Effects of amide creatine derivatives in brain hippocampal slices, and their possible usefulness for curing creatine transporter deficiency

Neurochemical Research

Volumn 39, Issue 1, 2014, Pages 37-45

  Garbati, Patrizia ^a   Adriano, Enrico ^a   Salis, Annalisa ^a   Ravera, Silvia ^a   Damonte, Gianluca ^a   Millo, Enrico ^a   Balestrino, Maurizio ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

Creatine; Creatine derivatives; Creatine transporter deficiency; Glycine damage; Hippocampal slices; Neuroprotection

Indexed keywords

AMIDE; CREATINE; CREATINE ALANINE METHYL ESTER; CREATINE ETHYL AMIDE; CREATINE GLYCINE ETHYL ESTER; CREATINE KINASE; CREATINE PHOSPHATE; CREATINE THREONINE METHYL; NEUROPROTECTIVE AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN SLICE; CELL MEMBRANE; CONTROLLED STUDY; CREATINE TRANSPORTER DEFICIENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; EXCITATORY POSTSYNAPTIC POTENTIAL; HIPPOCAMPAL CA1 REGION; IN VITRO STUDY; LIPOPHILICITY; MALE; MOUSE; NEUROPROTECTION; NONHUMAN; PH; PRIORITY JOURNAL; STOICHIOMETRY; X CHROMOSOME LINKED DISORDER;

ANIMALS; BRAIN DISEASES, METABOLIC, INBORN; CREATINE; HIPPOCAMPUS; HUMANS; MALE; MEMBRANE TRANSPORT PROTEINS; MENTAL RETARDATION, X-LINKED; MICE; NEUROPROTECTIVE AGENTS; PHOSPHOCREATINE; PLASMA MEMBRANE NEUROTRANSMITTER TRANSPORT PROTEINS;

EID: 84892679913     PISSN: 03643190     EISSN: 15736903     Source Type: Journal    
DOI: 10.1007/s11064-013-1188-8     Document Type: Article

References (38)

