Rapid uptake of lipophilic triphenylphosphonium cations by mitochondria in vivo following intravenous injection: Implications for mitochondria-specific therapies and probes
Abstract
Background Mitochondrial dysfunction contributes to a range of pathologies, consequently there is a need to monitor mitochondrial function and to intervene pharmacologically to prevent mitochondrial damage. One approach to this is to deliver antioxidants, probes and pharmacophores to mitochondria by conjugation to the lipophilic triphenylphosphonium (TPP) cation that is taken up selectively by mitochondria driven by the membrane potential.Conclusions Oral administration of TPP-conjugated antioxidants protects against mitochondrial damage in vivo. However, there is also a need to deliver molecules rapidly to mitochondria to respond quickly to pathologies and for the real-time assessment of mitochondrial function.Methods To see if this was possible we investigated how rapidly TPP cations were taken up by mitochondria in vivo following intravenous (iv) administration.Results AlkylTPP cations were accumulated selectively by mitochondria within mice within 5 min of iv injection. The extent of uptake was enhanced 10-30-fold relative to simple alkylTPP cations by attaching functional groups to the TPP cation via long, hydrophobic alkyl chains. Conclusions: Mitochondria-targeted antioxidants, probes and pharmacophores can be delivered into mitochondria within minutes of iv administration.General significance These findings greatly extend the utility of mitochondria-targeted lipophilic cations as therapies and probes.
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Triphenylphosphonium cations drive accumulation within cardiac mitochondria within minutes of intravenous administration.
“As triphenylphosphonium cations drive accumulation within cardiac mitochondria within minutes of intravenous administration14”
From Cardioprotection by S-nitrosation of a cysteine switch on mitochondrial complex I (2013) · cites this paper as [14]
Cites
Measurement of protein using bicinchoninic acid
Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gartner, F. H., Provenzano, M. D., Fujimoto, E. K., Goeke, N. M., Olson, B. J., & Klenk, D. C. (1985) · Analytical Biochemistry · doi:10.1016/0003-2697(85)90442-7 · Cited by 18,482 · see citing works
Effect of Cyclosporine on Reperfusion Injury in Acute Myocardial Infarction
Piot, C. A., Croisille, P., Staat, P., Thibault, H., Rioufol, G., Mewton, N., Belghiti, R. E., Cung, T. T., Bonnefoy‐Cudraz, E., Angoulvant, D., et al. (2008) · New England Journal of Medicine · doi:10.1056/nejmoa071142 · Cited by 1,339 · see citing works
Targeting Antioxidants to Mitochondria by Conjugation to Lipophilic Cations
Murphy, M. P., & Smith, R. A. J. (2007) · Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pharmtox.47.120505.105110 · Cited by 1,173 · see citing works
Self-citationSelective Targeting of a Redox-active Ubiquinone to Mitochondria within Cells
Kelso, G. F., Porteous, C. M., Coulter, C. V., Hughes, G., Porteous, W. K., Ledgerwood, E. C., Smith, R. A. J., & Murphy, M. P. (2001) · Journal of Biological Chemistry · doi:10.1074/jbc.m009093200 · Cited by 1,091 · see citing works
Self-citationMitochondrial Membrane Potential in Living Cells
Chen, L. B. (1988) · Annual Review of Cell Biology · doi:10.1146/annurev.cb.04.110188.001103 · Cited by 1,039 · see citing works
Selective fluorescent imaging of superoxide <i>in vivo</i> using ethidium-based probes
Robinson, K. M., Janes, M. S., Pehar, M., Monette, J. S., Ross, M. F., Hagen, T. M., Murphy, M. P., & Beckman, J. S. (2006) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0601945103 · Cited by 777 · see citing works
Self-citationDelivery of bioactive molecules to mitochondria <i>in</i> <i>vivo</i>
Smith, R. A. J., Porteous, C. M., Gane, A. M., & Murphy, M. P. (2003) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0931245100 · Cited by 725 · see citing works
Self-citationA Targetable Fluorescent Probe for Imaging Hydrogen Peroxide in the Mitochondria of Living Cells
Dickinson, B. C., & Chang, C. J. (2008) · Journal of the American Chemical Society · doi:10.1021/ja802355u · Cited by 642 · see citing works
Targeting an antioxidant to mitochondria decreases cardiac ischemia-reperfusion injury
Adlam, V. J., Harrison, J. C., Porteous, C. M., James, A. M., Smith, R. A. J., Murphy, M. P., & Sammut, I. A. (2005) · The FASEB Journal · doi:10.1096/fj.05-3718com · Cited by 618 · see citing works
Self-citationSnow, B. J., Rolfe, F. L., Lockhart, M. M., Frampton, C. M., O'Sullivan, J. D., Fung, V., Smith, R. A. J., Murphy, M. P., Taylor, K. M., & On behalf of the Protect Study Group (2010) · Movement Disorders · doi:10.1002/mds.23148 · Cited by 606 · see citing works
