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Chemical Compound Review:

CHEMBL11139 2-[[4-[(4-amino-2-oxo-3,5,7...

Synonyms: NSC-344279, AC1Q5SFW, NSC344279, AR-1J8797, NSC 344279, ...

Stone, S.R. et al., Davies, J.F. et al., Piper, J.R. et al., Rosowsky, A. et al.

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Disease relevance of NSC344279

In bacterial studies on the 2-amino-4-oxo analogues, 5-deazafolic acid proved to be a potent inhibitor of Lactobacillus casei DHFR and also the growth of both L. casei ATCC 7469 and Streptococcus faecium ATCC 8043 [1].
Folate behaved as a classical, steady-state inhibitor of both enzymes, whereas 5-deazafolate exhibited slow-binding inhibition (Mechanism B) with the enzyme from E. coli and classical, steady-state inhibition with the enzyme from chicken liver [2].

High impact information on NSC344279

The 5-deazafolate analogues were inhibitors of mouse liver FPGS, and the DATHF analogues inhibited both mouse FPGS and mouse leukemic cell GARFT [3].
The 2.3-A crystal structure of recombinant human dihydrofolate reductase (EC 1.5.1.3, DHFR) has been solved as a binary complex with folate (a poor substrate at neutral pH) and also as a binary complex with an inhibitor, 5-deazafolate [4].
By contrast, 5-deazafolate was bound about 4000 times more tightly than folate to the enzyme from E. coli and about 30 times more tightly than folate to the chicken-liver enzyme [2].

Associations of NSC344279 with other chemical compounds

Crystal structures of recombinant human dihydrofolate reductase complexed with folate and 5-deazafolate [4].

References

Syntheses and antifolate activity of 5-methyl-5-deaza analogues of aminopterin, methotrexate, folic acid, and N10-methylfolic acid. Piper, J.R., McCaleb, G.S., Montgomery, J.A., Kisliuk, R.L., Gaumont, Y., Sirotnak, F.M. J. Med. Chem. (1986) [Pubmed]
Inhibition of dihydrofolate reductase from bacterial and vertebrate sources by folate, aminopterin, methotrexate and their 5-deaza analogues. Stone, S.R., Montgomery, J.A., Morrison, J.F. Biochem. Pharmacol. (1984) [Pubmed]
Side chain modified 5-deazafolate and 5-deazatetrahydrofolate analogues as mammalian folylpolyglutamate synthetase and glycinamide ribonucleotide formyltransferase inhibitors: synthesis and in vitro biological evaluation. Rosowsky, A., Forsch, R.A., Reich, V.E., Freisheim, J.H., Moran, R.G. J. Med. Chem. (1992) [Pubmed]
Crystal structures of recombinant human dihydrofolate reductase complexed with folate and 5-deazafolate. Davies, J.F., Delcamp, T.J., Prendergast, N.J., Ashford, V.A., Freisheim, J.H., Kraut, J. Biochemistry (1990) [Pubmed]

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