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MedKoo Cat#: 563761 | Name: MitoNeoD
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Description:

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

MitoNeoD is a novel mitochondria-targeted O2(⋅−) probe that can be used in vivo. It prevents DNA intercalation. MitoNeoD incorporates a carbon-deuterium bond, and enhances O2(⋅−) selectivity. MitoNeoD comprises a O2⋅--sensitive reduced phenanthridinium moiety modified to prevent DNA intercalation, as well as a carbon-deuterium bond to enhance its selectivity for O2⋅- over non-specific oxidation, and a triphenylphosphonium lipophilic cation moiety leading to the rapid accumulation within mitochondria. MitoNeoD is a versatile and robust probe to assess changes in mitochondrial O2⋅- from isolated mitochondria to animal models, thus offering a way to examine the many roles of mitochondrial O2⋅- production in health and disease.

Chemical Structure

MitoNeoD
MitoNeoD
CAS#2375088-89-2 (bromide)

Theoretical Analysis

MedKoo Cat#: 563761

Name: MitoNeoD

CAS#: 2375088-89-2 (bromide)

Chemical Formula: C53H62DBrN3P

Exact Mass: 773.4817

Molecular Weight: 853.99

Elemental Analysis: C, 74.54; H, 7.55; Br, 9.36; N, 4.92; P, 3.63

Price and Availability

Size Price Availability Quantity
1mg USD 90.00 Ready to ship
5mg USD 225.00 Ready to ship
10mg USD 405.00 Ready to ship
25mg USD 850.00 Ready to ship
50mg USD 1,450.00 Ready to ship
100mg USD 2,450.00 Ready to ship
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Related CAS #
2375088-89-2 (cation) 2375088-89-2 (bromide)
Synonym
MitoNeoD; Mito-NeoD; Mito Neo D; Mito-Neo-D; Mito Neo-D
IUPAC/Chemical Name
(6-(3,8-Bis(neopentylamino)-6-phenylphenanthridin-5(6H)-yl-6-d)hexyl)triphenylphosphonium bromide
InChi Key
FMTMQUAQVIOWNQ-UTANGQNASA-M
InChi Code
InChI=1S/C53H63N3P.BrH/c1-52(2,3)39-54-42-31-33-47-48-34-32-43(55-40-53(4,5)6)38-50(48)56(51(49(47)37-42)41-23-13-9-14-24-41)35-21-7-8-22-36-57(44-25-15-10-16-26-44,45-27-17-11-18-28-45)46-29-19-12-20-30-46;/h9-20,23-34,37-38,51,54-55H,7-8,21-22,35-36,39-40H2,1-6H3;1H/q+1;/p-1/i51D;
SMILES Code
CC(C)(C)CNC1=CC(C(C2=CC=CC=C2)([2H])N(CCCCCC[P+](C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)C6=CC(NCC(C)(C)C)=CC=C76)=C7C=C1.[Br-]
Appearance
Solid powder
Purity
>95% (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
>3 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
Mitochondrial superoxide (O2⋅-) underlies much oxidative damage and redox signaling. Fluorescent probes can detect O2⋅-, but are of limited applicability in vivo, while in cells their usefulness is constrained by side reactions and DNA intercalation.
Biological target:
TBD
In vitro activity:
This study next determined whether MitoNeoD could detect mitochondrial O2⋅− production within cells by confocal fluorescence microscopy (Figures 6E and 6F). The background rates of oxidation of MitoNeoH or MitoNeoD by unstressed cells were low, with MitoNeoD being more stable (Figure 6E, inset). MitoNeoH was more sensitive to oxidation by O2⋅− than MitoNeoD (Figure 6E). However, the oxidation of MitoNeoD is a more reliable readout of O2⋅− levels than MitoNeoH, due to its lower sensitivity to non-specific oxidation to MitoNeo. MitoNeoD was oxidized by the mitochondria-targeted redox cycler MitoPQ, which generates O2⋅− by redox cycling at complex I (Figure 6G). This study concludes that, while the increase in fluorescence upon oxidation of MitoNeoD is less than that for MitoSOX Red, it is a more selective indicator of mitochondrial O2⋅− formation. Reference: Cell Chem Biol. 2017 Oct 19; 24(10): 1285–1298.e12. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278870/
In vivo activity:
To see if MitoNeoD can assess mitochondrial O2⋅− formation in vivo this study focused on the mouse heart, because mitochondrial ROS production has been implicated in a multitude of cardiac pathologies. This study assessed this by injecting MitoNeoD into mice intravenously by a tail vein and then measured MitoNeoOH and MitoNeo in the heart and expressed this as Σ MitoNeo× over time (Figure 7E). This showed a very rapid uptake of MitoNeoD into the heart within a few minutes of injection that was then gradually lost over time, with a half-life of ∼1 hr, consistent with other TPP compounds. Interestingly, MitoNeoOH was a small proportion of Σ MitoNeo× in the heart, consistent with low levels of mitochondrial O2⋅− production in the normoxic heart and the relative stability of MitoNeoD in vivo (Figure 7E). To see if MitoNeoOH levels responded to an increase in mitochondrial O2⋅− production in vivo, this study administered MitoNeoD to mice at the same time as MitoPQ, which selectively induces mitochondrial O2⋅− production in the heart (Robb et al., 2015). MitoPQ increased the MitoNeoOH/Σ MitoNeo× ratio markedly in the hearts (Figure 7F). Therefore, MitoNeoD can be used to assess mitochondrial O2⋅− production in vivo. Reference: Cell Chem Biol. 2017 Oct 19; 24(10): 1285–1298.e12. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278870/

Preparing Stock Solutions

The following data is based on the product molecular weight 853.99 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. Shchepinova MM, Cairns AG, Prime TA, Logan A, James AM, Hall AR, Vidoni S, Arndt S, Caldwell ST, Prag HA, Pell VR, Krieg T, Mulvey JF, Yadav P, Cobley JN, Bright TP, Senn HM, Anderson RF, Murphy MP, Hartley RC. MitoNeoD: A Mitochondria-Targeted Superoxide Probe. Cell Chem Biol. 2017 Oct 19;24(10):1285-1298.e12. doi: 10.1016/j.chembiol.2017.08.003. Epub 2017 Sep 7. PMID: 28890317; PMCID: PMC6278870.
In vitro protocol:
1. Shchepinova MM, Cairns AG, Prime TA, Logan A, James AM, Hall AR, Vidoni S, Arndt S, Caldwell ST, Prag HA, Pell VR, Krieg T, Mulvey JF, Yadav P, Cobley JN, Bright TP, Senn HM, Anderson RF, Murphy MP, Hartley RC. MitoNeoD: A Mitochondria-Targeted Superoxide Probe. Cell Chem Biol. 2017 Oct 19;24(10):1285-1298.e12. doi: 10.1016/j.chembiol.2017.08.003. Epub 2017 Sep 7. PMID: 28890317; PMCID: PMC6278870.
In vivo protocol:
1. Shchepinova MM, Cairns AG, Prime TA, Logan A, James AM, Hall AR, Vidoni S, Arndt S, Caldwell ST, Prag HA, Pell VR, Krieg T, Mulvey JF, Yadav P, Cobley JN, Bright TP, Senn HM, Anderson RF, Murphy MP, Hartley RC. MitoNeoD: A Mitochondria-Targeted Superoxide Probe. Cell Chem Biol. 2017 Oct 19;24(10):1285-1298.e12. doi: 10.1016/j.chembiol.2017.08.003. Epub 2017 Sep 7. PMID: 28890317; PMCID: PMC6278870.
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