Self-citationRoss, M. F., Kelso, G. F., Blaikie, F. H., James, A. M., Cochemé, H. M., Filipovska, A., Ros, T. D., Hurd, T. R., Smith, R. A. J., & Murphy, M. P. (2005) · Biochemistry (Moscow) · doi:10.1007/s10541-005-0104-5 · Cited by 495 · see citing works
Self-citationSelective targeting of an antioxidant to mitochondria
Smith, R. A. J., Porteous, C. M., Coulter, C. V., & Murphy, M. P. (1999) · European Journal of Biochemistry · doi:10.1046/j.1432-1327.1999.00543.x · Cited by 466 · see citing works
Self-citationDrug delivery to mitochondria: the key to mitochondrial medicine
Murphy, M. P., & Smith, R. A. J. (2000) · Advanced Drug Delivery Reviews · doi:10.1016/s0169-409x(99)00069-1 · Cited by 426 · see citing works
Self-citationSubcellular components: preparation and fractionation;
Birnie, G. D. (1972) · Cited by 422 · see citing works
Gane, E. J., Weilert, F., Orr, D. W., Keogh, G. F., Gibson, M., Lockhart, M. M., Frampton, C. M., Taylor, K. M., Smith, R. A. J., & Murphy, M. P. (2010) · Liver International · doi:10.1111/j.1478-3231.2010.02250.x · Cited by 379 · see citing works
Self-citationGraham, D., Huynh, N. N., Hamilton, C. A., Beattie, E., Smith, R. A. J., Cochemé, H. M., Murphy, M. P., & Dominiczak, A. F. (2009) · Hypertension · doi:10.1161/hypertensionaha.109.130351 · Cited by 367 · see citing works
Self-citationSelective targeting of bioactive compounds to mitochondria
Murphy, M. P. (1997) · Trends in Biotechnology · doi:10.1016/s0167-7799(97)01068-8 · Cited by 366 · see citing works
Self-citationJames, A. M., Cochemé, H. M., Smith, R. A. J., & Murphy, M. P. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m501527200 · Cited by 353 · see citing works
Self-citationMurphy, M. P., Echtay, K. S., Blaikie, F. H., Asin-Cayuela, J., Cochemé, H. M., Green, K., Buckingham, J. A., Taylor, E. R., Hurrell, F., Hughes, G., et al. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m308529200 · Cited by 304 · see citing works
Self-citationLowes, D. A., Thottakam, B. M. V., Webster, N. R., Murphy, M. P., & Galley, H. F. (2008) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2008.09.003 · Cited by 261 · see citing works
Self-citationPrime, T. A., Blaikie, F. H., Evans, C., Nadtochiy, S. M., James, A. M., Dahm, C. C., Vitturi, D. A., Patel, R. P., Hiley, C. R., Abakumova, I., et al. (2009) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0903250106 · Cited by 222 · see citing works
Self-citationRodriguez-Cuenca, S., Cochemé, H. M., Logan, A., Abakumova, I., Prime, T. A., Rose, C., Vidal-Puig, A., Smith, A. C., Rubinsztein, D. C., Fearnley, I. M., et al. (2010) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2009.10.039 · Cited by 218 · see citing works
Self-citationRapid and extensive uptake and activation of hydrophobic triphenylphosphonium cations within cells
Ross, M. F., Prime, T. A., Abakumova, I., James, A. M., Porteous, C. M., Smith, R. A. J., & Murphy, M. P. (2008) · Biochemical Journal · doi:10.1042/bj20080063 · Cited by 206 · see citing works
Self-citationDhanasekaran, A., Kotamraju, S., Karunakaran, C., Kalivendi, S. V., Thomas, S., Joseph, J., & Kalyanaraman, B. (2005) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2005.04.016 · Cited by 189 · see citing works
Fine-tuning the hydrophobicity of a mitochondria-targeted antioxidant
Asin-Cayuela, J., Manas, A.-R. B., James, A. M., Smith, R. A. J., & Murphy, M. P. (2004) · FEBS Letters · doi:10.1016/j.febslet.2004.06.045 · Cited by 184 · see citing works
Self-citationSpecific Modification of Mitochondrial Protein Thiols in Response to Oxidative Stress
Lin, T., Hughes, G., Muratovska, A., Blaikie, F. H., Brookes, P. S., Darley-Usmar, V. M., Smith, R. A. J., & Murphy, M. P. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m110797200 · Cited by 180 · see citing works
Self-citationDoxorubicin Inactivates Myocardial Cytochrome c Oxidase in Rats: Cardioprotection by Mito-Q
Chandran, K., Aggarwal, D., Migrino, R. Q., Joseph, J., McAllister, D. M., Konorev, E. A., Antholine, W. E., Zielonka, J., Srinivasan, S., Avadhani, N. G., et al. (2009) · Biophysical Journal · doi:10.1016/j.bpj.2008.10.042 · Cited by 171 · see citing works
Pandya, J. D., Pauly, J. R., Nukala, V. N., Sebastian, A. H., Day, K. M., Korde, A. S., Maragos, W. F., Hall, E. D., & Sullivan, P. G. (2007) · Journal of Neurotrauma · doi:10.1089/neu.2006.3673 · Cited by 147 · see citing works
PREPARATION OF MITOCHONDRIA FROM ANIMAL TISSUES AND YEASTS
Chappell, J., & Hansford, R. G. (1972) · Elsevier eBooks · doi:10.1016/b978-0-408-70360-4.50009-2 · Cited by 136 · see citing works
Korde, A. S., Pettigrew, L. C., Craddock, S. D., & Maragos, W. F. (2005) · Journal of Neurochemistry · doi:10.1111/j.1471-4159.2005.03328.x · Cited by 126 · see citing works
