Novel mitochondria-targeted antioxidants: Plastoquinone conjugated with cationic plant alkaloids berberine and palmatine

Pharmaceutical Research

Volumn 28, Issue 11, 2011, Pages 2883-2895

  Lyamzaev, Konstantin G ^a   Pustovidko, Antonina V ^a   Simonyan, Ruben A ^a   Rokitskaya, Tatyana I ^a   Domnina, Lidia V ^a   Ivanova, Olga Yu ^a   Severina, Inna I ^a   Sumbatyan, Natalia V ^a   Korshunova, Galina A ^a   Tashlitsky, Vadim N ^a   Roginsky, Vitaly A ^b   Antonenko, Yuriy N ^a   Skulachev, Maxim V ^a   Chernyak, Boris V ^a   Skulachev, Vladimir P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

Antioxidant; Berberine; Mitochondria; Palmatine; Plastoquinone; SkQ

Indexed keywords

13 (DECYLOXYCARBONYLMETHYL)BERBERINE; 13 (DECYLOXYCARBONYLMETHYL)PALMATINE; 13 [9 (6 PLASTOQUINONYL)NONYLOXYCARBONYLMETHYL]BERBERINE; 13 [9 (6 PLASTOQUINONYL)NONYLOXYCARBONYLMETHYL]PALMATINE; ALKALOID; ANTIOXIDANT; HYDROGEN PEROXIDE; LIPOSOME; SCAVENGER; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CELL ISOLATION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG CONJUGATION; DRUG MECHANISM; DRUG STRUCTURE; FRAGMENTATION REACTION; HUMAN; HUMAN CELL; LIPID PEROXIDATION; MICELLE; PHOSPHOLIPID MEMBRANE; PRIORITY JOURNAL;

ANTIOXIDANTS; BERBERINE; BERBERINE ALKALOIDS; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; FIBROBLASTS; HELA CELLS; HUMANS; LIPID BILAYERS; MITOCHONDRIA; MODELS, CHEMICAL; MOLECULAR TARGETED THERAPY; PHYTOTHERAPY; PLANT PREPARATIONS; PLASTOQUINONE;

EID: 84856231290     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-011-0504-8     Document Type: Article

References (49)

