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Visomitin (SKQ-1)

Alias: SKQ1 SKQ-1 SKQ 1 PDTP Plastoquinonyl decyltriphenyl phosphonium bromide Visomitin
Cat No.:V19746 Purity: ≥98%
Visomitin (SKQ1; plastoquinonyl decyltriphenyl phosphonium; PDTP) is a higly potent mitochondria-targeted antioxidant and topical cardiolipin peroxidation inhibitor with excellent mitochondrion membrane penetrating ability.
Visomitin (SKQ-1)
Visomitin (SKQ-1) Chemical Structure CAS No.: 934826-68-3
Product category: Reactive Oxygen Species
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Visomitin (SKQ1; plastoquinonyl decyltriphenyl phosphonium; PDTP) is a higly potent mitochondria-targeted antioxidant and topical cardiolipin peroxidation inhibitor with excellent mitochondrion membrane penetrating ability. SKQ1 is also an active pharmaceutical ingredient/API for making eye drop drug called Visomitin. SKQ1 showed activities as follows: (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. For the convenience of use, SKQ1 is supplied as solution of 200mg / mL in ethanol-water (1:1, v/v). As of Dec 2021, FDA has granted orphan drug designation (ODD) for Visomitin for the treatment of Leber's Hereditary Optic Neuropathy (LHON), a rare inherited condition that can lead to blindness.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Visomitin (SkQ1) administration of tumor-infiltrating leukocytes does not affect their cytotoxicity against Panc02 cells. At 500 nM concentration, visomitin significantly inhibits the growth of human PDAC cells while having no effect on the viability of the cell lines[1].
ln Vivo
In reference to systemic angiogenic factors, KC is shown to be lower in the group receiving continuous therapy with visomitin (SkQ1) in the serum of mice having pancreatic ductal adenocarcinoma (PDAC). Visomitin treatment raises the quantity of VEGF molecules in the mice. Prolactin and MIP1a levels are lowered following the follow-up treatment or in all Visomitin treatment groups, respectively. Furthermore, IL-6 and IL-13 levels are higher in the groups that received visomitin treatment. The pretreatment setting results in a decrease in TGF-b levels. Conversely, every Visomitin treatment plan reduces the percentage of NKT cells. The PDAC-bearing mice's median survival has increased with Visomitin treatment, however the change is not statistically significant[1].
Cell Assay
Panc02 cells are treated 48 h with different concentrations of Visomitin (SkQ1). Cell viability after Visomitin treatment is measured with an EZ4U Kit as described by the manufacturers. Briefly, 20,000 cells per well are seeded in 96-wellplates and let grow overnight. Afterwards, cells are treated without the medium exchange. A substrate compound from the kit is added and the cells are further incubated for 5 hr at 37°C to convert the yellow colored tetrazolium to its red formazan derivate by living cells. The absorbance is measured at 450 nm[1].
References
[1]. Bazhin AV, et al. 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.
[2]. Weniger M, et al. The Analgesic Effect of the Mitochondria-Targeted Antioxidant SkQ1 in Pancreatic Inflammation. Oxid Med Cell Longev. 2016;2016:4650489
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C36H42BRO2P
Molecular Weight
617.61
CAS #
934826-68-3
Related CAS #
934826-68-3 (bromide);934960-96-0 (cation);1372443-45-2 (chloride);1372443-48-5 (sulfate); 714085-40-1 (iodide);
Appearance
Typically exists as solids (or liquids in special cases) at room temperature
SMILES
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-]
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,3-8,12,19-20,27H2,1-2H31H/q+1/p-1
Chemical Name
(10-(4,5-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl)triphenylphosphonium bromide
Synonyms
SKQ1 SKQ-1 SKQ 1 PDTP Plastoquinonyl decyltriphenyl phosphonium bromide Visomitin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~161.92 mM)
Ethanol : ~50 mg/mL (~80.96 mM)
H2O : ~3.33 mg/mL (~5.39 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.05 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (4.05 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (4.05 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one),clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.


Solubility in Formulation 4: ≥ 2.5 mg/mL (4.05 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one),clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix well.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

Solubility in Formulation 5: ≥ 2.5 mg/mL (4.05 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one),clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.6191 mL 8.0957 mL 16.1914 mL
5 mM 0.3238 mL 1.6191 mL 3.2383 mL
10 mM 0.1619 mL 0.8096 mL 1.6191 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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