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CCK-4

propanoic acid

CCK-4
(IUPAC) ime
(3S)-3-[(2S)-2-amino-3-phenylpropanamido]-3[(1S)-1[(1S)-1-carboxy -2-(indol-3-yl)ethyl]carbamoyl3-(methylsulfanyl)propyl]carbamoyl
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| image = Cck-4.svg | width = 240 | image2 = | width2 = | CAS_number_Ref =  DaY | CAS_number = 1947-37-1 | ATC_prefix = | ATC_suffix = | PubChem = | IUPHAR_ligand = | ChEMBL_Ref = | ChEMBL = | DrugBank_Ref = | DrugBank = | C=29|H=35|N=5|O=7|S=1 | molecular_weight = 597.681 g/mol | smiles = c3cccc1c3ncc1CC(C(=O)O)NC(=O)C(CCSC)NC(=O)C(CC(O)=O)NC(=O)C(N)Cc2ccccc2 | InChI = | InChIKey = | StdInChI_Ref =  DaY | StdInChI = 1S/C29H35N5O7S/c1-42-12-11-22(27(38)34-24(29(40)41)14-18-16-31-21-10-6-5-9-19(18)21)32-28(39)23(15-25(35)36)33-26(37)20(30)13-17-7-3-2-4-8-17/h2-10,16,20,22-24,31H,11-15,30H2,1H3,(H,32,39)(H,33,37)(H,34,38)(H,35,36)(H,40,41)/t20-,22-,23-,24-/m0/s1 | StdInChIKey_Ref =  DaY | StdInChIKey = LQHGVXZMXPZBOC-UHFFFAOYSA-N | bioavailability = 100% | protein_bound = | metabolism = proteaze plazme | elimination_half-life = 13 minuta | excretion = N/A | pregnancy_AU = | pregnancy_US = | pregnancy_category= | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = IV }}

CCK-4 (holecistokininski tetrapeptid, Trp-Met-Asp-Phe-NH2; ili PTK7) je peptidni fragment izveden iz većeg peptidnog hormona holecistokinina. Za razliku od holecistokina koji ima niz uloga u gastrointestinalnom sistemu kao i u centralnom nervnom sistemu, CCK-4 deluje prvenstveno u mozgu kao stimulator anksioznosti. On pokazuje slabe GI efekte, za razliku od CCK-8 ili polipeptida pune dužine, CCK-58.

CCK-4 proizvodi jake simptome anksioznosti u malim dozama, kao što je 50 μg,[1] i često se koristi u naučnim istraživanjima za indukovanje paničnih napada s ciljem testiranja novih anksiolitika.[2][3][4][5] Pošto je on peptid, CCK-4 mora biti administriran putem injekcije. U telu se brzo razlaže, tako da ima kratkotrajno dejstvo.[6] Brojni sintetički analozi sa modifikovanim osobinama su poznati.[7][8][9][10][11][12][13][14][15][16][17]