Accumulation of lipophilic dications by mitochondria and cells
Ross, M. F., Ros, T. D., Blaikie, F. H., Prime, T. A., Porteous, C. M., Severina, I. I., Skulachev, V. P., Kjaergaard, H. G., Smith, R. A. J., & Murphy, M. P. (2006) · Biochemical Journal · doi:10.1042/bj20060919 · Cited by 124 · see citing works
Self-citationMadar, I., Ravert, H. T., Du, Y., Hilton, J., Volokh, L., Dannals, R. F., Frost, J. J., & Hare, J. M. (2006) · PubMed · Cited by 115 · see citing works
Burns, R. J., Smith, R. A. J., & Murphy, M. P. (1995) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1995.1436 · Cited by 111 · see citing works
Self-citationComplex I Dysfunction and Tolerance to Nitroglycerin
Esplugues, J. V., Rocha, M., Nuñez, C., Boscá, I., Ibiza, S., Herance, J. R., Ortega, Á., Serrador, J. M., D’Ocón, P., & Víctor, V. M. (2006) · Circulation Research · doi:10.1161/01.res.0000250430.62775.99 · Cited by 103 · see citing works
Neužil, J., Widén, C., Gellert, N., Swettenham, E., Zobalová, R., Dong, L., Wang, X., Lidebjer, C., Dalen, H., Headrick, J. P., et al. (2007) · Redox Report · doi:10.1179/135100007x200227 · Cited by 91 · see citing works
Ross, M. F., Filipovska, A., Smith, R. A. J., Gait, M. J., & Murphy, M. P. (2004) · Biochemical Journal · doi:10.1042/bj20041095 · Cited by 90 · see citing works
Self-citationTargeting coenzyme Q derivatives to mitochondria
Smith, R. A. J., Kelso, G. F., James, A. M., & Murphy, M. P. (2004) · Methods in Enzymology · doi:10.1016/s0076-6879(04)82003-2 · Cited by 87 · see citing works
Self-citationHydrated Tetrabutylammonium Fluoride as a Powerful Nucleophilic Fluorinating Agent
Albanese, D. C. M., Landini, D., & Penso, M. (1998) · The Journal of Organic Chemistry · doi:10.1021/jo981522o · Cited by 82 · see citing works
Plotnikov, E. Y., Vasileva, A. K., Arkhangelskaya, A. A., Pevzner, I. B., Skulachev, V. P., & Zorov, D. B. (2008) · FEBS Letters · doi:10.1016/j.febslet.2008.08.002 · Cited by 66 · see citing works
Detection, Characterization, and Decay Kinetics of ROS and Thiyl Adducts of Mito-DEPMPO Spin Trap
Hardy, M., Rockenbauer, A., Vasquez-Vivar, J. M., Felix, C. C., López, M., Srinivasan, S., Avadhani, N. G., Tordo, P., & Kalyanaraman, B. (2007) · Chemical Research in Toxicology · doi:10.1021/tx700101d · Cited by 62 · see citing works
Toxic Fluorine Compounds. III.1 ι-Fluoroalcohols
Pattison, F. L. M., Howell, W. C., Mcnamara, A. J., SCHNEIDER, J. C., & Walker, J. F. (1956) · The Journal of Organic Chemistry · doi:10.1021/jo01113a006 · Cited by 57 · see citing works
Manetta, A., Gamboa, G., Nasseri, A., Podnos, Y. D., Emma, D., Dorion, G. E., Rawlings, L., Carpenter, P. M., Bustamante, A., Patel, J., et al. (1996) · Gynecologic Oncology · doi:10.1006/gyno.1996.0026 · Cited by 53 · see citing works
Hardy, M., Chalier, F., Ouari, O., Finet, J., Rockenbauer, A., Kalyanaraman, B., & Tordo, P. (2007) · Chemical Communications · doi:10.1039/b616076j · Cited by 48 · see citing works
Chemoselective fluorination for primary alcohols
Shimizu, M., Nakahara, Y., & Yoshioka, H. (1985) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)98993-7 · Cited by 44 · see citing works
Xu, Y., & Kalyanaraman, B. (2006) · Free Radical Research · doi:10.1080/10715760600911147 · Cited by 43 · see citing works
Enhanced uptake of [11C]TPMP in canine brain tumor: a PET study.
Madar, I., Anderson, J. H., Szabó, Z. R., Scheffel, U., Kao, P. F., Ravert, H. T., & Dannals, R. F. (1999) · PubMed · Cited by 34 · see citing works
Korde, A. S., Sullivan, P. G., & Maragos, W. F. (2005) · Journal of Neurotrauma · doi:10.1089/neu.2005.22.1142 · Cited by 32 · see citing works
Specific targeting of a DNA‐alkylating reagent to mitochondria
James, A. M., Blaikie, F. H., Smith, R. A. J., Lightowlers, R. N., Smith, P., & Murphy, M. P. (2003) · European Journal of Biochemistry · doi:10.1046/j.1432-1033.2003.03660.x · Cited by 24 · see citing works
Self-citationLi, Y., Zhang, H., Fawcett, J. P., & Tucker, I. G. (2007) · Rapid Communications in Mass Spectrometry · doi:10.1002/rcm.3048 · Cited by 24 · see citing works
Patel, J., Rideout, D. C., McCarthy, M. R., Calogeropoulou, T., Wadwa, K. S., & Oseroff, A. R. (1994) · PubMed · Cited by 21 · see citing works
Effects of phosphonium compounds on Schistosoma mansoni
McAllister, P. R., Dotson, M. J., Grim, S. O., & Hillman, G. R. (1980) · Journal of Medicinal Chemistry · doi:10.1021/jm00182a010 · Cited by 19 · see citing works
Trujillo, J. G., Ceballos, G. M., Yañez, R., & Joseph‐Nathan, P. (1991) · Synthetic Communications · doi:10.1080/00397919108020837 · Cited by 9 · see citing works
Flagged first, then by citations
3 of the 55 references couldn’t be matched to a known paper.
