Synthesis of aminoanthraquinone derivatives and their in vitro evaluation as potential anti-cancer drugs

Jehoshua Katzhendler*, Keria Fiorella Gean, Gidon Bar-Ad, Zeev Tashma, Raphael Ben-Shoshan, Israel Ringel, Uriel Bachrach, Avner Ramu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

Anthraquinones, monosubstituted by aminoalkylamino side chains at positions 1, 2 or disubstituted at positions 1, 5 or 1, 8 were prepared. Their in vitro cytotoxic activity (ED50) was evaluated using: 1) P388 murine leukemia cells and 2) a subline of these cells resistant to doxorubicin (P388/ADR). The results of the structure-activity relationship analysis indicated that monosubstitution in position 1 or 2 showed a decrease of the activity when compared to adryamicin. Disubstitution in positions 1, 5 by N,N-dimethyl ethylenediamine side chain led to optimal activity, whereas the presence of cyclic dialkylamino substituents in the same positions resulted in a corresponding decrease in the anti-tumor activity. Disubstitution in positions 1,8 did not show any improvement in the cytotoxic activity.

Original languageEnglish
Pages (from-to)23-30
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Volume24
Issue number1
DOIs
StatePublished - 1989

Keywords

  • aminoantraquinones
  • anti-cancer
  • DNA
  • intercalation

Fingerprint

Dive into the research topics of 'Synthesis of aminoanthraquinone derivatives and their in vitro evaluation as potential anti-cancer drugs'. Together they form a unique fingerprint.

Cite this