MitoE10 | CAS#1810703-64-0 | antioxidant

MedKoo Cat#: 522665 | Name: MitoE10

Description:

WARNING: This product is for research use only, not for human or veterinary use.

MitoE10 is a potent mitochondria-targeted antioxidant. Structurally, MitoE10 is a lipophilic triphenylphosphonium cation attached to the antioxidant chroman moiety of vitamin E by a linear C10 carbon linker. itoE. MitoE10 can efficiently accumulate in mitochondria and preliminary biological data demonstrate that MitoE10 shows greater efficacy in preventing lipid peroxidation, mitochondrial oxidative damage and damage to mitochondrial DNA than non-targeted compounds.

Chemical Structure

MitoE10

CAS#1810703-64-0 (mesylate)

Theoretical Analysis

MedKoo Cat#: 522665

Name: MitoE10

CAS#: 1810703-64-0 (mesylate)

Chemical Formula: C42H55O5PS

Exact Mass:

Molecular Weight: 702.93

Elemental Analysis: C, 71.77; H, 7.89; O, 11.38; P, 4.41; S, 4.56

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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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

Appearance

Solid powder

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.

Instruction

View handling instruction

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.