Cyclophosphamide

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Cyclophosphamide

本产品不向个人销售，仅用作科学研究，不用于任何人体实验及非科研性质的动物实验。

CAS NO:

50-18-0

包装与价格：

包装	价格(元)
10mM (in 1mL DMSO)	电议
50mg	电议
200mg	电议
500mg	电议
5g	电议
10g	电议

产品介绍

化学性质

Physical Appearance	A solid
Storage	Store at -20°C
M.Wt	261.09
Cas No.	50-18-0
Formula	C₇H₁₅Cl₂N₂O₂P
Solubility	≥11.85 mg/mL in H2O with gentle warming and ultrasonic; ≥13.05 mg/mL in DMSO; ≥50.8 mg/mL in EtOH
Chemical Name	N,N-bis(2-chloroethyl)-2-oxo-1,3,2λ5-oxazaphosphinan-2-amine
Canonical SMILES	C1CNP(=O)(OC1)N(CCCl)CCCl
运输条件	蓝冰运输或根据您的需求运输。
一般建议	为了使其更好的溶解，请用37℃加热试管并在超声波水浴中震动片刻。不同厂家不同批次产品溶解度各有差异，仅做参考。若实验所需浓度过大至产品溶解极限，请添加助溶剂助溶或自行调整浓度。溶液形式一般不宜长期储存，请尽快用完。

资料参考

Cyclophosphamide, an inactive prodrug, is a kind of nitrogen mustard alkylating agent. Cyclophosphamide requires enzymatic and chemical activation. As a result, nitrogen mustard is produced. It causes DNA cross-linking that accounts for its cytotoxic properties.^[1]IC₅₀of cytotoxicity in mouse embryo BALB/c 3T3 cells is 37.6 μM,^[2]IC₅₀of cytotoxicity against human HL60 cells is 8.79 μM measured by MTT assay.^[3]

Cyclophosphamide attaches the alkyl group to the guanine base of DNA causing its crosslinking, strand breakage and inducing mutations.

In vitro, cyclophosphamide has a dose-dependent, bimodal effect on the immune system. Low-dose cyclophosphamide not only decreases cell number but leads to decreased functionality of regulatory T cells (T_REGs). Cyclophosphamide treatment enhances apoptosis and decreases homeostatic proliferation of these cells. Expression of GITR and FoxP3, which are involved in the suppressive activity of T_REGs, is down-regulated after cyclophosphamide administration.^[4]In primary human hepatocyte cultures, cyclophosphamide increases CYP3A4, CYP2C8, and CYP2C9 protein levels, causing its 4-hydroxylation rate enhance.^[5] In somatic cells, cyclophosphamide produces gene mutations, chromosome aberrations, micronuclei and sister chromatid exchanges in a variety of cultured cells in the presence of metabolic activation as well as sister chromatid exchanges without metabolic activation.^[6]

In vivo, it has produced chromosome damage and micronuclei in rats, mice and Chinese hamsters, and gene mutations in the mouse spot test and in the transgenic lacZ construct of Muta^(TM)Mouse.^[6]

References:

[1] Emadi A, Jones RJ, Brodsky RA. Cyclophosphamide and cancer: golden anniversary. Nat Rev Clin Oncol. 2009 Nov; 6 (11):638-47.

[2] Moon KY, Kwon CH. N3-methyl-mafosfamide as a chemically stable, alternative prodrug of mafosfamide. Bioorg Med Chem Lett. 1998 Jul 7; 8 (13):1673-8.

[3] Patel MM, Mali MD, Patel SK. Bernthsen synthesis, antimicrobial activities and cytotoxicity of acridine derivatives. Bioorg Med Chem Lett. 2010 Nov 1; 20 (21):6324-6.

[4] Lutsiak ME, Semnani RT, De Pascalis R,et al. Inhibition of CD4(+)25+ T regulatory cell function implicated in enhanced immune response by low-dose cyclophosphamide. Blood. 2005 Apr 1; 105 (7):2862-8. Epub 2004 Dec 9.

[5] Chang TK, Yu L, Maurel P, Waxman DJ. Enhanced cyclophosphamide and ifosfamide activation in primary human hepatocyte cultures: response to cytochrome P-450 inducers and autoinduction by oxazaphosphorines. Cancer Res. 1997 May 15; 57 (10):1946-54.

[6] Anderson D, Bishop JB, Garner RC, et al. Cyclophosphamide: review of its mutagenicity for an assessment of potential germ cell risks. Mutat Res. 1995 Aug; 330 (1-2):115-81.

试验操作

Cell experiment:[1]
Cell lines	9L gliosarcoma cells retrovirally transduced withCYP2B6
Reaction Conditions	1 mM cyclophosphamide for 48 h incubation
Applications	Cyclophosphamide was shown to cause tumor cell death by stimulating apoptosis, as evidenced by the induction of plasma membrane blebbing, DNA fragmentation, and cleavage of the caspase 3 and caspase 7 substrate poly(ADP-ribose) polymerase in drug-treated cells.
Animal experiment:[2]
Animal models	Female C57BL/6 mice, 8 weeks of age
Dosage form	2 mg Injected intraperitoneally
Applications	Low-dose cyclophosphamide not only decreased the number of regulatory T cells (T_REGs), but also led to decreased functionality of T_REGs. Cyclophosphamide treatment enhanced apoptosis and decreased homeostatic proliferation of these cells.
Note	The technical data provided above is for reference only.
	References: 1. Schwartz PS, Waxman DJ. Cyclophosphamide induces caspase 9-dependent apoptosis in 9L tumor cells. Molecular Pharmacology, 2001, 60(6): 1268-1279. 2. Lutsiak ME, Semnani RT, De Pascalis R, et al. Inhibition of CD4(+)25+ T regulatory cell function implicated in enhanced immune response by low-dose cyclophosphamide. Blood, 2005, 105(7): 2862-2868.