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Synthesis and antitumor activity of 1-β-D-arabinofuranosylcytosine conjugates of cortisol and cortisone

Authors
Journal
Biochemical and Biophysical Research Communications
0006-291X
Publisher
Elsevier
Publication Date
Volume
88
Issue
4
Identifiers
DOI: 10.1016/0006-291x(79)91110-0

Abstract

Abstract Superior antitumor activity of 1-β-D-arabinofuranosylcytosine (ara-C) conjugates of prednisolone and prednisone against L1210 leukemic mice, based on ara-C content, has encouraged us to synthesize 5′-(cortisone-21-phosphoryl)-1-β-D-arabinofuranosylcytosine (I) and 5′-(cortisone-21-phosphoryl)-1-β- d-arabinofuranosylcytosine (II) by condensation of N 4,2′,3′-triacetyl-1-β- d-arabinofuranosylcytosine 5′-monophosphate with cortisol and cortisone in the presence of N,N′-dicyclohexylcarbodiimide at room temperature followed by removing the acetyl groups in 2 N methanolic ammonia in 20% yield. The conjugates I and II inhibited the in vitro growth of L1210 by 50% (ED 50) at 0.25 μM and 0.07 μM, respectively, while ara-C showed ED 50 0.1 μM. However, the conjugates I and II exhibited 287% and 238% of T C at 50 mg/kg/day × 5 doses against L1210 leukemic mice, respectively, while ara-C at 25 mg and 50 mg/kg/day × 5 gave the respective 127% and 110% of T C .

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