1. Skulachev VP. Mitochondrial physiology and pathology; concepts of programmed death of organelles, cells and organisms. Mol Aspects Med. 1999;20:139-84. (Pubitemid 29505239)
2. Yousif LF, Stewart KM, Kelley SO. Targeting mitochondria with organelle-specific compounds: strategies and applications. Chembiochem. 2009;10:1939-50.
3. Liberman EA, Topaly VP, Tsofina LM, Jasaitis AA, Skulachev VP. Mechanism of coupling of oxidative phosphorylation and the membrane potential of mitochondria. Nature. 1969;222:1076-8.
4. Mitchell P. Coupling of phosphorylation to electron and hydrogen transfer by a chemi-osmotic type of mechanism. Nature. 1961;191:144-8.
5. Severin SE, Skulachev VP, Iaguzhinskii LS. Possible role of carnitine in the transport of fatty acids through the mitochondrial membrane. Biokhimiia (rus). 1970;35:1250-3.
6. Skulachev VP. Membrane bioenergetics. Berlin: Springer; 1988. p. 442.
7. Kelso GF, Porteous CM, Coulter CV, Hughes G, Porteous WK, Ledgerwood EC, et al. Selective targeting of a redox-active ubiquinone to mitochondria within cells: Antioxidant and antiapoptotic properties. J Biol Chem. 2001;276:4588-96.
8. Skulachev VP. A biochemical approach to the problem of aging: "Megaproject" on membrane-penetrating ions. The first results and prospects. Biochemistry (Mosc). 2007;72:1385-96.
9. Antonenko YN, Avetisyan AV, Bakeeva LE, Chernyak BV, Chertkov VA, Domnina LV, et al. Skulachev VP. Mitochondriatargeted plastoquinone derivatives as tools to interrupt execution of the aging program. 1. Cationic plastoquinone derivatives: synthesis and in vitro studies. Biochemistry (Mosc). 2008;73:1273-87.
10. Bakeeva LE, Barskov IV, Egorov MV, Isaev NK, Kapelko VI, Kazachenko AV, et al. Mitochondria-targeted plastoquinone derivatives as tools to interrupt execution of the aging program. 2. Treatment of some ROS- and age-related diseases (heart arrhythmia, heart infarctions, kidney ischemia, and stroke). Biochemistry (Mosc). 2008;73:1288-99.
11. Agapova LS, Chernyak BV, Domnina LV, Dugina VB, Efimenko AY, Fetisova EK, et al. Mitochondria-targeted plastoquinone derivatives as tools to interrupt execution of the aging program. 3. Inhibitory effect of SkQ1 on tumor development from p53-deficient cells. Biochemistry (Mosc). 2008;73:1300-16.
12. Neroev VV, Archipova MM, Bakeeva LE, Fursova A, Grigorian EN, Grishanova AY, et al. Mitochondria-targeted plastoquinone derivatives as tools to interrupt execution of the aging program. 4. Age-related eye disease. SkQ1 returns vision to blind animals. Biochemistry (Mosc). 2008;73:1317-28.
13. Anisimov VN, Bakeeva LE, Egormin PA, Filenko OF, Isakova EF, Manskikh VN, et al. Mitochondria-targeted plastoquinone derivatives as tools to interrupt execution of the aging program. 5. SkQ1 prolongs lifespan and prevents development of traits of senescence. Biochemistry (Mosc). 2008;73:1329-42.
14. Skulachev VP, Anisimov VN, Antonenko YN, Bakeeva LE, Chernyak BV, Erichev VP, et al. An attempt to prevent senescence: a mitochondrial approach. Biochim Biophys Acta. 2009;1787:437-61.
15. Skulachev MV, Antonenko YN, Anisimov VN, Chernyak BV, Cherepanov DA, Chistyakov VA, et al. Mitochondrial-targeted plastoquinone derivatives. Effect on senescence and acute agerelated pathologies. Current Drug Targets. 2011; (accepted).
16. Johnson LV, Walsh ML, Chen LB. Localization of mitochondria in living cells with rhodamine 123. Proc Natl Acad Sci USA. 1980;77:990-4. (Pubitemid 10105043)
17. Rokitskaya TI, Klishin SS, Severina II, Skulachev VP, Antonenko YN. Kinetic analysis of permeation of mitochondria-targeted antioxidants across bilayer lipid membranes. J Membr Biol. 2008;224:9-19.
18. Plotnikov EY, Silachev DN, Chupyrkina AA, Danshina MI, Jankauskas SS, Morosanova MA, et al. New-generation Skulachev ions exhibiting nephroprotective and neuroprotective properties. Biochemistry (Mosc). 2010;75:145-50.
19. Taylor CT, Baird AW. Berberine inhibition of electrogenic ion transport in rat colon. Br J Pharmacol. 1995;116:2667-72.
20. Ckless K, Schlottfeldt JL, Pasqual M, Moyna P, Henriques JA, Wajner M. Inhibition of invitro lymphocyte transformation by the isoquinoline alkaloid berberine. J Pharm Pharmacol. 1995;47:1029-31. (Pubitemid 26048174)
21. Zhou J, Zhou S, Tang J, Zhang K, Guang L, Huang Y, et al. Protective effect of berberine on beta cells in streptozotocin- and high-carbohydrate/high- fat diet-induced diabetic rats. Eur J Pharmacol. 2009;606:262-8.
22. Hong Y, Hui SC, Chan TY, Hou JY. Effect of berberine on regression of pressure-overload induced cardiac hypertrophy in rats. Am J Chin Med. 2002;30:589-99. (Pubitemid 41758886)
23. Lin CC, Ng LT, Hsu FF, Shieh DE, Chiang LC. Cytotoxic effects of Coptis chinensis and Epimedium sagittatum extracts and their major constituents (berberine, coptisine and icariin) on hepatoma and leukaemia cell growth. Clin Exp Pharmacol Physiol. 2004;31:65-9. (Pubitemid 38230750)
24. Serafim TL, Oliveira PJ, Sardao VA, Perkins E, Parke D, Holy J. Different concentrations of berberine result in distinct cellular localization patterns and cell cycle effects in a melanoma cell line. Cancer Chemother Pharmacol. 2008;61:1007-18. (Pubitemid 351423129)
25. Hwang JM, Wang CJ, Chou FP, Tseng TH, Hsieh YS, Lin WL, et al. Inhibitory effect of berberine on tert-butyl hydroperoxideinduced oxidative damage in rat liver. Arch Toxicol. 2002;76:664-70.
