SMB01361

Phosphoramide mustard cyclohexylamine

≥95% (HPLC)

• Synonym(s): N,N-Bis(2-Chloroethyl)phosphorodiamidic acid, cyclohexylamine, Friedman acid, cyclohexylamine, PAM cyclohexylamine, PM cyclohexylamine, PMC, Phosphamide mustard, Cyclohexylamine, Phosphorodiamidic mustard, Cyclohexylamine
• Linear Formula: C₄H₁₁Cl₂N₂O₂P · C₆H₁₃N
• CAS Number: 1566-15-0
• MDL number: MFCD00866429
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Quality Level: 200
• Assay: ≥95% (HPLC)
• form: solid
• storage temp.: -10 to -25°C
• SMILES string: ClCCN(P(N)(O)=O)CCCl.NC1CCCCC1
• InChI: 1S/C6H13N.C4H11Cl2N2O2P/c7-6-4-2-1-3-5-6;5-1-3-8(4-2-6)11(7,9)10/h6H,1-5,7H2;1-4H2,(H3,7,9,10)
• InChI key: BGTIPRUDEMNRIP-UHFFFAOYSA-N

Description

General description

Phosphoramide mustard cyclohexanamine, a potent cytotoxic metabolite derived from the anticancer drug cyclophosphamide, acts as a remarkable alkylating agent. It is generated from cyclophosphamide through the ring-opened tautomer of the cytochrome P450 (CYP) isoform-formed intermediate 4-hydroxycyclophosphamide. This metabolite exerts its cytotoxic effects by inducing DNA crosslinking, guanine alkylation, and the formation of DNA-protein conjugates. In a concentration-dependent manner, it specifically targets HT-1080 human fibrosarcoma cells, triggering DNA damage. An essential contributor to Cyclophosphamide′s anticancer activity, Phosphoramide Mustard Cyclohexanamine exhibits great promise for cancer research, as it has the potential to induce DNA adduct formation and activate the ovarian DNA repair response in granulosa cells.

Application

Used in the development of chemotherapeutic drugs that are known to treat cancer.

Biochem/physiol Actions

Phosphoramide mustard cyclohexanamine induces cytotoxicity by forming cross-linked DNA adducts that hinder DNA strand separation during replication. This compound destroys rapidly dividing cells and leads to DNA damage. In a study with rat ovarian granulosa cells (SIGCs), it reduced cell viability and increased DNA damage response (DDR) gene expression and protein levels. In animal models, it exhibited significant anticancer activity by inhibiting tumor growth. These findings highlight the potential of Phosphoramide mustard cyclohexanamine in cancer research

Features and Benefits

• High quality compound suitable for multiple research applications
• Compatible with a wide variety of chromatographic and spectrometry techniques

Other Notes

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This product is intended for research purposes only, and it is not meant for human consumption.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable