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Melphalan

In stock
Catalog No.
A4473
DNA alkylating agent
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$80.00
In stock
50mg
$80.00
In stock

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Melphalan is a DNA alkylating agent and inhibits DNA and RNA synthesis [1].

DNA alkylating agent attaches the alkyl group to the guanine base of DNA and inhibits DNA and RNA synthesis, which is necessary for cells to survive.

In PC-3 cells, melphalan inhibited cells growth with IC50 values of 0.074 μg/ml and 0.77 μg/ml for sequential dosing and single dosing, respectively, which suggested the sequential dosing was more effective [1].

In 12 patients with androgen-independent prostate cancer, melphalan provided some clinical benefits with manageable toxicity and the median survival was 23 weeks [1]. In 381 myeloma patients who received melphalan-based autologous stem cell transplant (Mel-ASCT), melphalan (200 mg/m2 body surface area (BSA)) led to oral mucositis (OM) in 75% of patients. And OM was severe in 21% patients. Patients with renal dysfunction have the greatest risk for severe OM when received a high mg/kg melphalan dose [2].

References:
[1].  Mougenot P, Bressolle F, Culine S, et al. In vitro cytotoxic effect of melphalan and pilot phase II study in hormone-refractory prostate cancer. Anticancer Res, 2006, 26(3B): 2197-2203.
[2].  Grazziutti ML, Dong L, Miceli MH, et al. Oral mucositis in myeloma patients undergoing melphalan-based autologous stem cell transplantation: incidence, risk factors and a severity predictive model. Bone Marrow Transplant, 2006, 38(7): 501-506.

Chemical Properties

Physical AppearanceA solid
StorageStore at RT
M.Wt305.2
Cas No.148-82-3
FormulaC13H18Cl2N2O2
Solubility≥6.85mg/mL in DMSO
Chemical Name(2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid
SDFDownload SDF
Canonical SMILESC1=CC(=CC=C1CC(C(=O)O)N)N(CCCl)CCCl
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Protocol

Cell experiment [1]:

Cell lines

Human myeloma cell line RPMI 8226, neuroblastoma cell lines; SH-SY5Y, SK-N-AS, and SK-N-BE

Preparation method

The solubility of this compound in DMSO is >6.9 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

30-min

Applications

Melphalan (5 and 10 pmol/l) resulted in an out-growth delay during the first 48 post-treatment. Melphalan treatment disclosed a relative increase of cells in S- and G-phases at 24 h followed by an accumulation of cells in G,-phase at 48 h. Treatment with high melphalan concentrations (20 and 40 pmol/l) the accumulation in the G-phase was more persistent. Melphalan treatment (20 pmol/l) dramatically decreased late S- and G,-phases. Exposure of a myeloma cell line (RPMI 8226) to a 30-minute pulse of melphalan (1-phenylalanine-mustard) resulted in a cell cycle progression delay characteristic for DNA cross-linking agents. Melphalan bound to DNA, RNA, and protein in cells in vitro. Melphalan induced chromosomal aberrations, sister chromatid exchange, micronuclei, mutations at the HPRT gene, and DNA damage in human cells in vitro. Melphalan induced transformation of C3H 10T1/2 and other cells. In cultured rodent cells, it induced chromosomal aberrations, sister chromatid exchange, gene mutations, and DNA damage. Melphalan induced aneuploidy and sex-linked recessive lethal mutations in Drosophila, and mutation in bacteria.

Animal experiment [3]:

Animal models

Immunodeficient mice bearing human ovarian tumors from A2780 cells

Dosage form

Intraperitoneal injection, 11.7 mg/kg

Application

In immunodeficient mice bearing human ovarian tumors from A2780 cells, melphalan (11.7 mg/kg, i.p.) severely inhibited the growth of previously untreated tumors, whereas the growth of tumors which had received prior treatment with melphalan was unaffected by the subsequent high dose.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Fernberg J O, Lewensohn R, Skog S. Cell cycle arrest and DNA damage after melphalan treatment of the human myeloma cell line RPMI 8226[J]. European journal of haematology, 1991, 47(3): 161-167.

[2]. MELPHALAN. Pharmaceuticals.Bookshelf

[3]. Caffrey P B, Zhang Y, Frenkel G D. Rapid development of drug resistance in human ovarian tumor xenografts after a single treatment with melphalan in Vivo[J]. Anticancer research, 1998, 18(4C): 3021-3025.

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