메뉴 건너뛰기




Volumn 55, Issue 1, 2012, Pages 378-389

Chemical modification of the multitarget neuroprotective compound fisetin

Author keywords

[No Author keywords available]

Indexed keywords

3 (3,4 DIHYDROXYPHENYL) 1 (2 HYDROXY 4,5 DIMETHYLPHENYL)PROP 2 EN 1 ONE; 3 HYDROXY 2 [3 HYDROXY 4 (PYRROLIDIN 1 YL)PHENYL] 4H BENZO[H]CHROMEN 4 ONE; 4 [4 (CYCLOPENTYLOXY)QUINOLIN 2 YL)BENZENE 1,2 DIOL; FISETIN; FLAVONOL DERIVATIVE; GLUTATHIONE; NEUROPROTECTIVE AGENT; UNCLASSIFIED DRUG;

EID: 84855854014     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2012563     Document Type: Article
Times cited : (86)

References (44)
  • 3
    • 0032845121 scopus 로고    scopus 로고
    • Ischemic death in brain neurons
    • Lipton, P. Ischemic death in brain neurons Physiol. Rev. 1999, 79, 1431-1568
    • (1999) Physiol. Rev. , vol.79 , pp. 1431-1568
    • Lipton, P.1
  • 4
    • 79959315559 scopus 로고    scopus 로고
    • Central nervous system agents for ischemic stroke: Neuroprotection mechanisms
    • [Online early access]. DOI: 10.2174/187152411796011321, Apr 27
    • Pandya, R. S.; Mao, L.; Zhou, H.; Zhou, S.; Zeng, J.; Popp, A. J.; Wang, X. Central nervous system agents for ischemic stroke: neuroprotection mechanisms. Cent. Nerv. Syst. Agents Med. Chem. [Online early access]. DOI: 10.2174/187152411796011321, Apr 27, 2011.
    • (2011) Cent. Nerv. Syst. Agents Med. Chem.
    • Pandya, R.S.1    Mao, L.2    Zhou, H.3    Zhou, S.4    Zeng, J.5    Popp, A.J.6    Wang, X.7
  • 5
    • 33745955359 scopus 로고    scopus 로고
    • Therapeutic strategies for the treatment of stroke
    • Green, A. R.; Shuaib, A. Therapeutic strategies for the treatment of stroke Drug Discovery Today 2006, 11, 681-693
    • (2006) Drug Discovery Today , vol.11 , pp. 681-693
    • Green, A.R.1    Shuaib, A.2
  • 6
    • 71949125029 scopus 로고    scopus 로고
    • Modulation of multiple pathways involved in the maintenance of neuronal function during aging by fisetin
    • Maher, P. Modulation of multiple pathways involved in the maintenance of neuronal function during aging by fisetin Genes Nutr. 2009, Sep, 10
    • (2009) Genes Nutr. , pp. 10
    • Maher, P.1
  • 7
    • 34548855340 scopus 로고    scopus 로고
    • A novel approach for new neuroprotective compounds for the treatment of dtroke
    • Maher, P.; Salgado, K. F.; Zivin, J. A.; Lapchak, P. A. A novel approach for new neuroprotective compounds for the treatment of dtroke Brain Res. 2007, 1173, 117-125
    • (2007) Brain Res. , vol.1173 , pp. 117-125
    • Maher, P.1    Salgado, K.F.2    Zivin, J.A.3    Lapchak, P.A.4
  • 8
    • 0027133428 scopus 로고
    • 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors
    • Sogawa, S.; Nihro, Y.; Ueda, H.; Izumi, A.; Miki, T.; Matsumoto, H.; Satoh, T. 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors J. Med. Chem. 1993, 36, 3904-3909
    • (1993) J. Med. Chem. , vol.36 , pp. 3904-3909
    • Sogawa, S.1    Nihro, Y.2    Ueda, H.3    Izumi, A.4    Miki, T.5    Matsumoto, H.6    Satoh, T.7
  • 9
    • 1342302800 scopus 로고    scopus 로고
    • Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids
    • Chu, H. W.; Wu, H. T.; Lee, J. Y. Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids Tetrahedron 2004, 60, 2647-2655
    • (2004) Tetrahedron , vol.60 , pp. 2647-2655
