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Targeting studies using the anti-cancer agent neocarzinostatin (NCS), conjugated to anti­ bodies have shown relatively poor specificity. From the literature, it is unclear whether NCS mediates its effects either in conjugated or unconjugated form. In the present work we have used a conjugate of NCS with transferrin, a biological ligand with a well defined endocytic route, to probe these mechanisms. NCS was covalently coupled to transferrin using the heter­ obifunctional reagent sulfo-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) and 2-iminothiolane to give a stable thioether-linked conjugate with a ratio of 1.6 mol of NCS per mole of transferrin. The binding activity of transferrin was completely retained. Conjugation of NCS to transferrin resulted in an apparent enhancement of cytotoxicity. However, incubation with excess transferrin had no influence on the observed enhanced toxicity, indicating that endocytosis is not responsible.

Mechanism of Free and Conjugated Neocarzinostatin Activity: Studies on Chromophore and Protein Uptake Using a Transferrin-Neocarzinostatin Conjugate