Spermidine → Spermidine Bis-Acridine

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The scheme for directing nucleic acids to certain sites of the body is based upon the intercalation of a ligand which interacts with a cell surface component into the double stranded DNA. A procedure for selective N4-acylation of spermidine, using N1,N8-bis(t-butoxycarbonyl) spermidine as starting material, has been reported. R. J. Bergeron et al., Synthesis (1982) 689-692. We have used this procedure (FIG. 8) to link the acid functionalized galactosyl derivatives 9(n=1) and 9′(n=4) to the secondary amino group of N1,N8-tBoc-protected spermidine (15) and the resulting galactosylated spermidines 17 and 17′ were, after deprotection, further alkylated with 9-phenoxyacridine by a standard chemical procedure to transform them into bis-intercalator compounds 21 and 21′. The synthesis of the carboxylic acid functionalized galactosyl derivatives is detailed (J. Haensler et al., Biochim Biophys Acta (1988) 946:95-105) and is easily applicable to a wide range of carbohydrate ligands (M. M. Ponpipom et al., J Med Chem (1981) 24:1388-1395). The title compounds were obtained in an overall yield of 30% and the NMR and mass spectrometry data are consistent with the proposed structure.

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