1. Wyss M, Kaddurah-Daouk R (2000) Creatine and creatinine metabolism. Physiol Rev 80(3):1107-1213 (Pubitemid 30452013)
2. Greenhaff PL (2001) The creatine-phosphocreatine system: there's more than one song in its repertoire. J Physiol 537(3):657. doi: 10.1113/jphysiol. 2001.013478 (Pubitemid 34026597)
3. Balestrino M, Lensman M, Parodi M, Perasso L, Rebaudo R, Melani R, Polenov S, Cupello A (2002) Role of creatine and in neuronal protection from anoxic and ischemic damage. Amino Acids 23(1-3):221-229. doi: 10.1007/s00726-001-0133-3
4. Perasso L, Spallarossa P, Gandolfo C, Ruggeri P, Balestrino M (2013) Therapeutic use of creatine in brain or heart ischemia: available data and future perspectives. Med Res Rev 33(2):336-363. doi: 10.1002/med.20255
5. Klivenyi P, Ferrante RJ, Matthews RT, Bogdanov MB, Klein AM, Andreassen OA, Mueller G, Wermer M, Kaddurah-Daouk R, Beal MF (1999) Neuroprotective effects of creatine in a transgenic animal model of amyotrophic lateral sclerosis. Nat Med 5:347-350. doi: 10.1038/6568 (Pubitemid 29124375)
6. Adhihetty PJ, Beal MF (2008) Creatine and its potential therapeutic value for targeting cellular energy impairment in neurodegenerative diseases. Neuromol Med 10(4):275-290. doi: 10.1007/s12017-008-8053-y
7. Beal MF (2011) Neuroprotective effects of creatine. Amino Acids 40(5):1305-1313. doi: 10.1007/s00726-011-0851-0
8. Wang J, Xiao Y, Chen S, Zhong C, Luo M, Luo H (2012) Creatine for Parkinson's disease. Cochrane Database Syst Rev Issue 2. doi: 10.1002/14651858.CD009646
9. Perasso L, Cupello A, Lunardi GL, Principato C, Gandolfo C, Balestrino M (2003) Kinetics of creatine in blood and brain after intraperitoneal injection in the rat. Brain Res 974(1-2):37-42. doi: 10.1016/S0006-8993(03)02547-2 (Pubitemid 36549218)
10. Lunardi G, Parodi A, Perasso L, Pohvozcheva AV, Scarrone S, Adriano E, Florio T, Gandolfo C, Cupello A, Burov SV, Balestrino M (2006) The creatine transporter mediates the uptake of creatine by brain tissue, but not the uptake of two creatine-derived compounds. Neuroscience 142(4):991-997. doi: 10.1016/j.neuroscience.2006.06.058 (Pubitemid 44636048)
11. Snow RJ, Murphy RM (2001) Creatine and the creatine transporter: a review. Mol Cell Biochem 224(1-2):169-181. doi: 10.1023/A:1011908606819 (Pubitemid 32962663)
12. deGrauw TJ, Cecil KM, Byars AW, Salomons GS, Ball WS, Jakobs C (2003) The clinical syndrome of creatine transporter deficiency. Mol Cell Biochem 244(1-2):45-48. doi: 10.1023/A:1022487218904 (Pubitemid 36411051)
13. Salomons GS, van Dooren SJ, Verhoeven NM, Marsden D, Schwartz C, Cecil KM, DeGrauw TJ, Jakobs C (2003) X-linked creatine transporter defect: an overview. J Inherit Metab Dis 26(2-3):309-318 (Pubitemid 36889750)
14. Rosenberg EH, Almeida LS, Kleefstra T, deGrauw RS, Yntema HG, Bahi N, Moraine C, Ropers HH, Fryns JP, deGrauw TJ, Jakobs C, Salomons GS (2004) High prevalence of SLC6A8 deficiency in X-linked mental retardation. Am J Hum Genet 75(1):97-105. doi: 10.1086/422102 (Pubitemid 38801905)
15. Newmeyer A, Cecil KM, Schapiro M, Clark JF, Degrauw TJ (2005) Incidence of brain creatine transporter deficiency in males with developmental delay referred for brain magnetic resonance imaging. J Dev Behav Pediatr 26(4):276-282. doi: 10.1097/00004703-200508000-00003 (Pubitemid 41272187)
16. Clark AJ, Rosenberg EH, Almeida LS, Wood TC, Jakobs C, Stevenson RE, Schwartz CE, Salomons GS (2006) X-linked creatine transporter (SLC6A8) mutations in about 1% of males with mental retardation of unknown etiology. Hum Genet 119(6):604-610. doi: 10.1007/s00439-006-0162-9 (Pubitemid 43805836)
17. Lion-François L, Cheillan D, Pitelet G, Acquaviva-Bourdain C, Bussy G, Cotton F, Guibaud L, Gérard D, Rivier C, Vianey-Saban C, Jakobs C, Salomons GS, des Portes V (2006) High frequency of creatine deficiency syndromes in patients with unexplained mental retardation. Neurology 67(9):1713-1714. doi: 10.1212/01.wnl.0000239153.39710.81 (Pubitemid 44747959)
