Amsacrine (synonyms: m-AMSA, acridinyl anisidide) is an antineoplastic agent. It has been used in

acute lymphoblastic leukemia Acute lymphoblastic leukemia (ALL) is a cancer of the lymphoid line of blood cells characterized by the development of large numbers of immature lymphocytes. Symptoms may include feeling tired, pale skin color, fever, easy bleeding or bruisin ...

Mechanism

Its planar fused ring system can

intercalate Intercalation may refer to: *Intercalation (chemistry), insertion of a molecule (or ion) into layered solids such as graphite * Intercalation (timekeeping), insertion of a leap day, week or month into some calendar years to make the calendar foll ...

into the DNA of tumor cells, thereby altering the major and minor groove proportions. These alterations to DNA structure inhibit both DNA replication and transcription by reducing association between the affected DNA and: DNA polymerase, RNA polymerase and transcription factors. Amsacrine also expresses topoisomerase inhibitor activity, specifically inhibiting topoisomerase II. In contrast, the structurally similar o-AMSA differing in the position of the methoxy substituent group on the anilino-ring have little ability to poison topoisomerase II despite its intercalative behavior, suggesting that intercalation of the molecule in itself is insufficient to trap topoisomerase II as a covalent complex on DNA.

References

Sulfonamides Antineoplastic drugs IARC Group 2B carcinogens Acridines O-methylated phenols DNA intercalaters Topoisomerase inhibitors {{antineoplastic-drug-stub