Mutations in adenosine deaminase-like (ADAL) protein confer resistance to the antiproliferative agents N6-cyclopropyl-PMEDAP and GS-9219

Anticancer Res. 2013 May;33(5):1899-912.

Abstract

Background/aim: GS 9219 is a double prodrug of antiproliferative nucleotide analog 9-(2-Phosphonylmethoxyethyl)guanine (PMEG), with potent in vivo efficacy against various hematological malignancies. This study investigates the role of adenosine deaminase-like (ADAL) protein in the intracellular activation of GS-9219.

Materials and methods: A cell line resistant to 9-(2-Phosphonylmethoxyethyl)-N(6)-cyclopropyl-2,6-diaminopurine (cPrPMEDAP), an intermediate metabolite of GS-9219, was generated and characterized.

Results: The resistant cell line was cross-resistant to cPrPMEDAP and GS-9219, due to a defect in the deamination of cPrPMEDAP to PMEG. Mutations in the ADAL gene (H286R and S180N) were identified in the resistant cells that adversely-affected its enzymatic activity. Introduction of the wild-type ADAL gene re-sensitized resistant cells to both cPrPMEDAP and GS-9219.

Conclusion: The ADAL protein plays an essential role in the intracellular activation of GS-9219 by catalyzing the deamination of cPrPMEDAP metabolite to PMEG. Mutations affecting the activity of ADAL confer resistance to both GS-9219 and its metabolite cPrPMEDAP.

Keywords: ADAL; GS-9219; PMEG; deamination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / pharmacology
  • Alanine / analogs & derivatives*
  • Alanine / pharmacology
  • Amino Acid Sequence
  • Antineoplastic Agents / pharmacology
  • Blotting, Western
  • Drug Resistance, Neoplasm / genetics*
  • Female
  • Humans
  • Molecular Sequence Data
  • Mutation / genetics*
  • Nucleoside Deaminases / chemistry
  • Nucleoside Deaminases / genetics*
  • Nucleoside Deaminases / metabolism
  • Prodrugs / pharmacology
  • Protein Conformation
  • Purines / pharmacology*
  • Sequence Homology, Amino Acid
  • Tumor Cells, Cultured
  • Uterine Cervical Neoplasms / drug therapy
  • Uterine Cervical Neoplasms / genetics*

Substances

  • Antineoplastic Agents
  • Prodrugs
  • Purines
  • rabacfosadine
  • 9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine
  • ADAL protein, human
  • Nucleoside Deaminases
  • Adenine
  • Alanine