WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 314201
CAS#: 934826-68-3 (bromide)
Description: SKQ1, also known as Visomitin, plastoquinonyl decyltriphenyl phosphonium or PDTP, is a potent mitochondria-targeted antioxidant. SKQ1 is also an API for making eye drop drug called Visomitin. SKQ1 showed activities (1) to prevent amyloid-β-induced impairment of long-term potentiation in rat hippocampal slices; (2) to reverse aging-related biomarkers in rats; (3) to slow down the development of age-dependent destructive processes in retina and vascular layer of eyes of wistar and OXYS rats; (4) to increase the lifespan of male rodents under LP or SPF conditions. SKQ1 can penetrate cell membranes , and is proposed as an anti-aging treatment. Visomitin, which API is SKQ1, is currently under clinical trials for treating glaucoma in Russia. Note: For the convenience of use, SKQ1 is supplied as solution of 200mg / mL in ethanol-water (1:1, v/v).
MedKoo Cat#: 314201
Name: SKQ1 (Visomitin), ethanol solution
CAS#: 934826-68-3 (bromide)
Chemical Formula: C36H42BrO2P
Molecular Weight: 617.61
Elemental Analysis: C, 70.01; H, 6.85; Br, 12.94; O, 5.18; P, 5.02
Related CAS #: 934826-68-3 (bromide) 934960-96-0 (cation) 1372443-45-2 (chloride) 1372443-48-5 (sulfate) 714085-40-1 (iodide)
Synonym: SKQ1; PDTP; Plastoquinonyl decyltriphenyl phosphonium bromide;Visomitin
IUPAC/Chemical Name: (10-(4,5-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl)triphenylphosphonium bromide
InChi Key: WYHFWTRUGAFNKW-UHFFFAOYSA-M
InChi Code: InChI=1S/C36H42O2P.BrH/c1-29-30(2)36(38)31(28-35(29)37)20-12-7-5-3-4-6-8-19-27-39(32-21-13-9-14-22-32,33-23-15-10-16-24-33)34-25-17-11-18-26-34;/h9-11,13-18,21-26,28H,3-8,12,19-20,27H2,1-2H3;1H/q+1;/p-1
SMILES Code: O=C(C(CCCCCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)=C4)C(C)=C(C)C4=O.[Br-]
Appearance: Yellow to light brown in ethanol solution (SKQ1, in pure form is a yellow to brown waxy / sticky and highly hydroscopic solid)
Purity: >98% (or refer to the Certificate of Analysis), supplied as 200 mg/mL solution in ethanol-wate (1:1, v/v).
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: >2 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).
HS Tariff Code: 2934.99.9001
|Biological target:||Visomitin (SKQ1) is a mitochondrial-targeted antioxidant with the high mitochondrion membrane penetrating ability and potent antioxidant capability.|
|In vitro activity:||SkQ1 treatment inhibited the growth of fibrosarcoma and rhabdomyosarcoma cells. Growth suppression in HT1080 cells was accompanied by decreased number of mitoses and multinucleation, that indicated problems with mitosis exit. RD cells were identified to have increased apoptosis that could be responsible for growth inhibition after SkQ1 treatment. Lipophilic cation C12TPP without plastoquinolyl residue did not influence proliferation and ploidy of HT1080 and RD cells. Non-targeted antioxidant NAC (1 mM) had similar growth inhibition action on HT1080 and RD cells. SkQ1 had no detrimental effect on normal human subcutaneous diploid ﬁbroblasts growth. In addition to the growth inhibition, mitochondria-targeted antioxidant SkQ1 induced dramatic changes in the morphology of HT1080 tumour cells. Cytoplasmic β- and γ-actin cytoskeleton rearrangement was accompanied by cell area enlargement. Reference: Cell Cycle. 2018;17(14):1797-1811. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6133338/|
