Transfer RNA bindings to antitumor estradiol-platinum(II) hybrid and cisplatin

DNA Cell Biol. 2008 Jun;27(6):337-43. doi: 10.1089/dna.2008.0727.

Abstract

The anticancer platinum (Pt) drugs exert their antitumor activity by direct or indirect Pt-DNA binding. It has been shown that Pt drugs can induce major DNA damage and minor RNA damage during cancer treatment. A recent report showed that a new anticancer estradiol-Pt(II) hybrid molecule (CD-37) binds DNA bases indirectly, while being more effective than cis-diaminedichloroplatinum(II) (cisplatin) against several types of cancer. In this report, we examine the bindings of CD-37 and cisplatin drugs with transfer RNA (tRNA) in vitro and compare the results to those of the corresponding Pt-DNA complexes. Solutions containing various CD-37 or cisplatin concentrations were reacted with tRNA at physiological pH. Using Fourier transform infrared (FTIR), UV-visible, and circular dichroism spectroscopic methods, the drug binding mode, the binding constant, and RNA structural variations are determined for Pt-tRNA complexes in aqueous solution. Structural analysis showed direct binding of cisplatin drug to guanine and adenine N7 sites, while both direct and indirect interactions of CD-37 with tRNA bases and the backbone phosphate group were observed. The overall binding constants estimated were K(CD-37) = 2.77 (+/-0.90) x 10(4) M(1) and K(cisplatin) = 1.72 (+/-0.50) x 10(4) M(1). Major aggregation of tRNA occurs at high CD-37 concentrations, while RNA remains in the A-family structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / metabolism*
  • Binding Sites
  • Circular Dichroism
  • Cisplatin / metabolism*
  • Estradiol / analogs & derivatives*
  • Estradiol / metabolism
  • Humans
  • In Vitro Techniques
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Nucleic Acid Conformation
  • Organoplatinum Compounds / metabolism*
  • RNA, Fungal / chemistry
  • RNA, Fungal / metabolism
  • RNA, Transfer / chemistry
  • RNA, Transfer / metabolism*
  • Spectrophotometry, Ultraviolet
  • Spectroscopy, Fourier Transform Infrared

Substances

  • 17beta-estradiol platinum(II)
  • Antineoplastic Agents
  • Organoplatinum Compounds
  • RNA, Fungal
  • Estradiol
  • RNA, Transfer
  • Cisplatin