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Zielonka, J., Joseph, J., Sikora, A., Hardy, M., Ouari, O., Vasquez-Vivar, J., Cheng, G., Lopez, M., & Kalyanaraman, B. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00042 · Cited by 1,683 · see citing works
Cardioprotection by S-nitrosation of a cysteine switch on mitochondrial complex I
Chouchani, E. T., Methner, C., Nadtochiy, S. M., Logan, A., Pell, V. R., Ding, S., James, A. M., Cochemé, H. M., Reinhold, J., Lilley, K. S., et al. (2013) · Nature Medicine · doi:10.1038/nm.3212 · Cited by 619 · see citing works
Self-citationSmith, R. A. J., Hartley, R. C., Cochemé, H. M., & Murphy, M. P. (2012) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2012.03.010 · Cited by 501 · see citing works
Self-citationZhang, W., Hu, X., Shen, Q., & Xing, D. (2019) · Nature Communications · doi:10.1038/s41467-019-09566-3 · Cited by 446 · see citing works
Mitochondria-Targeted Small Molecule Therapeutics and Probes
Smith, R. A. J., Hartley, R. C., & Murphy, M. P. (2011) · Antioxidants & Redox Signaling · doi:10.1089/ars.2011.3969 · Cited by 399 · see citing works
Self-citationCochemé, H. M., Quin, C., McQuaker, S. J., Cabreiro, F., Logan, A., Prime, T. A., Abakumova, I., Patel, J. V., Fearnley, I. M., James, A. M., et al. (2011) · Cell Metabolism · doi:10.1016/j.cmet.2011.02.003 · Cited by 313 · see citing works
Self-citationMolecular Strategies for Targeting Antioxidants to Mitochondria: Therapeutic Implications
Apostolova, N., & Víctor, V. M. (2014) · Antioxidants and Redox Signaling · doi:10.1089/ars.2014.5952 · Cited by 303 · see citing works
Dodani, S. C., Leary, S. C., Cobine, P. A., Winge, D. R., & Chang, C. J. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2004158 · Cited by 300 · see citing works
Vendrov, A. E., Vendrov, K. C., Smith, A., Yuan, J., Sumida, A., Robidoux, J., Runge, M. S., & Madamanchi, N. R. (2015) · Antioxidants and Redox Signaling · doi:10.1089/ars.2014.6221 · Cited by 219 · see citing works
Dare, A. J., Bolton, E. A., Pettigrew, G. J., Bradley, J. A., Saeb-Parsy, K., & Murphy, M. P. (2015) · Redox Biology · doi:10.1016/j.redox.2015.04.008 · Cited by 202 · see citing works
Self-citationLi, W., Wu, J., Xiang, D., Luo, S., Hu, X.-B., Tang, T., Sun, T., & Liu, X.-Y. (2019) · International Journal of Nanomedicine · doi:10.2147/ijn.s219670 · Cited by 187 · see citing works
Hearn, J. M., Romero‐Canelón, I., Qamar, B., Liu, Z., Hands-Portman, I., & Sadler, P. J. (2013) · ACS Chemical Biology · doi:10.1021/cb400070a · Cited by 164 · see citing works
Understanding and preventing mitochondrial oxidative damage
Murphy, M. P. (2016) · Biochemical Society Transactions · doi:10.1042/bst20160108 · Cited by 160 · see citing works
Self-citationThe Mitochondrial Complex(I)ty of Cancer
Urra, F. A., Muñoz, F., Lovy, A., & Cárdenas, C. (2017) · Frontiers in Oncology · doi:10.3389/fonc.2017.00118 · Cited by 149 · see citing works
Molecular Vehicles for Mitochondrial Chemical Biology and Drug Delivery
Jean, S. R., Tulumello, D. V., Wisnovsky, S., Lei, E. K., Pereira, M. P., & Kelley, S. O. (2014) · ACS Chemical Biology · doi:10.1021/cb400821p · Cited by 144 · see citing works
Gruber, J., Fong, S., Chen, C.-B., Yoong, S. L., Pastorin, G., Schaffer, S., Cheah, I. K.-M., & Halliwell, B. B. (2012) · Biotechnology Advances · doi:10.1016/j.biotechadv.2012.09.005 · Cited by 137 · see citing works
Cochemé, H. M., Logan, A., Prime, T. A., Abakumova, I., Quin, C., McQuaker, S. J., Patel, J. V., Fearnley, I. M., James, A. M., Porteous, C. M., et al. (2012) · Nature Protocols · doi:10.1038/nprot.2012.035 · Cited by 128 · see citing works
Self-citationPower of mitochondrial drug delivery systems to produce innovative nanomedicines
Yamada, Y., Satrialdi, S., Hibino, M., Sasaki, D., Abe, J., & Harashima, H. (2020) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2020.09.010 · Cited by 129 · see citing works
Rovira‐Llopis, S., Apostolova, N., Bañuls, C., Muntané, J., Rocha, M., & Víctor, V. M. (2017) · Antioxidants and Redox Signaling · doi:10.1089/ars.2017.7313 · Cited by 120 · see citing works
Dare, A. J., Logan, A., Prime, T. A., Rogatti, S., Goddard, M., Bolton, E. M., Bradley, J. A., Pettigrew, G. J., Murphy, M. P., & Saeb-Parsy, K. (2015) · The Journal of Heart and Lung Transplantation · doi:10.1016/j.healun.2015.05.007 · Cited by 119 · see citing works
Self-citationManganese Superoxide Dismutase Dysfunction and the Pathogenesis of Kidney Disease
Kitada, M., Xu, J., Ogura, Y., Monno, I., & Koya, D. (2020) · Frontiers in Physiology · doi:10.3389/fphys.2020.00755 · Cited by 117 · see citing works
