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the 13th letter of the Roman alphabet (同)m

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Michigan / Military Intelligence 陸軍情報部
Mach number / mark[s] / Monsieur

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/10 03:54:17」(JST)

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Melanocyte-inhibiting factor (also known as Pro-Leu-Gly-NH₂, Melanostatin, MSH release-inhibiting hormone or MIF-1) is an endogenous peptide fragment derived from cleavage of the hormone oxytocin, but having generally different actions in the body.^[1]^[2] MIF-1 produces multiple effects, both blocking the effects of opioid receptor activation,^[3]^[4]^[5]^[6]^[7]^[8] while at the same time acting as a positive allosteric modulator of the D₂ and D₄ dopamine receptor subtypes,^[9]^[10]^[11]^[12]^[13]^[14]^[15]^[16]^[17] as well as inhibiting release of other neuropeptides such as alpha-MSH,^[18]^[19]^[20] and potentiating melatonin activity.^[21]

This complex mix of actions produces a profile of antidepressant,^[22]^[23]^[24] nootropic,^[25]^[26]^[27]^[28] and anti-Parkinsonian effects when MIF-1 is administered,^[29]^[30]^[31] and it has been investigated for various medical uses. MIF-1 is unusually resistant to metabolism in the bloodstream,^[32] and crosses the blood–brain barrier easily,^[33]^[34] though it is poorly active orally and is usually injected. Several other closely related peptides with important actions in the body include Tyr-MIF-1 and endomorphin-1 and -2.^[35]^[36]^[37]^[38]^[39]

