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Chemical Compound Review:

IAHQ (2S)-2-[[4-[[(2-amino-4-oxo- 1H-quinazolin...

Synonyms: NSC-285571, AR-1J3168, NSC 289517, AC1L2J3Z, 56239-21-5, ...

Sobrero, A.F. et al., Fernandes, D.J. et al., Tsang, K.Y. et al., Mini, E. et al., Hynes, J.B. et al.

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Disease relevance of IAHQ

The uptake and metabolism of radiolabeled 5,8-dideazaisofolic acid (IAHQ) (N-[p- ([(2-amino-4-hydroxy-6-quinazolinyl)amino]methyl)benzoyl]-L-glutamic acid), a new antifol targeted to thymidylate synthase, has been investigated in the human colon adenocarcinoma cell line HCT-8 [1].
Effects of 5,8-dideazaisopteroylglutamate (IAHQ) on L1210 leukemia in mice when given alone and in combination with methotrexate, probenecid, or verapamil [2].

High impact information on IAHQ

However, in tumor cells incubated with growth-inhibitory concentrations of either FdUrd or 5,8-dideazaisofolic acid for 48 h, the rate of thymidylate synthase activity was between 15- and 17-fold greater than the rate of DNA synthesis [3].
Both natural killer cell activity and phytohemagglutinin (PHA)-induced lymphocyte proliferation were decreased in hamsters injected with these compounds, with 5,8-dideazaisofolic acid being the most potent in this regard [4].

Associations of IAHQ with other chemical compounds

All three methotrexate-resistant sublines showed minor cross-resistance to isoaminohydroxyquinazoline (IAHQ, NSC 289517; 5,8-dideazaisopteroylglutamate), a folate antagonist inhibitor of thymidylate synthase [5].

References

Uptake and metabolism of 5,8-dideazaisofolic acid in human colon carcinoma cells. Sobrero, A.F., McGuire, J.J., Bertino, J.R. Biochem. Pharmacol. (1988) [Pubmed]
Effects of 5,8-dideazaisopteroylglutamate (IAHQ) on L1210 leukemia in mice when given alone and in combination with methotrexate, probenecid, or verapamil. Hynes, J.B., Smith, A.B., Gale, G.R. Cancer Chemother. Pharmacol. (1986) [Pubmed]
Dissociation of thymidylate biosynthesis from DNA biosynthesis by 5-fluoro-2'-deoxyuridine and 5,8-dideazaisofolic acid. Fernandes, D.J., Cranford, S.K. Cancer Res. (1986) [Pubmed]
Effects of three new folate antagonists on human breast adenocarcinoma cells in vitro and on immune responses in vivo. Tsang, K.Y., Hynes, J.B., Fudenberg, H.H., Pan, J.F. Chemotherapy. (1984) [Pubmed]
Cytotoxic effects of folate antagonists against methotrexate-resistant human leukemic lymphoblast CCRF-CEM cell lines. Mini, E., Moroson, B.A., Franco, C.T., Bertino, J.R. Cancer Res. (1985) [Pubmed]

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