A phenazine analog of actinomycin D

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Abstract
An analog of actinomycin D (1) in which the phenoxazone chromophore was replaced by a phenazine, was synthesized and characterized. Although this compound (2) lacks the 2-amino group and does not possess the quinoid structure of 1, it does bind to DNA, but less tightly than either 1 or the 2-deamino derivative of 1. NMR and CD [circular dichroism] spectra indicate that the peptide conformations in 2 are approximately as in 1; there was no apparent asymmetry of the 2 peptide rings. Compound 2 inhibited nucleic acid synthesis in mouse leukemia L1210 cell more effectively than does 2-deaminoactinomycin D, but 1/10 as well as does actinomycin D.

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