioid receptor]], and along with [[endomorphin-2]] (EM-2), has been proposed to be the actual endogenous [[ligand (biochemistry)|ligand]] of the [[mu receptor|μ-receptor]].<ref name="BodnarCommons2002" /><ref name="KrammerSinger2000">{{cite book| vauthors = Krammer HJ, Singer MV |title=Neurogastroenterology - From the Basics to the Clinics|url=https://books.google.com/books?id=ghjN0L47QbwC&pg=PA76|date=31 May 2000|publisher=Springer Science & Business Media|isbn=978-0-7923-8757-2|pages=76–}}</ref><ref name="BrainMoore1999" /><ref name="OffermannsRosenthal2008">{{cite book| vauthors = Offermanns S, Rosenthal W |title=Encyclopedia of Molecular Pharmacology|url=https://books.google.com/books?id=fGe6NDIGQpsC&pg=PA904|date=14 August 2008|publisher=Springer Science & Business Media|isbn=978-3-540-38916-3|pages=904–}}</ref> EM-1 produces [[analgesia]] in animals and is [[equipotent]] with [[morphine]] in this regard.<ref name="BrainMoore1999">{{cite book| vauthors = Brain S, Moore PK |title=Pain and Neurogenic Inflammation|url=https://books.google.com/books?id=6TNSAeTpkUMC&pg=PA28|year=1999|publisher=Springer Science & Business Media|isbn=978-3-7643-5875-4|pages=28–}}</ref> The [[gene]] encoding for EM-1 has not yet been identified,<ref name="OffermannsRosenthal2008" /> and it has been suggested that endomorphins could be synthesized by an enzymatic, non-ribosomal mechanism.<ref>{{cite journal | vauthors = Terskiy A, Wannemacher KM, Yadav PN, Tsai M, Tian B, Howells RD | title = Search of the human proteome for endomorphin-1 and endomorphin-2 precursor proteins | journal = Life Sciences | volume = 81 | issue = 23–24 | pages = 1593–601 | date = November 2007 | pmid = 17964607 | pmc = 2144908 | doi = 10.1016/j.lfs.2007.09.025 }}</ref>
'''Endomorphin-1''' ('''EM-1''') ([[amino acid sequence]] Tyr-Pro-Trp-Phe-NH<sub>2</sub>) is an [[endogenous]] [[opioid peptide]] and one of the two [[endomorphin]]s.<ref name="BodnarCommons2002">{{cite book| vauthors = Bodnar RJ, Commons KG, Pfaff DW |title=Central Neural States Relating Sex and Pain|url=https://books.google.com/books?id=4KeQEC4nHSkC&pg=PA67|date=3 April 2002|publisher=JHU Press|isbn=978-0-8018-6827-6|pages=67–}}</ref> It is a high [[affinity (pharmacology)|affinity]], highly selective [[agonist]] of the [[μ-opioid receptor]], and along with [[endomorphin-2]] (EM-2), has been proposed to be the actual endogenous [[ligand (biochemistry)|ligand]] of the [[mu receptor|μ-receptor]].<ref name="BodnarCommons2002" /><ref name="KrammerSinger2000">{{cite book| vauthors = Krammer HJ, Singer MV |title=Neurogastroenterology - From the Basics to the Clinics|url=https://books.google.com/books?id=ghjN0L47QbwC&pg=PA76|date=31 May 2000|publisher=Springer Science & Business Media|isbn=978-0-7923-8757-2|pages=76–}}</ref><ref name="BrainMoore1999" /><ref name="OffermannsRosenthal2008">{{cite book| vauthors = Offermanns S, Rosenthal W |title=Encyclopedia of Molecular Pharmacology|url=https://books.google.com/books?id=fGe6NDIGQpsC&pg=PA904|date=14 August 2008|publisher=Springer Science & Business Media|isbn=978-3-540-38916-3|pages=904–}}</ref> EM-1 produces [[analgesia]] in animals and is [[equipotent]] with [[morphine]] in this regard.<ref name="BrainMoore1999">{{cite book| vauthors = Brain S, Moore PK |title=Pain and Neurogenic Inflammation|url=https://books.google.com/books?id=6TNSAeTpkUMC&pg=PA28|year=1999|publisher=Springer Science & Business Media|isbn=978-3-7643-5875-4|pages=28–}}</ref> The [[gene]] encoding for EM-1 has not yet been identified,<ref name="OffermannsRosenthal2008" /> and it has been suggested that endomorphins could be synthesized by an enzymatic, non-ribosomal mechanism.<ref>{{cite journal | vauthors = Terskiy A, Wannemacher KM, Yadav PN, Tsai M, Tian B, Howells RD | title = Search of the human proteome for endomorphin-1 and endomorphin-2 precursor proteins | journal = Life Sciences | volume = 81 | issue = 23–24 | pages = 1593–601 | date = November 2007 | pmid = 17964607 | pmc = 2144908 | doi = 10.1016/j.lfs.2007.09.025 }}</ref>

