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Chemical Compound Review:

CHEMBL49436 N-phenylacridin-9-amine

Synonyms: AC1L2CQF, LS-14214, ZINC03899979, AKOS002710482, BRN 0210868, ...

Atwell, G.J. et al., Zwelling, L.A. et al., Baguley, B.C. et al., Auparakkitanon, S. et al., Fan, J.Y. et al., et al.

Baguley, Wakelin, Jacintho, Kovacic,

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Disease relevance of N-phenylacridin-9-amine

An equation was also derived for the acute toxicities of 643 derivatives of 9-anilinoacridine [1].
The mutagenicity of a series of derivatives of 9-anilinoacridine, including the clinical antitumour agent amsacrine, has been assessed using a bacterial frameshift tester strain (Salmonella typhimurium TA1537) and a yeast petite colony assay (Saccharomyces cerevisiae 5178B) [2].

High impact information on N-phenylacridin-9-amine

We tested the cytotoxic and DNA-cleaving activities of two amsacrine analogues which were derivatives of 9-anilinoacridine (1'-methylcarbamate and 1'-benzenesulfonamide) against an amsacrine-resistant human leukemia cell line (HL-60/AMSA) whose resistance is due to an amsacrine-resistant topoisomerase II [3].
Amsacrine is a 9-anilinoacridine derivative that appears to act as an electron donor in ET reactions on DNA, while N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) may act as an electron acceptor [4].
These studies open up the novel possibility of development of 9-anilinoacridine antimalarials that target not only DNA topoisomerase II but also beta-hematin formation, which should help delay the rapid onset of resistance to drugs acting at only a single site [5].
A series of bis(hydroxymethyl)-substituted imidazoles, thioimidazoles, and pyrrolizines and related bis(carbamates), linked to either 9-anilinoacridine (intercalating) or 4-(4-quinolinylamino)benzamide (minor groove binding) carriers, were synthesized and evaluated for sequence-specific DNA alkylation and cytotoxicity [6].
This series was developed as the result of previous quantitative structure-activity relationship (QSAR) studies of the antitumor activity of 9-anilinoacridine derivatives [7].

Biological context of N-phenylacridin-9-amine

A series of N-mustard derivatives of 9-anilinoacridine was synthesized for antitumor and structure-activity relationship studies [8].
Kinetics and mechanism of general acid-catalysed thiolytic cleavage of 9-anilinoacridine [9].

Anatomical context of N-phenylacridin-9-amine

Two types of 9-anilinoacridine-linked mustards, containing aniline mustard side chains linked either at the 4-position of the intercalating acridine chromophore (type A) or at the 1'-position of the 9-anilino group (type B), were reacted with calf thymus DNA [10].

Associations of N-phenylacridin-9-amine with other chemical compounds

The ability of various 9-anilinoacridine derivatives to quench the fluorescence of DNA-bound ethidium appears to be related to the electron donor properties of the substituents on the anilino ring, as well as to experimental antitumour activity [11].

References

Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents. Denny, W.A., Cain, B.F., Atwell, G.J., Hansch, C., Panthananickal, A., Leo, A. J. Med. Chem. (1982) [Pubmed]
Inverse correlation between bacterial frameshift mutagenicity and yeast mitochondrial effects of antitumour anilinoacridines. Baguley, B.C., Ferguson, L.R. Chem. Biol. Interact. (1985) [Pubmed]
Relative activity of structural analogues of amsacrine against human leukemia cell lines containing amsacrine-sensitive or -resistant forms of topoisomerase II: use of computer simulations in new drug development. Zwelling, L.A., Mitchell, M.J., Satitpunwaycha, P., Mayes, J., Altschuler, E., Hinds, M., Baguley, B.C. Cancer Res. (1992) [Pubmed]
Mechanisms of action of DNA intercalating acridine-based drugs: how important are contributions from electron transfer and oxidative stress? Baguley, B.C., Wakelin, L.P., Jacintho, J.D., Kovacic, P. Current medicinal chemistry. (2003) [Pubmed]
Antimalarial 9-anilinoacridine compounds directed at hematin. Auparakkitanon, S., Noonpakdee, W., Ralph, R.K., Denny, W.A., Wilairat, P. Antimicrob. Agents Chemother. (2003) [Pubmed]
DNA-Directed alkylating agents. 7. Synthesis, DNA interaction, and antitumor activity of bis(hydroxymethyl)- and bis(carbamate)-substituted pyrrolizines and imidazoles. Atwell, G.J., Fan, J.Y., Tan, K., Denny, W.A. J. Med. Chem. (1998) [Pubmed]
Potential antitumor agents. 38. 3-substituted 5-carboxamido derivatives of amsacrine. Denny, W.A., Atwell, G.J., Baguley, B.C. J. Med. Chem. (1983) [Pubmed]
Potent antitumor 9-anilinoacridines bearing an alkylating N-mustard residue on the anilino ring: synthesis and biological activity. Bacherikov, V.A., Chou, T.C., Dong, H.J., Zhang, X., Chen, C.H., Lin, Y.W., Tsai, T.J., Lee, R.Z., Liu, L.F., Su, T.L. Bioorg. Med. Chem. (2005) [Pubmed]
Kinetics and mechanism of general acid-catalysed thiolytic cleavage of 9-anilinoacridine. Khan, M.N., Kuliya-Umar, A.F. Bioorg. Med. Chem. (1995) [Pubmed]
DNA adducts of 9-anilinoacridine mustards: characterization by NMR. Fan, J.Y., Ohms, S.J., Boyd, M., Denny, W.A. Chem. Res. Toxicol. (1999) [Pubmed]
Electron donor properties of the antitumour drug amsacrine as studied by fluorescence quenching of DNA-bound ethidium. Davis, L.M., Harvey, J.D., Baguley, B.C. Chem. Biol. Interact. (1987) [Pubmed]

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