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Revision as of 08:57, 29 July 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox valida← Previous edit		Latest revision as of 01:19, 22 October 2024 edit undo76.174.0.57 (talk) Add pharmaceutical development.
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			{{short description|Neurotransmitter}}
	{{chembox
			{{Chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 428117777		| verifiedrevid = 442009113
	|ImageFile=leu-enkaphalin.png		| ImageFile= Leu-enkephalin Structure.svg
	|ImageSize=300px		| ImageSize=300px
	|IUPACName=(2''R'')-2-<nowiki>amino]acetyl]<br>amino]acetyl]amino]-3-phenylpropanoyl]<br>amino]-4-methylpentanoic acid		| IUPACName=(2''R'')-2-<nowiki>amino]acetyl]<wbr>amino]acetyl]amino]-3-phenylpropanoyl]<wbr>amino]-4-methylpentanoic acid
			| OtherNames= enkephalin; enkephalin;
	|OtherNames=
	|Section1= {{Chembox Identifiers		|Section1={{Chembox Identifiers
		⚫	| PubChem = 461776
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChEBI = 89656
⚫	| ChemSpiderID = 21106451
		⚫	| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫	| InChI1 = 1/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22+,23-/m0/s1
		⚫	| ChemSpiderID = 406229
⚫	| InChIKey1 = URLZCHNOLZSCCA-ZRBLBEILBT
			| SMILES = O=C(O)(NC(=O)(NC(=O)CNC(=O)CNC(=O)(N)Cc1ccc(O)cc1)Cc2ccccc2)CC(C)C
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22+,23-/m0/s1		| InChI = 1/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1
		⚫	| InChIKey = URLZCHNOLZSCCA-VABKMULXBR
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫	| StdInChIKey = URLZCHNOLZSCCA-ZRBLBEILSA-N
		⚫	| StdInChI = 1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1
		⚫	| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
		⚫	| StdInChIKey = URLZCHNOLZSCCA-VABKMULXSA-N
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=58822-25-6		| CASNo=58822-25-6
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem=10415290
			| UNII = RI01R707R6
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 8234
	| IUPHAR_ligand = 1613		| IUPHAR_ligand = 1613
	| SMILES = Oc2ccc(C(N)C(=O)NCC(=O)NCC(=O)N(Cc1ccccc1)C(=O)N(CC(C)C)C(O)=O)cc2
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
	| Formula= C<sub>28</sub>H<sub>37</sub>N<sub>5</sub>O<sub>7</sub>		| Formula= C<sub>28</sub>H<sub>37</sub>N<sub>5</sub>O<sub>7</sub>
			| MolarMass=555.62 g/mol<ref name="pmid24980599">{{cite journal | vauthors = Colaianni L, Kung SC, Taggart DK, Picca RA, Greaves J, Penner RM, Cioffi N | title = Reduction of spectral interferences using ultraclean gold nanowire arrays in the LDI-MS analysis of a model peptide | journal = Analytical and Bioanalytical Chemistry | volume = 406 | issue = 19 | pages = 4571–83 | date = July 2014 | pmid = 24980599 | doi = 10.1007/s00216-014-7876-7 | s2cid = 24046957 }}</ref>
	| MolarMass=555.62268 g/mol
	| Appearance=		| MeltingPt=
	| Density=		| BoilingPt=
	| MeltingPt=		| Solubility=
	| BoilingPt=
	| Solubility=
	}}		}}
	|Section3= {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
			'''Leu-enkephalin''' is an ] ] ] with the ] Tyr-Gly-Gly-Phe-Leu that is found naturally in the brains of many animals, including humans.<ref name="pmid1064883">{{cite journal | vauthors = Lazarus LH, Ling N, Guillemin R | title = beta-Lipotropin as a prohormone for the morphinomimetic peptides endorphins and enkephalins | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 73 | issue = 6 | pages = 2156–9 | date = June 1976 | pmid = 1064883 | pmc = 430469 | doi = 10.1073/pnas.73.6.2156| bibcode = 1976PNAS...73.2156L | doi-access = free }}</ref><ref name="pmid9142421">{{cite journal | vauthors = Hughes J, Kosterlitz HW, Smith TW | title = The distribution of methionine-enkephalin and leucine-enkephalin in the brain and peripheral tissues. 1977 | journal = British Journal of Pharmacology | volume = 120 | issue = 4 Suppl | pages = 428–36; discussion 426–7 | date = February 1997 | pmid = 9142421 | pmc = 3224324 | doi = 10.1111/j.1476-5381.1997.tb06829.x}}</ref> It is one of the two forms of ]; the other is ].<ref name="pmid1064883" /> The ] residue at position 1 is thought to be analogous to the 3-hydroxyl group on ].<ref name="pmid870028">{{cite journal | vauthors = Schiller PW, Yam CF, Lis M | title = Evidence for topographical analogy between methionine-enkephalin and morphine derivatives | journal = Biochemistry | volume = 16 | issue = 9 | pages = 1831–8 | date = May 1977 | pmid = 870028 | doi=10.1021/bi00628a011}}</ref> Leu-enkephalin has ]ic actions at both the ] and ]s, with significantly greater preference for the latter. It has little to no effect on the ].<ref name="pmid6086883">{{cite journal | vauthors = Porreca F, Mosberg HI, Hurst R, Hruby VJ, Burks TF | title = Roles of mu, delta and kappa opioid receptors in spinal and supraspinal mediation of gastrointestinal transit effects and hot-plate analgesia in the mouse | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 230 | issue = 2 | pages = 341–8 | date = August 1984 | pmid = 6086883 }}</ref><ref name="pmid8114680">{{cite journal | vauthors = Raynor K, Kong H, Chen Y, Yasuda K, Yu L, Bell GI, Reisine T | title = Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors | journal = Molecular Pharmacology | volume = 45 | issue = 2 | pages = 330–4 | date = February 1994 | pmid = 8114680 }}</ref>
	'''Leu-enkephalin''' is an ] ] ] found naturally in the brains of many animals, including humans. It is one of the two forms of ]; the other is ]. The ] residue at position 1 is thought to be analogous to the 3-hydroxyl group on ].
			A ] ] of leu-enkephalin (developmental code names NES-100, NM-0127, NM-127, PES-200; proposed brand name Envelta) is under development by Virpax Pharmaceuticals for the treatment of ] and ] (PTSD).<ref name="AdisInsight">{{cite web | title=Leucine enkephalin - Virpax Pharmaceuticals | website=AdisInsight | date=20 November 2023 | url=https://adisinsight.springer.com/drugs/800046784 | access-date=22 October 2024}}</ref> As of November 2023, it is up to the ] for these indications.<ref name="AdisInsight" />
	Leu-Enkephalin is a peptide whose sequence is: Tyr - Gly - Gly - Phe - Leu. It produces pharmacological effects at both the mu and delta opioid receptors, showing selectivity for the delta receptor.
			== See also ==
	It has a much higher selectivity for δ opioid receptors than μ receptors, and has little to no effect on κ opioid receptors.
			* ]
			== References ==
⚫	]
			{{Reflist|2}}
⚫	]
⚫	]
⚫	{{biochem-stub}}
	{{Neuropeptides}}		{{Neuropeptides}}
			{{Opioid receptor modulators}}
		⚫	]
		⚫	]
		⚫	]
		⚫	{{biochemistry-stub}}
	]