| Size | Price | Stock | Qty |
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| 1mg |
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| 1g | |||
| Other Sizes |
| Targets |
ASTA-6496 targets DNA by forming crosslinks. As an alkylating agent, it adds alkyl groups to the guanine base of DNA, leading to the formation of intra-strand and inter-strand crosslinks. This DNA damage prevents DNA replication and transcription, ultimately leading to cell death. It also induces T cell apoptosis independent of death receptor activation, but activates mitochondrial death pathways through ROS production.
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|---|---|
| ln Vitro |
In vitro, 4-Hydroperoxy cyclophosphamide induces T cell apoptosis and forms crosslinks in DNA. It triggers mitochondrial death pathways by generating ROS. It also increases levels of glutaminase and aspartate aminotransferase, enhances inflammatory factors and oxidative markers, and inhibits oxidoreductase activity. It mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptotic factors AIF and EndoG.
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| ln Vivo |
In vivo, 4-Hydroperoxy cyclophosphamide possesses potent antitumor and immunosuppressive effects. It is used as an antitumor drug, immunosuppressant, and alkylating agent. It can be used to study the effects of cyclophosphamide without relying on liver metabolism for activation. However, specific published in vivo efficacy studies for ASTA-6496 are not detailed in the current literature.
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| Enzyme Assay |
The in vitro DNA crosslinking assay for 4-Hydroperoxy cyclophosphamide involves incubating the compound with DNA and then measuring the formation of crosslinks using techniques such as alkaline elution or comet assay. T cell apoptosis is assessed in T cell lines or primary T cells by flow cytometry using Annexin V/PI staining. ROS production is measured using fluorescent probes such as DCFH-DA. Caspase-independent apoptosis is confirmed by using caspase inhibitors.
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| Cell Assay |
Cellular assays for 4-Hydroperoxy cyclophosphamide are conducted in T cells and other cell lines. Cells are treated with varying concentrations of the compound. Apoptosis is assessed by flow cytometry using Annexin V/PI staining and by measuring the activation of caspases or the release of mitochondrial factors such as AIF and EndoG. DNA damage is evaluated by detecting γ-H2AX foci or by comet assay. ROS levels are measured using fluorescent probes.
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| Animal Protocol |
In vivo studies for 4-Hydroperoxy cyclophosphamide are typically conducted in animal models of cancer or autoimmune diseases. The compound is administered via intraperitoneal or intravenous injection. Efficacy is assessed by measuring tumor growth inhibition or immunosuppression. However, specific published in vivo protocols for ASTA-6496 are not detailed in the available literature. The compound is primarily used as a research tool to study the active metabolite of cyclophosphamide.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 4-Hydroperoxy cyclophosphamide indicates that it is the active metabolite of cyclophosphamide. It has a molecular weight of 293.08 and a molecular formula of C7H15Cl2N2O4P. It is typically administered via injection for in vivo studies. Detailed PK parameters such as half-life and bioavailability are not extensively reported in the provided sources.
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| Toxicity/Toxicokinetics |
Toxicity data for 4-Hydroperoxy cyclophosphamide is derived from its use as an active metabolite of cyclophosphamide. It is a potent alkylating agent and can cause significant toxicity, including immunosuppression, myelosuppression, and genotoxicity. It may also cause 4-autoimmune diseases and lymphomas. As with all research compounds, it is intended for research use only and not for human therapeutic applications.
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| References | |
| Additional Infomation |
4-Hydroperoxycyclophosphamide is a phosphoridamide and the active metabolite of the nitrogen mustard drug cyclophosphamide. It possesses potent antitumor and immunosuppressive effects. It can be used as an antitumor drug, immunosuppressant, alkylating agent, metabolite, and drug allergen. It is a phosphoridamide, nitrogen mustard, peroxyl, and organochlorine compound.
See also: Perphosphamide (note moved to). ASTA-6496 (4-Hydroperoxy cyclophosphamide; CAS 39800-16-3) is the active metabolite of the prodrug Cyclophosphamide. It is a potent alkylating agent that induces T cell apoptosis and forms DNA crosslinks. It triggers mitochondrial death pathways by generating ROS and possesses potent antitumor and immunosuppressive effects. ASTA-6496 is a valuable research tool for studying the mechanisms of action of cyclophosphamide. |
| Molecular Formula |
C7H15CL2N2O4P
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|---|---|
| Molecular Weight |
293.085
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| Exact Mass |
292.015
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| Elemental Analysis |
C, 28.69; H, 5.16; Cl, 24.19; N, 9.56; O, 21.84; P, 10.57
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| CAS # |
39800-16-3
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| Related CAS # |
4-Hydroperoxy Cyclophosphamide-d4;1246816-71-6
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| PubChem CID |
38347
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| Appearance |
White to yellow solid powder
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| Density |
1.465g/cm3
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| Boiling Point |
419.946ºC at 760 mmHg
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| Melting Point |
100-103ºC
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| Flash Point |
207.776ºC
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| Index of Refraction |
1.525
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| LogP |
2.028
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
16
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| Complexity |
253
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClCCN(P1(OCCC(OO)N1)=O)CCCl
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| InChi Key |
VPAWVRUHMJVRHU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)
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| Chemical Name |
N,N-bis(2-chloroethyl)-4-hydroperoxy-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
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| Synonyms |
ASTA-6496; 4-OOH-CY; ASTA 6496; ASTA6496; 4-hydroperoxy Cyclophosphamide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~170.6 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (8.53 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.53 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.53 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4119 mL | 17.0596 mL | 34.1192 mL | |
| 5 mM | 0.6824 mL | 3.4119 mL | 6.8238 mL | |
| 10 mM | 0.3412 mL | 1.7060 mL | 3.4119 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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