Targeting mitochondria with small molecules: The preparation of MitoB and MitoP as exomarkers of mitochondrial hydrogen peroxide

Methods in Molecular Biology

Volumn 1265, Issue , 2015, Pages 25-50

  Cairns, Andrew G ^a   McQuaker, Stephen J ^a   Murphy, Michael P ^a   Hartley, Richard C ^a  

^a NONE

Author keywords

Chemical biology; Exomarker; Hydrogen peroxide; Mass spectrometry; Mitochondria; Oxidative stress; Reactive oxygen species; Targeting

Indexed keywords

HYDROGEN PEROXIDE; MEMBRANE PROTEIN; MITOB PROTEIN; MITOP PROTEIN; UNCLASSIFIED DRUG; MITOB COMPOUND; MITOP COMPOUND; ORGANOPHOSPHORUS COMPOUND; PHENOL DERIVATIVE; REACTIVE OXYGEN METABOLITE;

ARTICLE; DROSOPHILA MELANOGASTER; LIMIT OF QUANTITATION; MEMBRANE POTENTIAL; MITOCHONDRION; NONHUMAN; PRIORITY JOURNAL; PROTEIN PURIFICATION; SENSOR; SYNTHESIS; DRUG DEVELOPMENT; DRUG EFFECTS; ISOLATION AND PURIFICATION; METABOLISM; OXIDATION REDUCTION REACTION; PROCEDURES;

DRUG DISCOVERY; HYDROGEN PEROXIDE; MITOCHONDRIA; ORGANOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION; PHENOLS; REACTIVE OXYGEN SPECIES;

EID: 84958622777     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4939-2288-8_3     Document Type: Article

References (58)

