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Paper | Regular issue | Vol 75, No. 8, 2008, pp.1943-1952
Published online, 8th April, 2008
DOI: 10.3987/COM-08-11346
Synthesis of Acridine Analogues as Intercalating Crosslinkers and Evaluation of Their Potential Anticancer Properties

Toshinori Higashi, Maki Sakamoto, and Masataka Mochizuki*

*Faculty of Pharmacy, Keio University, 1-5-30, Shiba-koen, Minato-ku, Tokyo 105-8512, Japan


We synthesized 4,5-bis(halomethyl)acridines, which contain an acridine skeleton for DNA intercalation and two halomethyl groups for DNA crosslinking. 4,5-Bis(bromomethyl)acridine and 4,5-bis(chloromethyl)acridine intercalated in DNA and mediated interstrand DNA crosslinking. Both compounds were cytotoxic to CCRF-HSB-2 cells, a human T cell leukemia cell line. Molecular modeling of 4,5-bis(bromomethyl)acridine intercalated in 5’-GC-3’ base pairs of DNA indicated that the bromomethyl group, which mediates alkylation, is in close proximity to N7 of guanine.