    • Chu, H.W.1    Wu, H.T.2    Lee, J.Y.3
  • 11
    • 0022998223 scopus 로고
    • Syntheses of 5,6,7- and 5,7,8-trioxygenated 3′,4′- dihydroxyflavones having alkoxy groups and their inhibitory activities against arachidonate 5-lipoxygenase
    • Horie, T.; Tsukayama, M.; Kourai, H.; Yokoyama, C.; Furukawa, M.; Yoshimoto, T.; Yamamoto, S.; Watanabe-Kohno, S.; Ohataf, K. Syntheses of 5,6,7- and 5,7,8-trioxygenated 3′,4′-dihydroxyflavones having alkoxy groups and their inhibitory activities against arachidonate 5-lipoxygenase J. Med. Chem. 1986, 29, 2256-2262
    • (1986) J. Med. Chem. , vol.29 , pp. 2256-2262
    • Horie, T.1    Tsukayama, M.2    Kourai, H.3    Yokoyama, C.4    Furukawa, M.5    Yoshimoto, T.6    Yamamoto, S.7    Watanabe-Kohno, S.8    Ohataf, K.9
  • 12
    • 41149144696 scopus 로고    scopus 로고
    • Understanding the cardioprotective effects of flavonols: Discovery of relaxant flavonols without antioxidant activity
    • Qin, C. X.; Chen, X.; Hughes, R. A.; Williams, S. J.; Woodman, O. L. Understanding the cardioprotective effects of flavonols: discovery of relaxant flavonols without antioxidant activity J. Med. Chem. 2008, 51, 1874-1884
    • (2008) J. Med. Chem. , vol.51 , pp. 1874-1884
    • Qin, C.X.1    Chen, X.2    Hughes, R.A.3    Williams, S.J.4    Woodman, O.L.5
  • 13
    • 62749156417 scopus 로고    scopus 로고
    • Sulfuric acid promoted condensation cyclization of 2-(2-(trimethylsilyl) ethynyl) anilines with arylaldehydes in alcoholic solvents: An efficient one-pot synthesis of 4-alkoxy-2-arylquinolines
    • Wang, Y.; Peng, C.; Liu, L.; Zhao, J.; Su, L.; Zhu, Q. Sulfuric acid promoted condensation cyclization of 2-(2-(trimethylsilyl) ethynyl) anilines with arylaldehydes in alcoholic solvents: an efficient one-pot synthesis of 4-alkoxy-2-arylquinolines Tetrahedron Lett. 2009, 50, 2261-2265
    • (2009) Tetrahedron Lett. , vol.50 , pp. 2261-2265
    • Wang, Y.1    Peng, C.2    Liu, L.3    Zhao, J.4    Su, L.5    Zhu, Q.6
  • 14
    • 34347403252 scopus 로고    scopus 로고
    • Drug development for CNS disorders: Strategies for balancing risk and reducing attrition
    • Pangalos, M. N.; Schechter, L. E.; Hurko., O. Drug development for CNS disorders: strategies for balancing risk and reducing attrition Nat. Rev. Drug Discovery 2007, 6, 521-532
    • (2007) Nat. Rev. Drug Discovery , vol.6 , pp. 521-532
    • Pangalos, M.N.1    Schechter, L.E.2    Hurko, O.3
  • 15
    • 0037693727 scopus 로고    scopus 로고
    • Modulation of the Pasteur effect in retinal cells: Implications for understanding compensatory metabolic mechanisms
    • Winkler, B. S.; Sauer, M. W.; Starnes, C. A. Modulation of the Pasteur effect in retinal cells: implications for understanding compensatory metabolic mechanisms Exp. Eye Res. 2003, 76, 715-723
    • (2003) Exp. Eye Res. , vol.76 , pp. 715-723
    • Winkler, B.S.1    Sauer, M.W.2    Starnes, C.A.3
  • 16
    • 0031444147 scopus 로고    scopus 로고
    • Activation and inhibition of protein kinase C protect rat neuronal cultures against ischemia-reperfusion insult
    • Reshef, A.; Sperling, O.; Zoref-Shani, E. Activation and inhibition of protein kinase C protect rat neuronal cultures against ischemia-reperfusion insult Neurosci. Lett. 1997, 238, 37-40
    • (1997) Neurosci. Lett. , vol.238 , pp. 37-40