26. Shia CS, Hou YC, Juang SH, Tsai SY, Hsieh PH, Ho LC, et al. Metabolism and pharmacokinetics of san-huang-xie-xin-tang, a polyphenol-rich chinese medicine formula, in rats and ex-vivo antioxidant activity. Evid Based Complement Alternat Med. 2009
27. Shirwaikar A, Rajendran K, Punitha IS. In vitro antioxidant studies on the benzyl tetra isoquinoline alkaloid berberine. Biol Pharm Bull. 2006;29:1906-10. (Pubitemid 44338416)
28. Severina II, Muntyan MS, Lewis K, Skulachev VP. Transfer of cationic antibacterial agents berberine, palmatine, and benzalkonium through bimolecular planar phospholipid film and staphylococcus aureus membrane. IUBMB Life. 2001;52:321-4. (Pubitemid 33731079)
29. Pereira GC, Branco AF, Matos JA, Pereira SL, Parke D, Perkins EL, et al. Mitochondrially targeted effects of berberine [natural yellow 18, 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo (5,6-a) quinolizinium] on k1735-m2 mouse melanoma cells: comparison with direct effects on isolated mitochondrial fractions. J Pharmacol Exp Ther. 2007;323:636-49. (Pubitemid 350005145)
30. Samosorn S. Development of berberine-based derivatives as novel antimicrobal agents. Australia: Department of chemistry: University of Wollongong; 2005. p. 213.
31. Lombardo F, Shalaeva MY, Tupper KA, Gao F. Elogd: A tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds. J Med Chem. 2001;44:2490-7. (Pubitemid 32852170)
32. Martyushin AA, Tcarev DA, Grigorenko MA, Fedorov II, Ramenskaya GV, Tashlitsky VN, et al. Estimation of lipophilicity of new generation of antioxidants. Pharmacia. 2008;5:23-9 (Russ.).
33. Severina II. Nystatin-induced increase in photocurrent in the system 'bacteriorhodopsin proteoliposome/bilayer planar membrane'. Biochim Biophys Acta. 1982;681:311-7. (Pubitemid 13237069)
34. Roginsky V. Chain-breaking antioxidant activity of natural polyphenols as determined during the chain oxidation of methyl linoleate in Triton x-100 micelles. Arch Biochem Biophys. 2003;414:261-70. (Pubitemid 36627359)
35. Roginsky V, Barsukova T, Loshadkin D, Pliss E. Substituted phydroquinones as inhibitors of lipid peroxidation. Chem Phys Lipids. 2003;125:49-58. (Pubitemid 37414805)
36. Naguib YM. A fluorometric method for measurement of peroxyl radical scavenging activities of lipophilic antioxidants. Anal Biochem. 1998;265:290-8. (Pubitemid 29002074)
37. Zhu M, Qin ZJ, Hu D, Munishkina LA, Fink AL. Alpha-synuclein can function as an antioxidant preventing oxidation of unsaturated lipid in vesicles. Biochemistry. 2006;45:8135-42. (Pubitemid 43993234)
38. Palmer JW, Tandler B, Hoppel CL. Biochemical properties of subsarcolemmal and interfibrillar mitochondria isolated from rat cardiac muscle. J Biol Chem. 1977;252:8731-9. (Pubitemid 8243644)
39. Jentzsch AM, Bachmann H, Furst P, Biesalski HK. Improved analysis of malondialdehyde in human body fluids. Free Radic Biol Med. 1996;20:251-6. (Pubitemid 26021882)
40. Antonenko YN, Roginsky VA, Pashkovskaya AA, Rokitskaya TI, Kotova EA, Zaspa AA, et al. Protective effects of mitochondriatargeted antioxidant SkQ in aqueous and lipid membrane environments. J Membr Biol. 2008;222:141-9.
41. Martinez LA, Rios JL, Paya M, Alcaraz MJ. Inhibition of nonenzymic lipid peroxidation by benzylisoquinoline alkaloids. Free Radic Biol Med. 1992;12:287-92.
42. Skulachev VP, Antonenko YN, Cherepanov DA, Chernyak BV, Izyumov DS, Khailova LS, et al. Prevention of cardiolipin oxidation and fatty acid cycling as two antioxidant mechanisms of cationic derivatives of plastoquinone (SkQs). Biochim Biophys Acta. 2010;1797:878-89.
43. Mikes V, Yaguzhinskij LS. Interaction of fluorescent berberine alkyl derivatives with respiratory chain of rat liver mitochondria. J Bioenerg Biomembr. 1985;17:23-32. (Pubitemid 15146343)
44. Chernyak BV, Izyumov DS, Lyamzaev KG, Pashkovskaya AA, Pletjushkina OY, Antonenko YN, et al. Production of reactive oxygen species in mitochondria of HeLa cells under oxidative stress. Biochim Biophys Acta. 2006;1757:525-34. (Pubitemid 43993847)
45. Fetisova EK, Avetisyan AV, Izyumov DS, Korotetskaya MV, Chernyak BV, Skulachev VP. Mitochondria-targeted antioxidant SkQR1 selectively protects MDR (Pgp 170)-negative cells against oxidative stress. FEBS Lett. 2010;584:562-6.
46. Izyumov DS, Domnina LV, Nepryakhina OK, Avetisyan AV, Golyshev SA, Ivanova OY, et al. Mitochondria as source of reactive oxygen species under oxidative stress. Study with novel mitochondria-targeted antioxidants-the "Skulachev-ion" derivatives. Biochemistry (Mosc). 2010;75:123-9.
47. Skulachev VP, Bakeeva LE, Chernyak BV, Domnina LV, Minin AA, Pletjushkina OY, et al. Thread-grain transition of mitochondrial reticulum as a step of mitoptosis and apoptosis. Mol Cell Biochem. 2004;256-257:341-58. (Pubitemid 38181257)
48. Belousov VV, Fradkov AF, Lukyanov KA, Staroverov DB, Shakhbazov KS, Terskikh AV, et al. Genetically encoded fluorescent indicator for intracellular hydrogen peroxide. Nat Methods. 2006;3:281-6.
49. Zorov DB, Filburn CR, Klotz LO, Zweier JL, Sollott SJ. Reactive oxygen species (ROS)-induced ROS release: a new phenomenon accompanying induction of the mitochondrial permeability transition in cardiac myocytes. J Exp Med. 2000;192:1001-14.