Research progress in mitochondria-targeted antioxidants

FAN Pengcheng; GE Yue; Jiang Wei; JING Linlin; MA Huiping; JIA Zhengping

doi:10.3969/j.issn.1006-0111.2015.01.001

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2015 > 33(1): 1-4,8

FAN Pengcheng, GE Yue, Jiang Wei, JING Linlin, MA Huiping, JIA Zhengping. Research progress in mitochondria-targeted antioxidants[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(1): 1-4,8. doi: 10.3969/j.issn.1006-0111.2015.01.001

Citation:

FAN Pengcheng, GE Yue, Jiang Wei, JING Linlin, MA Huiping, JIA Zhengping. Research progress in mitochondria-targeted antioxidants[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(1): 1-4,8. doi: 10.3969/j.issn.1006-0111.2015.01.001

Research progress in mitochondria-targeted antioxidants

doi: 10.3969/j.issn.1006-0111.2015.01.001

1.
Department of Pharmacy, Lanzhou General Hospital of Lanzhou Region, Lanzhou 730050, China;Key Laboratory of Entire Army Plateau Environment Injury Prevention Research, Lanzhou 730050, China
2.
Meternal and Child Health Care of Baota District, Yan'an 716000, China

Received Date: 2013-11-28
Rev Recd Date: 2014-03-26

Abstract

Mitochondria are the main places of cellular respiration as well as the citric acid cycle and oxidative phosphorylation.It plays an important role in controlling the life and death of cells.Mitochondrial dysfunction leads to a series of human diseases such as ischemia-reperfusion injury,sepsis and diabetes.Mitochondrial become an attractive target for drug transporters strategy and therapeutic targets for neurodegeneration.Although the molecular mechanisms responsible for mitochondria mediated disease processes are not fully elucidated yet,the oxidative stress appears to be critical.Accordingly,strategies are being developed for the targeted delivery of antioxidants to mitochondria.The prospect of development of mitochondrial targeted drugs with anti-oxidative stress protection is tempting.Mitochondrial targeting antioxidants were the antioxidant drugs which took mitochondria as the target site.In this review,weintroduced the conception and classification of mitochondrial targeted antioxidants and the research progress of disease treatment by mitochondrial targeted antioxidants.
- mitochondria-targeted,
- antioxidant,
- reactive oxygen species,
- oxidative stress