References

^ Celis ME, Taleisnik S, Walter R (July 1971). "Regulation of formation and proposed structure of the factor inhibiting the release of melanocyte-stimulating hormone". Proceedings of the National Academy of Sciences of the United States of America 68 (7): 1428–33. doi:10.1073/pnas.68.7.1428. PMC 389210. PMID 5283931.
^ Petersson M, Uvnäs-Moberg K (December 2004). "Prolyl-leucyl-glycinamide shares some effects with oxytocin but decreases oxytocin levels". Physiology & Behavior 83 (3): 475–81. doi:10.1016/j.physbeh.2004.08.034. PMID 15581670.
^ Chiu S, Mishra RK (January 1979). "Antagonism of morphine-induced catalepsy by L-prolyl-L-leucyl-glycinamide". European Journal of Pharmacology 53 (2): 119–25. doi:10.1016/0014-2999(79)90156-0. PMID 32058.
^ Dickinson SL, Slater P (1980). "Opiate receptor antagonism by L-prolyl-L-leucyl-glycinamide, MIF-I". Peptides 1 (4): 293–9. doi:10.1016/0196-9781(80)90006-6. PMID 6117839.
^ Contreras PC, Takemori AE (June 1984). "Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence". Life Sciences 34 (26): 2559–66. doi:10.1016/0024-3205(84)90041-9. PMID 6146083.
^ Ehrensing RH, Kastin AJ, Michell GF (December 1984). "Antagonism of morphine analgesia by prolyl-leucyl-glycinamide (MIF-1) in humans". Pharmacology, Biochemistry, and Behavior 21 (6): 975–8. doi:10.1016/S0091-3057(84)80083-0. PMID 6151672.
^ Galina ZH, Kastin AJ (December 1986). "Existence of antiopiate systems as illustrated by MIF-1/Tyr-MIF-1". Life Sciences 39 (23): 2153–9. doi:10.1016/0024-3205(86)90391-7. PMID 2878336.
^ Bocheva A, Dzambazova-Maximova E (November 2004). "Antiopioid properties of the TYR-MIF-1 family". Methods and Findings in Experimental and Clinical Pharmacology 26 (9): 673–7. doi:10.1358/mf.2004.26.9.872564. PMID 15632952.
^ Kostrzewa RM, Spirtes MA, Klara JW, Christensen CW, Kastin AJ, Joh TH (1976). "Effects of L-prolyl-L-leucyl-glycine amide (MIF-I) on dopaminergic neurons". Pharmacology, Biochemistry, and Behavior 5 (Suppl 1): 125–7. doi:10.1016/0091-3057(76)90340-3. PMID 13412.
^ Singhal RL, Rastogi RB (February 1982). "MIF-1: effects on norepinephrine, dopamine and serotonin metabolism in certain discrete brain regions". Pharmacology, Biochemistry, and Behavior 16 (2): 229–33. doi:10.1016/0091-3057(82)90153-8. PMID 6122214.
^ Chiu P, Rajakumar G, Chiu S, Johnson RL, Mishra RK (1985). "Mesolimbic and striatal dopamine receptor supersensitivity: prophylactic and reversal effects of L-prolyl-L-leucyl-glycinamide (PLG)". Peptides 6 (2): 179–83. doi:10.1016/0196-9781(85)90036-1. PMID 2863809.
^ Xu DL, Yu WC, Pan GB, Chen SD (1987). "Mechanism of action of L-leucyl-glycinamide and its effect on Parkinson's disease". Advances in Neurology 45: 587–90. PMID 2881450.
^ Verma V, Mann A, Costain W, Pontoriero G, Castellano JM, Skoblenick K, Gupta SK, Pristupa Z, Niznik HB, Johnson RL, Nair VD, Mishra RK (December 2005). "Modulation of agonist binding to human dopamine receptor subtypes by L-prolyl-L-leucyl-glycinamide and a peptidomimetic analog". The Journal of Pharmacology and Experimental Therapeutics 315 (3): 1228–36. doi:10.1124/jpet.105.091256. PMID 16126839.
^ Fisher A, Mann A, Verma V, Thomas N, Mishra RK, Johnson RL (January 2006). "Design and synthesis of photoaffinity-labeling ligands of the L-prolyl-L-leucylglycinamide binding site involved in the allosteric modulation of the dopamine receptor". Journal of Medicinal Chemistry 49 (1): 307–17. doi:10.1021/jm050644n. PMC 2533518. PMID 16392815.