Logan, A., Pell, V. R., Shaffer, K. J., Evans, C., Stanley, N., Robb, E. L., Prime, T. A., Chouchani, E. T., Cochemé, H. M., Fearnley, I. M., et al. (2015) · Cell Metabolism · doi:10.1016/j.cmet.2015.11.014 · Cited by 107 · see citing works
Self-citationReddy, C. A., Venkateswarlu, S., Golakoti, T., Kanugula, A. K., Karnewar, S., Karthikraj, R., Nagarjuna, V., Prabhakar, S., Kuppusamy, P., Kotamraju, S., et al. (2014) · PLoS ONE · doi:10.1371/journal.pone.0089351 · Cited by 107 · see citing works
A mitochondria-targeted inhibitor of cytochrome c peroxidase mitigates radiation-induced death
Atkinson, J., Kapralov, A. A., Yanamala, N. V. K., Tyurina, Y. Y., Amoscato, A. A., Pearce, L. L., Peterson, J., Huang, Z., Jiang, J., Samhan-Arias, A. K., et al. (2011) · Nature Communications · doi:10.1038/ncomms1499 · Cited by 106 · see citing works
Zang, Q. S., Sadek, H. A., Maass, D. L., Martinez, B., Ma, L., Kilgore, J. A., Williams, N. S., Frantz, D. E., Wigginton, J. G., Nwariaku, F. E., et al. (2012) · American Journal of Physiology-Heart and Circulatory Physiology · doi:10.1152/ajpheart.00203.2011 · Cited by 103 · see citing works
Moving Forwards by Blocking Back-Flow
Pell, V. R., Chouchani, E. T., Murphy, M. P., Brookes, P. S., & Krieg, T. (2016) · Circulation Research · doi:10.1161/circresaha.115.306569 · Cited by 101 · see citing works
Self-citationMitoNeoD: A Mitochondria-Targeted Superoxide Probe
Shchepinova, M. M., Cairns, A. G., Prime, T. A., Logan, A., James, A. M., Hall, A. R., Vidoni, S., Arndt, S., Caldwell, S. T., Prag, H. A., et al. (2017) · Cell chemical biology · doi:10.1016/j.chembiol.2017.08.003 · Cited by 99 · see citing works
Self-citationTriphenylphosphonium (TPP)‐Based Antioxidants: A New Perspective on Antioxidant Design
Wang, J., Li, J. Q., Xiao, Y., Fu, B., & Qin, Z. (2020) · ChemMedChem · doi:10.1002/cmdc.201900695 · Cited by 99 · see citing works
Coenzyme Q10 Analogues: Benefits and Challenges for Therapeutics
Suarez-Rivero, J. M., Pastor‐Maldonado, C. J., Povea-Cabello, S., Álvarez-Córdoba, M., Villalón-García, I., Munuera-Cabeza, M., Suárez-Carrillo, A., Talaverón-Rey, M., & Sánchez-Alcázar, J. A. (2021) · Antioxidants · doi:10.3390/antiox10020236 · Cited by 94 · see citing works
Strategies for oral delivery and mitochondrial targeting of CoQ10
Zaki, N. M. (2014) · Drug Delivery · doi:10.3109/10717544.2014.993747 · Cited by 85 · see citing works
Villamena, F. A., Das, A. K., & Nash, K. M. (2012) · Future Medicinal Chemistry · doi:10.4155/fmc.12.74 · Cited by 79 · see citing works
Flavonoids and mitochondrial pharmacology: A new paradigm for cardioprotection
Testai, L. (2015) · Life Sciences · doi:10.1016/j.lfs.2015.04.017 · Cited by 77 · see citing works
Mitochondrial Potassium Channels as Pharmacological Target for Cardioprotective Drugs
Testai, L., Rapposelli, S., Martelli, A., Breschi, M. C., & Calderone, V. (2014) · Medicinal Research Reviews · doi:10.1002/med.21332 · Cited by 74 · see citing works
TPP-based mitocans: a potent strategy for anticancer drug design
Wang, J., Li, J., Xiao, Y., Fu, B., & Qin, Z. (2020) · RSC Medicinal Chemistry · doi:10.1039/c9md00572b · Cited by 71 · see citing works
Paleos, C. M., Tsiourvas, D., & Sideratou, Z. (2016) · Molecular Pharmaceutics · doi:10.1021/acs.molpharmaceut.6b00237 · Cited by 67 · see citing works
Finichiu, P. G., James, A. M., Larsen, L., Smith, R. A. J., & Murphy, M. P. (2012) · Journal of Bioenergetics and Biomembranes · doi:10.1007/s10863-012-9493-5 · Cited by 65 · see citing works
Self-citationChen, W., Gong, W., Ye, Z., Yuan, L., & Ning, G. (2013) · Dalton Transactions · doi:10.1039/c3dt50832c · Cited by 65 · see citing works
Atamna, H., Mackey, J., & Dhahbi, J. M. (2012) · BioFactors · doi:10.1002/biof.197 · Cited by 64 · see citing works
Monitoring clinical progression with mitochondrial disease biomarkers
Steele, H. E., Horváth, R., Lyon, J. J., & Chinnery, P. F. (2017) · Brain · doi:10.1093/brain/awx168 · Cited by 62 · see citing works
Using exomarkers to assess mitochondrial reactive species in vivo
Logan, A., Cochemé, H. M., Pun, P. B. L., Apostolova, N., Smith, R. A. J., Larsen, L., Larsen, D. S., James, A. M., Fearnley, I. M., Rogatti, S., et al. (2013) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2013.05.026 · Cited by 58 · see citing works
Self-citationKuznetsova, D. A., Gaynanova, G. A., Vasileva, L. A., Sibgatullina, G., Samigullin, D. V., Sapunova, А. S., Voloshina, A. D., Galkina, I. V., Petrov, K. A., & Zakharova, L. Y. (2019) · Journal of Materials Chemistry B · doi:10.1039/c9tb01853k · Cited by 56 · see citing works