|In vivo activity:||Mitochondria-targeted antioxidant plastoquinonyl-decyltriphenylphosphonium (SkQ1) at nanomolar concentrations can prevent, slow down, or partially alleviate AD-like pathology in accelerated-senescence OXYS rats. Here it’s confirmed that dietary supplementation with SkQ1 during active progression of AD-like pathology in OXYS rats (aged 12-18 months) suppresses AD-like pathology progression and its effects are associated with suppression of p38 MAPK signaling pathway (MAPKsp) activity. Transcriptome analysis, western blotting, and immunofluorescent staining revealed that SkQ1 suppresses p38 MAPKsp activity in the hippocampus at the level of expression of genes involved in the p38 MAPKsp and reduces the phosphorylation of intermediate kinases (p38 MAPK and MK2) and a downstream protein (αB-crystallin). Thus, the anti-AD effects of SkQ1 are associated with improvement in the functioning of relevant signaling pathways and intracellular processes, thus making it a promising therapeutic agent for human AD. Reference: Antioxidants (Basel). 2020 Jul 28;9(8):676. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7463502/|
|Solvent||Max Conc. mg/mL||Max Conc. mM|
The following data is based on the product molecular weight 617.61 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|
|Formulation protocol:||1. Bazhin AV, Yang Y, D'Haese JG, Werner J, Philippov PP, Karakhanova S. The novel mitochondria-targeted antioxidant SkQ1 modulates angiogenesis and inflammatory micromilieu in a murine orthotopic model of pancreatic cancer. Int J Cancer. 2016 Jul 1;139(1):130-9. doi: 10.1002/ijc.30054. Epub 2016 Apr 4. PMID: 26914404. 2. Titova E, Shagieva G, Ivanova O, Domnina L, Domninskaya M, Strelkova O, Khromova N, Kopnin P, Chernyak B, Skulachev V, Dugina V. Mitochondria-targeted antioxidant SkQ1 suppresses fibrosarcoma and rhabdomyosarcoma tumour cell growth. Cell Cycle. 2018;17(14):1797-1811. doi: 10.1080/15384101.2018.1496748. Epub 2018 Jul 31. PMID: 29995559; PMCID: PMC6133338. 1. Bazhin AV, Yang Y, D'Haese JG, Werner J, Philippov PP, Karakhanova S. The novel mitochondria-targeted antioxidant SkQ1 modulates angiogenesis and inflammatory micromilieu in a murine orthotopic model of pancreatic cancer. Int J Cancer. 2016 Jul 1;139(1):130-9. doi: 10.1002/ijc.30054. Epub 2016 Apr 4. PMID: 26914404. 2. Muraleva NA, Stefanova NA, Kolosova NG. SkQ1 Suppresses the p38 MAPK Signaling Pathway Involved in Alzheimer's Disease-Like Pathology in OXYS Rats. Antioxidants (Basel). 2020 Jul 28;9(8):676. doi: 10.3390/antiox9080676. PMID: 32731533; PMCID: PMC7463502.|
|In vitro protocol:||1. Bazhin AV, Yang Y, D'Haese JG, Werner J, Philippov PP, Karakhanova S. The novel mitochondria-targeted antioxidant SkQ1 modulates angiogenesis and inflammatory micromilieu in a murine orthotopic model of pancreatic cancer. Int J Cancer. 2016 Jul 1;139(1):130-9. doi: 10.1002/ijc.30054. Epub 2016 Apr 4. PMID: 26914404. 2. Titova E, Shagieva G, Ivanova O, Domnina L, Domninskaya M, Strelkova O, Khromova N, Kopnin P, Chernyak B, Skulachev V, Dugina V. Mitochondria-targeted antioxidant SkQ1 suppresses fibrosarcoma and rhabdomyosarcoma tumour cell growth. Cell Cycle. 2018;17(14):1797-1811. doi: 10.1080/15384101.2018.1496748. Epub 2018 Jul 31. PMID: 29995559; PMCID: PMC6133338.|
|In vivo protocol:||1. Bazhin AV, Yang Y, D'Haese JG, Werner J, Philippov PP, Karakhanova S. The novel mitochondria-targeted antioxidant SkQ1 modulates angiogenesis and inflammatory micromilieu in a murine orthotopic model of pancreatic cancer. Int J Cancer. 2016 Jul 1;139(1):130-9. doi: 10.1002/ijc.30054. Epub 2016 Apr 4. PMID: 26914404. 2. Muraleva NA, Stefanova NA, Kolosova NG. SkQ1 Suppresses the p38 MAPK Signaling Pathway Involved in Alzheimer's Disease-Like Pathology in OXYS Rats. Antioxidants (Basel). 2020 Jul 28;9(8):676. doi: 10.3390/antiox9080676. PMID: 32731533; PMCID: PMC7463502.|
1: Samuilov VD, Kiselevsky DB. Effect of Cationic Plastoquinone SkQ1 on Electron Transfer Reactions in Chloroplasts and Mitochondria from Pea Seedlings. Biochemistry (Mosc). 2015 Apr;80(4):417-23. doi: 10.1134/S0006297915040045. PubMed PMID: 25869358.
2: Iomdina EN, Khoroshilova-Maslova IP, Robustova OV, Averina OA, Kovaleva NA, Aliev G, Reddy VP, Zamyatnin AA Jr, Skulachev MV, Senin II, Skulachev VP. Mitochondria-targeted antioxidant SkQ1 reverses glaucomatous lesions in rabbits. Front Biosci (Landmark Ed). 2015 Jan 1;20:892-901. PubMed PMID: 25553485.
