Maritoclax
Based on 6 publication(s) in Google Scholar
Maritoclax (Marinopyrrole A) is a novel and specific Mcl-1 inhibitor with an IC50 value of 10.1 μM, and shows >8 fold selectivity than BCL-xl (IC50 > 80 μM).
Para uso exclusivo en investigación. No vendemos a pacientes.
- Pureza: 99.52%
- No. CAS: 1227962-62-0
- Fòrmula: C22H12Cl4N2O4
- Peso molecular:510.15
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Almacenamiento:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year
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Actividad biológica
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Chemical Information
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Solvente y solubilidad
- Protocolo
- Pureza y Documentación
- Referencias
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Help & FAQs
Publications Citing Use of MedChemExpress (MCE) Maritoclax
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Actividad biológica
Descripciòn
IC50 & Target
[1]|
Mcl-1 10.1 μM (IC50) |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HCT-116 | IC50 |
8.8 μM
Compound: 40
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Anticancer activity against human HCT-116 cells assessed as cell growth inhibition
Anticancer activity against human HCT-116 cells assessed as cell growth inhibition
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[PMID: 36058089] |
| HeLa | IC50 |
20 μM
Compound: Marinopyrrole A
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Cytotoxicity against human HeLa cells assessed as reduction in cell viability after 72 hrs
Cytotoxicity against human HeLa cells assessed as reduction in cell viability after 72 hrs
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[PMID: 29407973] |
| RS4-11 | IC50 |
2 μM
Compound: Marinopyrrole A
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Cytotoxicity against human RS4:11 cells assessed as reduction in cell viability after 72 hrs
Cytotoxicity against human RS4:11 cells assessed as reduction in cell viability after 72 hrs
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[PMID: 29407973] |
In Vitro
Maritoclax (Marinopyrrole A) blocks the binding of Bim BH3 α-helix to Mcl-1 but not Bcl-XL. Maritoclax (Marinopyrrole A) markedly inhibits the viability of Mcl-1-IRES-BimEL cells (EC50=1.6 μM) with a selectivity greater than 40-fold over Bcl-2-IRES-BimEL (EC50=65.1 μM) and Bcl-XL-IRES-BimEL (EC50=70.0 μM) cells. Maritoclax (Marinopyrrole A) induces cell death selectively in Mcl-1-dependent but not Bcl-2- or Bcl-XL-dependent leukemia cells. Maritoclax (Marinopyrrole A) induces proteasome-mediated Mcl-1 degradation without induction of Mcl-1 phosphorylation and Noxa expression. Maritoclax (Marinopyrrole A) inhibits Mcl-1 interaction with Bim in intact cells and triggers cytochrome c release from isolated mitochondria. Maritoclax (Marinopyrrole A) synergistically sensitizes lymphoma/leukemia cells to ABT-737[1]. Maritoclax (Marinopyrrole A) shows activity against all tested S. aureus strains, including glycopeptide-intermediate and vancomycin-resistant MRSA, and has potent activities against other Gram-positive organisms. In addition, Maritoclax (Marinopyrrole A) is active against H. influenzae but is inactive against other tested Gram-negative strains. Maritoclax (Marinopyrrole A) displays substantial concentration-dependent killing against MRSA strain TCH1516 and is far more rapid in its antibiotic action than either vancomycin or linezolid. Maritoclax exhibits a favorable therapeutic index, with 50% inhibitory concentrations (IC50) in excess of 20× above the MIC in each case: 32 to 64 μg/mL against HeLa cells and 8 to 32 μg/mL against L929 cells[2]. Maritoclax (Marinopyrrole A) (3 μM) induced-cell death is associated with MCL1 decrease and translation inhibition. Maritoclax (Marinopyrrole A) induces a dephosphorylation of EIF4EBP1 concomitant to a decrease of EIF4E phosphorylation[3]. Maritoclax (Marinopyrrole A) is much more effective against Bcl-2-dependent RS4;11 cells (IC50: 2 μM) when compared to Mcl-1-dependent HeLa cells (IC50: 20 μM)[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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No. CAS 1227962-62-0
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Appearance Solid
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Peso molecular 510.15
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Fòrmula C22H12Cl4N2O4
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Color Light yellow to yellow
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SMILES
OC1=CC=CC=C1C(C2=C(N3C(C(C4=CC=CC=C4O)=O)=CC(Cl)=C3Cl)C(Cl)=C(Cl)N2)=O
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Synonyms
Marinopyrrole A
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Powder -20°C 3 years 4°C 2 years In solvent -80°C 2 years -20°C 1 year
Publications (6)
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Journal Impact Factor
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Most Recent
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Cell Metab
2019 May 7;29(5):1045-1060.e10. PMID: 30799288 -
Cell Rep Med
Venetoclax acts as an immunometabolic modulator to potentiate adoptive NK cell immunotherapy against leukemia. [Abstract]2024 Jun 18;5(6):101580. PMID: 38776913 -
Cell Death Differ
BH3 profiling discriminates on-target small molecule BH3 mimetics from putative mimetics. [Abstract]2020 Mar;27(3):999-1007. PMID: 31332296 -
Biochem Biophys Rep
BCL2 inhibitor ABT-199 and JNK inhibitor SP600125 exhibit synergistic cytotoxicity against imatinib-resistant Ph+ ALL cells. [Abstract]2018 Jul 13:15:69-75. PMID: 30073206 -
Trop Life Sci Res
Single Agent and Synergistic Activity of Maritoclax with ABT-263 in Nasopharyngeal Carcinoma (NPC) Cell Lines. [Abstract]2020 Oct;31(3):1-13. PMID: 33214852 -
Maritoclax purchased from MedChemExpress. Usage Cited in: bioRxiv. 2020 May.