1. Nielsen TE, Schreiber SL (2008) Diversityoriented synthesis—towards the optimal screening collection: a synthesis strategy. Angew Chem Int Ed 47:48–56
2. Smith RAJ, Hartley RC, Cochemé HM, Murphy MP (2012) Mitochondrial pharmacology. Trends Pharmacol Sci 33:341–352
3. Smith RAJ, Hartley RC, Murphy MP (2011) Mitochondria-targeted small molecule therapeutics and probes. Antioxid Redox Signal 15:3021–3038
4. Logan A, Shabalina IG, Prime TA et al (2014) In vivo levels of mitochondrial hydrogen peroxide increase with age in mtDNA mutator mice. Aging Cell 13:765–768
5. Lepez-Otin C, Blasco MA, Partridge L et al (2013) The hallmarks of aging. Cell 153: 1194–1217
6. Jean SR, Tulumello DV, Wisnovsky SP et al (2014) Molecular vehicles for mitochondria! Chemical biology and drug delivery. ACS Chem Biol 9:323–333
7. Weissig V, Boddapati SV, Cheng SM et al (2006) Liposomes and liposome-like vesicles for drug and DNA delivery to mitochondria. J Liposome Res 16:249–264
8. Boddapati SV, D’Souza GGM, Erdogan S et al (2008) Organelle-targeted nanocarriers: specifi c delivery of liposomal ceramide to mitochondria enhances its cytotoxicity in vitro and in vivo. Nano Lett 8:2559–2563
9. Marrache S, Dhar S (2012) Engineering of blended nanoparticle platform for delivery of mitochondria-acting therapeutics. Proc Natl Acad Sci U S A 109:16288–16293
10. Stewart KM, Horton KL, Kelley SO (2008) Cell-penetrating peptides as delivery vehicles for biology and medicine. Org Biomol Chem 6:2242–2255
11. Horobin RW (2010) Can QSAR models describing small-molecule xenobiotics give useful tips for predicting uptake and localization of nanoparticles in living cells? And if not, why not? In: Weissig V, D’Souza GG (eds) Organelle-specifi c pharmaceutical nanotechnology. Wiley, New York
12. Snow BJ, Rolfe FL, Lockhart MM et al (2010) A double-blind placebo-controlled study to assess the mitochondria-targeted antioxidant MitoQ as a disease-modifying therapy in Parkinson’s disease. Mov Disord 25:1670–1674
13. Ihmels H, Otto D (2005) Intercalation of organic dye molecules into double-stranded DNA general principles and recent developments. In: Wurthner F (ed) Supermolecular dye chemistry, vol 258. Springer, Heidelberg, pp 161–204
14. Finichiu PG, James AM, Larsen L et al (2013) Mitochondrial accumulation of a lipophilic cation conjugated to an ionisable group depends on membrane potential, pH gradient and pK(a): implications for the design of mitochondrial probes and therapies. J Bioenerg Biomembr 45:165–173
15. Kelso GF, Porteous CM, Coulter CV et al (2001) Selective targeting of a redox-active ubiquinone to mitochondria within cells— antioxidant and antiapoptotic properties. J Biol Chem 276:4588–4596
16. Chalmers S, Caldwell ST, Quin C et al (2012) Selective uncoupling of individual mitochondria within a cell using a mitochondria-targeted photoactivated protonophore. J Am Chem Soc 134:758–761
17. McQuaker SJ, Quinlan CL, Caldwell ST et al (2013) A prototypical small-molecule modulator uncouples mitochondria in response to endogenous hydrogen peroxide production. Chembiochem 14:993–1000
18. Murphy MP (2009) How mitochondria produce reactive oxygen species. Biochem J 417:1–13
19. Quinlan CL, Perevoschikova IV, Goncalves RLS et al (2013) The determination and analysis of site-specifi c rates of mitochondrial reactive oxygen species production. In: Cadenas E, Packer L (eds) Hydrogen peroxide and cell signaling, Part A, vol 526. Elsevier B. V, Amsterdam, pp 189–217
20. Pryde KR, Hirst J (2011) Superoxide is produced by the reduced fl avin in mitochondrial complex I a single, unifi ed mechanism that applies during both forward and reverse electron transfer. J Biol Chem 286:18056–18065
21. Hirst J (2013) Mitochondrial complex I. Annu Rev Biochem 82:551–575
22. Lambert AJ, Brand MD (2004) Superoxide production by NADH: ubiquinone oxidoreductase (complex I) depends on the pH gradient across the mitochondrial inner membrane. Biochem J 382:511–517
23. Halliwell B (2013) The antioxidant paradox: less paradoxical now? Br J Clin Pharmacol 75:637–644
24. Smith RAJ, Porteous CM, Coulter CV, Murphy MP (1999) Selective targeting of an antioxidant to mitochondria. Eur J Biochem 263:709–716
25. Dhanasekaran A, Kotamraju S, Karunakaran C et al (2005) Mitochondria superoxide dismutase mimetic inhibits peroxide-induced oxidative damage and apoptosis: role of mitochondrial superoxide. Free Radic Biol Med 39:567–583
26. Trnka J, Blaikie FH, Smith RAJ, Murphy MP (2008) A mitochondria-targeted nitroxide is reduced to its hydroxylamine by ubiquinol in mitochondria. Free Radic Biol Med 44: 1406–1419
27. Dikalova AE, Bikineyeva AT, Budzyn K et al (2010) Therapeutic targeting of mitochondrial superoxide in hypertension. Circ Res 107: 106–116
28. Dessolin J, Schuler M, Quinart A et al (2002) Selective targeting of synthetic antioxidants to mitochondria: towards a mitochondrial medicine for neurodegenerative diseases? Eur J Pharmacol 447:155–161
29. James AM, Sharpley MS, Manas AR et al (2007) Interaction of the mitochondriatargeted antioxidant MitoQ with phospholipid bilayers and ubiquinone oxidoreductases. J Biol Chem 282:14708–14718
30. Kelso GF, Maroz A, Cochemé HM et al (2012) A mitochondria-targeted macrocyclic Mn(II) superoxide dismutase mimetic. Chem Biol 19:1237–1246
