Analogs of a 4-aminothieno[2,3-d]pyrimidine lead (QB13) as modulators of P-glycoprotein substrate specificity

Bioorg Med Chem Lett. 2009 Nov 1;19(21):6102-5. doi: 10.1016/j.bmcl.2009.09.023. Epub 2009 Sep 11.

Abstract

P-glycoprotein (P-gp) is an important factor in the development of multidrug resistance (MDR) in cancer cells. In literature reports, a thieno[2,3-d]pyrimidine (QB13) was described as P-gp modulator and opposed effects on the cell accumulation of distinct P-gp substrates were postulated. On the basis of this lead structure, a series of 2-alkylthio-4-aminothieno[2,3-d]pyrimidines was prepared and tested in a daunorubicin accumulation assay. Modulation of substrate specificity was shown for selected compounds in cytotoxicity (MTT) assays.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism*
  • Antibiotics, Antineoplastic / metabolism
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Daunorubicin / metabolism
  • Drug Resistance, Neoplasm
  • Humans
  • Molecular Conformation
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology
  • Quinazolines / chemical synthesis
  • Quinazolines / chemistry
  • Quinazolines / pharmacology
  • Substrate Specificity

Substances

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Antibiotics, Antineoplastic
  • Pyrimidines
  • Quinazolines
  • thienopyrimidine
  • Daunorubicin