Maritoclax represses the anti-apoptotic proteins in a dose- and time-dependent manner.
Solvente y solubilidad
In Vitro:
DMSO : ≥ 43 mg/mL (84.29 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
* "≥" means soluble, but saturation unknown.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (4.90 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: 2.5 mg/mL (4.90 mM); Suspended solution; Need ultrasonic
This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocolo
Cell Assay[2]
Maritoclax (Marinopyrrole A) cytotoxicity is assessed by seeding 2×104 HeLa or L929 cells per well in sterile 96-well tissue culture-treated plates. After 24 h, the medium is replaced with fresh medium containing increasing concentrations of marinopyrrole A, and the plates are incubated at 37°C in 5% CO2 for 24 h. Cytotoxicity is assayed at 24 h by measuring the reduction of MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium] using the CellTiter 96 Aqueous nonradioactive cell proliferation assay according to the manufacturer's instructions.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Pureza y Documentación
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Ficha de datos (288 KB)
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SDS (758 KB)
- English - EN (758 KB)
- Français - FR (758 KB)
- Deutsch - DE (758 KB)
- Norwegian - NO (758 KB)
- Español - ES (758 KB)
- Swedish - SV (758 KB)
- Italian - IT (758 KB)
- Korean - KR (758 KB)
- Portuguese - PT (758 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Doi K, et al. Discovery of marinopyrrole A (maritoclax) as a selective Mcl-1 antagonist that overcomes ABT-737 resistance by binding to and targeting Mcl-1 for proteasomal degradation. J Biol Chem. 2012 Mar 23;287(13):10224-35. [Content Brief]
[2]. Haste NM, et al. Pharmacological properties of the marine natural product marinopyrrole A against methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2011 Jul;55(7):3305-12. [Content Brief]
[3]. Gomez-Bougie P, et al. The selectivity of Marinopyrrole A to induce apoptosis in MCL1high BCL2low expressing myeloma cells is related to its ability to impair protein translation. Br J Haematol. 2016 Aug 14. [Content Brief]
[4]. Eichhorn JM, et al. Purported Mcl-1 inhibitor marinopyrrole A fails to show selective cytotoxicity for Mcl-1-dependent cell lines. Cell Death Dis. 2013 Oct 24;4:e880 [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
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| DMSO | 1 mM | 1.9602 mL | 9.8010 mL | 19.6021 mL | 49.0052 mL |
| 5 mM | 0.3920 mL | 1.9602 mL | 3.9204 mL | 9.8010 mL | |
| 10 mM | 0.1960 mL | 0.9801 mL | 1.9602 mL | 4.9005 mL | |
| 15 mM | 0.1307 mL | 0.6534 mL | 1.3068 mL | 3.2670 mL | |
| 20 mM | 0.0980 mL | 0.4901 mL | 0.9801 mL | 2.4503 mL | |
| 25 mM | 0.0784 mL | 0.3920 mL | 0.7841 mL | 1.9602 mL | |
| 30 mM | 0.0653 mL | 0.3267 mL | 0.6534 mL | 1.6335 mL | |
| 40 mM | 0.0490 mL | 0.2450 mL | 0.4901 mL | 1.2251 mL | |
| 50 mM | 0.0392 mL | 0.1960 mL | 0.3920 mL | 0.9801 mL | |
| 60 mM | 0.0327 mL | 0.1634 mL | 0.3267 mL | 0.8168 mL | |
| 80 mM | 0.0245 mL | 0.1225 mL | 0.2450 mL | 0.6126 mL |
Maritoclax Related Classifications
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