4-hydroperoxy Cyclophosphamide (Synonyms: 4-OOH-CY) |
رقم الكتالوجGC42401
One-Click Copy Product Info
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Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 39800-16-3
Sample solution is provided at 25 µL, 10mM.
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4-hydroperoxy Cyclophosphamide, the active metabolite of cyclophosphamide, can cross-link DNA and induce T cell apoptosis independently of caspase receptor activation. It also activates the mitochondrial death pathway through the production of reactive oxygen species (ROS). 4-hydroperoxy Cyclophosphamide is useful in research on rheumatoid arthritis and autoimmune diseases[1-2].
4-hydroperoxy Cyclophosphamide(1 μg/mL, 72-96 h), along with methotrexate, suppresses RANKL expression in IL-6/sIL-6R-stimulated fibroblast-like synoviocytes by inhibiting the JAK2/STAT3 and p38MAPK signaling pathways[3]. 4-hydroperoxy Cyclophosphamide (3 μg/ml; 48h) treatment resulted in the production of reactive oxygen species, increased levels of Bax, and the translocation of mitochondrial factors apoptosis-inducing factor (AIF) and endonuclease G (EndoG) to the nucleus. This treatment causes caspase-independent cell death in human CTL [4].
4-hydroperoxy Cyclophosphamide (200 mg/kg; i.p; 5 days) induced caspase-independent cell death in mouse T cells and B cells[4]. 4-hydroperoxy Cyclophosphamide (50-200 μg) intradermal injection at the sensitized site in guinea pig models of in-vivo contact sensitivity resulted in a significant enhancement of contact hypersensitivity [5].
References:
[1]. Fleer R, Brendel M. Toxicity, interstrand cross-links and DNA fragmentation induced by 'activated' cyclophosphamide in yeast: comparative studies on 4-hydroperoxy-cyclophosphamide, its monofunctional analogon, acrolein, phosphoramide mustard, and nor-nitrogen mustard. Chem Biol Interact. 1982 Mar 1;39(1):1-15. doi: 10.1016/0009-2797(82)90002-3. PMID: 7037214.
[2]. Chen Y, Ai L, et,al. The EZH2-H3K27me3 axis modulates aberrant transcription and apoptosis in cyclophosphamide-induced ovarian granulosa cell injury. Cell Death Discov. 2023 Nov 14;9(1):413. doi: 10.1038/s41420-023-01705-6. PMID: 37963880; PMCID: PMC10646043.
[3]. Niu HQ, Zhao WP, et,al. Combination of 4-hydroperoxy cyclophosphamide and methotrexate inhibits IL-6/sIL-6R-induced RANKL expression in fibroblast-like synoviocytes via suppression of the JAK2/STAT3 and p38MAPK signaling pathway. Int Immunopharmacol. 2018 Aug;61:45-53. doi: 10.1016/j.intimp.2018.05.014. Epub 2018 May 24. PMID: 29803913.
[4]. Strauss G, Westhoff MA, et,al. 4-hydroperoxy-cyclophosphamide mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptogenic factors AIF and EndoG. Cell Death Differ. 2008 Feb;15(2):332-43. doi: 10.1038/sj.cdd.4402272. Epub 2007 Nov 23. PMID: 18034189.
[5]. Boerrigter GH, de Groot J, et,al. Intradermal administration of 4-hydroperoxy-cyclophosphamide during contact sensitization potentiates effector T cell responsiveness in draining lymph nodes. Immunopharmacology. 1986 Feb;11(1):13-20. doi: 10.1016/0162-3109(86)90060-3. PMID: 3485619.
| Cell experiment [1]: | |
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Cell lines |
Primary human cytotoxic T cells (CTL) |
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Preparation Method |
Cell were cultured in the absence (untreated) or presence of 4-hydroperoxy Cyclophosphamide (3 μg/ml) for 48 h. |
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Reaction Conditions |
3 μg/ml；48h |
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Applications |
4-hydroperoxy Cyclophosphamide induces caspase-independent death of human cytotoxic T lymphocytes (CTL) after treatment. |
| Animal experiment [2]: | |
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Animal models |
BALB/c mice |
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Preparation Method |
Mice were injected i.p. with 200 mg/kg 4-hydroperoxy Cyclophosphamide. |
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Dosage form |
200 mg/kg; i.p; 5days |
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Applications |
4-hydroperoxy Cyclophosphamide treatment induces caspase-independent death in mouse T cells and B cells. |
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References: [1]. Strauss G, Westhoff MA, et,al. 4-hydroperoxy-cyclophosphamide mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptogenic factors AIF and EndoG. Cell Death Differ. 2008 Feb;15(2):332-43. doi: 10.1038/sj.cdd.4402272. Epub 2007 Nov 23. PMID: 18034189. |
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| Cas No. | 39800-16-3 | SDF | |
| المرادفات | 4-OOH-CY | ||
| Chemical Name | 2-[bis(2-chloroethyl)amino]tetrahydro-2-oxido-2H-1,3,2-oxazaphosphorin-4-yl, hydroperoxide | ||
| Canonical SMILES | O=P1(N(CCCl)CCCl)OCCC(OO)N1 | ||
| Formula | C7H15Cl2N2O4P | M.Wt | 293.1 |
| الذوبان | DMSO : 50 mg/mL (170.60 mM; Need ultrasonic) | Storage | -80°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.4118 mL | 17.059 mL | 34.118 mL |
| 5 mM | 682.4 μL | 3.4118 mL | 6.8236 mL |
| 10 mM | 341.2 μL | 1.7059 mL | 3.4118 mL |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
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Quality Control & SDS
- View current batch:
- Purity: >95.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 21 reference(s) in Google Scholar.)