Original: Mitoquinone mesylate, ethanol solution 845959-50-4 , stock more than 100g

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Description: Mitoquinone mesylate, also known as MitoQ or MitoQ10; is a mitochondria-targeted antioxidant designed to accumulate within mitochondria in vivo in order to protect against oxidative damage. MitoQ comprises a positively charged lipophilic cation that drives its extensive accumulation within the negatively charged mitochondria inside cells. The active antioxidant component of MitoQ is ubiquinone, which is identical to the active antioxidant in Coenzyme Q10. It is this approximately thousand-fold greater concentration of MitoQ within mitochondria that makes it more effective at preventing mitochondrial oxidative damage when compared to untargeted antioxidants such as Coenzyme Q10. NOTE: For the convenience of use, this product is supplied as 200mg /mL solution in ethanol-water (1:1, v/v) solution since pure MitoQ10 is a tar-like or waxy semi-solid and very hard to transfer between containers.

Name: Mitoquinone mesylate, ethanol solution 
CAS#: 845959-50-4 (mesylate) 
Chemical Formula: C38H47O7PS 
Exact Mass: 583.29717 
Molecular Weight: 678.82 
Elemental Analysis: C, 67.24; H, 6.98; O, 16.50; P, 4.56; S, 4.72

Related CAS #: 845959-50-4 (mesylate)   845959-52-6 (beta-CD complex)   444890-41-9 (cation)   336184-91-9 (bromide)    

Synonym: MitoQ; Mito Q10; MitoQ10; MitoQ-10; Mitoubiquinone mesylate; Mitoquinone methanesulfonate; Mitoquinone mesylate

IUPAC/Chemical Name: (10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl)triphenylphosphonium methanesulfonate

InChi Key: GVZFUVXPTPGOQT-UHFFFAOYSA-M

InChi Code: 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

SMILES Code: O=C(C(CCCCCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)=C4C)C(OC)=C(OC)C4=O.CS(=O)([O-])=O

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 and ethanol.

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO or ethanol.

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code: 293490

ADDITIONAL INFORMATION

MitoQ is the first molecule specifically designed to decrease mitochondrial oxidative damage to have undergone clinical trials in humans.

MitoQ was designed in the late 1990s as a mitochondria-targeted antioxidant by Michael P. Murphy and Robin A. J. Smith. At the time, both were at the University of Otago, Dunedin, New Zealand where Murphy was a mitochondrial biochemist in the Department of Biochemistry and Smith was an organic chemist at the Department of Chemistry. The molecule was made by a PhD student in Smith’s lab, Geoffrey Kelso, and the first publication on MitoQ was in 2001. Since then over 180 publications on MitoQ have been recorded. MitoQ is the first physiologically active form of CoQ10 specifically targeted to mitochondria in order to decrease oxidative damage to have undergone clinical trials in human patients.

MitoQ was designed to accumulate extensively within mitochondria in vivo in order to increase the local antioxidant capacity and thereby decrease mitochondrial oxidative damage. To do this MitoQ incorporates a lipophilic cation, that is a positively charged component that is sufficiently hydrophobic, or “oily”, to be able to pass directly through biological membranes. The lipophilic cation used is based on the triphenylphosphonium structure, which is well known to accumulate within the negative mitochondrial matrix. In the solid form of MitoQ the positive charge is neutralised with a negatively charged anion, typically mesylate, to form a salt. MitoQ is present in two different forms, the oxidised ubiquinone form, MitoQuinone and the reduced ubiquinol form, MitoQuinol. MitoQ can refer to either form or to a mixture of the forms.

One on the Phase II clinical trials was on Parkinson's disease where patients were given an oral MitoQ dose of 40 or 80 mg per day for a year and compared with placebo. This trial was registered on clinicaltrials.gov as NCT00329056. 

The Parkinson’s Disease trial did not show a benefit of MitoQ, probably because the irreversible neuronal damage was too great by the time the patients were diagnosed; however, this study did provide a year’s safety data. In the other trial patients with hepatitis C virus who were not responding to antiviral treatments were assessed for prevention of liver inflammation. This trial was registered on clinicaltrials.gov as NCT00433108. The trial in hepatitis C virus patients did show liver protection. These two trials showed that it was safe to target mitochondria in humans long term and other trials for MitoQ are now planned.

The development of MitoQ has led to two further developments. One was a skin cream incorporating MitoQ which is used to combat the signs of skin ageing (mitoq.com). The other was an oral supplement containing a low dose of MitoQ which can be used as a nutritional supplement. (from https://en.wikipedia.org/wiki/MitoQ).

REFERENCES

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2: Pokrzywinski KL, Biel TG, Kryndushkin D, Rao VA. Therapeutic Targeting of the Mitochondria Initiates Excessive Superoxide Production and Mitochondrial Depolarization Causing Decreased mtDNA Integrity. PLoS One. 2016 Dec 28;11(12):e0168283. doi: 10.1371/journal.pone.0168283. PubMed PMID: 28030582; PubMed Central PMCID: PMC5193408.