3: Manskikh VN, Krasilshchikova MS, Vygodin VA, Egorov MV. Effect of the mitochondria-targeted antioxidant SkQ1 on development of spontaneous tumors in BALB/c mice. Biochemistry (Mosc). 2014 Oct;79(10):1136-9. doi: 10.1134/S0006297914100162. PubMed PMID: 25519073.
4: Myasoedova KN, Silachev DN. Therapeutic doses of SkQ1 do not induce cytochromes P450 in rat liver. Biochemistry (Mosc). 2014 Oct;79(10):1130-2. doi: 10.1134/S0006297914100149. PubMed PMID: 25519071.
5: Rogovin KA, Khrushcheva AM, Shekarova ON, Ushakova MV, Manskikh VN, Sokolova OV, Vasilieva NY. Effects of mitochondria-targeted plastoquinone derivative antioxidant (SkQ1) on demography of free-breeding Campbell dwarf hamsters (Phodopus campbelli) kept in outdoor conditions. reproduction and lifespan: explanation in the framework of ultimate loads. Biochemistry (Mosc). 2014 Oct;79(10):1117-29. doi: 10.1134/S0006297914100137. PubMed PMID: 25519070.
6: Rogovin KA, Khrushcheva AM, Shekarova ON, Ushakova MV, Manskikh VN, Vasilieva NY. Mitochondria-targeted antioxidant SkQ1 accelerates maturation in Campbell dwarf hamsters (Phodopus campbelli). Biochemistry (Mosc). 2014 Oct;79(10):1111-6. doi: 10.1134/S0006297914100125. PubMed PMID: 25519069.
7: Novikova YP, Gancharova OS, Eichler OV, Philippov PP, Grigoryan EN. Preventive and therapeutic effects of SkQ1-containing Visomitin eye drops against light-induced retinal degeneration. Biochemistry (Mosc). 2014 Oct;79(10):1101-10. doi: 10.1134/S0006297914100113. PubMed PMID: 25519068.
8: Muraleva NA, Kozhevnikova OS, Zhdankina AA, Stefanova NA, Karamysheva TV, Fursova AZ, Kolosova NG. The mitochondria-targeted antioxidant SkQ1 restores αB-crystallin expression and protects against AMD-like retinopathy in OXYS rats. Cell Cycle. 2014;13(22):3499-505. doi: 10.4161/15384101.2014.958393. PubMed PMID: 25483086.
9: Manskikh VN, Gancharova OS, Nikiforova AI, Krasilshchikova MS, Shabalina IG, Egorov MV, Karger EM, Milanovsky GE, Galkin II, Skulachev VP, Zinovkin RA. Age-associated murine cardiac lesions are attenuated by the mitochondria-targeted antioxidant SkQ1. Histol Histopathol. 2015 Mar;30(3):353-60. Epub 2014 Oct 17. PubMed PMID: 25323729.
10: Rumyantseva YV, Ryabchikova EI, Fursova AZ, Kolosova NG. Ameliorative effects of SkQ1 eye drops on cataractogenesis in senescence-accelerated OXYS rats. Graefes Arch Clin Exp Ophthalmol. 2015 Feb;253(2):237-48. doi: 10.1007/s00417-014-2806-0. Epub 2014 Sep 30. PubMed PMID: 25267419.
11: Perepechaeva ML, Grishanova AY, Rudnitskaya EA, Kolosova NG. The Mitochondria-Targeted Antioxidant SkQ1 Downregulates Aryl Hydrocarbon Receptor-Dependent Genes in the Retina of OXYS Rats with AMD-Like Retinopathy. J Ophthalmol. 2014;2014:530943. doi: 10.1155/2014/530943. Epub 2014 Jul 14. PubMed PMID: 25132985; PubMed Central PMCID: PMC4123489.
12: Vays VB, Eldarov CM, Vangely IM, Kolosova NG, Bakeeva LE, Skulachev VP. Antioxidant SkQ1 delays sarcopenia-associated damage of mitochondrial ultrastructure. Aging (Albany NY). 2014 Feb;6(2):140-8. PubMed PMID: 24519884; PubMed Central PMCID: PMC3969282.
13: Solovieva AD, Frolova OY, Solovyev AG, Morozov SY, Zamyatnin AA Jr. Effect of mitochondria-targeted antioxidant SkQ1 on programmed cell death induced by viral proteins in tobacco plants. Biochemistry (Mosc). 2013 Sep;78(9):1006-12. doi: 10.1134/S000629791309006X. PubMed PMID: 24228922.