18. Arias A, Corbella M, Fons C, Sempere A, García-Villoria J, Ormazabal A, Poo P, Pineda M, Vilaseca MA, Campistol J, Briones P, Pàmpols T, Salomons GS, Ribes A, Artuch R (2007) Creatine transporter deficiency: prevalence among patients with mental retardation and pitfalls in metabolite screening. Clin Biochem 40(16-17):1328-1331. doi: 10.1016/j.clinbiochem.2007.07.010 (Pubitemid 47566420)
19. Burov S, Leko M, Dorosh M, Dobrodumov A, Veselkina O (2011) Creatinyl amino acids - new hybrid compounds with neuroprotective activity. J Pept Sci 17(9):620-626. doi: 10.1002/psc.1379
20. Perasso L, Lunardi G, Risso F, Pohvozcheva A, Leko M, Gandolfo C, Florio T, Cupello A, Burov S, Balestrino M (2008) Protective effects of some creatine derivatives in brain tissue anoxia. Neurochem Res 33:765-775. doi: 10.1007/s11064-007-9492-9 (Pubitemid 351423140)
21. Balestrino M, Rebaudo R, Lunardi G (1999) Exogenous creatine delays anoxic depolarization and protects from hypoxic damage: dose-effect relationship. Brain Res 816:124-130. doi: 10.1016/S0006-8993(98)01131-7 (Pubitemid 29225430)
22. Millo E, Balestrino M, Damonte G, Garbati P, Adriano E, Salis A (2012) Procedimento per sintetizzare derivati della creatina. Patent number TO2012 A001098
23. Garbati P, Salis A, Adriano E, Galatini A, Damonte G, Balestrino M, Millo E (2013) A new method to synthesize creatine derivatives. Amino Acids 44(6):1-13. doi: 10.1007/s00726-013-1525-x
24. Adriano E, Garbati P, Damonte G, Salis A, Armirotti A, Balestrino M (2011) Searching for a therapy of creatine transporter deficiency: some effects of creatine ethyl ester in brain slices in vitro. Neuroscience 199:386-393. doi: 10.1016/j.neuroscience.2011.09.018
25. Andersen P, Bliss TV, Skrede KK (1971) Unit analysis of hippocampal population spikes. Exp Brain Res 13:208-221. doi: 10.1007/BF00234086
26. Ballanyi K (1999) In vitro preparations. In: Windhorst U, Johansson H (eds) Modern techniques in neuroscience research. Springer, Heidelberg, pp 307-326
27. Whittingham TS, Lipton P (1981) Cerebral synaptic transmission during anoxia is protected by creatine. J Neurochem 37:1618-1621 (Pubitemid 12219012)
28. Kass IS, Lipton P (1989) Protection of hippocampal slices from young rats against anoxic transmission damage is due to better maintenance of ATP. J Physiol 413:1-11 (Pubitemid 19144864)
29. Schedel JM, Tanaka H, Kiyonaga A, Shindo M, Schutz Y (1999) Acute creatine ingestion in human: consequences on serum creatine and creatinine concentrations. Life Sci 65(23):2463-2470. doi: 10.1016/S0024-3205(99)00512-3
30. Dai W, Vinnakota S, Qian X, Kunze DL, Sarkar HK (1999) Molecular characterization of the human CRT-1 creatine transporter expressed in Xenopus oocytes. Arch Biochem Biophys 361:75-84. doi: 10.1006/abbi.1998.0959 (Pubitemid 29393716)
31. Smith PK, Krohon RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, Fujimoto EK, Goeke NM, Olson BJ, Klenk DC (1985) Measurement of protein using bicinchoninic acid. Anal Biochem 150(1):76-85 (Pubitemid 16258399)
32. Bergmeyer HU (1974) In: Bergmeyer HV (ed) Methods of enzymatic analysis, vol 1. Verlag Chemie/Academic Press, New York/London, pp 425-426
33. Song W, Chattipakorn SC, McMahon LL (2006) Glycine-gated chloride channels depress synaptic transmission in rat hippocampus. J Neurophysiol 95(4):2366-2379. doi: 10.1152/jn.00386.2005
34. Betz H (1992) Structure and function of inhibitory glycine receptors. Q Rev Biophys 25:381-394 (Pubitemid 23078701)
35. Kirsch J (2006) Glycinergic transmission. Cell Tissue Res 326(2):535-540. doi: 10.1007/s00441-006-0261-x (Pubitemid 44435824)
36. Barth A, Nguyen LB, Barth L, Newell DW (2004) Glycine-induced neurotoxicity in organotypic hippocampal slice cultures. Exp Brain Res 161(3):351-357. doi: 10.1007/s00221-004-2079-7
37. Saransaari P, Oja SS (2001) Characteristics of hippocampal glycine release in cell-damaging conditions in the adult and developing mouse. Neurochem Res 26(7):845-852. doi: 10.1023/A:1011624421505 (Pubitemid 32845978)
38. Prass K, Royl G, Lindauer U, Freyer D, Megow D, Dirnagl U, Stöckler-Ipsiroglu G, Wallimann T, Priller J (2007) Improved reperfusion and neuroprotection by creatine in a mouse model of stroke. J Cereb Blood Flow Metab 27(3):452-459. doi: 10.1038/sj.jcbfm.9600351