Potent antitumor N-mustard derivatives of 9-anilinoacridine, synthesis and antitumor evaluation

Bioorg Med Chem Lett. 2004 Sep 20;14(18):4719-22. doi: 10.1016/j.bmcl.2004.06.080.

Abstract

A series of 9-anilinoacridine N-mustard derivatives, in which the alkylating N-mustard residue was linked to the C-3' or C-4' position of the anilino ring with an O-ethylene spacer, was synthesized and evaluated for cytotoxicity against human lymphoblastic leukemic cells (CCRF-CEM) in culture. The results showed that all of the new compounds exhibited potent cytotoxicity with IC(50) values ranging from 0.002 to 0.7 microM, which were as potent or significantly more potent than 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA). Compound 9 did not exhibit cross-resistance against both vinblastine-resistant (CCRF-CEM/VBL) and taxol-resistant (CCRF-CEM/taxol) cells. Additionally, compound 9 demonstrated potent antitumor effect in nude mice bearing human breast carcinoma MX-1 xenografts, resulting in complete tumor remission in two out of three mice at the maximal dose of 1-2mg/kg (Q3Dx7) or 3mg/kg (Q4Dx5) via intravenous injection.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amsacrine / administration & dosage
  • Amsacrine / analogs & derivatives*
  • Amsacrine / chemical synthesis
  • Amsacrine / pharmacology*
  • Animals
  • Antineoplastic Agents / administration & dosage
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Breast Neoplasms / drug therapy
  • Dose-Response Relationship, Drug
  • Drug Resistance, Neoplasm
  • Humans
  • Injections, Intravenous
  • Mice
  • Mice, Nude
  • Nitrogen Mustard Compounds / administration & dosage
  • Nitrogen Mustard Compounds / chemical synthesis
  • Nitrogen Mustard Compounds / pharmacology*
  • Paclitaxel / pharmacology
  • Structure-Activity Relationship
  • Tumor Cells, Cultured
  • Vinblastine / pharmacology
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Nitrogen Mustard Compounds
  • Amsacrine
  • 9-anilinoacridine
  • Vinblastine
  • Paclitaxel