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MedKoo Cat#: 577472 | Name: Mitoquinol mesylate

Description:

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

Mitoquinol, also known as MitoQ, is a mitochondrially targeted antioxidant. Mitoquinol is a reduced form of mitoquinone. MitoQ replenished mitochondrial SOD, GPx and GSH indicating its strong antioxidant effect in addition to its energy preservation manifested by the elevated ATP. MitoQ inhibited the intrinsic apoptosis via diminution of Bax, cytochrome-c and caspase-3 and alleviation of Bcl-2. MitoQ modulates expression of Nrf2 and enhances activity of mitochondrial SDH in cirrhotic-HCC rats via its interaction with key amino acid residues in the active pocket of BTB and KELCH domains of KEAP1 as well as amino residues at the active site of SDH. MitoQ may have potential usage for the treatment/management of liver cirrhosis and HCC.

Chemical Structure

Mitoquinol mesylate
Mitoquinol mesylate
CAS#845959-55-9 (mesylate)

Theoretical Analysis

MedKoo Cat#: 577472

Name: Mitoquinol mesylate

CAS#: 845959-55-9 (mesylate)

Chemical Formula: C38H49O7PS

Exact Mass: 680.2937

Molecular Weight: 680.84

Elemental Analysis: C, 67.04; H, 7.25; O, 16.45; P, 4.55; S, 4.71

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 #
747398-82-9 (cation) 845959-55-9 (mesylate)
Synonym
Mitoquinol mesylate; MitoQ;
IUPAC/Chemical Name
(10-(2,5-dihydroxy-3,4-dimethoxy-6-methylphenyl)decyl)triphenylphosphonium methanesulfonate
InChi Key
WPMXVYGZUOSRAN-UHFFFAOYSA-N
InChi Code
InChI=1S/C37H45O4P.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,(H-,38,39);1H3,(H,2,3,4)
SMILES Code
CC1=C(CCCCCCCCCC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C(O)=C(OC)C(OC)=C1O.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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 680.84 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.