31. Filipovska A, Kelso GF, Brown SE et al (2005) Synthesis and characterization of a triphenylphosphonium- conjugated peroxidase mimetic—insights into the interaction of ebselen with mitochondria. J Biol Chem 280:24113–24126
32. Prime TA, Blaikie FH, Evans C et al (2009) A mitochondria-targeted S-nitrosothiol modulates respiration, nitrosates thiols, and protects against ischemia-reperfusion injury. Proc Natl Acad Sci U S A 106:10764–10769
33. Chouchani ET, Methner C, Nadtochiy SM et al (2013) Cardioprotection by S-nitrosation of a cysteine switch on mitochondrial complex I. Nat Med 19:753–759
34. Quin C, Robertson L, McQuaker SJ et al (2010) Caged mitochondrial uncouplers that are released in response to hydrogen peroxide. Tetrahedron 66:2384–2389
35. Murphy MP, Holmgren A, Larsson NG et al (2011) Unraveling the biological roles of reactive oxygen species. Cell Metab 13:361–366
36. Murphy MP, Echtay KS, Blaikie FH et al (2003) Superoxide activates uncoupling proteins by generating carbon-centered radicals and initiating lipid peroxidation—studies using a mitochondria-targeted spin trap derived from alpha-phenyl-N-tert-butylnitrone. J Biol Chem 278:48534–48545
37. Quin C, Trnka J, Hay A et al (2009) Synthesis of a mitochondria-targeted spin trap using a novel Parham-type cyclization. Tetrahedron 65:8154–8160
38. Xu YK, Kalyanaraman B (2007) Synthesis and ESR studies of a novel cyclic nitrone spin trap attached to a phosphonium group—a suitable trap for mitochondria-generated ROS? Free Radic Res 41:1–7
39. Hardy M, Chalier F, Ouari O et al (2007) Mito-DEPMPO synthesized from a novel NH2-reactive DEPMPO spin trap: a new and improved trap for the detection of superoxide. Chem Commun 1083–1085
40. Hardy M, Rockenbauer A, Vasquez-Vivar J et al (2007) Detection, characterization, and decay kinetics of ROS and thiyl adducts of Mito-DEPMPO spin trap. Chem Res Toxicol 20:1053–1060
41. Dickinson BC, Srikun D, Chang CJ (2010) Mitochondrial-targeted fl uorescent probes for reactive oxygen species. Curr Opin Chem Biol 14:50–56
42. Robinson KM, Janes MS, Pehar M et al (2006) Selective fl uorescent imaging of superoxide in vivo using ethidium-based probes. Proc Natl Acad Sci U S A 103:15038–15043
43. Kalyanaraman B, Dranka BP, Hardy M et al (2014) HPLC-based monitoring of products formed from hydroethidine-based fl uorogenic probes—the ultimate approach for intra- and extracellular superoxide detection. Biochim Biophys Acta 1840:739–744
44. Cairns AG, Senn HM, Murphy MP, Hartley RC (2014) Expanding the palette of phenanthridinium cations. Chemistry 20:3742–3751
45. Dickinson BC, Lin VS, Chang CJ (2013) Preparation and use of MitoPY1 for imaging hydrogen peroxide in mitochondria of live cells. Nat Protoc 8:1249–1259
46. Dickinson BC, Chang CJ (2008) A targetable fl uorescent probe for imaging hydrogen peroxide in the mitochondria of living cells. J Am Chem Soc 130:9638–9639
47. Van de Bittner GC, Bertozzi CR, Chang CJ (2013) Strategy for dual-analyte luciferin imaging: in vivo bioluminescence detection of hydrogen peroxide and caspase activity in a murine model of acute infl ammation. J Am Chem Soc 135:1783–1795
48. Van de Bittner GC, Dubikovskaya EA, Bertozzi CR, Chang CJ (2010) In vivo imaging of hydrogen peroxide production in a murine tumor model with a chemoselective bioluminescent reporter. Proc Natl Acad Sci U S A 107:21316–21321
49. Cochemé HM, Quin C, McQuaker SJ et al (2011) Measurement of H 2 O 2 within living Drosophila during aging using a ratiometric mass spectrometry probe targeted to the mitochondrial matrix. Cell Metab 13:340–350
50. Cochemé HM, Logan A, Prime TA et al (2012) Using the mitochondria-targeted ratiometric mass spectrometry probe MitoB to measure H 2 O 2 in living Drosophila. Nat Protoc 7:946–958
51. Sikora A, Zielonka J, Lopez M et al (2009) Direct oxidation of boronates by peroxynitrite: mechanism and implications in fl uorescence imaging of peroxynitrite. Free Radic Biol Med 47:1401–1407
52. Sikora A, Zielonka J, Adamus J et al (2013) Reaction between peroxynitrite and triphenylphosphonium- substituted arylboronic acid isomers: identifi cation of diagnostic marker products and biological implications. Chem Res Toxicol 26:856–867
53. Turowski M, Yamakawa N, Meller J et al (2003) Deuterium isotope effects on hydrophobic interactions: the importance of dispersion interactions in the hydrophobic phase. J Am Chem Soc 125:13836–13849
54. Eltayar N, Vandewaterbeemd H, Gryllaki M et al (1984) The lipophilicity of deuterium atoms—a comparison of shake-fl ask and HPLC methods. Int J Pharm 19:271–281
55. Tanaka N, Thornton ER (1976) Isotopeeffects in hydrophobic binding measured by high-pressure liquid-chromatography. J Am Chem Soc 98:1617–1619
56. Logan A, Cochemé HM, Pun PBL et al (2014) Using exomarkers to assess mitochondrial reactive species in vivo. Biochim Biophys Acta 1840:923–930
57. Pun PBL, Logan A, Darley-Usmar V et al (2014) A mitochondria-targeted mass spectrometry probe to detect glyoxals: implications for diabetes. Free Radic Biol Med 67:437–450
58. Dawson MI, Hobbs PD, Kuhlmann K et al (1980) Retinoic acid analogs—synthesis and potential as cancer chemopreventive agents. J Med Chem 23:1013–1022