Ikeda, K., Marutani, E., Hirai, S., Wood, M. E., Whiteman, M., & Ichinose, F. (2015) · Nitric Oxide · doi:10.1016/j.niox.2015.05.001 · Cited by 54 · see citing works
A mitochondria-targeted mass spectrometry probe to detect glyoxals: implications for diabetes
Pun, P. B. L., Logan, A., Darley-Usmar, V. M., Chacko, B. K., Johnson, M. S., Huang, G. W., Rogatti, S., Prime, T. A., Methner, C., Krieg, T., et al. (2013) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2013.11.025 · Cited by 53 · see citing works
Self-citationRocha, M., Apostolova, N., Herance, J. R., Rovira‐Llopis, S., Hernández‐Mijares, A., & Víctor, V. M. (2013) · Medicinal Research Reviews · doi:10.1002/med.21285 · Cited by 51 · see citing works
Li, Q., Zhou, T. J., Wu, F., Li, N., Wang, R., Zhao, Q. S., Ma, Y., Zhang, J., & Ma, B. (2018) · Drug Metabolism Reviews · doi:10.1080/03602532.2018.1512614 · Cited by 49 · see citing works
Martel, C., Huynh, L. H., Garnier, A., Ventura‐Clapier, R., & Brenner, C. (2012) · Biochemistry Research International · doi:10.1155/2012/213403 · Cited by 45 · see citing works
Dube, H., Selwood, D. L., Malouitre, S. D. M., Capano, M., Simone, M. I., & Crompton, M. (2011) · Biochemical Journal · doi:10.1042/bj20111301 · Cited by 45 · see citing works
Long-Circulating Amphiphilic Doxorubicin for Tumor Mitochondria-Specific Targeting
Xi, J., Li, M. C., Jing, B., An, M., Yu, C., Pinnock, C. B., Zhu, Y., Lam, M. T., & Liu, H. (2018) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.8b17399 · Cited by 45 · see citing works
Fluorescent Polymers Conspectus
Ahumada, G., & Borkowska, M. (2022) · Polymers · doi:10.3390/polym14061118 · Cited by 43 · see citing works
Dunn, E. A., Roxburgh, M., Larsen, L., Smith, R. A. J., McLellan, A. D., Heikal, A., Murphy, M. P., & Cook, G. M. (2014) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2014.07.050 · Cited by 43 · see citing works
Self-citationMiljković, J. L., Burger, N., Gawel, J. M., Mulvey, J. F., Norman, A. A. I., Nishimura, T., Tsujihata, Y., Logan, A., Sauchanka, O., Caldwell, S. T., et al. (2022) · Redox Biology · doi:10.1016/j.redox.2022.102429 · Cited by 39 · see citing works
Self-citationA BODIPY‐Based Water‐Soluble Fluorescent Probe for Mitochondria Targeting
Sui, B., Tang, S. Y., Woodward, A. W., Kim, B., & Belfield, K. D. (2016) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201600238 · Cited by 40 · see citing works
Arndt, S., Baeza-Garza, C. D., Logan, A., Rosa, T., Wedmann, R., Prime, T. A., Martin, J. L., Saeb‐Parsy, K., Krieg, T., Filipović, M. R., et al. (2017) · Journal of Biological Chemistry · doi:10.1074/jbc.m117.784678 · Cited by 38 · see citing works
Self-citationLiu, X., Murphy, M. P., Xing, W., Wu, H., Zhang, R., & Sun, H. (2017) · Magnetic Resonance in Medicine · doi:10.1002/mrm.26772 · Cited by 37 · see citing works
Self-citationHamed, M. O., Logan, A., Gruszczyk, A. V., Beach, T. E., James, A. M., Dare, A. J., Barlow, A. D., Martin, J. L., Georgakopoulos, N., Gane, A., et al. (2021) · British journal of surgery · doi:10.1093/bjs/znab108 · Cited by 37 · see citing works
Self-citationMitoQ Inhibits Human Breast Cancer Cell Migration, Invasion and Clonogenicity
Capelôa, T., Krzystyniak, J., d’Hose, D., Rodriguez, A. C., Payen, V. L., Zampieri, L. X., de Velde, J. A. V., Benyahia, Z., Pranzini, E., Vazeille, T., et al. (2022) · Cancers · doi:10.3390/cancers14061516 · Cited by 35 · see citing works
Self-citationDelocalized Lipophilic Cation Triphenyl Phosphonium: Promising Molecule for Mitochondria Targeting
Pawar, A., Korake, S., Pawar, A., & Kamble, R. N. (2022) · Current Drug Delivery · doi:10.2174/1567201819666220525092527 · Cited by 35 · see citing works
Young, K. A., Hosseini, M., Mistry, J. J., Morganti, C., Mills, T., Cai, X., James, B., Nye, G. J., Fournier, N. R., Voisin, V., et al. (2025) · Nature Communications · doi:10.1038/s41467-025-57238-2 · Cited by 36 · see citing works
Dai, F., Jin, F., Long, Y., Jin, X., & Zhou, B. (2018) · Free Radical Research · doi:10.1080/10715762.2018.1446530 · Cited by 33 · see citing works
Sonocatalytic Optimization of Titanium‐Based Therapeutic Nanomedicine
Zhou, R.-R., Chang, M., Shen, M., Cong, Y., Chen, Y., & Wang, Y. (2023) · Advanced Science · doi:10.1002/advs.202301764 · Cited by 32 · see citing works
Teranishi, R., Matsuda, T., Yuba, E., Kono, K., & Harada, A. (2019) · Macromolecular Bioscience · doi:10.1002/mabi.201800365 · Cited by 32 · see citing works
Is metabolic stress a common denominator in inflammatory bowel disease?