    • Reshef, A.1    Sperling, O.2    Zoref-Shani, E.3
  • 17
    • 0242499511 scopus 로고    scopus 로고
    • Reactive oxygen species play an important role in iodoacetate-induced neurotoxicity in primary rat neuronal cultures and in differentiated PC12 cells
    • Sperling, O.; Bromberg, Y.; Oelsner, H.; Zoref-Shani, E. Reactive oxygen species play an important role in iodoacetate-induced neurotoxicity in primary rat neuronal cultures and in differentiated PC12 cells Neursci. Lett. 2003, 351, 137-140
    • (2003) Neursci. Lett. , vol.351 , pp. 137-140
    • Sperling, O.1    Bromberg, Y.2    Oelsner, H.3    Zoref-Shani, E.4
  • 18
    • 0032964352 scopus 로고    scopus 로고
    • Distinct glycolysis inhibitors determine retinal cell sensitivity to glutamate-mediated injury
    • Rego, A. C.; Areias, F. M.; Santos, M. S.; Oliveira, C. R. Distinct glycolysis inhibitors determine retinal cell sensitivity to glutamate-mediated injury Neurochem. Res. 1999, 24, 351-358
    • (1999) Neurochem. Res. , vol.24 , pp. 351-358
    • Rego, A.C.1    Areias, F.M.2    Santos, M.S.3    Oliveira, C.R.4
  • 19
    • 0034457992 scopus 로고    scopus 로고
    • VIP-related protection against iodoacetate toxicity in pheochromocytoma (PC12) cells: A model for ischemic/hypoxic injury
    • Sigalov, E.; Fridkin, M.; Brenneman, D. E.; Gozes, I. VIP-related protection against iodoacetate toxicity in pheochromocytoma (PC12) cells: a model for ischemic/hypoxic injury J. Mol. Neurosci. 2000, 15, 147-154
    • (2000) J. Mol. Neurosci. , vol.15 , pp. 147-154
    • Sigalov, E.1    Fridkin, M.2    Brenneman, D.E.3    Gozes, I.4
  • 20
    • 0025185799 scopus 로고
    • A pharmacological model of ischemia in the hippocampal slice
    • Reiner, P. B.; Laycock, A. G.; Doll, C. J. A pharmacological model of ischemia in the hippocampal slice Neurosci. Lett. 1990, 119, 175-178
    • (1990) Neurosci. Lett. , vol.119 , pp. 175-178
    • Reiner, P.B.1    Laycock, A.G.2    Doll, C.J.3
  • 21
    • 67650745031 scopus 로고    scopus 로고
    • Potential neuroprotective drugs in cerebral ischemia: New saturated and polyunsaturated lipids coupled to hydrophilic moieties: Synthesis and biological activity
    • Biraboneye, A. C.; Madonna, S.; Laras, Y.; Maher, P.; Kraus, J. L. Potential neuroprotective drugs in cerebral ischemia: new saturated and polyunsaturated lipids coupled to hydrophilic moieties: synthesis and biological activity J. Med. Chem. 2009, 52, 4358-4369
    • (2009) J. Med. Chem. , vol.52 , pp. 4358-4369
    • Biraboneye, A.C.1    Madonna, S.2    Laras, Y.3    Maher, P.4    Kraus, J.L.5
  • 22
    • 74849115609 scopus 로고    scopus 로고
    • Neuroprotective effects of N -alkyl-1,2,4-oxadiazolidine-3,5-diones and their corresponding synthetic intermediates N -alkylhydroxylamines and N -1-alkyl-3-carbonyl-1-hydroxyureas against in vitro cerebral ischemia
    • Biraboneye, A. C.; Madonna, S.; Maher, P.; Kraus, J. L. Neuroprotective effects of N -alkyl-1,2,4-oxadiazolidine-3,5-diones and their corresponding synthetic intermediates N -alkylhydroxylamines and N -1-alkyl-3-carbonyl-1- hydroxyureas against in vitro cerebral ischemia Chem. Med. Chem. 2010, 5, 79-85
    • (2010) Chem. Med. Chem. , vol.5 , pp. 79-85
    • Biraboneye, A.C.1    Madonna, S.2    Maher, P.3    Kraus, J.L.4
  • 23
    • 0032845121 scopus 로고    scopus 로고
