Melanocyte-inhibiting factor

Melanocyte-inhibiting factor
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
Pregnancy cat.  ?
Legal status  ?
Routes IV
Pharmacokinetic data
Bioavailability 100% (injected)
Metabolism plasma protease enzymes
Excretion N/A
Identifiers
CAS number 2002-44-0
ATC code  ?
PubChem CID 3896043
Synonyms L-propyl-L-leucyl-glycinamide
Chemical data
Formula C13H24N4O3 
Mol. mass 284.355 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

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]

See also

References

  1. ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=389210. 
  2. ^ 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. 
  3. ^ 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. PMID 32058. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ Galina ZH, Kastin AJ (December 1986). "Existence of antiopiate systems as illustrated by MIF-1/Tyr-MIF-1". Life Sciences 39 (23): 2153–9. PMID 2878336. 
  8. ^ 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. PMID 15632952. 
  9. ^ 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. PMID 13412. 
  10. ^ 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. 
  11. ^ 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. 
  12. ^ 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. 
  13. ^ 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. 
  14. ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2533518. 
  15. ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2529021. 
  16. ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2712934. 
  17. ^ 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. PMID 20639138. 
  18. ^ 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. 
  19. ^ 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. PMID 2907121. 
  20. ^ 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. PMID 8100849. 
  21. ^ 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. PMID 1979968. 
  22. ^ 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. 
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  24. ^ 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. 
  25. ^ 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. 
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  30. ^ 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. 
  31. ^ 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. 
  32. ^ 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. 
  33. ^ Reed GW, Olson GA, Olson RD (1994). "The Tyr-MIF-1 family of peptides". Neuroscience and Biobehavioral Reviews 18 (4): 519–25. PMID 7708364. 
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  35. ^ 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. PMID 7891114. 
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  39. ^ 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. PMID 21036015. 


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