메뉴 건너뛰기




Volumn 6, Issue 1, 2013, Pages 54-69

A potent (R)-alpha-bis-lipoyl derivative containing 8-hydroxyquinoline scaffold: Synthesis and biological evaluation of its neuroprotective capabilities in SH-SY5Y human neuroblastoma cells

Author keywords

(R) alpha lipoic acid; 8 hydroxyquinoline; Antioxidants; Neurodegenerative diseases; Neuroprotective agent

Indexed keywords

1 [5 [1,2] DITHIOLAN 3 YL PEMTANOYL]PYRROLIDINE 2,5 DIONE; 5 HYDROXYMETHYL 8 HYDROXYQUINOLINE; 8 QUINOLINOL; ALPHA BIS LIPOYL DERIVATIVE; NEUROPROTECTIVE AGENT; REACTIVE OXYGEN METABOLITE; TETRAZOLIUM; THIOCTIC ACID; UNCLASSIFIED DRUG;

EID: 84872164177     PISSN: None     EISSN: 14248247     Source Type: Journal    
DOI: 10.3390/ph6010054     Document Type: Article
Times cited : (25)

References (39)
  • 1
    • 1842504355 scopus 로고    scopus 로고
    • Metal-catalyzed disruption of membrane protein and lipid signaling in the pathogenesis of neurodegenerative disorders
    • Mark, P.M. Metal-catalyzed disruption of membrane protein and lipid signaling in the pathogenesis of neurodegenerative disorders. Ann. N.Y. Acad. Sci. 2004, 1012, 37-50.
    • (2004) Ann. N.Y. Acad. Sci , vol.1012 , pp. 37-50
    • Mark, P.M.1
  • 2
    • 0142010013 scopus 로고    scopus 로고
    • General aspects of neurodegeneration
    • Jellinger, K.A. General aspects of neurodegeneration. J. Neural Transm. Suppl. 2003, 65, 101-144.
    • (2003) J. Neural Transm. Suppl , vol.65 , pp. 101-144
    • Jellinger, K.A.1
  • 3
    • 0027980511 scopus 로고
    • Quenching of the tyrosyl free radical of ribonucleotide reductase by nitric oxide
    • Lepoivre, M.; Flaman, J.M.; Bobè, P.; Lemaire, G.; Henry, Y. Quenching of the tyrosyl free radical of ribonucleotide reductase by nitric oxide. J. Bio. Chem. 1994, 269, 21891-21897.
    • (1994) J. Bio. Chem , vol.269 , pp. 21891-21897
    • Lepoivre, M.1    Flaman, J.M.2    Bobè, P.3    Lemaire, G.4    Henry, Y.5
  • 4
    • 0034035616 scopus 로고    scopus 로고
    • Metals and neuroscience
    • Bush, A.I. Metals and neuroscience. Curr. Opin. Chem. Biol. 2000, 4, 184-191.
    • (2000) Curr. Opin. Chem. Biol , vol.4 , pp. 184-191
    • Bush, A.I.1
  • 5
    • 41949095459 scopus 로고    scopus 로고
    • Metal based neurodegenerative diseases - From molecular mechanism to therapeutic strategies
    • Cricthton, R.R.; Dexter, D.T.; Ward, R.J. Metal based neurodegenerative diseases - From molecular mechanism to therapeutic strategies. Coordin. Chem. Rev. 2008, 252, 1189-1199.
    • (2008) Coordin. Chem. Rev , vol.252 , pp. 1189-1199
    • Cricthton, R.R.1    Dexter, D.T.2    Ward, R.J.3
  • 12
    • 67649868135 scopus 로고    scopus 로고
    • Cyclo(His-Pro) promotes cytoprotection by activating Nrf2-mediated up-regulation of antioxidant defence
    • Minelli, A.; Conte, C.; Grottelli, S.; Bellezza, I.; Cacciatore, I.; Bolaños, J. Cyclo(His-Pro) promotes cytoprotection by activating Nrf2-mediated up-regulation of antioxidant defence. J. Cell. Mol. Med. 2009, 13, 1149-1161.
    • (2009) J. Cell. Mol. Med , vol.13 , pp. 1149-1161
    • Minelli, A.1    Conte, C.2    Grottelli, S.3    Bellezza, I.4    Cacciatore, I.5    Bolaños, J.6