References

[1]	Jordan J,de Groot PW,Galindo MF.Mitochondria:the headquarters in ischemia-induced neuronal death[J].Cent Nerv Syst Agents Med Chem,2011,11:98-106.
[2]	Finkel T.Radical medicine:treating ageing to cure disease[J].Nat Rev Mol Cell Biol,2005,6:971-976.
[3]	Fantinelli JC,Perez Nunez IA,Gonzalez Arbelaez LF,et al.Participation of mitochondrial permeability transition pore in the effects of ischemic preconditioning in hypertrophied hearts:role of NO and mitoK(ATP)[J].Int J Cardiol,2011,166:173-180.
[4]	Larsen GA,Skjellegrind HK,Berg-Johnsen J,et al.Depolarization of mitochondria in isolated CA1 neurons during hypoxia,glucose deprivation and glutamate excitotoxicity[J].Brain Res,2006,1077:153-160.
[5]	Lee DR,Helps SC,Macardle PJ,et al.Alterations in membrane potential in mitochondria isolated from brain subregions during focal cerebral ischemia and early reperfusion:evaluation using flow cytometry[J].Neurochem Res,2009,34:1857-1866.
[6]	Dave KR,Bhattacharya SK,Saul I,et al.Activation of protein kinase C delta following cerebral ischemia leads to release of cytochrome C from the mitochondria via bad pathway[J].PLoS One,2011,6(7):e22057.
[7]	Moreira PI,Zhu X,Wang X,et al.Mitochondria:a therapeutic target in neurodegeneration[J].Biochim Biophys Acta,2010,1802:212-220.
[8]	Diogo CV,Grattagliano I,Oliveira PJ,et al.Re-wiring the circuit:mitochondria as a pharmacological target in liver disease[J].Curr Med Chem,2011,18:5448-5465.
[9]	Walters AM,Porter GAJ,Brookes PS.Mitochondria as a drug target in ischemic heart disease and cardiomyopathy[J].Circ Res,2012,111:1222-1236.
[10]	Reale M,Pesce M,Priyadarshini M,et al.Mitochondria as an easy target to oxidative stress events in Parkinson's disease[J].CNS Neurol Disord Drug Targets,2012,11:430-438.
[11]	Gruber J,Fong S,Chen CB,et al.Mitochondria-targeted antioxidants and metabolic modulators as pharmacological interventions to slow ageing[J].Biotechnol Adv,2012,31:563-592.
[12]	Mukhopadhyay P,Horvath B,Zsengeller Z,et al.Mitochondrial reactive oxygen species generation triggers inflammatory response and tissue injury associated with hepatic ischemia-reperfusion:therapeutic potential of mitochondrially targeted antioxidants[J].Free Radic Biol Med,2012,53:1123-1138.
[13]	Telford JE,Kilbride SM,Davey GP.Decylubiquinone increases mitochondrial function in synaptosomes[J].J Biol Chem,2010,285:8639-8645.
[14]	Coulter CV,Kelso GF,Lin TK,et al.Mitochondrially targeted antioxidants and thiol reagents[J].Free Radic Biol Med,2000,28:1547-1554.
[15]	Modica-Napolitano JS,Aprille JR.Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells[J].Adv Drug Deliv Rev,2001,49:63-70.
[16]	Sheu SS,Nauduri D,Anders MW.Targeting antioxidants to mitochondria:a new therapeutic direction[J].Biochim Biophys Acta,2006,1762:256-265.
[17]	Skulachev VP.Mitochondria-targeted antioxidants as promising drugs for treatment of age-related brain diseases[J].J Alzheimers Dis,2012,28:283-289.
[18]	Smith RA,Porteous CM,Coulter CV,et al.Selective targeting of an antioxidant to mitochondria[J].Eur J Biochem,1999,263:709-716.
[19]	Hughes G,Murphy MP,Ledgerwood EC.Mitochondrial reactive oxygen species regulate the temporal activation of nuclear factor kappaB to modulate tumour necrosis factor-induced apoptosis:evidence from mitochondria-targeted antioxidants[J].Biochem J,2005,389:83-89.
[20]	Kelso GF,Porteous CM,Coulter CV,et al.Selective targeting of a redox-active ubiquinone to mitochondria within cells:antioxidant and antiapoptotic properties[J].J Biol Chem,2001,276:4588-4596.
[21]	Solesio ME,Prime TA,Logan A,et al.The mitochondria-targeted anti-oxidant MitoQ reduces aspects of mitochondrial fission in the 6-OHDA cell model of Parkinson's disease[J].Biochim Biophys Acta,2013,1832:174-182.
[22]	Asin-Cayuela J,Manas AR,James AM,et al.Fine-tuning the hydrophobicity of a mitochondria-targeted antioxidant[J].FEBS Lett,2004,571:9-16.
[23]	Rodriguez-Cuenca S,Cocheme HM,Logan A,et al.Consequences of long-term oral administration of the mitochondria-targeted antioxidant MitoQ to wild-type mice[J].Free Radic Biol Med,2010,48:161-172.
[24]	Zelber-Sagi S,Lurie Y,Nitzan-Kaluski D,et al.Mitochondria-targeted antioxidants prevent liver injury in animal models of steatohepatitis and CCl₄ intoxication[J].Alcoholic Liver Dis,2006,S267.
[25]	Lowes DA,Thottakam BM,Webster NR,et al.The mitochondria-targeted antioxidant MitoQ protects against organ damage in a lipopolysaccharide-peptidoglycan model of sepsis[J].Free Radic Biol Med,2008,45:1559-1565.
[26]	Ghosh A,Chandran K,Kalivendi SV,et al.Neuroprotection by a mitochondria-targeted drug in a Parkinson's disease model[J].Free Radic Biol Med,2010,49:1674-1684.
[27]	Vergeade A,Mulder P,Vendeville-Dehaudt C,et al.Mitochondrial impairment contributes to cocaine-induced cardiac dysfunction:prevention by the targeted antioxidant MitoQ[J].Free Radic Biol Med,2010,49:748-756.
[28]	Wani WY,Gudup S,Sunkaria A,et al.Protective efficacy of mitochondrial targeted antioxidant MitoQ against dichlorvos induced oxidative stress and cell death in rat brain[J].Neuropharmacology,2011,61:1193-1201.
[29]	Zhao K,Zhao GM,Wu D,et al.Cell-permeable peptide antioxidants targeted to inner mitochondrial membrane inhibit mitochondrial swelling,oxidative cell death,and reperfusion injury[J].J Biol Chem,2004,279:34682-34690.
[30]	Wright JS,Carpenter DJ,McKay DJ,et al.Theoretical calculation of substituent effects on the O-H bond strength of phenolic antioxidants related to vitamin E[J].J Am Chem Soc,1997,119:4245-4252.
[31]	Schiller PW,Nguyen TM,Berezowska I,et al.Synthesis and in vitro opioid activity profiles of DALDA analogues[J].Eur J Med Chem,2000,35:895-901.
[32]	赵善民,何显教,晋玲,等.急性低氧对家兔血压心率微血管反应性及自由基的影响[J].中国应用生理学杂志,2003,19:341-344.
[33]	Chen Z,Putt DA,Lash LH.Enrichment and functional reconstitution of glutathione transport activity from rabbit kidney mitochondria:further evidence for the role of the dicarboxylate and 2-oxoglutarate carriers in mitochondrial glutathione transport [J].Arch Biochem Biophys,2000,373:193-202.

