Isopoptolidin, originally isolated from a Nocardiopsis sp., is a ring expanded isomer of apoptolidin. In water, an equilibrium mixture of apoptolidin:isoapoptolidin (~1.5:1) is formed within hours. In a rapid F0F1-ATPase assay, isoapoptolidin exhibited an IC50 of 17 μM compared to 0.7 μM for apoptolidin. Isoapoptolidin is an inhibitor of ATP5.
1. Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin. Wender P.A. et al. Org. Lett. 2002, 4, 3819. 2. Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin. Pennington J. D. et al. Org. Lett. 2002, 4, 3823. 3. Apoptolidin analogs and derivatives for inducing apoptosis in transformed cells. Wender P.A. et al. US Patent Application, 20040180841.
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