Mitoglitazone
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Hodoodo CAT#: H407197

CAS#: 146062-49-9 (racemic)

Description: Mitoglitazone, also known as CAY10415, is a novel peroxisome proliferator-activated receptor (PPAR)γ ligand. CAY10415 induced cell death and ROS generation in a PPARγ-independent manner. CAY10415 enhanced γ-radiation-induced apoptosis and caspase-3-mediated poly (ADP-ribose) polymerase (PARP) cleavage in vitro. The combined CAY10415 / γ-radiation treatment triggered caspase-8 activation, and this initiator caspase played an important role in the combination-induced apoptosis. The combined treatment of CAY10415 and γ-radiation synergistically induced DNA damage and apoptosis, which was regulated by ROS.


Chemical Structure

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Mitoglitazone
CAS# 146062-49-9 (racemic)

Theoretical Analysis

Hodoodo Cat#: H407197
Name: Mitoglitazone
CAS#: 146062-49-9 (racemic)
Chemical Formula: C19H18N2O4S
Exact Mass: 370.10
Molecular Weight: 370.423
Elemental Analysis: C, 61.61; H, 4.90; N, 7.56; O, 17.28; S, 8.65

Price and Availability

Size Price Availability Quantity
5g USD -1 2 Weeks
10mg USD 120 Same day
25mg USD 150 Same day
50mg USD 250 Same day
100mg USD 450 Same day
200mg USD 750 Same day
500mg USD 1650 Same day
1g USD 2650 Same day
2g USD 3650 2 Weeks
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Related CAS #: 1628078-14-7 (R-isomer)   146062-49-9 (racemic)   1628078-13-6 (S-isomer),  

Synonym: Mitoglitazone; CAY10415; CAY-10415; CAY 10415;

IUPAC/Chemical Name: 5-(4-(2-(5-ethylpyridin-2-yl)-2-oxoethoxy)benzyl)thiazolidine-2,4-dione

InChi Key: IRNJSRAGRIZIHD-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H18N2O4S/c1-2-12-5-8-15(20-10-12)16(22)11-25-14-6-3-13(4-7-14)9-17-18(23)21-19(24)26-17/h3-8,10,17H,2,9,11H2,1H3,(H,21,23,24)

SMILES Code: O=C(N1)SC(CC2=CC=C(OCC(C3=NC=C(CC)C=C3)=O)C=C2)C1=O

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, not in water

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:

Biological target: MSDC 0160 (Mitoglitazone) is a mitochondrial target of thiazolidinediones (mTOT)-modulating insulin sensitizer and a modulator of mitochondrial pyruvate carrier (MPC).
In vitro activity: Human islets were cultured with 5 mM glucose and MSDC-0160 (1–50 µM) for 24 h. Phosphorylation of mTOR was significantly decreased at 20 and 50 µM MSDC-0160 (Fig. 3A&B). This inhibition inversely correlated with increased phosphorylation of AMPK and its downstream target acetyl CoA carboxylase (ACC) (Fig. 3A, C, D). The effects of MSDC-0160 at 5 mM glucose were similar at 8 mM glucose (data not shown). Consistent with the reduction in the amount of phosphorylated mTOR, treatment with MSDC-0160 also produced a decrease in the phosphorylation of S6, a downstream indicator of the mTOR pathway. This was evident after 4 days of culture under these conditions (Fig. 3E), but occurred as early as 90 minutes into the treatment (Fig. 3F). Taken together, these data suggest that MSDC-0160 restores the insulin signaling pathway at least in part by modulating mTOR activity. Reference: PLoS One. 2013; 8(5): e62012. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3641131/
In vivo activity: This study applied this experimental approach to hormone-responsive, AR-driven VCaP and LuCaP78 PDX xenografts and again found the MSDC0160 diet inhibited xenograft growth (Fig. 6h). Similarly, MSDC0160 inhibited tumor growth in AR positive, castrate-resistant LuCaP35CR PDXs (Fig. 6i) Last, this study implanted VCaP xenografts into a cohort of intact animals, allowed tumor establishment, then castrated the cohort and randomized animals to MSDC0160 or a matched control diet. Castrate-resistant outgrowth was disrupted in animals maintained on the MSDC0160 diet (Fig. 6j, Supplementary Fig. 6d). Similar to in-vitro findings, this study found evidence for activation of the ISR in MSDC0160-treated tumors compared to control tumors (Fig. 6k, Supplementary Fig. 6e). Likewise, Ki67 staining was markedly decreased in tumors from mice maintained on the MSDC0160 diet (Fig. 6l, Supplementary Fig. 6f), suggesting delayed cell cycle progression resulting from ISR activation. Overall, these experiments demonstrate MPC suppression using a clinically viable small molecule suppresses tumor growth in several preclinical models of hormone-responsive and castrate-resistant PCa. Reference: Nat Metab. 2019 Jan; 1(1): 70–85. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6563330/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 53.99
DMSO:PBS (pH 7.2) (1:2) 0.3 0.81
DMF 30.0 80.99
Ethanol 0.5 1.35