  • 13
    • 77953026478 scopus 로고    scopus 로고
    • N-acetyl- L-methionyl-L-Dopa- methyl ester as a dual acting drug that relives L-Dopa-induced oxidative toxicity
    • Minelli, A.; Conte, C.; Prudenzi, E.; Cacciatore, I.; Cornacchia, C.; Taha, E.; Pinnen, F. N-acetyl- L-methionyl-L-Dopa- methyl ester as a dual acting drug that relives L-Dopa-induced oxidative toxicity. Free Radical Bio. Med. 2010, 49, 31-39.
    • (2010) Free Radical Bio. Med , vol.49 , pp. 31-39
    • Minelli, A.1    Conte, C.2    Prudenzi, E.3    Cacciatore, I.4    Cornacchia, C.5    Taha, E.6    Pinnen, F.7
  • 14
    • 84867044861 scopus 로고    scopus 로고
    • Molecular mechanism underlying the cerebral effect of Gly-Pro-Glu tripeptide bound to L-Dopa in a Parkinson's animal model
    • Minelli, A.; Conte, C.; Cacciatore, I.; Cornacchia, C.; Pinnen, F. Molecular mechanism underlying the cerebral effect of Gly-Pro-Glu tripeptide bound to L-Dopa in a Parkinson's animal model. Amino Acids 2012, 43, 1359-1367.
    • (2012) Amino Acids , vol.43 , pp. 1359-1367
    • Minelli, A.1    Conte, C.2    Cacciatore, I.3    Cornacchia, C.4    Pinnen, F.5
  • 17
    • 79952217204 scopus 로고    scopus 로고
    • The concept of privileged structures in rational drug design: Focus on acridine and quinoline scaffolds in neurodegenerative and protozoan diseases
    • Bongarzone, S.; Bolognesi, M.L. The concept of privileged structures in rational drug design: Focus on acridine and quinoline scaffolds in neurodegenerative and protozoan diseases. Expert Opin. Drug Dis. 2011, 6, 251-268.
    • (2011) Expert Opin. Drug Dis , vol.6 , pp. 251-268
    • Bongarzone, S.1    Bolognesi, M.L.2
  • 18
    • 0023214741 scopus 로고
    • A quinoline fluorescence method for visualizing and assayingthe hystochemically and reactive zinc (bouton zinc) in the brain
    • Frederickson, C.J.; Kasarskis, E.J.; Ringo, D.; Frederickson, R.E. A quinoline fluorescence method for visualizing and assayingthe hystochemically and reactive zinc (bouton zinc) in the brain. J. Neurosci. Methods 1987, 20, 91-103.
    • (1987) J. Neurosci. Methods , vol.20 , pp. 91-103
    • Frederickson, C.J.1    Kasarskis, E.J.2    Ringo, D.3    Frederickson, R.E.4
  • 19
    • 0009827905 scopus 로고
    • Stability constants of iron (III)-8-hydroxyquinoline complexes
    • Turnquist, T.D.; Sandell, E.B. Stability constants of iron (III)-8-hydroxyquinoline complexes. Anal. Chim. Acta 1968, 42, 239-245.
    • (1968) Anal. Chim. Acta , vol.42 , pp. 239-245
    • Turnquist, T.D.1    Sandell, E.B.2
  • 20
    • 0032523110 scopus 로고    scopus 로고
    • Comparative radical scavenging ability of bidentate iron (III) chelators
    • Kayyali, R.; Pannala, A.S.; Khodr, H.; Hider, R.C. Comparative radical scavenging ability of bidentate iron (III) chelators. Biochem. Pharmacol. 1998, 55, 1327-1332.
    • (1998) Biochem. Pharmacol , vol.55 , pp. 1327-1332
    • Kayyali, R.1    Pannala, A.S.2    Khodr, H.3    Hider, R.C.4
  • 21
    • 0346849912 scopus 로고    scopus 로고
    • Neuroprotection by a novel brain permeable iron chelator, VK-28, against 6-hydroxydopamine lesion in rats