By combining N-terminal guadino modifications, a new class of endonmorphin-1 was synthesized, the range of their bioactivities were measured by radioligand binding assay in order to conclude its potency as an opioid.<ref>{{Cite web|title=BrowZine|url=https://browzine.com/libraries/1453/journals/5448/issues/322551099|access-date=2021-11-02|website=browzine.com}}</ref> Endomorphin-1 has a Hight affinity and specificity for opioid receptors for behavioral, physiological and pharmacological assays, it is also a potent analgesic agent which brings effects on cardiovascular, respiratory and gastrointestinal functions as well as in immune system responses..<ref>{{Cite web|title=Endomorphin 1 - an overview {{!}} ScienceDirect Topics|url=https://www.sciencedirect.com/topics/neuroscience/endomorphin-1|access-date=2021-11-13|website=www.sciencedirect.com}}</ref>This endogenous opioid peptide can help with neuropathic pain without having the common side effects many neuropathic drugs caused which produces constipation. To make this drug side effect-free, a modification at the N-terminus by 2-aminodecainoic acid is made which in term showed an improve in the drug's metabolic stability along with improving its membrane permeability, while holding its high receptor binding affinity, helping the drug act as a potent agonist<ref>{{Cite journal|last=Varamini|first=Pegah|last2=Mansfeld|first2=Friederike M.|last3=Blanchfield|first3=Joanne T.|last4=Wyse|first4=Bruce D.|last5=Smith|first5=Maree T.|last6=Toth|first6=Istvan|date=2012-08-17|title=Lipo-Endomorphin-1 Derivatives with Systemic Activity against Neuropathic Pain without Producing Constipation|url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3422351/|journal=PLoS ONE|volume=7|issue=8|pages=e41909|doi=10.1371/journal.pone.0041909|issn=1932-6203|pmc=3422351|pmid=22912681}}</ref>


