Role of glutathione depletion in the mechanism of action of N-methylformamide and N,N-dimethylformamide in a cultured human colon carcinoma cell line. 1986

R F Cordeiro, and T M Savarese

The mechanism of the antitumor action of N-methylformamide (NMF), an agent currently undergoing clinical trials, and its congener, N,N-dimethylformamide (DMF), was examined in the DLD-1 Clone A human colon carcinoma cell line in vitro. The primary action of NMF and DMF on these cells is a depletion of cellular reduced glutathione levels which results in cytostasis. Evidence to support this hypothesis include (a) the extent of growth inhibition produced by NMF and DMF is directly proportional to the extent of depletion they effect on cellular reduced glutathione levels; (b) removal of NMF (170 mM) or DMF (103 mM) from the culture medium results in a parallel restoration of cell growth and cellular glutathione levels; (c) coaddition of the glutathione precursor, L-cysteine (0.5 mM), or certain precursors for this amino acid, significantly reverses NMF- and DMF-induced glutathione depletion and cytostasis; and (d) the specific glutathione-depleting agent, buthionine sulfoximine (7.5 mM) mimics the ability of NMF and DMF to induce cytostasis. In addition, NMF- and DMF-mediated reduced glutathione depletion accounts for the previously reported ability of these agents at high concentrations (less than 100 mM) to induce a more benign phenotype in DLD-1 Clone A human colon carcinoma cells. This is evidenced by the findings that (a) L-cysteine (0.5 mM) reverses NMF- and DMF-mediated (170 and 103 mM, respectively) increases in doubling time, decreases in saturation density, and decreases in clonogenicity; (b) buthionine sulfoximine (7.5 mM) mimics these actions of NMF and DMF; and (c) the tumorigenicity of DLD-1 Clone A cells in nude mice, which is completely eliminated by the in vitro treatment of these cells for 4 passages with 170 mM NMF prior to inoculation, is fully restored if the cells are passaged in the presence of 170 mM NMF and 0.5 mM L-cysteine. Thus, NMF- and DMF-induced depletion of cellular reduced glutathione is responsible for not only the cytostatic effect of these agents on human colon carcinoma cells but also for their ability to induce more benign characteristics in these cells.

UI MeSH Term Description Entries
D008717 Methionine Sulfoximine Sulfoximine, Methionine
D002453 Cell Cycle The complex series of phenomena, occurring between the end of one CELL DIVISION and the end of the next, by which cellular material is duplicated and then divided between two daughter cells. The cell cycle includes INTERPHASE, which includes G0 PHASE; G1 PHASE; S PHASE; and G2 PHASE, and CELL DIVISION PHASE. Cell Division Cycle,Cell Cycles,Cell Division Cycles,Cycle, Cell,Cycle, Cell Division,Cycles, Cell,Cycles, Cell Division,Division Cycle, Cell,Division Cycles, Cell
D002460 Cell Line Established cell cultures that have the potential to propagate indefinitely. Cell Lines,Line, Cell,Lines, Cell
D002945 Cisplatin An inorganic and water-soluble platinum complex. After undergoing hydrolysis, it reacts with DNA to produce both intra and interstrand crosslinks. These crosslinks appear to impair replication and transcription of DNA. The cytotoxicity of cisplatin correlates with cellular arrest in the G2 phase of the cell cycle. Platinum Diamminodichloride,cis-Diamminedichloroplatinum(II),cis-Dichlorodiammineplatinum(II),Biocisplatinum,Dichlorodiammineplatinum,NSC-119875,Platidiam,Platino,Platinol,cis-Diamminedichloroplatinum,cis-Platinum,Diamminodichloride, Platinum,cis Diamminedichloroplatinum,cis Platinum
D003110 Colonic Neoplasms Tumors or cancer of the COLON. Cancer of Colon,Colon Adenocarcinoma,Colon Cancer,Cancer of the Colon,Colon Neoplasms,Colonic Cancer,Neoplasms, Colonic,Adenocarcinoma, Colon,Adenocarcinomas, Colon,Cancer, Colon,Cancer, Colonic,Cancers, Colon,Cancers, Colonic,Colon Adenocarcinomas,Colon Cancers,Colon Neoplasm,Colonic Cancers,Colonic Neoplasm,Neoplasm, Colon,Neoplasm, Colonic,Neoplasms, Colon
D003545 Cysteine A thiol-containing non-essential amino acid that is oxidized to form CYSTINE. Cysteine Hydrochloride,Half-Cystine,L-Cysteine,Zinc Cysteinate,Half Cystine,L Cysteine
D004126 Dimethylformamide A formamide in which the amino hydrogens are replaced by methyl groups. N,N-Dimethylformamide,N,N Dimethylformamide
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D005559 Formamides A group of amides with the general formula of R-CONH2.
D005978 Glutathione A tripeptide with many roles in cells. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes, is involved in protein disulfide bond rearrangement and reduces peroxides. Reduced Glutathione,gamma-L-Glu-L-Cys-Gly,gamma-L-Glutamyl-L-Cysteinylglycine,Glutathione, Reduced,gamma L Glu L Cys Gly,gamma L Glutamyl L Cysteinylglycine

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