    • Ischemic death in brain neurons
    • Lipton, P. Ischemic death in brain neurons Physiol. Rev. 1999, 79, 1431-1568
    • (1999) Physiol. Rev. , vol.79 , pp. 1431-1568
    • Lipton, P.1
  • 24
    • 0025185799 scopus 로고
    • A pharmacological model of ischemia in the hippocampal slice
    • Reiner, P. B.; Laycock, A. G.; Doll, C. J. A pharmacological model of ischemia in the hippocampal slice Neurosci. Lett. 1990, 119, 175-178
    • (1990) Neurosci. Lett. , vol.119 , pp. 175-178
    • Reiner, P.B.1    Laycock, A.G.2    Doll, C.J.3
  • 25
    • 0030111288 scopus 로고    scopus 로고
    • The mechanism of cytoprotective action of lazaroids: I. Inhibition of reactive oxygen species formation and lethal cell injury during periods of energy depletion
    • Taylor, B. M.; Fleming, W. E.; Benjamin, C. W.; Wu, Y.; Mathews, R.; Sun, F. F. The mechanism of cytoprotective action of lazaroids: I. Inhibition of reactive oxygen species formation and lethal cell injury during periods of energy depletion J. Pharmacol. Exp. Ther. 1996, 276, 1224-1231
    • (1996) J. Pharmacol. Exp. Ther. , vol.276 , pp. 1224-1231
    • Taylor, B.M.1    Fleming, W.E.2    Benjamin, C.W.3    Wu, Y.4    Mathews, R.5    Sun, F.F.6
  • 26
    • 0037693727 scopus 로고    scopus 로고
    • Modulation of the Pasteur effect in retinal cells: Implications for understanding compensatory metabolic mechanisms
    • Winkler, B. S.; Sauer, M. W.; Starnes, C. A. Modulation of the Pasteur effect in retinal cells: implications for understanding compensatory metabolic mechanisms Exp. Eye Res. 2003, 76, 715-723
    • (2003) Exp. Eye Res. , vol.76 , pp. 715-723
    • Winkler, B.S.1    Sauer, M.W.2    Starnes, C.A.3
  • 27
    • 0242499511 scopus 로고    scopus 로고
    • Reactive oxygen species play an important role in iodoacetate-induced neurotoxicity in primary rat neuronal cultures and in differentiated PC12 cells
    • Sperling, O.; Bromberg, Y.; Oelsner, H.; Zoref-Shani, E. Reactive oxygen species play an important role in iodoacetate-induced neurotoxicity in primary rat neuronal cultures and in differentiated PC12 cells Neursci. Lett. 2003, 351, 137-140
    • (2003) Neursci. Lett. , vol.351 , pp. 137-140
    • Sperling, O.1    Bromberg, Y.2    Oelsner, H.3    Zoref-Shani, E.4
  • 28
    • 0242499511 scopus 로고    scopus 로고
    • Reactive oxygen species play an important role in iodoacetate-induced neurotoxicity in primary rat neuronal cultures and in differentiated PC12 cells
    • Sperling, O.; Bromberg, Y.; Oelsner, H.; Zoref-Shani, E. Reactive oxygen species play an important role in iodoacetate-induced neurotoxicity in primary rat neuronal cultures and in differentiated PC12 cells Neursci. Lett. 2003, 351, 137-140
    • (2003) Neursci. Lett. , vol.351 , pp. 137-140
    • Sperling, O.1    Bromberg, Y.2    Oelsner, H.3    Zoref-Shani, E.4
  • 30
    • 79959315559 scopus 로고    scopus 로고
    • Central nervous system agents for ischemic stroke: Neuroprotection mechanisms
    • [Online early access]. DOI: 10.2174/187152411796011321, Apr 27
    • Pandya, R. S.; Mao, L.; Zhou, H.; Zhou, S.; Zeng, J.; Popp, A. J.; Wang, X. Central nervous system agents for ischemic stroke: neuroprotection mechanisms. Cent. Nerv. Syst. Agents Med. Chem. [Online early access]. DOI: 10.2174/187152411796011321, Apr 27, 2011.
