Mitoquinone-cyclodextrin

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

MedKoo CAT#: 329610

CAS#: 845959-52-6 (beta-CD complex)

Description: Mitoquinone-cyclodextrin is a 1:1 molar ratio complex of Mitoquinone mesylate with cyclodextrin. 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. Note: pure MitoQ10 is a tar-like or waxy semi-solid and very hard to transfer between containers. For the convenience of use, we supply Mitoquinone mesylate-cyclodextrin as 1:1 molar ratio (or 1:1.67, w/w). Mitoquinone mesylate-cyclodextrin is a solid powder, which is more stable and convenience for use.


Price and Availability

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Mitoquinone mesylate-cyclodextrin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 329610
Name: Mitoquinone-cyclodextrin
CAS#: 845959-52-6 (beta-CD complex)
Chemical Formula: C80H117O42PS
Exact Mass:
Molecular Weight: 1813.8078
Elemental Analysis: C, 52.98; H, 6.50; O, 37.05; P, 1.71; S, 1.77


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

Synonym: Mitoquinone mesylate-cyclodextrin; 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 with cyclodextrin.

InChi Key: PQSSUSXOSOIMGL-PTOJYDMNSA-M

InChi Code: InChI=1S/C42H70O35.C37H44O4P.CH4O3S/c43-1-8-29-15(50)22(57)36(64-8)72-30-9(2-44)66-38(24(59)17(30)52)74-32-11(4-46)68-40(26(61)19(32)54)76-34-13(6-48)70-42(28(63)21(34)56)77-35-14(7-49)69-41(27(62)20(35)55)75-33-12(5-47)67-39(25(60)18(33)53)73-31-10(3-45)65-37(71-29)23(58)16(31)51;1-29-33(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/h8-63H,1-7H2;10-18,21-26H,4-9,19-20,27-28H2,1-3H3;1H3,(H,2,3,4)/q;+1;/p-1/t8-,9-,10-,11-,12+,13+,14+,15-,16-,17-,18+,19-,20+,21+,22-,23-,24-,25+,26-,27+,28+,29-,30-,31-,32-,33+,34+,35+,36-,37-,38-,39+,40-,41+,42+;;/m0../s1

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.O[C@@H]5[C@@H](O)[C@H](O[C@@H]6[C@H](O)[C@@H](O)[C@H](O7)[C@@H](CO)O6)[C@@H](CO)O[C@@H]5O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@@H]9[C@@H](O)[C@H](O)[C@H](O[C@@H]%10[C@@H](O)[C@H](O)[C@H](O[C@@H]%11[C@@H](O)[C@H](O)[C@H](O[C@@H]%12[C@@H](O)[C@H](O)[C@H]7O[C@H]%12CO)O[C@H]%11CO)O[C@H]%10CO)O[C@H]9CO)O[C@@H]8CO


Technical Data

Appearance:
Yellow to brown 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

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).

Harmonized System Code:
293490


Additional Information

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.


References

1: Tate AD, Antonelli PJ, Hannabass KR, Dirain CO. Mitochondria-Targeted Antioxidant Mitoquinone Reduces Cisplatin-Induced Ototoxicity in Guinea Pigs. Otolaryngol Head Neck Surg. 2017 Mar;156(3):543-548. doi: 10.1177/0194599816678381. PubMed PMID: 28248600.

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.

8: Lozano-Sepulveda SA, Bryan-Marrugo OL, Cordova-Fletes C, Gutierrez-Ruiz MC, Rivas-Estilla AM. Oxidative stress modulation in hepatitis C virus infected cells. World J Hepatol. 2015 Dec 18;7(29):2880-9. doi: 10.4254/wjh.v7.i29.2880. Review. PubMed PMID: 26692473; PubMed Central PMCID: PMC4678374.

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.

14: Chen S, Huang J, Zeng Q, Jia Y, Wang J. [Effect of autophagy and mitochondrial coenzyme Q on exocrine function of pancreas in rats with acute sepsis]. Zhonghua Wei Zhong Bing Ji Jiu Yi Xue. 2015 Feb;27(2):86-91. doi: 10.3760/cma.j.issn.2095-4352.2015.02.002. Chinese. PubMed PMID: 25665604.

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.

16: Ramsey H, Wu MX. Mitochondrial anti-oxidant protects IEX-1 deficient mice from organ damage during endotoxemia. Int Immunopharmacol. 2014 Dec;23(2):658-63. PubMed PMID: 25466275; PubMed Central PMCID: PMC4394602.

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.

19: Ramsey H, Zhang Q, Wu MX. Mitoquinone restores platelet production in irradiation-induced thrombocytopenia. Platelets. 2015;26(5):459-66. doi: 10.3109/09537104.2014.935315. PubMed PMID: 25025394; PubMed Central PMCID: PMC4382457.

20: Dongworth RK, Hall AR, Burke N, Hausenloy DJ. Targeting mitochondria for cardioprotection: examining the benefit for patients. Future Cardiol. 2014 Mar;10(2):255-72. doi: 10.2217/fca.14.6. Review. PubMed PMID: 24762253.