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MedKoo Cat#: 465700 | Name: SkQR1 Br

Description:

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

SkQR1 Br is a class of mitochondria-targeted antioxidant. It exhibited pro-oxidant properties stimulating ROS production and a pronounced anti-inflammatory effect.

Chemical Structure

SkQR1 Br
SkQR1 Br
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 465700

Name: SkQR1 Br

CAS#: unknown

Chemical Formula: C44H55BrN2O5

Exact Mass: 770.3294

Molecular Weight: 771.84

Elemental Analysis: C, 68.47; H, 7.18; Br, 10.35; N, 3.63; O, 10.36

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 #
No Data
Synonym
SkQR-1 Br; SkQR1 Br; SkQR 1 Br; SkQR1 bromide; SkQR 1 bromide; SkQR-1 bromide;
IUPAC/Chemical Name
(Z)-N-(9-(2-(((10-(2,5-dihydroxy-3,4-dimethylphenyl)decyl)oxy)carbonyl)phenyl)-6-(ethylamino)-2,7-dimethyl-3H-xanthen-3-ylidene)ethanaminium bromide
InChi Key
CLSFCGLWMCHZOR-JTSVEUPUSA-N
InChi Code
InChI=1S/C44H54N2O5.BrH/c1-7-45-37-26-40-35(23-28(37)3)42(36-24-29(4)38(46-8-2)27-41(36)51-40)33-20-16-17-21-34(33)44(49)50-22-18-14-12-10-9-11-13-15-19-32-25-39(47)30(5)31(6)43(32)48;/h16-17,20-21,23-27,45,47-48H,7-15,18-19,22H2,1-6H3;1H/b46-38-;
SMILES Code
CC1=C(O)C=C(CCCCCCCCCCOC(C2=C(C(C(C=C(C)C(NCC)=C3)=C3O4)=C5C4=C/C(C(C)=C5)=[NH+]/CC)C=CC=C2)=O)C(O)=C1C.[Br-]
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 771.84 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: Genrikhs EE, Stelmashook EV, Rogozin PD, Novikova SV, Aleksandrova OP, Sobolev VB, Skrebitsky VG, Isaev NK. SkQR1 Reduces Neurologic Deficit Caused by Rat Brain Compression Ischemia. Bull Exp Biol Med. 2021 Mar;170(5):590-593. doi: 10.1007/s10517-021-05112-8. Epub 2021 Mar 31. PMID: 33788100. 2: Zinovkina LA, Galivondzhyan AK, Prikhodko AS, Galkin II, Zinovkin RA. Mitochondria-targeted triphenylphosphonium-based compounds do not affect estrogen receptor α. PeerJ. 2020 Mar 25;8:e8803. doi: 10.7717/peerj.8803. PMID: 32257641; PMCID: PMC7102506. 3: Plotnikov EY, Pevzner IB, Zorova LD, Chernikov VP, Prusov AN, Kireev II, Silachev DN, Skulachev VP, Zorov DB. Mitochondrial Damage and Mitochondria- Targeted Antioxidant Protection in LPS-Induced Acute Kidney Injury. Antioxidants (Basel). 2019 Jun 14;8(6):176. doi: 10.3390/antiox8060176. PMID: 31197113; PMCID: PMC6617298. 4: Fujimoto C, Yamasoba T. Mitochondria-Targeted Antioxidants for Treatment of Hearing Loss: A Systematic Review. Antioxidants (Basel). 2019 Apr 24;8(4):109. doi: 10.3390/antiox8040109. PMID: 31022870; PMCID: PMC6523236. 5: Genrikhs EE, Stelmashook EV, Alexandrova OP, Novikova SV, Voronkov DN, Glibka YA, Skulachev VP, Isaev NK. The single intravenous administration of mitochondria-targeted antioxidant SkQR1 after traumatic brain injury attenuates neurological deficit in rats. Brain Res Bull. 2019 May;148:100-108. doi: 10.1016/j.brainresbull.2019.03.011. Epub 2019 Mar 29. PMID: 30935979. 6: Silachev DN, Plotnikov EY, Pevzner IB, Zorova LD, Balakireva AV, Gulyaev MV, Pirogov YA, Skulachev VP, Zorov DB. Neuroprotective Effects of Mitochondria- Targeted Plastoquinone in a Rat Model of Neonatal Hypoxic⁻Ischemic Brain Injury. Molecules. 2018 Jul 27;23(8):1871. doi: 10.3390/molecules23081871. PMID: 30060443; PMCID: PMC6222533. 7: Jankauskas SS, Andrianova NV, Alieva IB, Prusov AN, Matsievsky DD, Zorova LD, Pevzner IB, Savchenko ES, Pirogov YA, Silachev DN, Plotnikov EY, Zorov DB. Dysfunction of Kidney Endothelium after Ischemia/Reperfusion and Its Prevention by Mitochondria-Targeted Antioxidant. Biochemistry (Mosc). 