MedKoo Cat#: 530435 | Name: MitoPQ
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Description:

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

MitoPQ, also known as MitoParaquat, is a redox cycler. MitoParaquat (MitoPQ) that comprises a triphenylphosphonium lipophilic cation conjugated to the redox cycler paraquat. MitoPQ accumulates selectively in the mitochondrial matrix driven by the membrane potential. Within the matrix, MitoPQ produces superoxide by redox cycling at the flavin site of complex I, selectively increasing superoxide production within mitochondria. MitoPQ increased mitochondrial superoxide in isolated mitochondria and cells in culture ~a thousand-fold more effectively than untargeted paraquat. MitoPQ was also more toxic than paraquat in the isolated perfused heart and in Drosophila in vivo. MitoPQ enables the selective generation of superoxide within mitochondria and is a useful tool to investigate the many roles of mitochondrial superoxide in pathology and redox signaling in cells and in vivo.

Chemical Structure

MitoPQ
MitoPQ
CAS#1821370-28-8

Theoretical Analysis

MedKoo Cat#: 530435

Name: MitoPQ

CAS#: 1821370-28-8

Chemical Formula: C39H46I3N2P

Exact Mass: 0.0000

Molecular Weight: 954.50

Elemental Analysis: C, 49.08; H, 4.86; I, 39.89; N, 2.93; P, 3.25

Price and Availability

Size Price Availability Quantity
5mg USD 550.00 2 weeks
25mg USD 1,250.00 2 weeks
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Related CAS #
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Synonym
MitoPQ, MitoParaquat.
IUPAC/Chemical Name
1-methyl-1'-(10-(triphenylphosphonio)decyl)-[4,4'-bipyridine]-1,1'-diium iodide
InChi Key
AOZZGHKENAZYTD-UHFFFAOYSA-K
InChi Code
InChI=1S/C39H46N2P.3HI/c1-40-30-25-35(26-31-40)36-27-32-41(33-28-36)29-17-6-4-2-3-5-7-18-34-42(37-19-11-8-12-20-37,38-21-13-9-14-22-38)39-23-15-10-16-24-39;;;/h8-16,19-28,30-33H,2-7,17-18,29,34H2,1H3;3*1H/q+3;;;/p-3
SMILES Code
C[N+]1=CC=C(C2=CC=[N+](CCCCCCCCCC[P+](C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)C=C2)C=C1.[I-].[I-].[I-]
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
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).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
MitoPQ is a mitochondria-targeted redox cycler.
In vitro activity:
To confirm the generation of superoxide radicals in mitochondria of primary human keratinocytes, this study treated the HEKn cells with mPQ (MitoPQ) for 24 h. Mitochondrial O2•− was assessed by measuring MitoSOX Red fluorescence using fluorescence microscopy and flow cytometry. The results show that mPQ treatment significantly increased the MitoSOX Red flourescence in HEKn cells (Fig. 1A and B). Similarly, MitoSOX Red fluorescence was significantly increased in JB6 cells following mPQ treatment (Supplementary Fig. 1). Reference: Free Radic Biol Med. 2022 Feb 1;179:181-189. https://pubmed.ncbi.nlm.nih.gov/34968705/
In vivo activity:
This study treated WT mice with the mitochondria-targeted oxidant MitoParaquat (MitoPQ), which was previously reported to elevate mitochondrial ROS in cell lines and isolated mitochondria without affecting mitochondrial function (Robb et al., 2015) (Figure 6D). At day 2 post-MI, there was a modest (~25%) increase in ROS in CFs from MitoPQ-treated versus vehicle-treated mice, with no change in treated sham hearts, which must buffer oxidants appropriately (Figure 6E). Reference: Cell Stem Cell. 2022 Feb 3;29(2):281-297.e12. https://pubmed.ncbi.nlm.nih.gov/34762860/