Recalculate based on batch purity %
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: Sulaimon LA, Adisa RA, Samuel TA, Joel IY, Ayankojo AG, Abdulkareem FB, Olaniyi TO. Molecular mechanism of mitoquinol mesylate in mitigating the progression of hepatocellular carcinoma-in silico and in vivo studies. J Cell Biochem. 2021 Apr 28. doi: 10.1002/jcb.29937. Epub ahead of print. PMID: 33909925. 2: Rudolph TE, Mayorga EJ, Roths M, Rhoads RP, Baumgard LH, Selsby JT. The effect of Mitoquinol (MitoQ) on heat stressed skeletal muscle from pigs, and a potential confounding effect of biological sex. J Therm Biol. 2021 Apr;97:102900. doi: 10.1016/j.jtherbio.2021.102900. Epub 2021 Mar 6. PMID: 33863453. 3: Kageyama M, Ito J, Shirasuna K, Kuwayama T, Iwata H. Mitochondrial reactive oxygen species regulate mitochondrial biogenesis in porcine embryos. J Reprod Dev. 2021 Apr 21;67(2):141-147. doi: 10.1262/jrd.2020-111. Epub 2021 Feb 20. PMID: 33612552; PMCID: PMC8075724. 4: Cho SJ, Hong KS, Schenck E, Lee S, Harris R, Yang J, Choi AMK, Stout-Delgado H. Decreased IDO1-dependent tryptophan metabolism in aged lung during influenza. Eur Respir J. 2021 May 13;57(5):2000443. doi: 10.1183/13993003.00443-2020. PMID: 33243840; PMCID: PMC8147522. 5: Mansell E, Sigurdsson V, Deltcheva E, Brown J, James C, Miharada K, Soneji S, Larsson J, Enver T. Mitochondrial Potentiation Ameliorates Age-Related Heterogeneity in Hematopoietic Stem Cell Function. Cell Stem Cell. 2021 Feb 4;28(2):241-256.e6. doi: 10.1016/j.stem.2020.09.018. Epub 2020 Oct 20. PMID: 33086034. 6: Elswood J, Pearson SJ, Payne HR, Barhoumi R, Rijnkels M, W Porter W. Autophagy regulates functional differentiation of mammary epithelial cells. Autophagy. 2021 Feb;17(2):420-438. doi: 10.1080/15548627.2020.1720427. Epub 2020 Feb 5. PMID: 31983267; PMCID: PMC8007166. 7: Ibrahim AA, Karam HM, Shaaban EA, Safar MM, El-Yamany MF. MitoQ ameliorates testicular damage induced by gamma irradiation in rats: Modulation of mitochondrial apoptosis and steroidogenesis. Life Sci. 2019 Sep 1;232:116655. doi: 10.1016/j.lfs.2019.116655. Epub 2019 Jul 13. PMID: 31306659. 8: Fink BD, Herlein JA, Yorek MA, Fenner AM, Kerns RJ, Sivitz WI. Bioenergetic effects of mitochondrial-targeted coenzyme Q analogs in endothelial cells. J Pharmacol Exp Ther. 2012 Sep;342(3):709-19. doi: 10.1124/jpet.112.195586. Epub 2012 Jun 1. PMID: 22661629; PMCID: PMC3422527. 9: Nierobisz LS, McFarland DC, Mozdziak PE. MitoQ10 induces adipogenesis and oxidative metabolism in myotube cultures. Comp Biochem Physiol B Biochem Mol Biol. 2011 Feb;158(2):125-31. doi: 10.1016/j.cbpb.2010.10.003. Epub 2010 Oct 18. PMID: 20965270. 10: Mustapha NM, Tarr JM, Kohner EM, Chibber R. NADPH Oxidase versus Mitochondria-Derived ROS in Glucose-Induced Apoptosis of Pericytes in Early Diabetic Retinopathy. J Ophthalmol. 2010;2010:746978. doi: 10.1155/2010/746978. Epub 2010 Jun 28. PMID: 20652059; PMCID: PMC2905948. 11: Hobbs CE, Murphy MP, Smith RA, Oorschot DE. Neonatal rat hypoxia-ischemia: Effect of the anti-oxidant mitoquinol, and S-PBN. Pediatr Int. 2008 Aug;50(4):481-8. doi: 10.1111/j.1442-200X.2008.02705.x. PMID: 18937752. 12: Li Y, Fawcett JP, Zhang H, Tucker IG. Transport and metabolism of MitoQ10, a mitochondria-targeted antioxidant, in Caco-2 cell monolayers. J Pharm Pharmacol. 2007 Apr;59(4):503-11. doi: 10.1211/jpp.59.4.0004. PMID: 17430633. 13: O'Malley Y, Fink BD, Ross NC, Prisinzano TE, Sivitz WI. Reactive oxygen and targeted antioxidant administration in endothelial cell mitochondria. J Biol Chem. 2006 Dec 29;281(52):39766-75. doi: 10.1074/jbc.M608268200. Epub 2006 Oct 23. PMID: 17060316. 14: Kalivendi SV, Konorev EA, Cunningham S, Vanamala SK, Kaji EH, Joseph J, Kalyanaraman B. Doxorubicin activates nuclear factor of activated T-lymphocytes and Fas ligand transcription: role of mitochondrial reactive oxygen species and calcium. Biochem J. 2005 Jul 15;389(Pt 2):527-39. doi: 10.1042/BJ20050285. PMID: 15799720; PMCID: PMC1175131. 15: Bedogni B, Pani G, Colavitti R, Riccio A, Borrello S, Murphy M, Smith R, Eboli ML, Galeotti T. Redox regulation of cAMP-responsive element-binding protein and induction of manganous superoxide dismutase in nerve growth factor- dependent cell survival. J Biol Chem. 2003 May 9;278(19):16510-9. doi: 10.1074/jbc.M301089200. Epub 2003 Feb 27. PMID: 12609977. 16: Kelso GF, Porteous CM, Hughes G, Ledgerwood EC, Gane AM, Smith RA, Murphy MP. Prevention of mitochondrial oxidative damage using targeted antioxidants. Ann N Y Acad Sci. 2002 Apr;959:263-74. doi: 10.1111/j.1749-6632.2002.tb02098.x. PMID: 11976201. 17: Kelso GF, Porteous CM, Coulter CV, Hughes G, Porteous WK, Ledgerwood EC, Smith RA, Murphy MP. Selective targeting of a redox-active ubiquinone to mitochondria within cells: antioxidant and antiapoptotic properties. J Biol Chem. 2001 Feb 16;276(7):4588-96. doi: 10.1074/jbc.M009093200. Epub 2000 Nov 22. PMID: 11092892.

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