Cancer chemopreventive effect of quassinoid derivatives. Introduction of side chain to shinjulactone C for enhancement of inhibitory effect on Epstein-Barr virus activation

Cancer Lett. 2002 Nov 8;185(1):47-51. doi: 10.1016/s0304-3835(02)00302-6.

Abstract

A series of shinjulactone C (1) derivatives (2-8) were synthesized and evaluated for their anti-tumor promoting effects against Epstein-Barr virus early antigen activation introduced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. The succinate and 3',3'-dimethylsuccinate derivatives of 1 exhibited higher inhibitory effects than 1. From the point of view of structure-activity relationships, the succinate derivatives (2, 4) demonstrated better potency than the glutarate derivatives (3, 5-8). As substituted moieties of 3'-position became bulky, the inhibitory effects of the glutarate derivatives (7, 8) significantly decreased.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antigens, Viral / metabolism
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Chemoprevention
  • Dose-Response Relationship, Drug
  • Epstein-Barr Virus Infections / prevention & control*
  • Herpesvirus 4, Human / drug effects*
  • Herpesvirus 4, Human / physiology
  • Humans
  • Inhibitory Concentration 50
  • Lactones / isolation & purification
  • Lactones / pharmacology*
  • Plant Bark / chemistry
  • Quassins / pharmacology*
  • Structure-Activity Relationship
  • Tetradecanoylphorbol Acetate / pharmacology
  • Tumor Cells, Cultured
  • Virus Activation / drug effects*

Substances

  • Antigens, Viral
  • Antineoplastic Agents, Phytogenic
  • Epstein-Barr virus early antigen
  • Lactones
  • Quassins
  • Tetradecanoylphorbol Acetate