    • (2011) Cent. Nerv. Syst. Agents Med. Chem.
    • Pandya, R.S.1    Mao, L.2    Zhou, H.3    Zhou, S.4    Zeng, J.5    Popp, A.J.6    Wang, X.7
  • 31
    • 77949678956 scopus 로고    scopus 로고
    • Lactacidosis modulates glutathione metabolism and oxidative glutamate toxicity
    • Lewerenz, J.; Dargusch, R.; Maher, P. Lactacidosis modulates glutathione metabolism and oxidative glutamate toxicity J. Neurochem. 2010, 113, 502-504
    • (2010) J. Neurochem. , vol.113 , pp. 502-504
    • Lewerenz, J.1    Dargusch, R.2    Maher, P.3
  • 32
    • 0035756761 scopus 로고    scopus 로고
    • Oxytosis: A novel form of programmed cell death
    • Tan, S.; Schubert, D.; Maher, P. Oxytosis: a novel form of programmed cell death Curr. Top. Med. Chem. 2001, 1, 497-506
    • (2001) Curr. Top. Med. Chem. , vol.1 , pp. 497-506
    • Tan, S.1    Schubert, D.2    Maher, P.3
  • 33
    • 33749255399 scopus 로고    scopus 로고
    • A comparison of the neurotrophic activities of the flavonoid fisetin and some of its derivatives
    • Maher, P. A comparison of the neurotrophic activities of the flavonoid fisetin and some of its derivatives Free Radical Res. 2006, 40, 1105-1111
    • (2006) Free Radical Res. , vol.40 , pp. 1105-1111
    • Maher, P.1
  • 34
    • 39149120805 scopus 로고    scopus 로고
    • Suppressive effects of flavonoid fisetin on lipopolysaccharide-induced microglial activation and neurotoxicity
    • Zheng, L. T.; Ock, J.; Kwon, B. M.; Suk, K. Suppressive effects of flavonoid fisetin on lipopolysaccharide-induced microglial activation and neurotoxicity Int. Immunopharmacol. 2008, 8, 484-494
    • (2008) Int. Immunopharmacol. , vol.8 , pp. 484-494
    • Zheng, L.T.1    Ock, J.2    Kwon, B.M.3    Suk, K.4
  • 35
    • 4444360215 scopus 로고    scopus 로고
    • Induction of PC12 cell differentiation by flavonoids is dependent upon extracellular signal-regulated kinase activation
    • Sagara, Y.; Vanhnasy, J.; Maher, P. Induction of PC12 cell differentiation by flavonoids is dependent upon extracellular signal-regulated kinase activation J. Neurochem. 2004, 90, 1144-1155
    • (2004) J. Neurochem. , vol.90 , pp. 1144-1155
    • Sagara, Y.1    Vanhnasy, J.2    Maher, P.3
  • 36
    • 33845937770 scopus 로고    scopus 로고
    • Structure-brain exposure relationships
    • Hitchcock, S. A.; Pennington, L. D. Structure-brain exposure relationships J. Med. Chem. 2006, 49, 7559-7583
    • (2006) J. Med. Chem. , vol.49 , pp. 7559-7583
    • Hitchcock, S.A.1    Pennington, L.D.2
  • 37
    • 79952840767 scopus 로고    scopus 로고
    • Control of redox state and redox signaling by neural antioxidant systems
    • Lewerenz, J.; Maher, P. Control of redox state and redox signaling by neural antioxidant systems Antioxid. Redox Signaling 2011, 14, 1449-1465
    • (2011) Antioxid. Redox Signaling , vol.14 , pp. 1449-1465
    • Lewerenz, J.1    Maher, P.2
  • 38
    • 59849123367 scopus 로고    scopus 로고
    • Metabolism and pharmacokinetics of 3,3′,4′,7- tetrahydroxyflavone (fisetin), 5-hydroxyflavone, and 7-hydroxyflavone and antihemolysis effects of fisetin and its serum metabolites
