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In vitro and in vivo study of an albumin-binding prodrug of doxorubicin that is cleaved by cathepsin B

 

Khalid Abu Ajaj, Ralph Graeser, Iduna Fichtner, Felix Kratz

 

 

Cancer Chemotherapy & Pharmacology, 2009, 64 (2), 413–418

 

Keywords: albumin-binding prodrug; albumin; cathepsin B; 1,6-self-immolative spacer; doxorubicin

 

Abstract: Purpose: This study was designed to evaluate the in vitro and in vivo antitumor activity of an albumin-binding prodrug of doxorubicin 1 which incorporates a maleimide moiety and a para-aminobenzyloxycarbonyl (PABC) spacer coupled to the dipeptide Phe-Lys that is cleaved by cathepsin B. Methods: Cleavage of the albumin conjugate was studied with cathepsin B and in homogenates of MDA-MB 435 tumors. For in vivo studies, nude mice were injected with (a) glucose buffer, (b) doxorubicin (2 × 8 mg/kg, i.v, on days 10 and 17), or (c) compound 1 (3 × 24 mg/kg doxorubicin equivalent, on days 10, 17 and 24). Results: Prodrug 1 once bound to albumin was effectively cleaved by cathepsin B and in tumor homogenates releasing doxorubicin. Cytotoxicity assay of the albumin conjugate of 1 in two human tumor cell lines showed that doxorubicin was ~6 times more active than the conjugate. In contrast, in an in vivo study, the prodrug exhibited superior antitumor activity (T/C 15%) compared to doxorubicin (T/C 49%) in an equitoxic comparison. Conclusions: The cathepsin B cleavable spacer Phe-Lys-PABC incorporated in an albumin-binding prodrug is an effective way to increase the therapeutic index of doxorubicin.

 

 

 

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