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通讯作者: 陈斌, [email protected]

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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Research progress in mitochondria-targeted antioxidants

1. Department of Pharmacy, Lanzhou General Hospital of Lanzhou Region, Lanzhou 730050, China;Key Laboratory of Entire Army Plateau Environment Injury Prevention Research, Lanzhou 730050, China

2. Meternal and Child Health Care of Baota District, Yan'an 716000, China

Received Date: 2013-11-28

Rev Recd Date: 2014-03-26

Key words:

Abstract: Mitochondria are the main places of cellular respiration as well as the citric acid cycle and oxidative phosphorylation.It plays an important role in controlling the life and death of cells.Mitochondrial dysfunction leads to a series of human diseases such as ischemia-reperfusion injury,sepsis and diabetes.Mitochondrial become an attractive target for drug transporters strategy and therapeutic targets for neurodegeneration.Although the molecular mechanisms responsible for mitochondria mediated disease processes are not fully elucidated yet,the oxidative stress appears to be critical.Accordingly,strategies are being developed for the targeted delivery of antioxidants to mitochondria.The prospect of development of mitochondrial targeted drugs with anti-oxidative stress protection is tempting.Mitochondrial targeting antioxidants were the antioxidant drugs which took mitochondria as the target site.In this review,weintroduced the conception and classification of mitochondrial targeted antioxidants and the research progress of disease treatment by mitochondrial targeted antioxidants.

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Reference (33)

