Preparation and use of NHS-MAG3 for technetium-99m labeling of DNA

Nucl Med Biol. 1997 Jul;24(5):425-32. doi: 10.1016/s0969-8051(97)00027-9.

Abstract

The chelator mercaptoacetylglycylglycylglycine (MAG3) is on of several amidothiols that have been used successfully to radiolabeled proteins and other molecules with 99mTc. Prior to radiolabeling, the sulfur in these amidothiols is usually protected by a benzoyl group (i.e. S-benzoyl MAG3) which requires extreme alkaline pH or boiling water temperatures for rapid deprotection. As a result, the benzoyl-protected chelator is radiolabeled prior to conjugation (i.e. preconjugation labeling) in the case of carriers such as proteins or polypeptides which cannot withstand harsh conditions. We have employed a simple, two-step, synthesis of the N-hydroxysuccinimide ester of MAG3 in which the sulfur is protected with an acetyl group (i.e. S-acetyl NHS-MAG3). A single-stranded amine-derivitized DNA was coupled with NHS-S-acetyl MAG3. Radiolabeling was accomplished at room temperature and neutral pH by transchelation from 99mTc-tartrate. In comparison to labeled SHNH-DNA, the labeled MAG3-DNA was unstable to cysteine transchelation, however, in contrast to SHNH-DNA, no evidence for serum protein binding of the labeled MAG3-DNA was observed. We conclude that the S-acetyl NHS MAG3 bifunctional chelator may prove to be an attractive alternative method of radiolabeling DNA and other biologically important molecules with 99mTc.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Chelating Agents / metabolism*
  • Chromatography, High Pressure Liquid
  • DNA / metabolism*
  • Glycine / analogs & derivatives*
  • Glycine / metabolism
  • Isotope Labeling*
  • Magnetic Resonance Spectroscopy
  • Succinimides / metabolism*
  • Technetium*

Substances

  • Chelating Agents
  • Succinimides
  • N-(mercaptoacetyl)glycine
  • Technetium
  • DNA
  • N-hydroxysuccinimide
  • Glycine