2016 Dec;81(12):1538-1548. doi: 10.1134/S0006297916120154. PMID: 28259131. 8: Morosanova MA, Plotnikov EY, Zorova LD, Pevzner IB, Popkov VA, Silachev DN, Jankauskas SS, Babenko VA, Zorov DB. Mechanisms of Inflammatory Injury of Renal Tubular Cells in a Cellular Model of Pyelonephritis. Biochemistry (Mosc). 2016 Nov;81(11):1240-1250. doi: 10.1134/S000629791611002X. PMID: 27914450. 9: Galkin II, Pletjushkina OY, Zinovkin RA, Zakharova VV, Chernyak BV, Popova EN. Mitochondria-Targeted Antioxidant SkQR1 Reduces TNF-Induced Endothelial Permeability in vitro. Biochemistry (Mosc). 2016 Oct;81(10):1188-1197. doi: 10.1134/S0006297916100163. PMID: 27908243. 10: Isaev NK, Stelmashook EV, Genrikhs EE, Korshunova GA, Sumbatyan NV, Kapkaeva MR, Skulachev VP. Neuroprotective properties of mitochondria-targeted antioxidants of the SkQ-type. Rev Neurosci. 2016 Dec 1;27(8):849-855. doi: 10.1515/revneuro-2016-0036. PMID: 27559690. 11: Silva FS, Simoes RF, Couto R, Oliveira PJ. Targeting Mitochondria in Cardiovascular Diseases. Curr Pharm Des. 2016;22(37):5698-5717. doi: 10.2174/1381612822666160822150243. PMID: 27549376. 12: Kezic A, Spasojevic I, Lezaic V, Bajcetic M. Mitochondria-Targeted Antioxidants: Future Perspectives in Kidney Ischemia Reperfusion Injury. Oxid Med Cell Longev. 2016;2016:2950503. doi: 10.1155/2016/2950503. Epub 2016 May 24. PMID: 27313826; PMCID: PMC4894993. 13: Stelmashook EV, Stavrovskaya AV, Yamshchikova NG, Ol'shanskii AS, Kapay NA, Popova OV, Khaspekov LG, Skrebitsky VG, Isaev NK. Mitochondria-Targeted Plastoquinone Antioxidant SkQR1 Has Positive Effect on Memory of Rats. Biochemistry (Mosc). 2015 May;80(5):592-5. doi: 10.1134/S0006297915050119. PMID: 26071778. 14: Fetisova EK, Antoschina MM, Cherepanynets VD, Izumov DS, Kireev II, Kireev RI, Lyamzaev KG, Riabchenko NI, Chernyak BV, Skulachev VP. Radioprotective effects of mitochondria-targeted antioxidant SkQR1. Radiat Res. 2015 Jan;183(1):64-71. doi: 10.1667/RR13708.1. Epub 2014 Dec 12. PMID: 25496313. 15: Tábara LC, Poveda J, Martin-Cleary C, Selgas R, Ortiz A, Sanchez-Niño MD. Mitochondria-targeted therapies for acute kidney injury. Expert Rev Mol Med. 2014 Aug 8;16:e13. doi: 10.1017/erm.2014.14. Erratum in: Expert Rev Mol Med. 2014;16:e14. PMID: 25104110. 16: Omarova EO, Antonenko YN. Inhibition of oxidative hemolysis in erythrocytes by mitochondria-targeted antioxidants of SkQ series. Biochemistry (Mosc). 2014 Feb;79(2):139-45. doi: 10.1134/S0006297914020072. PMID: 24794729. 17: Galkin II, Pletjushkina OY, Zinovkin RA, Zakharova VV, Birjukov IS, Chernyak BV, Popova EN. Mitochondria-targeted antioxidants prevent TNFα-induced endothelial cell damage. Biochemistry (Mosc). 2014 Feb;79(2):124-30. doi: 10.1134/S0006297914020059. PMID: 24794727. 18: Galimov ER, Chernyak BV, Sidorenko AS, Tereshkova AV, Chumakov PM. Prooxidant properties of p66shc are mediated by mitochondria in human cells. PLoS One. 2014 Mar 11;9(3):e86521. doi: 10.1371/journal.pone.0086521. PMID: 24618848; PMCID: PMC3950296. 19: Fetisova EK, Antoshina MM, Cherepanynets VD, Izumov DS, Kireev II, Kireev RI, Lyamzaev KG, Riabchenko NI, Chernyak BV, Skulachev VP. [Mitochondria- targeted antioxidant SkQR1 selectively protects MDR-negative cells against ionizing radiation]. Tsitologiia. 2014;56(12):890-8. Russian. PMID: 25929130. 20: Skulachev VP. Cationic antioxidants as a powerful tool against mitochondrial oxidative stress. Biochem Biophys Res Commun. 2013 Nov 15;441(2):275-9. doi: 10.1016/j.bbrc.2013.10.063. Epub 2013 Oct 22. PMID: 24161394.