^ Vartak AP, Skoblenick K, Thomas N, Mishra RK, Johnson RL (December 2007). "Allosteric modulation of the dopamine receptor by conformationally constrained type VI beta-turn peptidomimetics of Pro-Leu-Gly-NH2". Journal of Medicinal Chemistry 50 (26): 6725–9. doi:10.1021/jm070895r. PMC 2529021. PMID 18052024.
^ Raghavan B, Skoblenick KJ, Bhagwanth S, Argintaru N, Mishra RK, Johnson RL (April 2009). "Allosteric modulation of the dopamine D2 receptor by Pro-Leu-Gly-NH2 peptidomimetics constrained in either a polyproline II helix or a type II beta-turn conformation". Journal of Medicinal Chemistry 52 (7): 2043–51. doi:10.1021/jm801575w. PMC 2712934. PMID 19271750.
^ Mann A, Verma V, Basu D, Skoblenick KJ, Beyaert MG, Fisher A, Thomas N, Johnson RL, Mishra RK (September 2010). "Specific binding of photoaffinity-labeling peptidomimetics of Pro-Leu-Gly-NH2 to the dopamine D2L receptor: evidence for the allosteric modulation of the dopamine receptor". European Journal of Pharmacology 641 (2-3): 96–101. doi:10.1016/j.ejphar.2010.05.018. PMC 2907365. PMID 20639138.
^ Scimonelli T, Celis ME (1982). "Inhibition by L-prolyl-L-leucyl-glycinamide (PLG) of alpha-melanocyte stimulating hormone release from hypothalamic slices". Peptides 3 (6): 885–9. doi:10.1016/0196-9781(82)90055-9. PMID 6132363.
^ McCullen RK, Peiffer RL, Jennes L, Hernandez DE (1988). "Inhibition by MIF-I of alpha-MSH induced increase of intraocular pressure and miosis in rabbits". Neuropeptides 12 (4): 213–7. doi:10.1016/0143-4179(88)90057-1. PMID 2907121.
^ Caballero C, Celis ME (May 1993). "The effect of the blockade of alpha-melanocyte-stimulating hormone on LH release in the rat". The Journal of Endocrinology 137 (2): 197–202. doi:10.1677/joe.0.1370197. PMID 8100849.
^ Sandyk R (May 1990). "MIF-induced augmentation of melatonin functions: possible relevance to mechanisms of action of MIF-1 in movement disorders". The International Journal of Neuroscience 52 (1-2): 59–65. doi:10.3109/00207459008994244. PMID 1979968.
^ Pignatiello MF, Olson GA, Kastin AJ, Ehrensing RH, McLean JH, Olson RD (March 1989). "MIF-1 is active in a chronic stress animal model of depression". Pharmacology, Biochemistry, and Behavior 32 (3): 737–42. doi:10.1016/0091-3057(89)90027-0. PMID 2568001.
^ Kostowski W, Danysz W, Dyr W, Jankowska E, Krzaścik P, Pałejko W, Stefański R, Płaźnik A (1991). "MIF-1 potentiates the action of tricyclic antidepressants in an animal model of depression". Peptides 12 (5): 915–8. doi:10.1016/0196-9781(91)90037-p. PMID 1686934.
^ Ehrensing RH, Kastin AJ, Wurzlow GF, Michell GF, Mebane AH (August 1994). "Improvement in major depression after low subcutaneous doses of MIF-1". Journal of Affective Disorders 31 (4): 227–33. doi:10.1016/0165-0327(94)90098-1. PMID 7989637.
^ Stratton LO, Kastin AJ (1975). "Increased acquisition of a complex appetitive task after MSH and MIF". Pharmacology, Biochemistry, and Behavior 3 (5): 901–4. doi:10.1016/0091-3057(75)90124-0. PMID 1801.
^ Davis JL, Pico RM, Cherkin A (November 1982). "Memory enhancement induced in chicks by L-prolyl-L-leucyl-glycinamide". Pharmacology, Biochemistry, and Behavior 17 (5): 893–6. doi:10.1016/0091-3057(82)90467-1. PMID 6129646.