[1]	Jordan J,de Groot PW,Galindo MF.Mitochondria:the headquarters in ischemia-induced neuronal death[J].Cent Nerv Syst Agents Med Chem,2011,11:98-106.
[2]	Finkel T.Radical medicine:treating ageing to cure disease[J].Nat Rev Mol Cell Biol,2005,6:971-976.
[3]	Fantinelli JC,Perez Nunez IA,Gonzalez Arbelaez LF,et al.Participation of mitochondrial permeability transition pore in the effects of ischemic preconditioning in hypertrophied hearts:role of NO and mitoK(ATP)[J].Int J Cardiol,2011,166:173-180.
[4]	Larsen GA,Skjellegrind HK,Berg-Johnsen J,et al.Depolarization of mitochondria in isolated CA1 neurons during hypoxia,glucose deprivation and glutamate excitotoxicity[J].Brain Res,2006,1077:153-160.
[5]	Lee DR,Helps SC,Macardle PJ,et al.Alterations in membrane potential in mitochondria isolated from brain subregions during focal cerebral ischemia and early reperfusion:evaluation using flow cytometry[J].Neurochem Res,2009,34:1857-1866.
[6]	Dave KR,Bhattacharya SK,Saul I,et al.Activation of protein kinase C delta following cerebral ischemia leads to release of cytochrome C from the mitochondria via bad pathway[J].PLoS One,2011,6(7):e22057.
[7]	Moreira PI,Zhu X,Wang X,et al.Mitochondria:a therapeutic target in neurodegeneration[J].Biochim Biophys Acta,2010,1802:212-220.
[8]	Diogo CV,Grattagliano I,Oliveira PJ,et al.Re-wiring the circuit:mitochondria as a pharmacological target in liver disease[J].Curr Med Chem,2011,18:5448-5465.
[9]	Walters AM,Porter GAJ,Brookes PS.Mitochondria as a drug target in ischemic heart disease and cardiomyopathy[J].Circ Res,2012,111:1222-1236.
[10]	Reale M,Pesce M,Priyadarshini M,et al.Mitochondria as an easy target to oxidative stress events in Parkinson's disease[J].CNS Neurol Disord Drug Targets,2012,11:430-438.
[11]	Gruber J,Fong S,Chen CB,et al.Mitochondria-targeted antioxidants and metabolic modulators as pharmacological interventions to slow ageing[J].Biotechnol Adv,2012,31:563-592.
[12]	Mukhopadhyay P,Horvath B,Zsengeller Z,et al.Mitochondrial reactive oxygen species generation triggers inflammatory response and tissue injury associated with hepatic ischemia-reperfusion:therapeutic potential of mitochondrially targeted antioxidants[J].Free Radic Biol Med,2012,53:1123-1138.
[13]	Telford JE,Kilbride SM,Davey GP.Decylubiquinone increases mitochondrial function in synaptosomes[J].J Biol Chem,2010,285:8639-8645.
[14]	Coulter CV,Kelso GF,Lin TK,et al.Mitochondrially targeted antioxidants and thiol reagents[J].Free Radic Biol Med,2000,28:1547-1554.
[15]	Modica-Napolitano JS,Aprille JR.Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells[J].Adv Drug Deliv Rev,2001,49:63-70.
[16]	Sheu SS,Nauduri D,Anders MW.Targeting antioxidants to mitochondria:a new therapeutic direction[J].Biochim Biophys Acta,2006,1762:256-265.
[17]	Skulachev VP.Mitochondria-targeted antioxidants as promising drugs for treatment of age-related brain diseases[J].J Alzheimers Dis,2012,28:283-289.
[18]	Smith RA,Porteous CM,Coulter CV,et al.Selective targeting of an antioxidant to mitochondria[J].Eur J Biochem,1999,263:709-716.
[19]	Hughes G,Murphy MP,Ledgerwood EC.Mitochondrial reactive oxygen species regulate the temporal activation of nuclear factor kappaB to modulate tumour necrosis factor-induced apoptosis:evidence from mitochondria-targeted antioxidants[J].Biochem J,2005,389:83-89.
[20]	Kelso GF,Porteous CM,Coulter CV,et al.Selective targeting of a redox-active ubiquinone to mitochondria within cells:antioxidant and antiapoptotic properties[J].J Biol Chem,2001,276:4588-4596.
[21]	Solesio ME,Prime TA,Logan A,et al.The mitochondria-targeted anti-oxidant MitoQ reduces aspects of mitochondrial fission in the 6-OHDA cell model of Parkinson's disease[J].Biochim Biophys Acta,2013,1832:174-182.
[22]	Asin-Cayuela J,Manas AR,James AM,et al.Fine-tuning the hydrophobicity of a mitochondria-targeted antioxidant[J].FEBS Lett,2004,571:9-16.
[23]	Rodriguez-Cuenca S,Cocheme HM,Logan A,et al.Consequences of long-term oral administration of the mitochondria-targeted antioxidant MitoQ to wild-type mice[J].Free Radic Biol Med,2010,48:161-172.
[24]	Zelber-Sagi S,Lurie Y,Nitzan-Kaluski D,et al.Mitochondria-targeted antioxidants prevent liver injury in animal models of steatohepatitis and CCl₄ intoxication[J].Alcoholic Liver Dis,2006,S267.
[25]	Lowes DA,Thottakam BM,Webster NR,et al.The mitochondria-targeted antioxidant MitoQ protects against organ damage in a lipopolysaccharide-peptidoglycan model of sepsis[J].Free Radic Biol Med,2008,45:1559-1565.
[26]	Ghosh A,Chandran K,Kalivendi SV,et al.Neuroprotection by a mitochondria-targeted drug in a Parkinson's disease model[J].Free Radic Biol Med,2010,49:1674-1684.
[27]	Vergeade A,Mulder P,Vendeville-Dehaudt C,et al.Mitochondrial impairment contributes to cocaine-induced cardiac dysfunction:prevention by the targeted antioxidant MitoQ[J].Free Radic Biol Med,2010,49:748-756.
[28]	Wani WY,Gudup S,Sunkaria A,et al.Protective efficacy of mitochondrial targeted antioxidant MitoQ against dichlorvos induced oxidative stress and cell death in rat brain[J].Neuropharmacology,2011,61:1193-1201.
[29]	Zhao K,Zhao GM,Wu D,et al.Cell-permeable peptide antioxidants targeted to inner mitochondrial membrane inhibit mitochondrial swelling,oxidative cell death,and reperfusion injury[J].J Biol Chem,2004,279:34682-34690.
[30]	Wright JS,Carpenter DJ,McKay DJ,et al.Theoretical calculation of substituent effects on the O-H bond strength of phenolic antioxidants related to vitamin E[J].J Am Chem Soc,1997,119:4245-4252.
[31]	Schiller PW,Nguyen TM,Berezowska I,et al.Synthesis and in vitro opioid activity profiles of DALDA analogues[J].Eur J Med Chem,2000,35:895-901.
[32]	赵善民,何显教,晋玲,等.急性低氧对家兔血压心率微血管反应性及自由基的影响[J].中国应用生理学杂志,2003,19:341-344.
[33]	Chen Z,Putt DA,Lash LH.Enrichment and functional reconstitution of glutathione transport activity from rabbit kidney mitochondria:further evidence for the role of the dicarboxylate and 2-oxoglutarate carriers in mitochondrial glutathione transport [J].Arch Biochem Biophys,2000,373:193-202.

Message Board

Research progress in mitochondria-targeted antioxidants

doi: 10.3969/j.issn.1006-0111.2015.01.001

Abstract

References

Proportional views

通讯作者: 陈斌, [email protected]

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Related

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