A new class of semisynthetic anthracycline glycoside antibiotics incorporating a squaric acid moiety

Ferenc Sztaricskai, Anita Sum, Erzsébet Roth, István F. Pelyvás, Szabolcs Sándor, Gyula Batta, Pál Herczegh, Judit Reményi, Zsanett Miklán, Ferenc Hudecz

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Treatment of the squaric acid amide esters (7, 9) of anthracycline glycoside antibiotics with aliphatic and aromatic primary and secondary amines, amino acids, peptides and aminodeoxy sugars furnished the new asymmetric diamides 16-19, 25-30, 32, 34 and 38-40 in stereoselective reactions which do not require protecting group-manipulations. The IC50 = 0.12 μM value measured for daunorubicin (1) on human leukemia (HL-60) cells is comparable to those obtained for the daunomycin-L-leucyl squaric acid diamide (30, IC50 = 0.18 μM) and the corresponding D-galactosamine derivative (40, IC50 = 0.22 μM).

Original languageEnglish
Pages (from-to)704-714
Number of pages11
JournalJournal of Antibiotics
Volume58
Issue number11
DOIs
Publication statusPublished - Nov 1 2005

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Keywords

  • Anthracycline glycoside antibiotics
  • HL-60 activity
  • Squaric acid amides

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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