Related CAS #
1810703-64-0 (mesylate),1810703-63-9 (cation)
Synonym
MitoE10; Mito E10; MitoE-10; Vitaman E-triphenylphosphonium conjugate.
IUPAC/Chemical Name
(10-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)decyl)triphenylphosphonium methanesulfonate
InChi Key
ZAYCMFYORHFHOR-UHFFFAOYSA-N
InChi Code
InChI=1S/C41H51O2P.CH4O3S/c1-32-33(2)40-38(34(3)39(32)42)28-30-41(4,43-40)29-20-9-7-5-6-8-10-21-31-44(35-22-14-11-15-23-35,36-24-16-12-17-25-36)37-26-18-13-19-27-37;1-5(2,3)4/h11-19,22-27H,5-10,20-21,28-31H2,1-4H3;1H3,(H,2,3,4)
SMILES Code
CC1=C(C)C(O)=C(C)C2=C1OC(CCCCCCCCCC[P+](C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)(C)CC2.CS(=O)([O-])=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Mitochondria are essential to the functioning of most eukaryotic cells because they provide the energy necessary for cell activities in the form of an elevated adenosine triphosphate/diphosphate ratio by oxidative phosphorylation. Because free radicals are produced as a side product of this respiration, mitochondrial localised oxidative damage accumulates faster than in the rest of the cell. Mitochondrial dysfunction due to oxidative damage has been implicated in a wide range of conditions from ageing, ischaemia-reperfusion injury, cancer, epilepsy and to neurodegenerative diseases such as amyotrophic lateral sclerosis16 and Alzheimer's and Parkinson's diseases. Because of the roles mitochondria play in a wide range of pathologies, the engineering of molecules to prevent mitochondrial oxidative damage has therapeutic potential.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
702.93
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Jameson VJ, Cochemé HM, Logan A, Hanton LR, Smith RA, Murphy MP. Synthesis of triphenylphosphonium vitamin E derivatives as mitochondria-targeted antioxidants. Tetrahedron. 2015 Nov 4;71(44):8444-8453. PubMed PMID: 26549895; PubMed Central PMCID: PMC4596152.
2: de Campos RP, Siegel JM, Fresta CG, Caruso G, da Silva JA, Lunte SM. Indirect detection of superoxide in RAW 264.7 macrophage cells using microchip electrophoresis coupled to laser-induced fluorescence. Anal Bioanal Chem. 2015 Sep;407(23):7003-12. doi: 10.1007/s00216-015-8865-1. Epub 2015 Jul 10. PubMed PMID: 26159570.
3: Ramis MR, Esteban S, Miralles A, Tan DX, Reiter RJ. Protective Effects of Melatonin and Mitochondria-targeted Antioxidants Against Oxidative Stress: A Review. Curr Med Chem. 2015;22(22):2690-711. PubMed PMID: 26087763.
4: Reily C, Mitchell T, Chacko BK, Benavides G, Murphy MP, Darley-Usmar V. Mitochondrially targeted compounds and their impact on cellular bioenergetics. Redox Biol. 2013;1(1):86-93. PubMed PMID: 23667828; PubMed Central PMCID: PMC3647698.
5: Lowes DA, Webster NR, Murphy MP, Galley HF. Antioxidants that protect mitochondria reduce interleukin-6 and oxidative stress, improve mitochondrial function, and reduce biochemical markers of organ dysfunction in a rat model of acute sepsis. Br J Anaesth. 2013 Mar;110(3):472-80. doi: 10.1093/bja/aes577. Epub 2013 Feb 4. PubMed PMID: 23381720; PubMed Central PMCID: PMC3570068.
6: Bai JZ, Lipski J. Differential expression of TRPM2 and TRPV4 channels and their potential role in oxidative stress-induced cell death in organotypic hippocampal culture. Neurotoxicology. 2010 Mar;31(2):204-14. doi: 10.1016/j.neuro.2010.01.001. Epub 2010 Jan 12. PubMed PMID: 20064552.
7: Leo S, Szabadkai G, Rizzuto R. The mitochondrial antioxidants MitoE(2) and MitoQ(10) increase mitochondrial Ca(2+) load upon cell stimulation by inhibiting Ca(2+) efflux from the organelle. Ann N Y Acad Sci. 2008 Dec;1147:264-74. doi: 10.1196/annals.1427.019. PubMed PMID: 19076448; PubMed Central PMCID: PMC2676430.