^ d'Amore A, Pieretti S, Palazzesi S, Pezzini G, Chiarotti F, Scorza T, Loizzo A (1990). "MIF-1 can accelerate neuromotor, EEG and behavioral development in mice". Peptides 11 (3): 527–32. doi:10.1016/0196-9781(90)90054-9. PMID 1974348.
^ Khan RS, Yu C, Kastin AJ, He Y, Ehrensing RH, Hsuchou H, Stone KP, Pan W (2010). "Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1)". International Journal of Peptides 2010. doi:10.1155/2010/537639. PMC 2915805. PMID 20721355.
^ Kastin AJ, Ehrensing RH, Olson RD, Coy DH (1980). "Neurological effects of MIF-1, MSH, and opiate peptides in clinical studies". International Journal of Neurology 14 (2-4): 205–9. PMID 6137465.
^ Katzenschlager R, Jackson MJ, Rose S, Stockwell K, Tayarani-Binazir KA, Zubair M, Smith LA, Jenner P, Lees AJ (April 2007). "Antiparkinsonian activity of L-propyl-L-leucyl-glycinamide or melanocyte-inhibiting factor in MPTP-treated common marmosets". Movement Disorders : Official Journal of the Movement Disorder Society 22 (5): 715–9. doi:10.1002/mds.21256. PMID 17373723.
^ Castellano JM, Batrynchuk J, Dolbeare K, Verma V, Mann A, Skoblenick KJ, Johnson RL, Mishra RK (October 2007). "MIF-1 and its peptidomimetic analogs attenuate haloperidol-induced vacuous chewing movements and modulate apomorphine-induced rotational behavior in 6-hydroxydopamine-lesioned rats". Peptides 28 (10): 2009–15. doi:10.1016/j.peptides.2007.07.026. PMID 17766011.
^ Kastin AJ, Hahn K, Erchegyi J, Zadina JE, Hackler L, Palmgren M, Banks WA (February 1994). "Differential metabolism of Tyr-MIF-1 and MIF-1 in rat and human plasma". Biochemical Pharmacology 47 (4): 699–709. doi:10.1016/0006-2952(94)90133-3. PMID 7907473.
^ Reed GW, Olson GA, Olson RD (1994). "The Tyr-MIF-1 family of peptides". Neuroscience and Biobehavioral Reviews 18 (4): 519–25. doi:10.1016/0149-7634(94)90005-1. PMID 7708364.
^ Banks WA, Kastin AJ (January 1994). "Opposite direction of transport across the blood–brain barrier for Tyr-MIF-1 and MIF-1: comparison with morphine". Peptides 15 (1): 23–9. doi:10.1016/0196-9781(94)90165-1. PMID 7912427.
^ Kastin AJ, Hahn K, Zadina JE, Banks WA, Hackler L (April 1995). "Melanocyte-stimulating hormone release-inhibiting factor-1 (MIF-1) can be formed from Tyr-MIF-1 in brain mitochondria but not in brain homogenate". Journal of Neurochemistry 64 (4): 1855–9. doi:10.1046/j.1471-4159.1995.64041855.x. PMID 7891114.
^ Zadina JE, Hackler L, Ge LJ, Kastin AJ (April 1997). "A potent and selective endogenous agonist for the mu-opiate receptor". Nature 386 (6624): 499–502. doi:10.1038/386499a0. PMID 9087409.
^ Pan W, Kastin AJ (December 2007). "From MIF-1 to endomorphin: the Tyr-MIF-1 family of peptides". Peptides 28 (12): 2411–34. doi:10.1016/j.peptides.2007.10.006. PMID 17988762.
^ Rotzinger S, Lovejoy DA, Tan LA (April 2010). "Behavioral effects of neuropeptides in rodent models of depression and anxiety". Peptides 31 (4): 736–56. doi:10.1016/j.peptides.2009.12.015. PMID 20026211.
^ Dyck B, Guest K, Sookram C, Basu D, Johnson R, Mishra RK (January 2011). "PAOPA, a potent analogue of Pro-Leu-glycinamide and allosteric modulator of the dopamine D2 receptor, prevents NMDA receptor antagonist (MK-801)-induced deficits in social interaction in the rat: implications for the treatment of negative symptoms in schizophrenia". Schizophrenia Research 125 (1): 88–92. doi:10.1016/j.schres.2010.09.025. PMC 3010311. PMID 21036015.