    • D. Kahana N. Kampel V. Warshawsky, A. Youdim, M.B. Neuroprotection by a novel brain permeable iron chelator, VK-28, against 6-hydroxydopamine lesion in rats. Neuropharmacology 2004, 46, 254-263.
    • (2004) Neuropharmacology , vol.46 , pp. 254-263
    • Kahana, D.N.1    Kampel, V.2    Warshawsky, A.3    Youdim, M.B.4
  • 22
    • 75649105423 scopus 로고    scopus 로고
    • A Prochelator activated by hydrogen peroxide prevents metal-induced amyloid beta aggregation
    • Dickens, M.G.; Franz, K.J. A Prochelator activated by hydrogen peroxide prevents metal-induced amyloid beta aggregation. Chem. Bio. Chem. 2010, 11, 59-62.
    • (2010) Chem. Bio. Chem , vol.11 , pp. 59-62
    • Dickens, M.G.1    Franz, K.J.2
  • 23
    • 2942750367 scopus 로고    scopus 로고
    • Clioquinol, a drug for Alzheimer's disease specifically interfering with brain metal metabolism: Structural characterization of its zinc(II) and copper(II) complexes
    • Di Vaira, M.; Bazzicalupi, C.; Orioli, P.; Messori, L.; Bruni, B.; Zatta, P. Clioquinol, a drug for Alzheimer's disease specifically interfering with brain metal metabolism: structural characterization of its zinc(II) and copper(II) complexes. Inorg. Chem. 2004, 43, 3795-3797.
    • (2004) Inorg. Chem , vol.43 , pp. 3795-3797
    • di Vaira, M.1    Bazzicalupi, C.2    Orioli, P.3    Messori, L.4    Bruni, B.5    Zatta, P.6
  • 25
    • 54549101998 scopus 로고    scopus 로고
    • Synthesis and characterization of 5-substituted 8-hydroxyquinoline derivatives and their metal complexes
    • Li, L.; Xu, B. Synthesis and characterization of 5-substituted 8-hydroxyquinoline derivatives and their metal complexes. Tetrahedron 2008, 64, 10986-10995.
    • (2008) Tetrahedron , vol.64 , pp. 10986-10995
    • Li, L.1    Xu, B.2
  • 26
    • 0001764778 scopus 로고
    • A novel activated ester in peptide syntheses
    • Nefkens, G.H. L.; Tesser, G.I. A novel activated ester in peptide syntheses. J. Am. Chem. Soc. 1961, 83, 1263-1263.
    • (1961) J. Am. Chem. Soc , vol.83 , pp. 1263
    • Nefkens, G.H.L.1    Tesser, G.I.2
  • 27
    • 77951240010 scopus 로고    scopus 로고
    • SH-SY5Y human neuroblastoma cells line: In vitro cell model of dopaminergic neurons in Parkinson's disease
    • Xie, H.; Hu, L.; Li, G. SH-SY5Y human neuroblastoma cells line: in vitro cell model of dopaminergic neurons in Parkinson's disease. Chin. Med. J. 2010, 123, 1086-1092.
    • (2010) Chin. Med. J , vol.123 , pp. 1086-1092
    • Xie, H.1    Hu, L.2    Li, G.3
  • 28
    • 0035078097 scopus 로고    scopus 로고
    • Resistance to induced apoptosis in the human neuroblastoma cell line SK-N-SH in relation to neuronal differentiation: Role of Bcl-2 protein family
    • Lombet, A.; Zujovic, V.; Kandouz, M.; Billardon, C.; Carvajal-Gonzalez, S.; Gompel, A.; Rostène, W. Resistance to induced apoptosis in the human neuroblastoma cell line SK-N-SH in relation to neuronal differentiation: Role of Bcl-2 protein family. Eur. J. Biochem. 2001, 268, 1352-1362.
    • (2001) Eur. J. Biochem , vol.268 , pp. 1352-1362
    • Lombet, A.1    Zujovic, V.2    Kandouz, M.3    Billardon, C.4    Carvajal-Gonzalez, S.5    Gompel, A.6    Rostène, W.7
  • 30