Schoultz, I., Söderholm, J. D., & McKay, D. M. (2010) · Inflammatory Bowel Diseases · doi:10.1002/ibd.21556 · Cited by 30 · see citing works
MitoQ Prevents Human Breast Cancer Recurrence and Lung Metastasis in Mice
Capelôa, T., Krzystyniak, J., Rodriguez, A. C., Payen, V. L., Zampieri, L. X., Pranzini, E., Derouane, F., Vazeille, T., Bouzin, C., Duhoux, F. P., et al. (2022) · Cancers · doi:10.3390/cancers14061488 · Cited by 31 · see citing works
Self-citationPrag, H. A., Kula‐Alwar, D., Pala, L., Caldwell, S. T., Beach, T. E., James, A. M., Saeb‐Parsy, K., Krieg, T., Hartley, R. C., & Murphy, M. P. (2020) · Molecular Pharmaceutics · doi:10.1021/acs.molpharmaceut.0c00533 · Cited by 30 · see citing works
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Barnoud, T., Leung, J. C., Leu, J. I.-J., Basu, S., Poli, A. N. R., Parris, J. L. D., Indeglia, A., Martynyuk, T., Good, M., Gnanapradeepan, K., et al. (2020) · Cancer Research · doi:10.1158/0008-5472.can-20-0397 · Cited by 30 · see citing works
Self-citationCytotoxic Triosmium Carbonyl Clusters: A Structure–Activity Relationship Study
Lee, H. Z. S., Leong, W. K., Top, S., & Vessières, A. (2014) · ChemMedChem · doi:10.1002/cmdc.201300394 · Cited by 29 · see citing works
One-Pot Multi-Tracer Synthesis of Novel 18 F-Labeled PET Imaging Agents
Haslop, A., Wells, L. A., Gee, A. D., Plisson, C., & Long, N. J. (2014) · Molecular Pharmaceutics · doi:10.1021/mp500324n · Cited by 29 · see citing works
A flow-cytometry-based protocol for detection of mitochondrial ROS production under hypoxia
Yang, Y., Zhang, G., Yang, T., Gan, J., Xu, L., & Yang, H. (2021) · STAR Protocols · doi:10.1016/j.xpro.2021.100466 · Cited by 27 · see citing works
Engineering Mitochondriotropic Carbon Dots for Targeting Cancer Cells
Kaminari, A., Nikoli, E., Αθανασόπουλος, Α., Sakellis, E., Sideratou, Z., & Tsiourvas, D. (2021) · Pharmaceuticals · doi:10.3390/ph14090932 · Cited by 27 · see citing works
Strategies to target bioactive molecules to subcellular compartments. Focus on natural compounds
Biasutto, L., Mattarei, A., Spina, M. L., Azzolini, M., Parrasia, S., Szabó, I., & Zoratti, M. (2019) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2019.07.060 · Cited by 26 · see citing works
Progress and Problems in Nutraceuticals Delivery
Zaki, N. M. (2014) · Journal of Bioequivalence & Bioavailability · doi:10.4172/jbb.10000183 · Cited by 26 · see citing works
Porteous, C. M., Menon, D. K., Aigbirhio, F. I., Smith, R. A. J., & Murphy, M. P. (2013) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2013.02.005 · Cited by 25 · see citing works
Self-citationSalin, K., Auer, S. K., Villasevil, E. M., Anderson, G. J., Cairns, A. G., Mullen, W., Hartley, R. C., & Metcalfe, N. B. (2017) · Scientific Reports · doi:10.1038/srep41228 · Cited by 25 · see citing works
Estimating the binding ability of onium ions with CO 2 and π systems: a computational investigation
Hussain, M. A., Mahadevi, A. S., & Sastry, G. N. (2014) · Physical Chemistry Chemical Physics · doi:10.1039/c4cp03434a · Cited by 21 · see citing works
Mitochondrial-Targeted Molecular Imaging in Cardiac Disease
Li, J., Lu, J., & Zhou, Y. (2017) · BioMed Research International · doi:10.1155/2017/5246853 · Cited by 21 · see citing works
Modulation of cellular redox environment as a novel therapeutic strategy for Parkinson's disease
Deus, C. M., Teixeira, J., Raimundo, N., Tucci, P., Borges, F., Saso, L., & Oliveira, P. J. (2022) · European Journal of Clinical Investigation · doi:10.1111/eci.13820 · Cited by 21 · see citing works
Multiple Triphenylphosphonium Cations as a Platform for the Delivery of a Pro-Apoptotic Peptide
Kolevzon, N., Kuflik, U., Shmuel, M., Benhamron, S., Ringel, I., & Yavin, E. (2011) · Pharmaceutical Research · doi:10.1007/s11095-011-0494-6 · Cited by 20 · see citing works
An Inhibitor of the Interaction of Survivin with Smac in Mitochondria Promotes Apoptosis
Park, S., Shin, I.-S., Park, S., Kim, N. D., & Shin, I. (2019) · Chemistry - An Asian Journal · doi:10.1002/asia.201900587 · Cited by 20 · see citing works
Flavonoids as new regulators of mitochondrial potassium channels: contribution to cardioprotection
Kampa, R. P., Sęk, A., Bednarczyk, P., Szewczyk, A. M., Calderone, V., & Testai, L. (2022) · Journal of Pharmacy and Pharmacology · doi:10.1093/jpp/rgac093 · Cited by 19 · see citing works
Chavarria, D., da Silva, O., Benfeito, S., Barreiro, S., Garrido, J. M. P. J., Cagide, F., Soares, P., Remião, F., Brazzolotto, X., Nachon, F., et al. (2021) · Antioxidants · doi:10.3390/antiox10020329 · Cited by 18 · see citing works
Chen, W., Zhang, D.-W., Gong, W., Lin, Y., & Ning, G. (2013) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2013.03.088 · Cited by 18 · see citing works
Kell, D. B. (2021) · Advances in microbial physiology/Advances in Microbial Physiology · doi:10.1016/bs.ampbs.2021.01.001 · Cited by 16 · see citing works
Urban, C., Charif, M., Goffin, E., Heugen, J.-C. V., Elmoualij, B., Chiap, P., Mouithys-Mickalad, A. A., Serteyn, D. A., Lebrun, P., Pirotte, B., et al. (2013) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2013.08.091 · Cited by 15 · see citing works
Wang, S., Yin, H., Huang, Y., & Guan, X. (2018) · Analytical Chemistry · doi:10.1021/acs.analchem.8b01469 · Cited by 13 · see citing works
Gheybi, H., Sattari, S., Bodaghi, A., Soleimani, K., Dadkhah, A., & Adeli, M. (2018) · Elsevier eBooks · doi:10.1016/b978-0-08-101750-0.00005-2 · Cited by 13 · see citing works
