MitoQ

MitoQ
Names

IUPAC name Phosphonium, [10-(4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien- 1-yl)decyl]triphenyl-, methanesulfonate
Other names mitoquinone mesylate, MitoQ10, mitoubiquinone mesylate
Identifiers
CAS Number	845959-50-4^Y
3D model (JSmol)	Interactive image
ChemSpider	9563239
PubChem CID	11388331
UNII	6E01CG547T^Y
InChI InChI=1S/C37H44O4P.CH4O3S/c1-29-33(35(39)37(41-3)36(40-2)34(29)38)27-19-8-6-4-5-7-9-20-28-42(30-21-13-10-14-22-30,31-23-15-11-16-24-31)32-25-17-12-18-26-32;1-5(2,3)4/h10-18,21-26H,4-9,19-20,27-28H2,1-3H3;1H3,(H,2,3,4)/q+1;/p-1 Key: GVZFUVXPTPGOQT-UHFFFAOYSA-M InChI=1/C37H44O4P.CH4O3S/c1-29-33(35(39)37(41-3)36(40-2)34(29)38)27-19-8-6-4-5-7-9-20-28-42(30-21-13-10-14-22-30,31-23-15-11-16-24-31)32-25-17-12-18-26-32;1-5(2,3)4/h10-18,21-26H,4-9,19-20,27-28H2,1-3H3;1H3,(H,2,3,4)/q+1;/p-1 Key: GVZFUVXPTPGOQT-REWHXWOFAQ
SMILES CC1=C(C(=O)C(=C(C1=O)OC)OC)CCCCCCCCCC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.CS(=O)(=O)[O-]
Properties
Chemical formula	C₃₈H₄₇O₇PS
Molar mass	678.82 g·mol⁻¹
Appearance	Viscous orange syrup
Solubility	dichloromethane, ethanol, methanol, chloroform, water(Insoluble in hexane, ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

MitoQ is a mitochondria-targeted antioxidant designed to protect against oxidative damage within mitochondria, an essential organelle within most cells that use oxygen to break down carbohydrates and fat to release energy in a form the cell can use. MitoQ was designed to decrease mitochondrial oxidative damage and has undergone clinical trials in humans with positive and negative results.^[1]^[2]^[3]

Design and synthesis

MitoQ was designed in the late 1990s as a mitochondria-targeted antioxidant by Michael P. Murphy and Robin A. J. Smith,^[4] and synthesised by Geoffrey Kelso.,^[4] at the University of Otago, Dunedin, New Zealand.

References

↑ E.J. Gane, F. Weilert, D.W. Orr, G.F. Keogh, M. Gibson, M.M. Lockhart, C.M. Frampton, K.M. Taylor, R.A. Smith, M.P. Murphy, The mitochondria-targeted anti-oxidant mitoquinone decreases liver damage in a phase II study of hepatitis C patients, Liver Int, 30 (2010) 1019–1026.
↑ B.J. Snow, F.L. Rolfe, M.M. Lockhart, C.M. Frampton, J.D. O'Sullivan, V. Fung, R.A. Smith, M.P. Murphy, K.M. Taylor, A double-blind, placebo-controlled study to assess the mitochondria-targeted antioxidant MitoQ as a disease-modifying therapy in Parkinson's disease, Movement disorders : official journal of the Movement Disorder Society, 25 (2010) 1670–1674.
↑ R.A. Smith, M.P. Murphy, Animal and human studies with the mitochondria-targeted antioxidant MitoQ, Annals of the New York Academy of Sciences, 1201 (2010) 96-103.
1 2 G.F. Kelso, C.M. Porteous, C.V. Coulter, G. Hughes, W.K. Porteous, E.C. Ledgerwood, R.A. Smith, M.P. Murphy, Selective targeting of a redox-active ubiquinone to mitochondria within cells: antioxidant and antiapoptotic properties, The Journal of biological chemistry, 276 (2001) 4588-4596.

External links

JBC Article – Interaction of the Mitochondria-targeted Antioxidant MitoQ with Phospholipid Bilayers and Ubiquinone Oxidoreductases
James, AM; Sharpley, MS; Manas, AR; Frerman, FE; Hirst, J; Smith, RA; Murphy, MP (May 18, 2007). "Interaction of the mitochondria-targeted antioxidant MitoQ with phospholipid bilayers and ubiquinone oxidoreductases.". The Journal of Biological Chemistry. 282 (20): 14708–18. PMID 17369262. doi:10.1074/jbc.m611463200.
Medical Research Council – Targeting Small Molecules to Mitochondria
http://www.mitoq.com — Official website

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