    • Shia, C. S.; Tsai, S, Y.; Kuo, S. C.; Hou, Y, C.; Chao, P. D. Metabolism and pharmacokinetics of 3,3′,4′,7-tetrahydroxyflavone (fisetin), 5-hydroxyflavone, and 7-hydroxyflavone and antihemolysis effects of fisetin and its serum metabolites J. Agric. Food Chem. 2009, 57, 83-89
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 83-89
    • Shia, C.S.1    Tsai, S.Y.2    Kuo, S.C.3    Hou, Y.C.4    Chao, P.D.5
  • 39
    • 78650525484 scopus 로고    scopus 로고
    • ERK activation by the polyphenols fisetin and resveratrol provides neuroprotection in multiple models of Huntingtons disease
    • Maher, P.; Dargusch, R.; Bodai, L.; Gerard, P. E.; Purcell, J. M.; Marsh, J. L. ERK activation by the polyphenols fisetin and resveratrol provides neuroprotection in multiple models of Huntingtons disease Hum. Mol. Genet. 2011, 20, 261-270
    • (2011) Hum. Mol. Genet. , vol.20 , pp. 261-270
    • Maher, P.1    Dargusch, R.2    Bodai, L.3    Gerard, P.E.4    Purcell, J.M.5    Marsh, J.L.6
  • 40
    • 79959596092 scopus 로고    scopus 로고
    • Fisetin lowers methylglyoxal dependent protein glycation and limits the complications of diabetes
    • Maher, P.; Dargusch, R.; Ehren, J. L.; Okada, S.; Sharma, K.; Schubert, D. Fisetin lowers methylglyoxal dependent protein glycation and limits the complications of diabetes PLoS One 2011, 6, e21226
    • (2011) PLoS One , vol.6 , pp. 21226
    • Maher, P.1    Dargusch, R.2    Ehren, J.L.3    Okada, S.4    Sharma, K.5    Schubert, D.6
  • 41
    • 33749255399 scopus 로고    scopus 로고
    • A comparison of the neurotrophic activities of the flavonoid fisetin and some of its derivatives
    • Maher, P. A comparison of the neurotrophic activities of the flavonoid fisetin and some of its derivatives Free Radical Res. 2006, 40, 1105-1111
    • (2006) Free Radical Res. , vol.40 , pp. 1105-1111
    • Maher, P.1
  • 42
    • 0024380087 scopus 로고
    • Rapid detection of octamer binding proteins with "mini- extracts", prepared from a small number of cells
    • Schreiber, E.; Matthias, P.; Muller, M. M.; Schaffner, W. Rapid detection of octamer binding proteins with "mini-extracts", prepared from a small number of cells Nucleic Acids Res. 1989, 17, 6419
    • (1989) Nucleic Acids Res. , vol.17 , pp. 6419
    • Schreiber, E.1    Matthias, P.2    Muller, M.M.3    Schaffner, W.4
  • 43
    • 25844495011 scopus 로고    scopus 로고
    • Medicinal chemical properties of successful central nervous system drugs
    • Pajouhesh, H.; Lenz, G. R. Medicinal chemical properties of successful central nervous system drugs NeuroRx 2005, 2, 541-553
    • (2005) NeuroRx , vol.2 , pp. 541-553
    • Pajouhesh, H.1    Lenz, G.R.2
  • 44
    • 0022523165 scopus 로고
    • A common structural model for central nervous system drugs and their receptors
    • Lloyed, E. J.; Andrews, P. R. A common structural model for central nervous system drugs and their receptors J. Med. Chem. 1986, 29, 453-462
    • (1986) J. Med. Chem. , vol.29 , pp. 453-462
    • Lloyed, E.J.1    Andrews, P.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.