    • 38349168650 scopus 로고    scopus 로고
    • The attenuating effect of memantine on staurosporine-, salsolinol- and doxorubicin- induced apoptosis in human neuroblastoma SH-SY5Y cells
    • Jantas, D.; Pytel, M.; Mozrzymas, J.W.; Leskiewicz, M.; Regulska, M.; Antkiewicz-Michaluk, L.; Lason, W. The attenuating effect of memantine on staurosporine-, salsolinol- and doxorubicin- induced apoptosis in human neuroblastoma SH-SY5Y cells. Neurochem. Int. 2008, 52, 864-877.
    • (2008) Neurochem. Int , vol.52 , pp. 864-877
    • Jantas, D.1    Pytel, M.2    Mozrzymas, J.W.3    Leskiewicz, M.4    Regulska, M.5    Antkiewicz-Michaluk, L.6    Lason, W.7
  • 31
    • 0033500322 scopus 로고    scopus 로고
    • Brain derived neurotrophic factor protects human neuroblastoma cells from DNA damaging agents
    • Middlemas, D.S.; Kihl, B.K.; Moody, N.M. Brain derived neurotrophic factor protects human neuroblastoma cells from DNA damaging agents. J. Neuro-Oncol. 1999, 45, 27-36.
    • (1999) J. Neuro-Oncol , vol.45 , pp. 27-36
    • Middlemas, D.S.1    Kihl, B.K.2    Moody, N.M.3
  • 32
    • 0033230212 scopus 로고    scopus 로고
    • Differential effects of staurosporine and retinoic acid on the vulnerability of the SH-SY5Y neuroblastoma cells: Involvement of Bcl-2 and p53 proteins
    • Tieu, K.; Zuo, D.M.; Yu, P.H. Differential effects of staurosporine and retinoic acid on the vulnerability of the SH-SY5Y neuroblastoma cells: Involvement of Bcl-2 and p53 proteins. J. Neurosci. Res. 1999, 58, 426-435.
    • (1999) J. Neurosci. Res , vol.58 , pp. 426-435
    • Tieu, K.1    Zuo, D.M.2    Yu, P.H.3
  • 33
    • 0026554428 scopus 로고
    • Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress
    • LeBel, C.P.; Ischiropoulos, H.; Bondy, S.C. Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress. Chem. Res. Toxicol. 1992, 5, 227-231.
    • (1992) Chem. Res. Toxicol , vol.5 , pp. 227-231
    • Lebel, C.P.1    Ischiropoulos, H.2    Bondy, S.C.3
  • 36
    • 33644657387 scopus 로고    scopus 로고
    • Dopamine transporter-mediated cytotoxicity of 6-hydroxydopamine in vitro depends on expression of mutant α-synucleins related to Parkinson's disease
    • Lehmensiek, V.; Tan, E.M.; Liebau, S.; Lenk, T.; Zettlmeisl, H.; Schwarz, J.; Storch, A. Dopamine transporter-mediated cytotoxicity of 6-hydroxydopamine in vitro depends on expression of mutant α-synucleins related to Parkinson's disease. Neurochem. Int. 2006, 48, 329-340.
    • (2006) Neurochem. Int , vol.48 , pp. 329-340
    • Lehmensiek, V.1    Tan, E.M.2    Liebau, S.3    Lenk, T.4    Zettlmeisl, H.5    Schwarz, J.6    Storch, A.7
  • 37
    • 2442426175 scopus 로고    scopus 로고
    • Terminally differentiated SH-SY5Y cells provide a model system for studying neuroprotective effects of dopamine agonists
    • Presgraves, S.P.; Ahmed, T.; Borwege, S.; Joyce, J.N. Terminally differentiated SH-SY5Y cells provide a model system for studying neuroprotective effects of dopamine agonists. Neurotox. Res. 2003, 5, 579-598.
    • (2003) Neurotox. Res , vol.5 , pp. 579-598
    • Presgraves, S.P.1    Ahmed, T.2    Borwege, S.3    Joyce, J.N.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.