Solvent mg/mL mM comments
Solubility
DMF 25.0 26.19
DMF:PBS (pH 7.2) (1:1) 0.3 0.35
DMSO 44.8 46.91
Ethanol 50.2 52.56
Water 75.0 78.58
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 954.50 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
Formulation protocol:
1. Dhar SK, Scott T, Wang C, Fan TWM, St Clair DK. Mitochondrial superoxide targets energy metabolism to modulate epigenetic regulation of NRF2-mediated transcription. Free Radic Biol Med. 2022 Feb 1;179:181-189. doi: 10.1016/j.freeradbiomed.2021.12.309. Epub 2021 Dec 28. PMID: 34968705; PMCID: PMC8765599. 2. Hinchy EC, Gruszczyk AV, Willows R, Navaratnam N, Hall AR, Bates G, Bright TP, Krieg T, Carling D, Murphy MP. Mitochondria-derived ROS activate AMP-activated protein kinase (AMPK) indirectly. J Biol Chem. 2018 Nov 2;293(44):17208-17217. doi: 10.1074/jbc.RA118.002579. Epub 2018 Sep 19. PMID: 30232152; PMCID: PMC6222118. 3. Janbandhu V, Tallapragada V, Patrick R, Li Y, Abeygunawardena D, Humphreys DT, Martin EMMA, Ward AO, Contreras O, Farbehi N, Yao E, Du J, Dunwoodie SL, Bursac N, Harvey RP. Hif-1a suppresses ROS-induced proliferation of cardiac fibroblasts following myocardial infarction. Cell Stem Cell. 2022 Feb 3;29(2):281-297.e12. doi: 10.1016/j.stem.2021.10.009. Epub 2021 Nov 10. PMID: 34762860; PMCID: PMC9021927. 4. Pinho BR, Reis SD, Hartley RC, Murphy MP, Oliveira JMA. Mitochondrial superoxide generation induces a parkinsonian phenotype in zebrafish and huntingtin aggregation in human cells. Free Radic Biol Med. 2019 Jan;130:318-327. doi: 10.1016/j.freeradbiomed.2018.10.446. Epub 2018 Oct 31. PMID: 30389496; PMCID: PMC6340810.
In vitro protocol:
1. Dhar SK, Scott T, Wang C, Fan TWM, St Clair DK. Mitochondrial superoxide targets energy metabolism to modulate epigenetic regulation of NRF2-mediated transcription. Free Radic Biol Med. 2022 Feb 1;179:181-189. doi: 10.1016/j.freeradbiomed.2021.12.309. Epub 2021 Dec 28. PMID: 34968705; PMCID: PMC8765599. 2. Hinchy EC, Gruszczyk AV, Willows R, Navaratnam N, Hall AR, Bates G, Bright TP, Krieg T, Carling D, Murphy MP. Mitochondria-derived ROS activate AMP-activated protein kinase (AMPK) indirectly. J Biol Chem. 2018 Nov 2;293(44):17208-17217. doi: 10.1074/jbc.RA118.002579. Epub 2018 Sep 19. PMID: 30232152; PMCID: PMC6222118.
In vivo protocol:
1. Janbandhu V, Tallapragada V, Patrick R, Li Y, Abeygunawardena D, Humphreys DT, Martin EMMA, Ward AO, Contreras O, Farbehi N, Yao E, Du J, Dunwoodie SL, Bursac N, Harvey RP. Hif-1a suppresses ROS-induced proliferation of cardiac fibroblasts following myocardial infarction. Cell Stem Cell. 2022 Feb 3;29(2):281-297.e12. doi: 10.1016/j.stem.2021.10.009. Epub 2021 Nov 10. PMID: 34762860; PMCID: PMC9021927. 2. Pinho BR, Reis SD, Hartley RC, Murphy MP, Oliveira JMA. Mitochondrial superoxide generation induces a parkinsonian phenotype in zebrafish and huntingtin aggregation in human cells. Free Radic Biol Med. 2019 Jan;130:318-327. doi: 10.1016/j.freeradbiomed.2018.10.446. Epub 2018 Oct 31. PMID: 30389496; PMCID: PMC6340810.
1: Robb EL, Gawel JM, Aksentijević D, Cochemé HM, Stewart TS, Shchepinova MM, Qiang H, Prime TA, Bright TP, James AM, Shattock MJ, Senn HM, Hartley RC, Murphy MP. Selective superoxide generation within mitochondria by the targeted redox cycler MitoParaquat. Free Radic Biol Med. 2015 Dec;89:883-94. doi: 10.1016/j.freeradbiomed.2015.08.021. PubMed PMID: 26454075.