Preparing Stock Solutions

The following data is based on the product molecular weight 370.42 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. Rohatgi N, Aly H, Marshall CA, McDonald WG, Kletzien RF, Colca JR, McDaniel ML. Novel insulin sensitizer modulates nutrient sensing pathways and maintains β-cell phenotype in human islets. PLoS One. 2013 May 1;8(5):e62012. doi: 10.1371/journal.pone.0062012. PMID: 23650507; PMCID: PMC3641131. 2. Bader DA, Hartig SM, Putluri V, Foley C, Hamilton MP, Smith EA, Saha PK, Panigrahi A, Walker C, Zong L, Martini-Stoica H, Chen R, Rajapakshe K, Coarfa C, Sreekumar A, Mitsiades N, Bankson JA, Ittmann MM, O'Malley BW, Putluri N, McGuire SE. Mitochondrial pyruvate import is a metabolic vulnerability in androgen receptor-driven prostate cancer. Nat Metab. 2019 Jan;1(1):70-85. doi: 10.1038/s42255-018-0002-y. Epub 2018 Nov 19. PMID: 31198906; PMCID: PMC6563330. 3. Ghosh A, Tyson T, George S, Hildebrandt EN, Steiner JA, Madaj Z, Schulz E, Machiela E, McDonald WG, Escobar Galvis ML, Kordower JH, Van Raamsdonk JM, Colca JR, Brundin P. Mitochondrial pyruvate carrier regulates autophagy, inflammation, and neurodegeneration in experimental models of Parkinson's disease. Sci Transl Med. 2016 Dec 7;8(368):368ra174. doi: 10.1126/scitranslmed.aag2210. PMID: 27928028.
In vitro protocol: 1. Rohatgi N, Aly H, Marshall CA, McDonald WG, Kletzien RF, Colca JR, McDaniel ML. Novel insulin sensitizer modulates nutrient sensing pathways and maintains β-cell phenotype in human islets. PLoS One. 2013 May 1;8(5):e62012. doi: 10.1371/journal.pone.0062012. PMID: 23650507; PMCID: PMC3641131.
In vivo protocol: 1. Bader DA, Hartig SM, Putluri V, Foley C, Hamilton MP, Smith EA, Saha PK, Panigrahi A, Walker C, Zong L, Martini-Stoica H, Chen R, Rajapakshe K, Coarfa C, Sreekumar A, Mitsiades N, Bankson JA, Ittmann MM, O'Malley BW, Putluri N, McGuire SE. Mitochondrial pyruvate import is a metabolic vulnerability in androgen receptor-driven prostate cancer. Nat Metab. 2019 Jan;1(1):70-85. doi: 10.1038/s42255-018-0002-y. Epub 2018 Nov 19. PMID: 31198906; PMCID: PMC6563330. 2. Ghosh A, Tyson T, George S, Hildebrandt EN, Steiner JA, Madaj Z, Schulz E, Machiela E, McDonald WG, Escobar Galvis ML, Kordower JH, Van Raamsdonk JM, Colca JR, Brundin P. Mitochondrial pyruvate carrier regulates autophagy, inflammation, and neurodegeneration in experimental models of Parkinson's disease. Sci Transl Med. 2016 Dec 7;8(368):368ra174. doi: 10.1126/scitranslmed.aag2210. PMID: 27928028.

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