3: Chu FF, Esworthy RS, Doroshow JH, Grasberger H, Donko A, Leto TL, Gao Q, Shen B. Deficiency in Duox2 activity alleviates ileitis in GPx1- and GPx2-knockout mice without affecting apoptosis incidence in the crypt epithelium. Redox Biol. 2017 Apr;11:144-156. doi: 10.1016/j.redox.2016.11.001. PubMed PMID: 27930931; PubMed Central PMCID: PMC5148781.

4: Escribano-Lopez I, Diaz-Morales N, Rovira-Llopis S, de Marañon AM, Orden S, Alvarez A, Bañuls C, Rocha M, Murphy MP, Hernandez-Mijares A, Victor VM. The mitochondria-targeted antioxidant MitoQ modulates oxidative stress, inflammation and leukocyte-endothelium interactions in leukocytes isolated from type 2 diabetic patients. Redox Biol. 2016 Dec;10:200-205. doi: 10.1016/j.redox.2016.10.017. PubMed PMID: 27810734; PubMed Central PMCID: PMC5094376.

5: Sakellariou GK, Pearson T, Lightfoot AP, Nye GA, Wells N, Giakoumaki II, Griffiths RD, McArdle A, Jackson MJ. Long-term administration of the mitochondria-targeted antioxidant mitoquinone mesylate fails to attenuate age-related oxidative damage or rescue the loss of muscle mass and function associated with aging of skeletal muscle. FASEB J. 2016 Nov;30(11):3771-3785. Epub 2016 Aug 22. PubMed PMID: 27550965; PubMed Central PMCID: PMC5067250.

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7: Liu L, Wang MJ, Yu TH, Cheng Z, Li M, Guo QW. [Mitochondria-targeted antioxidant Mitoquinone protects post-thaw human sperm against oxidative stress injury]. Zhonghua Nan Ke Xue. 2016 Mar;22(3):205-11. Chinese. PubMed PMID: 27172658.

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9: Maiti AK, Sharba S, Navabi N, Forsman H, Fernandez HR, Lindén SK. IL-4 Protects the Mitochondria Against TNFα and IFNγ Induced Insult During Clearance of Infection with Citrobacter rodentium and Escherichia coli. Sci Rep. 2015 Oct 20;5:15434. doi: 10.1038/srep15434. PubMed PMID: 26481427; PubMed Central PMCID: PMC4613366.

10: Dare AJ, Logan A, Prime TA, Rogatti S, Goddard M, Bolton EM, Bradley JA, Pettigrew GJ, Murphy MP, Saeb-Parsy K. The mitochondria-targeted anti-oxidant MitoQ decreases ischemia-reperfusion injury in a murine syngeneic heart transplant model. J Heart Lung Transplant. 2015 Nov;34(11):1471-80. doi: 10.1016/j.healun.2015.05.007. PubMed PMID: 26140808; PubMed Central PMCID: PMC4626443.

11: Li Y, Yang J, Chen MH, Wang Q, Qin MJ, Zhang T, Chen XQ, Liu BL, Wen XD. Ilexgenin A inhibits endoplasmic reticulum stress and ameliorates endothelial dysfunction via suppression of TXNIP/NLRP3 inflammasome activation in an AMPK dependent manner. Pharmacol Res. 2015 Sep;99:101-15. doi: 10.1016/j.phrs.2015.05.012. PubMed PMID: 26054569.

12: Huang W, Cash N, Wen L, Szatmary P, Mukherjee R, Armstrong J, Chvanov M, Tepikin AV, Murphy MP, Sutton R, Criddle DN. Effects of the mitochondria-targeted antioxidant mitoquinone in murine acute pancreatitis. Mediators Inflamm. 2015;2015:901780. doi: 10.1155/2015/901780. PubMed PMID: 25878403; PubMed Central PMCID: PMC4386569.

13: Galarreta CI, Forbes MS, Thornhill BA, Antignac C, Gubler MC, Nevo N, Murphy MP, Chevalier RL. The swan-neck lesion: proximal tubular adaptation to oxidative stress in nephropathic cystinosis. Am J Physiol Renal Physiol. 2015 May 15;308(10):F1155-66. doi: 10.1152/ajprenal.00591.2014. PubMed PMID: 25694483.

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15: Ng MR, Antonelli PJ, Joseph J, Dirain CO. Assessment of mitochondrial membrane potential in HEI-OC1 and LLC-PK1 cells treated with gentamicin and mitoquinone. Otolaryngol Head Neck Surg. 2015 Apr;152(4):729-33. doi: 10.1177/0194599814564934. PubMed PMID: 25550222.

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17: Fink BD, Herlein JA, Guo DF, Kulkarni C, Weidemann BJ, Yu L, Grobe JL, Rahmouni K, Kerns RJ, Sivitz WI. A mitochondrial-targeted coenzyme q analog prevents weight gain and ameliorates hepatic dysfunction in high-fat-fed mice. J Pharmacol Exp Ther. 2014 Dec;351(3):699-708. doi: 10.1124/jpet.114.219329. PubMed PMID: 25301169; PubMed Central PMCID: PMC4244581.

18: Jadidian A, Antonelli PJ, Ojano-Dirain CP. Evaluation of apoptotic markers in HEI-OC1 cells treated with gentamicin with and without the mitochondria-targeted antioxidant mitoquinone. Otol Neurotol. 2015 Mar;36(3):526-30. doi: 10.1097/MAO.0000000000000517. PubMed PMID: 25076226.

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