Isoquino[4,5-bc]acridines: design, synthesis and evaluation of DNA binding, anti-tumor and DNA photo-damaging ability

J Photochem Photobiol B. 2006 Sep 1;84(3):221-6. doi: 10.1016/j.jphotobiol.2006.03.005. Epub 2006 May 22.

Abstract

Several novel isoquino[4,5-bc]acridine derivatives have been designed and synthesized. Their DNA-binding, anti-tumor and DNA-photo-damaging properties were investigated. A4 exhibited the highest anti-tumor activities against both A 549 (human lung cancer cell) and P388 (murine leukemia cells). All these compounds were found to be more cytotoxic against P388 than against A549. Under 365-nm light irradiation, A3 damaged plasmid DNA pBR322 at <2 microM and cleaved DNA from form I to 100% form II by 50 microM. The mechanism studies revealed that A3 damaged DNA by electron transfer mechanism and singlet oxygen species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemical synthesis
  • Acridines / chemistry*
  • Acridines / metabolism
  • Acridines / pharmacology*
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • DNA Damage
  • DNA, Neoplasm / drug effects*
  • DNA, Neoplasm / metabolism
  • Drug Design
  • Humans
  • Intercalating Agents / chemical synthesis
  • Intercalating Agents / chemistry
  • Intercalating Agents / metabolism
  • Intercalating Agents / pharmacology
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry
  • Isoquinolines / metabolism
  • Isoquinolines / pharmacology
  • Leukemia P388 / drug therapy
  • Leukemia P388 / metabolism
  • Mice
  • Photobiology

Substances

  • Acridines
  • Antineoplastic Agents
  • DNA, Neoplasm
  • Intercalating Agents
  • Isoquinolines