Synthesis of methotrexate polyglutamates in L1210 murine leukemia cells. 1977

V M Whitehead

The ability of L1210 mouse leukemia cells and of a mutant methotrexate-resistant cell line (L1210/MTX) to synthesize methotrexate polyglutamates was studied. Host DBA/2 mice were treated with methotrexate, after which leukemic cells were harvested from ascitic fluid and levels of methotrexate and metabolites in them were determined by Sephadex G-15 gel chromatography. The level of methotrexate in L1210/MTX cells was 12.5 times greater than that in L1210 cells, reflecting the increased level of dihydrofolate reductase that characterizes this mutant cell line. Synthesis of methotrexate polyglutamates in each cell line required a dose of methotrexate (2.4 mg/kg) 10 times greater than the dose that yielded extensive methotrexate polyglutamate synthesis in rat liver and kidney in previous studies. Total methotrexate polyglutamates synthesized in 4 hr with this dose were the same in each cell line, demonstrating that this metabolism was not affected by differences in the level of dihydrofolate reductase. Methotrexate polyglutamates comprised 47+/-20% of the total methotrexate in L1210 cells. Methotrexate diglutamate was the predominant form. Levels of methotrexate monoglutamate and diglutamate were similar in L1210/MTX cells, whereas methotrexate monoglutamate was the predominant metabolite in host liver, kidney, and small intestine. These differences may reflect differences in substrate preference of pteroylpolyglutamate synthetase in these different tissues. Twenty-four hr after methotrexate administration, total methotrexate in L1210 cells was one-third of that at 4 hr; but the proportion of metabolites was the same, presumably reflecting cell death and division rather than loss of a freely exchangeable portion of intracellular methotrexate present at the earlier time. The affinity of methotrexate polyglutamates for dihydrofolate reductase was found to be similar to that of methotrexate, providing evidence that these metabolites may be as potent antagonists of folate metabolism as is methotrexate itself. Recent studies indicate that inhibition of folate metabolism in cells requires their exposure to high levels of methotrexate in order to achieve intracellular levels of methotrexate greater than needed to bind to dihydrofolate reductase. Such conditions conform to those required for synthesis of methotrexate polyglutamates. Thus, these metabolites may play a specific role in inhibiting folate metabolism, distinct from the antifolate potential that they appear to share with methotrexate.

UI MeSH Term Description Entries
D007939 Leukemia L1210 An experimental LYMPHOCYTIC LEUKEMIA of mice. Leukemia L 1210,L 1210, Leukemia,L1210, Leukemia
D008297 Male Males
D008727 Methotrexate An antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of TETRAHYDROFOLATE DEHYDROGENASE and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA. Amethopterin,Methotrexate Hydrate,Methotrexate Sodium,Methotrexate, (D)-Isomer,Methotrexate, (DL)-Isomer,Methotrexate, Dicesium Salt,Methotrexate, Disodium Salt,Methotrexate, Sodium Salt,Mexate,Dicesium Salt Methotrexate,Hydrate, Methotrexate,Sodium, Methotrexate
D008811 Mice, Inbred DBA An inbred strain of mouse. Specific substrains are used in a variety of areas of BIOMEDICAL RESEARCH such as DBA/1J, which is used as a model for RHEUMATOID ARTHRITIS. Mice, DBA,Mouse, DBA,Mouse, Inbred DBA,DBA Mice,DBA Mice, Inbred,DBA Mouse,DBA Mouse, Inbred,Inbred DBA Mice,Inbred DBA Mouse
D010452 Peptide Biosynthesis The production of PEPTIDES or PROTEINS by the constituents of a living organism. The biosynthesis of proteins on RIBOSOMES following an RNA template is termed translation (TRANSLATION, GENETIC). There are other, non-ribosomal peptide biosynthesis (PEPTIDE BIOSYNTHESIS, NUCLEIC ACID-INDEPENDENT) mechanisms carried out by PEPTIDE SYNTHASES and PEPTIDYLTRANSFERASES. Further modifications of peptide chains yield functional peptide and protein molecules. Biosynthesis, Peptide
D010455 Peptides Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS. Peptide,Polypeptide,Polypeptides
D011099 Polyglutamic Acid A peptide that is a homopolymer of glutamic acid. Polyglutamate
D005493 Folic Acid Antagonists Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033) Antifolate,Antifolates,Dihydrofolate Reductase Inhibitor,Folic Acid Antagonist,Dihydrofolate Reductase Inhibitors,Folic Acid Metabolism Inhibitors,Acid Antagonist, Folic,Acid Antagonists, Folic,Antagonist, Folic Acid,Antagonists, Folic Acid,Inhibitor, Dihydrofolate Reductase,Inhibitors, Dihydrofolate Reductase,Reductase Inhibitor, Dihydrofolate,Reductase Inhibitors, Dihydrofolate
D005971 Glutamates Derivatives of GLUTAMIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the 2-aminopentanedioic acid structure. Glutamic Acid Derivatives,Glutamic Acids,Glutaminic Acids
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
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