Halogenation of N⁶-benzyladenosine decreases its cytotoxicity in human leukemia cells

Toxicol In Vitro. 2010 Dec;24(8):2079-83. doi: 10.1016/j.tiv.2010.07.010. Epub 2010 Jul 15.

Abstract

Cytotoxicity of two halogen derivatives of N⁶-benzyladenosine (BAPR), N⁶-(3-iodobenzyl)-adenosine (I-BAPR) and 2-chloro-N⁶-(3-iodobenzyl)-adenosine (Cl-I-BAPR), was tested in human leukemia U937 cell line. Our results revealed that their cytotoxicity was surprisingly low. I-BAPR and also Cl-I-BAPR induced cell death with morphological and biochemical hallmarks of apoptosis, although the number of apoptotic cells was significantly lower than that found for BAPR. Our data strongly suggested that the decreased cytotoxic effect of halogenated derivatives of N⁶-benzyladenosine was related to their reduced intracellular phosphorylation by adenosine kinase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemistry
  • Adenosine / toxicity
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Cytotoxins / chemistry*
  • Cytotoxins / toxicity
  • Halogenation
  • Humans
  • U937 Cells

Substances

  • Cytotoxins
  • N(6)-benzyladenosine
  • Adenosine