== See also ==
== See also ==

Revision as of 04:11, 29 November 2021

Endomorphin-1
Names
IUPAC name
L-Tyrosyl-L-prolyl-L-tryptophyl-L-phenylalaninamide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C34H38N6O5/c35-26(17-22-12-14-24(41)15-13-22)34(45)40-16-6-11-30(40)33(44)39-29(19-23-20-37-27-10-5-4-9-25(23)27)32(43)38-28(31(36)42)18-21-7-2-1-3-8-21/h1-5,7-10,12-15,20,26,28-30,37,41H,6,11,16-19,35H2,(H2,36,42)(H,38,43)(H,39,44)/t26-,28-,29-,30-/m0/s1
    Key: ZEXLJFNSKAHNFH-SYKYGTKKSA-N
  • InChI=1/C34H38N6O5/c35-26(17-22-12-14-24(41)15-13-22)34(45)40-16-6-11-30(40)33(44)39-29(19-23-20-37-27-10-5-4-9-25(23)27)32(43)38-28(31(36)42)18-21-7-2-1-3-8-21/h1-5,7-10,12-15,20,26,28-30,37,41H,6,11,16-19,35H2,(H2,36,42)(H,38,43)(H,39,44)/t26-,28-,29-,30-/m0/s1
    Key: ZEXLJFNSKAHNFH-SYKYGTKKBN
  • c1ccc(cc1)C[C@@H](C(=O)N)NC(=O)[C@H](Cc2c[nH]c3c2cccc3)NC(=O)[C@@H]4CCCN4C(=O)[C@H](Cc5ccc(cc5)O)N
Properties
C34H38N6O5
Molar mass 610.703 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Endomorphin-1 (EM-1) (amino acid sequence Tyr-Pro-Trp-Phe-NH2) is an endogenous opioid peptide and one of the two endomorphins.[1] It is a high affinity, highly selective agonist of the μ-opioid receptor, and along with endomorphin-2 (EM-2), has been proposed to be the actual endogenous ligand of the μ-receptor.[1][2][3][4] EM-1 produces analgesia in animals and is equipotent with morphine in this regard.[3] The gene encoding for EM-1 has not yet been identified,[4] and it has been suggested that endomorphins could be synthesized by an enzymatic, non-ribosomal mechanism.[5]

By combining N-terminal guadino modifications, a new class of endonmorphin-1 was synthesized, the range of their bioactivities were measured by radioligand binding assay in order to conclude its potency as an opioid.[6] Endomorphin-1 has a Hight affinity and specificity for opioid receptors for behavioral, physiological and pharmacological assays, it is also a potent analgesic agent which brings effects on cardiovascular, respiratory and gastrointestinal functions as well as in immune system responses..[7]This endogenous opioid peptide can help with neuropathic pain without having the common side effects many neuropathic drugs caused which produces constipation. To make this drug side effect-free, a modification at the N-terminus by 2-aminodecainoic acid is made which in term showed an improve in the drug's metabolic stability along with improving its membrane permeability, while holding its high receptor binding affinity, helping the drug act as a potent agonist[8]

See also

References

  1. ^ a b Bodnar RJ, Commons KG, Pfaff DW (3 April 2002). Central Neural States Relating Sex and Pain. JHU Press. pp. 67–. ISBN 978-0-8018-6827-6.
  2. ^ Krammer HJ, Singer MV (31 May 2000). Neurogastroenterology - From the Basics to the Clinics. Springer Science & Business Media. pp. 76–. ISBN 978-0-7923-8757-2.
  3. ^ a b Brain S, Moore PK (1999). Pain and Neurogenic Inflammation. Springer Science & Business Media. pp. 28–. ISBN 978-3-7643-5875-4.
  4. ^ a b Offermanns S, Rosenthal W (14 August 2008). Encyclopedia of Molecular Pharmacology. Springer Science & Business Media. pp. 904–. ISBN 978-3-540-38916-3.
  5. ^ Terskiy A, Wannemacher KM, Yadav PN, Tsai M, Tian B, Howells RD (November 2007). "Search of the human proteome for endomorphin-1 and endomorphin-2 precursor proteins". Life Sciences. 81 (23–24): 1593–601. doi:10.1016/j.lfs.2007.09.025. PMC 2144908. PMID 17964607.
  6. ^ "BrowZine". browzine.com. Retrieved 2021-11-02.
  7. ^ "Endomorphin 1 - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2021-11-13.
  8. ^ Varamini, Pegah; Mansfeld, Friederike M.; Blanchfield, Joanne T.; Wyse, Bruce D.; Smith, Maree T.; Toth, Istvan (2012-08-17). "Lipo-Endomorphin-1 Derivatives with Systemic Activity against Neuropathic Pain without Producing Constipation". PLoS ONE. 7 (8): e41909. doi:10.1371/journal.pone.0041909. ISSN 1932-6203. PMC 3422351. PMID 22912681.{{cite journal}}: CS1 maint: unflagged free DOI (link)
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