Vidi još uredi

Reference uredi

  1. ↑ Daniela Eser et al. (2005). „Panic Induction with Cholecystokinin-Tetrapeptide (CCK-4) Increases Plasma Concentrations of the Neuroactive Steroid 3α, 5α Tetrahydrodeoxycorticosterone (3α, 5α-THDOC) in Healthy Volunteers”. Neuropsychopharmacology 30 (1): 192–195. DOI:10.1038/sj.npp.1300572. PMID 15467707. 
  2. ↑ Bradwejn J. (July 1993). „Neurobiological investigations into the role of cholecystokinin in panic disorder”. Journal of Psychiatry and Neuroscience 18 (4): 178–188. PMC 1188527. PMID 8104032. 
  3. ↑ Schunck T, Erb G, Mathis A, Gilles C, Namer IJ, Hode Y, Demaziere A, Luthringer R, Macher JP. (July 2006). „Functional magnetic resonance imaging characterization of CCK-4-induced panic attack and subsequent anticipatory anxiety”. NeuroImage 31 (3): 1197–1208. DOI:10.1016/j.neuroimage.2006.01.035. PMID 16600640. 
  4. ↑ Eser D, Schüle C, Baghai T, Floesser A, Krebs-Brown A, Enunwa M, de la Motte S, Engel R, Kucher K, Rupprecht R. (July 2007). „Evaluation of the CCK-4 model as a challenge paradigm in a population of healthy volunteers within a proof-of-concept study”. Psychopharmacology 192 (4): 479–487. DOI:10.1007/s00213-007-0738-7. PMID 17318504. 
  5. ↑ Eser D, Leicht G, Lutz J, Wenninger S, Kirsch V, Schüle C, Karch S, Baghai T, Pogarell O, Born C, Rupprecht R, Mulert C. (December 2007). „Functional neuroanatomy of CCK-4-induced panic attacks in healthy volunteers”. Human Brain Mapping 30 (2): 511–22. DOI:10.1002/hbm.20522. PMID 18095276. 
  6. ↑ Koulischer D, Moroder L, Deschodt-Lanckman M (August 1982). „Degradation of cholecystokinin octapeptide, related fragments and analogs by human and rat plasma in vitro”. Regulatory Peptides 4 (3): 127–139. DOI:10.1016/0167-0115(82)90080-5. PMID 6291099. 
  7. ↑ Blommaert AG, Dhôtel H, Ducos B, Durieux C, Goudreau N, Bado A, Garbay C, Roques BP (February 1997). „Structure-based design of new constrained cyclic agonists of the cholecystokinin CCK-B receptor”. Journal of Medicinal Chemistry 40 (5): 647–58. DOI:10.1021/jm9603072. PMID 9057851. 
  8. ↑ Bellier B, Million ME, DaNascimento S, Meudal H, Kellou S, Maigret B, Garbay C (October 2000). „Replacement of glycine with dicarbonyl and related moieties in analogues of the C-terminal pentapeptide of cholecystokinin: CCK(2) agonists displaying a novel binding mode”. Journal of Medicinal Chemistry 43 (20): 3614–23. DOI:10.1021/jm0000416. PMID 11020275. 
  9. ↑ Léna I, Dh tel H, Garbay C, Daugé V (January 2001). „Involvement of D2 dopamine receptors in the opposing effects of two CCK-B agonists in a spatial recognition memory task: role of the anterior nucleus accumbens”. Psychopharmacology 153 (2): 170–9. DOI:10.1007/s002130000517. PMID 11205416. 
  10. ↑ Bellier B, Garbay C (2003). „How a single inversion of configuration leads to a reversal of the binding mode: proposal of a novel arrangement of CCK2 ligands in their receptor, and contribution to the development of peptidomimetic or non-peptide CCK2 ligands”. European Journal of Medicinal Chemistry 38 (7-8): 671–86. DOI:10.1016/S0223-5234(03)00112-0. PMID 12932898. 
  11. ↑ Bellier B, Crété D, Million ME, Beslot F, Bado A, Garbay C, Daugé V (November 2004). „New CCK2 agonists confirming the heterogeneity of CCK2 receptors: characterisation of BBL454”. Naunyn-Schmiedeberg's Archives of Pharmacology 370 (5): 404–13. DOI:10.1007/s00210-004-0969-7. PMID 15480577. 
  12. ↑ Proskuriakova TV, Bespalova ZhD, Pal'keeva ME, Petrichenko OB, Pankratova NV, Shokhonova VA, Anokhina IP (2005). „[Biological activity of cholecystokinin-(30-33) tetrapeptide analogs]” (Russian). Bioorganicheskaia Khimiia 31 (2): 130–9. PMID 15889786. 
  13. ↑ Anokhina IP, Proskuriakova TV, Bespalova ZhD, Pal'keeva ME, Shokhonova VA, Petrichenko OB (2006). „[Effect of a cholecystokinin tetrapeptide analogue on opioid reception under acute and chronic morphine administration]” (Russian). Bioorganicheskaia Khimiia 32 (3): 276–83. PMID 16808170. 
  14. ↑ Agnes RS, Lee YS, Davis P, Ma SW, Badghisi H, Porreca F, Lai J, Hruby VJ (May 2006). „Structure-activity relationships of bifunctional peptides based on overlapping pharmacophores at opioid and cholecystokinin receptors”. Journal of Medicinal Chemistry 49 (10): 2868–75. DOI:10.1021/jm050921q. PMC 1484468. PMID 16686530. 
  15. ↑ Noble F (2007). „Pharmacology of CCKRs and SAR studies of peptidic analog ligands”. Current Topics in Medicinal Chemistry 7 (12): 1173–9. DOI:10.2174/156802607780960447. PMID 17584139. 
  16. ↑ García-López MT, González-Muñiz R, Martín-Martínez M, Herranz R (2007). „Strategies for design of non peptide CCK1R agonist/antagonist ligands”. Current Topics in Medicinal Chemistry 7 (12): 1180–94. DOI:10.2174/156802607780960537. PMID 17584140. 
  17. ↑ Kalindjian SB, McDonald IM (2007). „Strategies for the design of non-peptide CCK2 receptor agonist and antagonist ligand”. Current Topics in Medicinal Chemistry 7 (12): 1195–204. DOI:10.2174/156802607780960500. PMID 17584141. 

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