14: Stefanova NA, Muraleva NA, Skulachev VP, Kolosova NG. Alzheimer's disease-like pathology in senescence-accelerated OXYS rats can be partially retarded with mitochondria-targeted antioxidant SkQ1. J Alzheimers Dis. 2014;38(3):681-94. doi: 10.3233/JAD-131034. PubMed PMID: 24047616.
15: Kapay NA, Popova OV, Isaev NK, Stelmashook EV, Kondratenko RV, Zorov DB, Skrebitsky VG, Skulachev VP. Mitochondria-targeted plastoquinone antioxidant SkQ1 prevents amyloid-β-induced impairment of long-term potentiation in rat hippocampal slices. J Alzheimers Dis. 2013;36(2):377-83. doi: 10.3233/JAD-122428. PubMed PMID: 23735258.
16: Snytnikova OA, Tsentalovich YP, Stefanova NA, Fursova AZh, Kaptein R, Sagdeev RZ, Kolosova NG. The therapeutic effect of mitochondria-targeted antioxidant SkQ1 and Cistanche deserticola is associated with increased levels of tryptophan and kynurenine in the rat lens. Dokl Biochem Biophys. 2012 Nov-Dec;447:300-3. doi: 10.1134/S1607672912060087. Epub 2013 Jan 4. PubMed PMID: 23288574.
17: Chistyakov VA, Dem'yanenko SV, Alexandrova AA, Gutnikova LV, Prokof'ev VN, Kosheleva ON. Effect of plastoquinone derivative 10-(6'-plastoquinonyl) decyltriphenylphosphonium (SkQ1) on estrous cycle and 17β-estradiol level in rats. Biochemistry (Mosc). 2012 Dec;77(12):1382-6. doi: 10.1134/S0006297912120061. PubMed PMID: 23244734.
18: Il'yasova TM, Rokitskaya TI, Severina II, Antonenko YN, Skulachev VP. Substitution of ether linkage for ester bond in phospholipids increases permeability of bilayer lipid membrane for SkQ1-type penetrating cations. Biochemistry (Mosc). 2012 Sep;77(9):1038-43. doi: 10.1134/S0006297912090118. PubMed PMID: 23157264.
19: Kolosova NG, Stefanova NA, Muraleva NA, Skulachev VP. The mitochondria-targeted antioxidant SkQ1 but not N-acetylcysteine reverses aging-related biomarkers in rats. Aging (Albany NY). 2012 Oct;4(10):686-94. PubMed PMID: 23104863; PubMed Central PMCID: PMC3517939.
20: Krementsova AV, Roshina NV, Tsybul'ko EA, Rybina OY, Symonenko AV, Pasyukova EG. Reproducible effects of the mitochondria-targeted plastoquinone derivative SkQ1 on Drosophila melanogaster lifespan under different experimental scenarios. Biogerontology. 2012 Dec;13(6):595-607. doi: 10.1007/s10522-012-9404-5. Epub 2012 Oct 17. PubMed PMID: 23073710.
CAS#934826-68-3 (SKQ1 bromide);
CAS#934960-96-0 (SKQ1 cation)
Recent Work on SkQ1 and Vascular Inflammation: SkQ1 is a mitochondrially targeted antioxidant, and there is evidence to show that it can modestly extend life in mice. Mitochondria are important in the aging process, and one of the ways in which they interact with surrounding cell biology is by generating damaging reactive oxygen species (ROS). Too much ROS creation can harm a cell, a state called oxidative stress. Just a little more than usual can be beneficial, as the cell reacts with increased housekeeping for a net benefit - this is probably one of the mechanisms by which exercise improves health, for example. This signaling is a parallel mechanism to the most important harm likely caused by mitochondrial ROS, however, which is to damage mitochondrial DNA at their point of origin. This can lead to all sorts of persistent dysfunction in a small population of cells, which export harmful molecules to surrounding tissues. Mitochondrial antioxidants probably produce benefits to long term health by reducing the rate of this mitochondrial damage, but that isn't completely certain at this point because of the ROS signaling to other important aspects of cell metabolism. Biology is complex, and as for all small effects on longevity, the actual mechanism could be any one of a number of things. So these researchers are making use of SkQ1 as a way to better identify what exactly it is that changes in response to ROS levels, with a focus on dysfunction in blood vessel wall tissue (the vascular endothelium) that leads to age-related conditions such as atherosclerosis. (copied from https://www.fightaging.org/archives/2014/09/recent-work-on-skq1-and-vascular-inflammation.php).