Samiee, S., Bahmaie, M., Motamedi, H., Shiralinia, A., & Gable, R. W. (2020) · Polyhedron · doi:10.1016/j.poly.2020.114567 · Cited by 11 · see citing works
Ribeiro, J. A., Benfeito, S., Cagide, F., Teixeira, J., Oliveira, P. J., Borges, F., Silva, F., & Pereira, C. M. D. M. (2018) · Analytical Chemistry · doi:10.1021/acs.analchem.8b00787 · Cited by 11 · see citing works
Trends and methods for nanobased delivery for nutraceuticals
Rangan, A., Manjula, M. V., & Satyanarayana, K. G. (2016) · Elsevier eBooks · doi:10.1016/b978-0-12-804306-6.00017-9 · Cited by 9 · see citing works
Interdisciplinary advances reshape the delivery tools for effective NASH treatment
Chen, L., & Wang, Y. (2023) · Molecular Metabolism · doi:10.1016/j.molmet.2023.101730 · Cited by 9 · see citing works
Cytostatic Effect of a Novel Mitochondria-Targeted Pyrroline Nitroxide in Human Breast Cancer Lines
Andreidesz, K., Szabó, A., Kovács, D., Kőszegi, B., Vántus, V. B., Vámos, E., Isbera, M., Kálai, T., Bognár, Z., Kovács, K., et al. (2021) · International Journal of Molecular Sciences · doi:10.3390/ijms22169016 · Cited by 8 · see citing works
Mitochondria-Targeted Antioxidants
Smith, R. A. J., Hartley, R. C., & Murphy, M. P. (2012) · Oxidative stress and disease · doi:10.1201/b12308-8 · Cited by 7 · see citing works
Self-citationXu, Z., Qian, J., Ge, Y.-F., Wang, Y., & Chen, H. (2022) · Molecules · doi:10.3390/molecules27154858 · Cited by 8 · see citing works
Li, L., Brichard, L., Larsen, L., Menon, D. K., Smith, R. A. J., Murphy, M. P., & Aigbirhio, F. I. (2013) · Journal of Labelled Compounds and Radiopharmaceuticals · doi:10.1002/jlcr.3109 · Cited by 6 · see citing works
Self-citationBorodkin, S. A., Попов, Л. Д., Milenković, M. R., Milenković, M., Belošević, S., Anđelković, K., Tsaturyan, A. A., & Shcherbakov, I. N. (2017) · Phosphorus, sulfur, and silicon and the related elements · doi:10.1080/10426507.2017.1322592 · Cited by 6 · see citing works
Rapid mitochondrial repolarization upon reperfusion after cardiac ischemia
Giles, A. V., Covián, R., Prag, H. A., Burger, N., Lucotte, B. M., Yu, C. S., Sun, J., Murphy, E., Krieg, T., Murphy, M. P., et al. (2025) · Nature Cardiovascular Research · doi:10.1038/s44161-025-00752-9 · Cited by 5 · see citing works
Self-citationPriyanka, K., & Singh, S. K. (2019) · Journal of Drug Delivery Science and Technology · doi:10.1016/j.jddst.2019.05.002 · Cited by 5 · see citing works
Biomarkers of oxidative stress in antioxidant therapy
Rossi, W. M., Garrido, G., & Sellés, A. J. N. (2016) · Journal of Pharmacy & Pharmacognosy Research · doi:10.56499/jppres15.083_4.2.62 · Cited by 4 · see citing works
Novel Pt (II) Complexes With Anticancer Activity Against Pancreatic Ductal Adenocarcinoma Cells
Stefàno, E., Rovito, G., Cossa, L. G., Castro, F. D., Vergaro, V., Ali, A., My, G., Migoni, D., Muscella, A., Marsigliante, S., et al. (2024) · Bioinorganic Chemistry and Applications · doi:10.1155/bca/5588491 · Cited by 2 · see citing works
Synthesis, Structure, and Properties of Novel Enamine Containing Coumarin and Phosphonium Fragments
Попов, Л. Д., Shcherbakov, I. N., Borodkin, S. A., Revinskii, Y. V., Kazoyan, E. A., Шагинян, Г. А., Sarkisyan, A. R., & Markaryan, S. A. (2019) · Russian Journal of General Chemistry · doi:10.1134/s1070363219050086 · Cited by 2 · see citing works
Yu, E., Calvert, P. A., Mercer, J. R., Harrison, J. B., Baker, L. L., Figg, N. L., Kumar, S., Wang, J. J., Hurst, L. A., Obaid, D. R., et al. (2014) · Circulation · doi:10.1161/circulationaha.113.008032 · Cited by 2 · see citing works
Self-citation
- Authors
- Porteous, C. M., Logan, A., Evans, C., Ledgerwood, E. C., Menon, D. K., Aigbirhio, F., Smith, R. A. J., & Murphy, M. P.
- Affiliations
- University of Otago (NZ)
- MRC Mitochondrial Biology Unit (GB)
- University of Cambridge (GB)
- Corresponding author
- Murphy, Michael P.
- Venue
- Biochimica et Biophysica Acta (BBA) - General Subjects
- Publisher
- Elsevier BV
- Published
- 2010-09
- Volume
- 1800
- Issue
- 9
- Pages
- 1009-1017
- ISSN
- 0304-4165 (ISSN-L)
- OpenAlex
- W1971782930
- Cited by
- 121
- References
- 55
- Citations by year
- 2026: 4 · 2025: 7 · 2024: 1 · 2023: 4 · 2022: 9 · 2021: 8 · 2020: 7 · 2019: 10 · 2018: 6 · 2017: 12 · 2016: 7 · 2015: 7 · 2014: 12 · 2013: 11 · 2012: 9
- FWCI
- 3.52
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Biochimica et Biophysica Acta (BBA) - General Subjects (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institute for Health Research
- Asia New Zealand Foundation
- Medical Research Council
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Mitochondrial Function and Pathology
- Life Sciences › Neuroscience › Neurology › Neurological Disorders and Treatments
- Physical Sciences › Materials Science › Biomaterials › Nanoparticle-Based Drug Delivery
- Keywords
- triphenylphosphonium cation, mitochondrial membrane potential, mitochondrial uptake, mitochondria-targeted antioxidants, hydrophobic alkyl chains, mitochondrial dysfunction, mitochondrial damage, intravenous administration
- MeSH terms
- Animals, Antioxidants, Cations, Female, Injections, Intravenous, Mitochondria, Organophosphorus Compounds, Drug Delivery Systems, Mitochondrial Diseases, Mice, Membrane Potential, Mitochondrial
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