N-(5, 5-Diacetoxypent-l-yl) doxorubicin (DAPDOX)(3), a new, water-soluble analogue of doxorubicin, has been synthesized by coupling doxorubicin with 5-oxopentane-1, l-diacetate in the presence of NaBH&N. This analogue was designed to be converted to the corresponding aldehyde, N-(5-oxopent-l-yl) doxorubicin, in the presence of carboxylate hydrolases, enzymes that are ubiquitous in tissue. DAPDOX had a half-life of several days ...
