(-)-Irofulven
Based on 1 publication(s) in Google Scholar
(-)-Irofulven (MGI 114), an Illudin S analog, is a DNA alkylating agent. (-)-Irofulven inhibits the replication of DNA, induces tumor cells apoptosis, and has potent antitumor activity.
For research use only. We do not sell to patients.
- Purity : 95.55%
- CAS No.: 158440-71-2
- Formula: C15H18O3
- Molecular Weight:246.31
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Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Protocols
- Purity & Documentation
- References
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Help & FAQs
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Publications Citing Use of MedChemExpress (MCE) (-)-Irofulven
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Biological Activity
Description
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HEK293 | IC50 |
1.2 μM
Compound: (-)-HMAF
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Cytotoxicity against HEK293 cells by MTT assay
Cytotoxicity against HEK293 cells by MTT assay
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[PMID: 16610802] |
| HEK293 | IC50 |
55 nM
Compound: (-)-HMAF
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Cytotoxicity against HEK293 cells transfected with recombinant AOR by MTT assay
Cytotoxicity against HEK293 cells transfected with recombinant AOR by MTT assay
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[PMID: 16610802] |
| HL-60 | IC50 |
73 nM
Compound: 5, HMAF, MGI114
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Cytotoxicity against human HL60 cells after 48 hrs by trypan blue exclusion method
Cytotoxicity against human HL60 cells after 48 hrs by trypan blue exclusion method
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[PMID: 8864242] |
| HL-60 | IC50 |
73 nM
Compound: irofulven
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Cytotoxicity against human HL60 cells after 48 hrs by trypan blue exclusion assay
Cytotoxicity against human HL60 cells after 48 hrs by trypan blue exclusion assay
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[PMID: 12608875] |
In Vitro
(-)-Irofulven (2.8 μM; 1 hour) induces p53-dependent cell cycle arrest[1].
(-)-Irofulven (0.8 μM, 0.9 μM and 2.8 μM; 1 hour) induces CHK2 activation is related to p53 status in cells[1].
(-)-Irofulven inhibits DNA replication and induces chromosome aberrations (breaks and radials)[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
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Cell Line:A2780, CAOV3 and HCT116 cells
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Concentration:2.8 μM
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Incubation Time:1 hour
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Result:p53 wild-type cells mainly arrested at G1/S phases, while p53-mutated or p53-null cells arrested at S and G2/M phases.
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Cell Line:A2780, CAOV3 and HCT116 cells
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Concentration:0.8 μM, 0.9 μM and 2.8 μM
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Incubation Time:1 hour
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Result:Induced the Thr 68 phosphorylation of CHK2 kinase in cells.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Male and female athymic BALB/c mice (nu/nu genotype, 6 weeks old or older) injected with human glioblastoma multiforme[2].
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Dosage:7 mg/kg
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Administration:i.p; on days 1-5 and 8-12
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Result:Was active against all tumor lines.
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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CAS No. 158440-71-2
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Appearance Solid
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Molecular Weight 246.31
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Formula C15H18O3
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Color Yellow to orange
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SMILES
CC(C1(CC1)[C@@](O)(C2=O)C)=C3C2=CC(C)=C3CO
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Synonyms
MGI 114; 6-Hydroxymethylacylfulvene; NSC 683863
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Publications (1)
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Journal Impact Factor
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Most Recent
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Adv Sci (Weinh)
Glucose Deprivation-Induced Disulfidptosis via the SLC7A11-INF2 Axis: Pan-Cancer Prognostic Exploration and Therapeutic Validation. [Abstract]2025 Jul 25:e08556. PMID: 40709550
Solvent & Solubility
In Vitro:
DMSO : 50 mg/mL (203.00 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
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, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
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, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
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 (10.15 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 (10.15 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 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.
Protocols
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
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Subcutaneous Cell-Line-Derived Xenograft
Subcutaneous cell-line-derived xenograft (CDX) models are established by implanting cultured human cancer cell lines into immunodeficient mice, where the injected cells form localized tumors that can be monitored in vivo as a measure of tumorigenic potential, growth kinetics, and treatment response. These models are widely used in oncology research because they allow reproducible tumor formation and enable comparative assessment of tumor growth between different cell lines or genetic manipulations in a controlled in vivo microenvironment. Subcutaneous implantation of cancer cells in immunodeficient mice is a standard approach for evaluating tumor growth behavior and therapeutic response across multiple cancer types, including prostate, esophageal, pancreatic, and colon cancer models.
Purity & Documentation
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Data Sheet (279 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[1]. Yutian Wang, et al. Irofulven induces replication-dependent CHK2 activation related to p53 status. Biochem Pharmacol. 2007 Feb 15;73(4):469-80. [Content Brief]
[2]. H S Friedman, et al. Activity of irofulven (6-hydroxymethylacylfulvene) in the treatment of glioblastoma multiforme-derived xenografts in athymic mice. Cancer Chemother Pharmacol. 2001 Nov;48(5):413-6. [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, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 4.0600 mL | 20.3000 mL | 40.5999 mL | 101.4998 mL |
| 5 mM | 0.8120 mL | 4.0600 mL | 8.1200 mL | 20.3000 mL | |
| 10 mM | 0.4060 mL | 2.0300 mL | 4.0600 mL | 10.1500 mL | |
| 15 mM | 0.2707 mL | 1.3533 mL | 2.7067 mL | 6.7667 mL | |
| 20 mM | 0.2030 mL | 1.0150 mL | 2.0300 mL | 5.0750 mL | |
| 25 mM | 0.1624 mL | 0.8120 mL | 1.6240 mL | 4.0600 mL | |
| 30 mM | 0.1353 mL | 0.6767 mL | 1.3533 mL | 3.3833 mL | |
| 40 mM | 0.1015 mL | 0.5075 mL | 1.0150 mL | 2.5375 mL | |
| 50 mM | 0.0812 mL | 0.4060 mL | 0.8120 mL | 2.0300 mL | |
| 60 mM | 0.0677 mL | 0.3383 mL | 0.6767 mL | 1.6917 mL | |
| 80 mM | 0.0507 mL | 0.2537 mL | 0.5075 mL | 1.2687 mL | |
| 100 mM | 0.0406 mL | 0.2030 mL | 0.4060 mL | 1.0150 mL |
(-)-Irofulven Related Classifications
HY-14429 Related Classifications
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