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English Journal

From blood to brain through BBB and astrocytic signaling.

Pan W1.
Peptides.Peptides.2015 Oct;72:121-7. doi: 10.1016/j.peptides.2015.06.003. Epub 2015 Jun 22.
In this Festschrift, I discuss the career and guiding principles to which Abba J. Kastin has adhered during the last 20 years we worked together. I briefly describe the history of our joint laboratory group, the context of studies of peptide permeation across the blood-brain barrier (BBB), and newer
PMID 26111490

An extraordinary relationship involving MIF-1 and other peptides.

Ehrensing RH1.
Peptides.Peptides.2015 Oct;72:73-4. doi: 10.1016/j.peptides.2015.03.013. Epub 2015 Mar 25.
In commemoration of Abba J. Kastin's exceptional service as the founding editor for the international journal Peptides, I review our collaborative work on how neuropeptides are involved in depression and other neuropsychiatric behavior. A special focus is on MIF-1 (prolyl-leucyl-glycinamide) that wa
PMID 25817911

Identification and biochemical characterization of macrophage migration inhibitory factor-2 (MIF-2) homologue of human lymphatic filarial parasite, Wuchereria bancrofti.

Chauhan N1, Sharma R1, Hoti SL2.
Acta tropica.Acta Trop.2015 Feb;142:71-8. doi: 10.1016/j.actatropica.2014.10.009. Epub 2014 Oct 22.
Homologues of human macrophage migration inhibitory factor (hMIF) have been reported from vertebrates, invertebrates and prokaryotes, as well as plants. Filarial parasites produce two homologues of hMIF viz., MIF-1 and MIF-2, which play important role in the host immune modulation. Earlier, we have
PMID 25446175

Japanese Journal

Tyr-Pro-Trp-Gly-NH_2(Tyr-W-MIF-1)analogであるTyr-D-Pro-Trp-Gly-NH_2の抗侵害作用におけるμオピオイド受容体の関与について

中山大助,渡邉廣行,藤村務 [他],櫻田忍
東北薬科大学研究誌 53, 71-76, 2006-12
… previously reported that Tyr-D-Pro-Trp-Gly-NH_2 (D-Pro^2-Tyr-W-MIF-1) given spinally produces clearly a dose-dependent attenuation of the antinociception induced by Tyr-W-MIF-1 without affecting endomorphins- and[D-Ala^2, NMePhe^4, Gly(ol)^5]-enkephalin (DAMGO)-induced antinociception, and D-Pro^2-Tyr-W-MIF-1 at any doses used (0.025-1.2 nmol) does not show any antinociception or hyperalgesic …
NAID 110006392398

Effects of Tyr-MIF-1 on Stress-Induced Analgesia and the Blockade of Development of Morphine Tolerance by Stress in Mice

Fukunaga Hiroko,Takahashi Masakatsu,Kaneko Hiroshi [他],YOSHIKAWA Masaaki
The Japanese journal of pharmacology 79(2), 231-235, 1999-02-01
… The role of Tyr-MIF-1 (Tyr-Pro-Leu-Gly-NH<SUB>2</SUB>) in biological responses to stress exposure was examined in mice. … Intraperitoneal or intracerebroventricular administration of Tyr-MIF-1 attenuated not only footshock (FS)- and forced swimming (SW)-stress-induced analgesia (SIA) but also socio-psychological (PSY)-SIA that, when using the communication box, is produced without any direct physical nociceptions. …
NAID 10008682473

Differential effects of endomorphin-1, endomorphin-2, and Tyr-W-MIF-1 on activation of G-proteins in SH-SY5Y human neuroblastoma membranes

HARRISON LM.
Peptides 19, 749-753, 1998
NAID 30007594178

「MSH放出抑制ホルモン」

Melanocyte-inhibiting factor
Systematic (IUPAC) name
	(S)-N-((S)-1-(2-amino-2-oxoethylamino)-4-methyl-1-oxopentan-2-yl)pyrrolidine-2-carboxamide
Clinical data
MedlinePlus	a605038
Routes of; administration	IV
Pharmacokinetic data
Bioavailability	100% (injected)
Metabolism	plasma protease enzymes
Excretion	N/A
Identifiers
CAS Registry Number	2002-44-0
PubChem	CID: 92910
ChemSpider	83871
UNII	3KY24B4Q62
Chemical data
Formula	C13H24N4O3
Molecular mass	284.355 g/mol
	SMILES NC(CNC([C@H](CC(C)C)NC([C@@H]1CCCN1)=O)=O)=O;
	InChI InChI=1S/C13H24N4O3/c1-8(2)6-10(12(19)16-7-11(14)18)17-13(20)9-4-3-5-15-9/h8-10,15H,3-7H2,1-2H3,(H2,14,18)(H,16,19)(H,17,20)/t9-,10-/m0/s1 ; Key:NOOJLZTTWSNHOX-UWVGGRQHSA-N ;
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